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Oldsmar Cottages

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    Don't let other travellers get your favourite Oldsmar area holiday rental. You're so close to securing your perfect getaway. Book today.
    19 Matching Rentals in the Oldsmar AreaView all 521 rentals
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    The following rentals are within 15 kilometres of Oldsmar.
    Cottage On The Water With Boat Dock1 / 18
    (2)Excellent
    Tarpon Springs
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Clearwater Beach Hideaway Cottage, 3 bedrooms, Pets OK, Steps to the sand.1 / 35
    (7)Very good
    Clearwater
    3 Bedrooms, 1 Bathroom, Sleeps 10 Quick View
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    Corner Cottage, 120 steps to the beach, Historic Beach House, sleeps  5, Pets ok1 / 34
    (34)Very good
    Clearwater
    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
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    Pink Dolphin Cottage 100 Steps to the Beach Sleeps 7, Pets Okay, Value1 / 28
    (1)Average
    Clearwater
    2 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    Amenities & Details
    • Hot Tub
    • Cable/satellite TV
    • Grill
    • Wi-Fi
    • DVD Player
    • Housekeeping Included
    • Air Conditioning
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 November 2017
    The house was small for 4 people but the location was worth it, just a very short walk to the beach, also pets were allowed.
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    About this property
    Restored Beach Cottage, daily rentals, Private wood deck Tropical Backyard Just remodeled 1925 beach cottage 100 steps from the beach. Pink Dolphin Cottage features Samsung Smart Stainless Steel appliances, granite countertops with white beaded pine cabinets. Families have enjoyed these cute...
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    Location Information
    Clearwater, Florida 33767
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 7
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    Charming Cottage in Clearwater1 / 46
    (7)Very good
    Clearwater
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • Wi-Fi
    • Washer
    • DVD Player
    • Shared Garden
    • Outdoor Dining Area
    • Air Conditioning
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 April 2015
    The cottage was exactly as pictured and the owner was very quick to respond to all of our needs in the booking process. Check in was simple and the cottage was clean. My only...
    Reviewed 21 September 2014
    Very cute little cottage. Close to the beach.Perfect for one or couple looking to be out of typical hotel scene. Lovely garden and surroundings.Would definitely rebook.
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    About this property
    Charming cottage in a quiet neighborhood near many attractions. 5 miles from Clearwater Beach and 1 miles to delightful downtown Dunedin! Full kitchen-Stove, fridge, sink, microwave. Generously stocked with cookware and servingware. The cottage has it's own private driveway with room for...
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    Clearwater, Florida 33755
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Restored Beach Cottage , Beach Block, Pets Okay, Sleeps 6, Tiki Hut1 / 26
    (1)Excellent
    Clearwater
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Private Garden
    • Parking
    • DVD Player
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Great Value for familiy, 2 adults , up to 4 kids and pets, Beach side , 1925 Real Beach Cottage just 200 steps to the sand, Clearwater Beach, 5 blocks walk to Pier 60, in quiet historic part of Clearwater Beach called Clearwater Cottages, where there are several beach houses. 2016 remodel White...
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    Location Information
    Clearwater, Florida 33767
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 6
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    Coconut Cabana 2/1 Cottage, sleeps 5, Two heated pools, Walk to Beach1 / 14
    (12)Excellent
    Clearwater
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Washer
    • Porch
    • Grill
    • Cable/satellite TV
    • DVD Player
    • Patio
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Coconut Cabana is a fully equipped and supplied, 2 bedroom, 1 bath vacation rental. This cottage has central A/C, WiFI, complimentary W/D and more. The cottage has a living room, flatscreen cable Smart TV, full kitchen, table, two bedrooms, each with queen bed, closets, ceiling fans, bathroom...
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    Location Information
    Clearwater, Florida 33767
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Cozy Cottage Clearwater1 / 15
    (2)Excellent
    Clearwater
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • Private Garden
    • Secure Parking
    • Air Conditioning
    • Patio
    • Outdoor Dining Area
    • Cable/satellite TV
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 April 2017
    Sharon and John were wonderful hosts. The cottage was immaculate and well equipped. The bed was very comfortable. We especially enjoyed our morning coffee on the front, private...
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    About this property
    Centrally Located in a Beautiful Part of Clearwater, Florida minutes from the coast and award winning beaches. The Cottage offers a Fully Equipped kitchen with Full size appliances. Also included is High speed wireless internet and Brand New Flat Screened TV's. There is a separate bedroom with a...
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    Location Information
    Clearwater, Florida 33755
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Pelican Cottage: A Tropical Paradise1 / 21
    (4)Excellent
    Tarpon Springs
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • DVD Player
    • Cable/satellite TV
    • Outdoor Dining Area
    • Parking
    • Wi-Fi
    • Air Conditioning
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 February 2017
    Nice and close to the sponge docks. Clean and comfortable-everything we could need. Our dog had her own private fenced yard. Would stay there again.
    Reviewed 12 June 2016
    This Cottage is exactly as represented. Clean and comfortable with everything you could need for a fun stay. Owners Kerrie & Jerry are so nice and helpful. We will definitely...
