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Holiday Homes near Sail San Diego

2646 Shelter Island Dr, San Diego, California 92106-3116
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    Travellers to San Diego are booking May dates now. Secure your holiday rental today, and have the perfect trip.
    All 100 Rentals in San Diego
    BEACH HOUSE includes WHITE WATER OCEAN VIEWS and Air Conditioning!!1 / 25
    (7)Excellent
    Point Loma
    2.6 kilometres from Sail San Diego
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Ocean View Dream Vacation 1 bedroom in San Diego California1 / 100
    (22)Excellent
    Ocean Beach
    3.3 kilometres from Sail San Diego
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    1.8 kilometres from Sail San Diego
    6 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    Ocean Beach
    2.8 kilometres from Sail San Diego
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Wi-Fi
    • Private Garden
    • Parking
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The house has lots of spaces. Open concept Livng , dining and Kitchen. great for social gatherings. There are 2 studio size bedrooms. Each with couch, good for hanging out. Beautiful back yard. And views views views. Walk to over 50 Restuarants, Walk to the Beach, Walk to the Ocean beach Street...
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    San Diego, California
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    2.8 kilometres from Sail San Diego
    5 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    • Ocean Views
    • DVD Player
    • Wi-Fi
    • Washer
    • Waterfront
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Breathtaking View of Pacific Ocean--Dramatic Sunsets Welcome to Villa Mar Vista's big backyard with POOL and JACUZZI--Among the largest backyards of Oceanfront Homes in San Diego Your family can relax in comfort with ocean views from your living room. Villa Mar Vista encompasses over 3600 square...
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    San Diego, California
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 14
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    The Whole House is Yours with Views Galore! - Enjoy our newly built guest house1 / 8
    (4)Excellent
    2.9 kilometres from Sail San Diego
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Mountain Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 January 2018
    This is a pleasant one-bedroom place on top of a garage. It is separated from the owner's house next door with lots of privacy. The house is very clean and pleasant. The owner...
    Reviewed 22 October 2017
    We stayed at the Little Pumpkin Guest House through the summer and our stay could not have been better. The guest house appeared to be brand new and was impeccable. Upon arrival...
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    About this property
    Come be one of the first to stay in our new two story guest house. We built it just for you! You’ll love our place because of the comfy bed, the coziness, the full kitchen, the quiet neighborhood, and the views. We are minutes from downtown, Sea World, Liberty Station and beaches. Plenty of great...
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    San Diego, California
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Slipaway - Boat Bed and Breakfast1 / 12
    (44)Excellent
    0.6 kilometres from Sail San Diego
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • DVD Player
    • Wi-Fi
    • Ocean Views
    • Grill
    • Washer
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    • Waterfront
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 February 2018
    You know it might be romantic to think about living on a boat ... well we had a great stay, but it did convince me sailboat life is not for the 60 year old crowd! While for a...
    Reviewed 14 September 2017
    My husband and 2 boys (age 10 and 13) stayed on Slipaway for 3 nights and it was amazing! My husband could not stop thanking me for this trip, he said it was very relaxing and...
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    About this property
    Come experience what it is like to stay in our beautiful SLIPAWAY, Boat B&B. This is perfect for that romantic getaway for two or bring the whole family. This yacht accommodates up to 5 persons dockside with 1 Queen Stateroom aft, 2 single bunks midship and 1 double berth forward. This yacht has...
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    San Diego, California
    Private Room - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    BOAT, BED & BREAKFAST - Ohana - Sleeps 61 / 30
    (6)Average
    0.6 kilometres from Sail San Diego
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Air Conditioning
    • Washer
    • Ocean Views
    • Mountain Views
    • DVD Player
    • Wi-Fi
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 February 2018
    What a fantastic 2 days on this boat in such a perfect location. My only regret is not finding such a holiday sooner and being on the boat longer ! Additionally Shaun the...
    Reviewed 25 September 2017
    We've stayed at quite a few boat bnb's over the years and this was one of our favorite. Great location. Close to everything on the water. Shaun had some great information for...
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    About this property
    'OHANA' is an All-American Beauty - a 42' Carver with a wide open floor plan. Her spacious interior and aft deck will please even the most discriminating taste. She boasts 2 comfortable staterooms plus a double convertible sofa in the Salon that offer tons of comfort and space for up to 6...
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    San Diego, California
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    'FIRST CLASS' - Boat, Bed & Breakfast1 / 14
    (2)Very good
    0.6 kilometres from Sail San Diego
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Waterfront
    • DVD Player
    • Balcony
    • Ocean Views
    • Grill
    • Washer
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 August 2018
    Just when I thought I had experienced the best of San Diego, I discovered Boat B&B! A beautiful, well stocked boat at Shelter Island, was five days of pure delight. I had...
    Reviewed 4 January 2018
    Boat was definitely First Class on a great Marina. Perfect location for sea kayaking. Shaun and staff very helpful
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    About this property
    Beautiful 38' Technema designed with passion and craftsmanship. Her beautiful stainless port holes and elegant wood throughout define the quality of the Italian marine architects. She sleeps up to 4 people with a Queen forward and 2 twin bunks starboard. The spacious head has plenty of counter...
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    San Diego, California
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    BOAT BED & BREAKFAST - 'MAGIC' - 43' HUNTER - Sleeps 41 / 11
    (11)Very good
    0.6 kilometres from Sail San Diego
    3 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Central Heating
    • Wi-Fi
    • DVD Player
    • Washer
    • Grill
    • Ocean Views
    • Waterfront
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 April 2018
    My parents and I stayed on the Magic for 2 nights. It was fun to have happy hour in the cockpit of the boat. The beds were nice. It was just very tight. You have to walk to the...
    Reviewed 16 October 2017
    We had such a great time this past July on Seas the Day, a 34' catamaran that had so much space for four adult males. Shelter Cove Marina is really clean and fun to walk around...
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    About this property
    Beautiful 43' Hunter - available for overnight accommodations. This sailing yacht is spacious with plenty of head room throughout. Big spacious cockpit as you board to relax and enjoy the fabulous San Diego weather - large seating area around the helm/cockpit area. As you enter the main cabin you...
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    Location Information
    San Diego, California
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 4
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    Ocean Beach Garden Cottage1 / 36
    (10)Excellent
    Ocean Beach
    2.9 kilometres from Sail San Diego
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    • Cable/satellite TV
    • Grill
    • Ocean Views
    • Wi-Fi
    • Central Heating
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 August 2018
    We absolutely loved our two weeks at Rodney's Ocean Beach Garden Cottage!! We would 100 % go for this cottage again!!!! My husband and I,with our 21 year old son and 17 year old...
    Reviewed 31 July 2018
    This is our 1st time having a rental. It was nice to be able to have the extra room that you don't get in a hotel. The house was very clean and walking distance to a few...
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    About this property
    Welcome to Ocean Beach, where the sun sets on San Diego! This bright and breezy beach bungalow whispers 'summer' all year round and is a short walk to beaches, shops, restaurants, and weekly farmer's market. Your home away from home lends itself to a relaxing and fun visit, vacation, or...
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    San Diego, California
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Cottage 3 - The Seaview Lookout1 / 15
    (2)Very good
    Ocean Beach
    3.1 kilometres from Sail San Diego
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Waterfront
    • Patio
    • Parking
    • Internet Access
    • Cable/satellite TV
    • Hot Tub
    • Grill
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 October 2016
    My wife and I were looking for a special place to celebrate our 34th Anniversary and we were not disappointed! Spectacular views! Quiet! Private! Affordable! Close to...
    Reviewed 28 August 2015
    So wonderful from coffee in the morning till glass of wine at nite- perfect hangout! Beautiful sunsets right from the location
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    About this property
    Beautifully remodeled cottage with granite counters, new fixtures, flooring and whitewater views from the dining and living areas. Enjoy the shared yard on the bluff overlooking the beautiful Sunset Cliffs area of Ocean Beach and drink in the whole of the Pacific ocean while using this amazing area...
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    San Diego, California
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Ocean Views, 3 Blocks to the Beach, Newly Remodeled1 / 42
    (2)Excellent
    Ocean Beach
    2.8 kilometres from Sail San Diego
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Private Garden
    • Parking
    • Wi-Fi
    • Balcony
    • Terrace
    • Washer
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 November 2018
    My girlfriend and I decided to spend a month in Ocean Beach this summer. We needed a place that was dog friendly and that was walkable to the beach and shops because we planned...
    Reviewed 25 June 2018
    Wow! What a vacation, three blocks from the ocean. Minutes from San Diego airport. Walking distance from the best food to have. 5 minutes from Sea World. Most convenient spot...
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    About this property
    Enjoy your stay at this completely renovated beach house just a few blocks away from the ocean, downtown Ocean Beach, and Sunset Cliffs Natural Park. It's newly remodeled inside and has ocean views. This cozy beach house is perfect for families with children as it can accommodate many people, and...
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    San Diego, California
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Ocean Front Dream Vacation 1 bedroom in San Diego, California1 / 45
    (8)Excellent
    Ocean Beach
    3.3 kilometres from Sail San Diego
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
    • DVD Player
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    • Cable/satellite TV
    • Waterfront
    • Grill
    • Central Heating
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    When they say dream vacation, they are not kidding!! This was our dream vacation!! From start to finish, Tim and Kathy went above and beyond to make sure we had everything we...
    Reviewed 22 October 2018
    We loved staying here. The views were amazing, the sounds of the ocean were relaxing, and it was a perfect home base - close to everything we wanted to do. It was comfortable...
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    About this property
    Location: Ocean Beach, San Diego County, California, USA (Ocean Beach is centrally located in San Diego) Accommodations: Apartment, 1 Bedroom + Convertible bed(s), 1 Bath (Sleeps 4) This beautiful ocean view rental apartment is located in Ocean Beach, a beach community in the heart of San...
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    San Diego, California
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Point Loma
    1.0 kilometres from Sail San Diego
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    At this Sonder, you'll love the airy decor, open-concept living area, and fully-equipped kitchen. Located close to Shelter Island and the Bay. Every booking is instantly confirmed. Every call or message is answered within minutes. Every home is equipped with crisp linens, high-speed Wi-Fi, and...
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    San Diego, California
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Hidden Beach Oasis1 / 46
    (1)Excellent
    Ocean Beach
    2.6 kilometres from Sail San Diego
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
    • Housekeeping Included
    • Ocean Views
    • Balcony
    • Grill
    • Parking
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 October 2017
    Stayed at wonderful rental Hidden Beach Oasis. Ocean view from the master and outside deck was so nice. House was just the right size for our family of 8. We had 5 adults and 3...
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    About this property
    Private Home in Sunset Cliffs . 3 Large bedrooms and 2 smaller bedrooms that are connected so one must walk through the other to access the other room, 3 Baths one is a full with deep tub. This contemporary beach house SLEEPS 10-12 in 8 beds. 2 blocks to Sunset Cliffs and 5 minute drive or 10...
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    Location Information
    San Diego, California
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    1.8 kilometres from Sail San Diego
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Stay blocks to a very secluded beach in the seaside community of Point Loma in San Diego. This comfortable, stylish three bedroom apartment will be a convenient and comfortable home base while experiencing San Diego for work or pleasure. The Space: With so much of the this seaside community to...
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    Location Information
    Coronado, California
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Ocean Beach
    3.0 kilometres from Sail San Diego
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 September 2016
    Unit is a good size as we travelled with our two adult children.Great to have kitchen if you like to cook for yourselves. Location is fantastic! Bed in master unfortunately...
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    About this property
    This is a beautiful 4 units next-door-to-each-other that makes a great place for a 1-4 family vacation comes with full kitchen appliances, furniture, paint and beautifully landscaped. They are only 3 minutes walk to the secluded Bermuda Beach. Each of our cottage is fully furnished is remodeled...
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    San Diego, California
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Point Loma Carleton1 / 43
    (1)Excellent
    0.9 kilometres from Sail San Diego
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Patio
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    Pet friendly
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    About this property
    I love sitting by the pool and listening to the wind pass through the trees. At our house, Point Loma Carleton, you can do this every day! It's a beautiful, mid-century modern house that's unlike anything you've stayed at before. Don't let the - ahem - interesting look outside discourage you from...
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    Location Information
    San Diego, California
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Steps to Point Loma Nazarene Univ., Mid-Century Modern Home, Sleeps 91 / 47
    (1)Average
    2.3 kilometres from Sail San Diego
    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Terrace
    • Mountain Views
    • Balcony
    • Washer
    • Central Heating
    • Hot Tub
    • Ocean Views
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 November 2018
    The price doesn't match the quality:- both sanitary units must be updated they look and work like in 70's: master bedroom water doesn't flow properly. The switch that must...
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    About this property
    Fabulous Sweeping Ocean View Home with Fully Wooded and Canyon Grounds. You feel like you are in the trees in this home by Award-winning Architect. Wood and Glass enhance your views of nature. Walk to pocket beaches, tide pools, small cafes and shops. Sweeping Panoramic Ocean Views from all 3...
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    Location Information
    San Diego, California
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 9
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    Point Loma
    2.2 kilometres from Sail San Diego
    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Balcony
    • Wi-Fi
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    • Central Heating
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    • Ocean Views
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Light and Bright House, Old World Charm Close to All Area Attractions. Sunset Cliffs Vacation Rental on the hill. Close to Point Loma and Ocean beach. Ocean views with 4 off street parking. Old world charm with vintage touches throughout. This 4 bedroom , 2 bathroom home is in a prime location,...
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    Location Information
    San Diego, California
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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    Point Loma
    2.7 kilometres from Sail San Diego
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Grill
    • Wi-Fi
    • Parking
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    At this Sonder, you'll love the spacious living area, outdoor pool, and private balcony with stunning views. This apartment is located in Point Loma and comes with a private parking space. Every booking is instantly confirmed. Every call or message is answered within minutes. Every home is...
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    Location Information
    San Diego, California
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Steps to Pier/Beach Gated 2 Bedroom Condo1 / 10
    (1)Excellent
    Ocean Beach
    3.6 kilometres from Sail San Diego
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 July 2018
    We were steps to the beach and pier. The town is also steps away so we had plenty of restaurants to choose from. There is a small grocery store and a CVS pharmacy so food and...
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    About this property
    Anyone who wishes to be FOOTSTEPS from the sandy beach SURF will be thrilled with this CHARMING, clean 2bdrm gem. Located on the same avenue as the Ocean Beach pier, it is 1/4 block from the pier and 1/2 block to all the best eats, shops and HOT NIGHTLIFE this town has GOING ON. Condo sits in a...
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    Location Information
    San Diego, California
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    0.4 kilometres from Sail San Diego
    2 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    About this property
    A unique beach cottage steps from San Diego's most sought after destinations. Our Point Loma Cottage is 15 minutes from everywhere you want to be. Whether you're headed to the beach, SeaWorld, the Zoo, downtown to the Gaslamp, or everywhere in between, our cottage is perfectly suited for every...
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    Location Information
    San Diego, California
    Cabin Holiday Rental - 2 Bedrooms, 1 Bathroom, Sleeps 7
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    0.4 kilometres from Sail San Diego
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Internet Access
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    Pet friendly
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    Smoking allowed
    About this property
    Come enjoy the tranquility, peace and serenity of a night on the water aboard a beautiful sailboat with all the creature comforts. Located 10 minutes from the airport, downtown, and convention center. This is central location with views of the bay fireworks walking distance to several fine...
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    Location Information
    San Diego, California
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Cottage 4 - Sea la vie1 / 20
    (2)Excellent
    3.1 kilometres from Sail San Diego
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Grill
    • Hot Tub
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    • Waterfront
    • Cable/satellite TV
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 November 2015
    The cottage is very clean and stocked with most everything you will need. We enjoyed our mini-vacation here and we will be coming back. We really appreciated the prompt replies...
    Reviewed 4 February 2015
    My wife and I went down for a conference in San Diego. We found this place to be very nice. We stayed 5 nights and very much enjoyed the view from the shared back yard. I was a...
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    About this property
    Beautifully remodeled cottage with granite counters, new fixtures, flooring and whitewater views from the dining and living areas. Enjoy the shared yard on the bluff overlooking the beautiful Sunset Cliffs area of Ocean Beach and drink in the whole of the Pacific ocean while using this amazing area...
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    Location Information
    San Diego, California
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Cottage 1 - Whitewater Cliff Cottage1 / 19
    (3)Very good
    Ocean Beach
    3.1 kilometres from Sail San Diego
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    • Wi-Fi
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    • Ocean Views
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 October 2016
    The rental is great for two with a great outside area with unrivalled views of the Pacific sunset. Facilities are great and the location in Ocean Beach is ideal for Newport St...
    Reviewed 30 May 2016
    I loved this little cottage. Perfect for a little get away! Family and friends visited and we were able to hang out on the cliff and bbq. Other guest sharing the space were...
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    About this property
    Beautifully remodeled cottage with granite counters, new fixtures, flooring and whitewater views from the dining and living areas. Enjoy the shared yard on the bluff overlooking the beautiful Sunset Cliffs area of Ocean Beach and drink in the whole of the Pacific ocean while using this amazing area...
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    Location Information
    San Diego, California
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Welcome to our Ocean Beach Oasis!1 / 7
    (2)Very good
    Ocean Beach
    3.5 kilometres from Sail San Diego
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Reviewed 24 October 2017
    Just what I needed.Short walk to beaches and food and anything else that you might need .Clean,quiet.Thanks.
    Reviewed 24 July 2017
    Place was awesome! Perfect location and place was clean and my daughter and I loved it. Only one small issue was no AC and it was a little hot in the room but not a big deal...
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    About this property
    Located in the heart of one of San Diego's most famous beach communities and within walking distance to the ocean and to the heart of the Ocean Beach community, our place offers everything you might need to rest, rejuvenate and have some fun in San Diego! Not only are we right down the street from...
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    Location Information
    San Diego, California
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Point Loma
    3.3 kilometres from Sail San Diego
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
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    Pet friendly
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    About this property
    San Diego is the city of jewel in southern California with sunshine. This unit has 2 bedrooms, 1.5 Bath, 1 over sized shower, full kitchen + on site laundry, approx. 880 sf with cute and cozy atmosphere with very convenient location which is very close to sea world, beaches, free way and many more...
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    Location Information
    San Diego, California
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    San Diego Ocean View Point Loma Beach House1 / 28
    (1)Excellent
    2.2 kilometres from Sail San Diego
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 January 2015
    From beginning to end, the owners were excellent hosts. The home has been completely remodeled with great detail and taste. The location is close to all major activities and...
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    About this property
    Enjoy your vacation in this fully-furnished, newly-remodeled three bedroom, two bath beach house located on a hill overlooking the Pacific Ocean. This home is perfect for spending relaxing evenings at home with the family in the spacious open-layout living and dining area with top-of-the-line...
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    Location Information
    San Diego, California
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Ocean Beach
    3.0 kilometres from Sail San Diego
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Bermuda Beach is our Luxury Beachfront House Vacation Rental - 3 bedroom, 2 bathrooms- a stunning beachfront Sunset Cliffs home designed for the traveler seeking a memorable escape to modern luxury, direct oceanfront accommodation, brand new furnishings & appliances, private beachfront...
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    Location Information
    San Diego, California
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Stunning Houseboat on the San Diego Bay1 / 26
    (1)Excellent
    2.1 kilometres from Sail San Diego
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    Reviewed 15 July 2018
    This is the time we have stayed on the Zolna Yacht houseboat. It's located in Cortez Marina on Harbor Island just south of the airport. We usually bring our kayak and bikes...
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    About this property
    Welcome to Zolna Yachts of San Diego, offering yachts and a houseboat for lodging and San Diego Bay charters. This delightful Suite Paradise Houseboat is a “prototype” that was completely renovated to beautiful contemporary standards. Suite Paradise is located in the same marina as our yachts,...
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    Location Information
    San Diego, California
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    LUXURY YACHT - 'ELEGANTE'  BOAT, BED and BREAKFAST1 / 54
    (8)Excellent
    0.6 kilometres from Sail San Diego
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 June 2018
    We have stayed in resorts, rented houses with awesome views , but NEVER stayed on a luxury yacht before. My family really enjoyed it. The smooth rocking of the boat as boats...
    Reviewed 15 February 2018
    We spent five nights aboard this beautiful luxury classic yacht. We had a fabulous view of downtown San Diego with the city nights that's better than any of the hotels we've...
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    About this property
    Elegante is a beautiful 'Classic' 82' all wood McQueen with a panoramic view of downtown San Diego. Her classy sleek lines are adorned with teak flooring throughout and 4 staterooms to accommodate up to 10. Master King aft with private en-suite bath w/jetted tub. Midship you will find a Queen...
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    Location Information
    San Diego, California
    Private Room - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Ocean Beach Sunset Cottage1 / 36
    (8)Excellent
    Ocean Beach
    2.8 kilometres from Sail San Diego
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 April 2018
    Cute cottage - perfect for San Diego stay. ★ ★ ★ ★ ★ We had a great stay at this cute cottage in San Diego. It was nice and clean and very nicely decorated as well. Rodney...
    Reviewed 13 June 2017
    This cottage was in beautiful condition in a quiet neighborhood close to the beach - and a ocean view from the front porch. What more do you need? It was centrally located to...
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    About this property
    Welcome to Ocean Beach, where the sun sets on San Diego! This bright and breezy beach bungalow whispers 'summer' all year round and is a short walk to beaches, shops, restaurants, and weekly farmer's market. Your home away from home lends itself to a relaxing and fun visit, vacation, or...
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    Location Information
    San Diego, California
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    0.7 kilometres from Sail San Diego
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Mountain Views
    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Grab a craft beer and head out to the front patio and take in the sights of San Diego Bay from your San Diego home. At our 3-bed, 2 bath home, 10 guests can sleep in total coastal comfort. Large windows open up views to the bay, Coronado Bridge, the city skyline, and so much more. From the...
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    Location Information
    San Diego, California
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    1.6 kilometres from Sail San Diego
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Cable/satellite TV
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    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This lovely condo in La Playa, is nestled at the point in Point Loma. it is far away from the HUSTLE AND BUSTLE, which truly makes you feel like you are on a vacation. THIS UPGRADED LOVELY CONDO offers luxurious, SPACIOUS LIVING, TOP OF THE LINE APPLIANCES. MY LARGE 2 BEDROOM is a corner unit ON...
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    Location Information
    San Diego, California
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    2.1 kilometres from Sail San Diego
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Sauna
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    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    IMPORTANT NOTE Cruises are mandatory on all yachts from June 1st through September 30th and all holidays. The minimum 2 hour cruise on the Ohana Pacific yacht is $590 plus tax. All cruises come with a Captain and a Crew. All catering, food, drinks and 15% crew gratuities are additional and we're...
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    Location Information
    San Diego, California
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    The B*itchin Ocean Beach Bungalow!1 / 8
    (1)Excellent
    Ocean Beach
    3.4 kilometres from Sail San Diego
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Reviewed 26 July 2018
    This home was perfect for our family of 4. It was around 3 blocks away from the beach and restaurants all around us. The home was exactly what we expected it to be. Drew and...
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    About this property
    It's a little bit funky, it's a little bit retro, and it's ALL beachy fun! Located in the heart of one of San Diego's most famous beach communities and within walking distance to the ocean and to the heart of the Ocean Beach community, our place offers everything you might need to rest, rejuvenate...
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    Location Information
    San Diego, California
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Ocean Beach
    3.4 kilometres from Sail San Diego
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    Pet friendly
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    Smoking allowed
    About this property
    Newly gutted house with brand new furnishings, available for rent April 14, 2018. THE SETTING: Quiet residential street. Freestanding house (no attached units, no shared entry). A peaceful oasis all to yourself! Private gated entryway. HOUSE OVERVIEW: 1,000 sq. ft. beach house with an open floor...
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    Location Information
    San Diego, California
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    BOAT, BED & BREAKFAST - 'SELL SELL SELL'  YACHT - Sleeps 41 / 41
    (10)Very good
    0.6 kilometres from Sail San Diego
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 July 2018
    The boat was very well appointed. Spacious interior with a nice kitchen stocked with spices and cookware as well as fresh fruit and ice on our arrival. The location of the...
    Reviewed 3 July 2017
    Whenever I’m in San Diego, Boat Bed and Breakfast has become my home. They have great boats, all in Bristol condition. Sell Sell Sell is an excellent example. She's a spacious...
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    About this property
    This beautiful Maxum 46' (recent name change from Czech Mate to Sell Sell Sell) is sleek and sexy and will accommodate up to 4 persons overnight and is all about beauty; starting with the master stateroom with a queen-size bed and private shower w/ tub. Guest suite is a twin side-by-side berth...
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    Location Information
    San Diego, California
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2.0 kilometres from Sail San Diego
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    IMPORTANT NOTE Cruises are mandatory on all yachts from June 1st through September 30th and all holidays. The minimum 2 hour cruise on the Hula Kai yacht is $690 plus tax. All cruises come with a Captain and a Crew. All catering, food, drinks and 15% crew gratuities are additional and we're happy...
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    Location Information
    San Diego, California
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    0.6 kilometres from Sail San Diego
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Waterfront
    • Mountain Views
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Boat, Bed & Breakfast - Located on beautiful San Diego Bay. Come experience what it is like to stay aboard a beautiful classic yacht. SLIPAWAY is perfect for that romantic getaway for two or bring the whole family. This yacht accommodates up to 5 persons with 1 Queen Stateroom aft, 2 single bunks...
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    Location Information
    San Diego, California
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Views Views and more Views!1 / 20
    (3)Excellent
    0.9 kilometres from Sail San Diego
    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Ocean Views
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    In order to read reviews of this stunning home, please inquire with owner to be directed to the site. This Classic lofty hillside residence with 4 Master Bedrooms & 4.5 baths was entirely renovated and redesigned in 2014 for Architectural Digest AD 100 architect John Ike for his own personal San...
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    Location Information
    San Diego, California
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    Ocean Beach
    3.5 kilometres from Sail San Diego
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    About this property
    Step back in time (without sacrificing comfort). This place has all the charm of the original period in the 1930's when it was built and lots of modern upgrades. The place is filled with natural light. The living room is very spacious and perfect for all to socialize and reflect after a day of fun...
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    Location Information
    San Diego, California
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Ocean Beach
    3.0 kilometres from Sail San Diego
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    Point Loma Paradise Point Loma Paradise is a wonderful updated beach cottage close to it all. If you are looking for a short weekend escape or a relaxing long stay you will quickly make yourself at home in this renovated 2 bedroom, 1 bath cottage with all the modern amenities. Situated on a...
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    Location Information
    San Diego, California
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2200ft2 - 5BR/3BA Spacious, Bright Home1 / 46
    (2)Excellent
    Ocean Beach
    3.4 kilometres from Sail San Diego
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Secure Parking
    • Washer
    • Private Garden
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    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 May 2018
    The home was absolutely beautiful! It was perfect for our weekend getaway and celebration for my best friend before her weekend. The home was comfortable, well maintained, and...
    Reviewed 22 September 2017
    The place was just lovely. There were 7 women in our group and we all agreed. I would definitely recommend this place to a friend.
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    About this property
    The Space This urban, modern house has five bedrooms and three bathrooms. It's bright and has an open, spacious floor plan -- which makes it great for larger families getting together or friends meeting up. The Neighborhood Point Loma is a seaside neighborhood, bordering Ocean Beach. Known as...
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    Location Information
    San Diego, California
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    Two Quiet, Relaxing Cottages Close To Beach1 / 47
    (3)Excellent
    Ocean Beach
    2.9 kilometres from Sail San Diego
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Grill
    • Central Heating
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    • Balcony
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 August 2018
    This was our groups first time staying in a home rather than separate hotel rooms. We very much enjoyed having the group in one area where we could relax and enjoy our time...
    Reviewed 16 August 2018
    My extended family (parents, husband and sister and nephews) stayed at the property for a week in July.The cottages are beautifully decorated and well-appointed and even though...
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    About this property
    Welcome to Ocean Beach, where the sun sets on San Diego! These two (2) bright and breezy beach bungalows whisper 'summer' all year round and are a short walk to beaches, shops, restaurants, and weekly farmer's market. Cottages are tastefully furnished and offer all the elements of classic coastal...
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    Location Information
    San Diego, California
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Point Loma
    2.3 kilometres from Sail San Diego
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Grill
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    Pet friendly
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    Smoking allowed
    About this property
    Point Loma Oasis Welcome to Point Loma Oasis, your family-friendly San Diego retreat. This gorgeous, recently-remodeled 2 bedroom, 1.5 bathroom home in eclectic Loma Portal is perfect for couples or families of 4-5 with kids. With the feel of a beach bungalow and all the modern conveniences you...
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    Location Information
    San Diego, California
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    0.7 kilometres from Sail San Diego
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Parking
    • Ocean Views
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    • Waterfront
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Boat, Bed & Breakfast - Located on beautiful San Diego Bay Come experience what it is like to stay aboard a beautiful classic yacht. SLIPAWAY is perfect for that romantic getaway for two or bring the whole family. This yacht accommodates up to 6 persons with 1 Queen Stateroom aft, 2 single bunks...
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    Location Information
    San Diego, California
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Ocean Beach
    3.5 kilometres from Sail San Diego
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Terrace
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Outstanding Ocean Beach condo less than a block to the ocean and only two blocks to a variety of restaurants and shops. This home offers ocean views from the roof top deck, high vaulted ceilings, big windows that open to the sky, and a spacious floor plan to include a living room with a fireplace &...
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    Location Information
    San Diego, California
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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