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    About this property
    Tucked neatly into the NE corner of our property, sun-drenched Pelican Cottage offers everything you'll need for a private, relaxing, quiet getaway within walking distance to the Sponge Docks, Spring Bayou, the Pinellas Trail & more in beautiful Tarpon Springs, Florida. The Space The 528 sq. ft....
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    Location Information
    Tarpon Springs, Florida 34689
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Clearwater
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Patio
    • Air Conditioning
    • Cable/satellite TV
    • Balcony
    • Parking
    • Housekeeping Included
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    One bedroom Renovated Beach Cottage, Beach Bungalow, Luxury Beach Cabin,B&B ( free breakfast for 2, daily one week guests ) Lemon Cottage is cute as a button. With no streets to cross you are just 300 steps to the beach, and 5 blocks walk to Famous Pier 60. Enjoy a Classic Beach Cottage with...
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    Location Information
    Clearwater, Florida 33767
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Exclusive Quiet Beach Cottage - Monthly rental1 / 20
    (1)Excellent
    Clearwater
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Grill
    • Patio
    • Cable/satellite TV
    • Air Conditioning
    • Porch
    • DVD Player
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you like exclusive quiet beaches, this is it! This cute, 2 bedroom house is 2 blocks from a private beach in an exclusive area on north Clearwater Beach. There is a private entrance to the beach with a shower. The house has a private, fenced backyard and is located across the street from the...
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    Location Information
    Clearwater, Florida 33767
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Cottage Clearwater Bch, Heated Pool, 2/2 Tangerine Dream1 / 16
    (41)Excellent
    Clearwater
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Grill
    • Washer
    • Air Conditioning
    • Porch
    • Cable/satellite TV
    • Internet Access
    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 November 2017
    The cottage was very clean and is located at the quiet end of Clearwater Beach. The beds were comfortable as was the living room furniture. All the comforts of home were...
    Reviewed 15 June 2017
    This is a fantastic cottage with everything you could possibly need to enjoy your stay! The location is perfect and the cottage is very clean and well stocked with towels...
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    About this property
    Our 2/2 Tangerine Dream vacation rental is part of a family friendly cottage resort located on the quiet Cyprus Avenue behind the Chapel by the Sea Church on the Island of Clearwater Beach. These beautiful homes are landscaped together in a tropical garden, with 2 heated pools, patio, and all...
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    Location Information
    Clearwater, Florida 33767
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Banana Breeze/Lazy Lemon Cottage-2 heated Pools, Clearwater Beach,Gulf of Mexico1 / 20
    (39)Excellent
    Clearwater
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Amenities & Details
    • Air Conditioning
    • Porch
    • Cable/satellite TV
    • Wi-Fi
    • Patio
    • Grill
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 November 2017
    We enjoyed five days on Clearwater Beach, staying at Lazy Lemon on friends' recommendation. We spent the first few days without a rental car, so it was great that we had easy...
    Reviewed 21 November 2017
    Our 2nd year, so love the cottages, pools and location. A very clean and comfortable place. Great owners and friendly people at other cottages. We will see you next year, Thanks!
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    About this property
    Our 2/1 Banana Breeze/Lazy Lemon vacation home is part of a family friendly self-catering 7 cottage resort located on the quiet Cyprus Avenue behind the Chapel by the Sea Church, on Clearwater Beach Island. These beautiful homes are landscaped together in a tropical garden, with 2 new heated pools,...
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    Location Information
    Clearwater, Florida 33767
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    A perfect place for a couple, Mango Tango Cottage1 / 12
    (24)Excellent
    Clearwater
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • Patio
    • Grill
    • DVD Player
    • Porch
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 February 2018
    Mango Tango Cottage is small but perfect for one person or a couple. Owners Teresa and Max are very helpful and the property is well maintained. Cottage has a well stocked...
    Reviewed 13 July 2017
    Located within steps of the wonderful Clearwater beach, this condo is small but functional. Everything worked as advertised and the owners were a joy to work with. We would go...
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    About this property
    What a great place for a couple. Our tropical Mango Tango, one bedroom, one bathroom vacation rental is part of a cottage resort complex located on the quiet Cyprus Avenue behind the Chapel By The Sea Church. These beautiful homes are landscaped together in a tropical garden, with palm trees and...
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    Location Information
    Clearwater, Florida 33767
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2BR Beach BlueJay Bungalow, Clearwater—Minutes to Sugar-white Sands & Dining1 / 24
    (1)Excellent
    Clearwater
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This cute 2BR, 1BA beach cottage in Clearwater (sleeps 4) is artfully decorated with new furnishings and shabby-chic décor. Within a 10-minute drive—or short bike ride—to Dunedin, restaurants, art festivals, and one of the top-rated beaches in the country. This home is less than a mile from the...
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    Location Information
    Clearwater, Florida 33755
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Orange Blossom-Key Lime Cottage-2 Pools-Clwtr Beach1 / 17
    (55)Excellent
    Clearwater
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Amenities & Details
    • Grill
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    • Porch
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 February 2017
    A perfect get away with everything nearby. There were no surprises other than it is really more beautiful than pictured on this site. Everything is close by and the cottages...
    Reviewed 10 October 2016
    Loved the location, a small walk to the beach, a gas station real close and the little deli on corner was great.... The only thing I was disappointed in was the choices in...
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    About this property
    This bright large 2 bedroom,1 bath vacation rental is part of a 7 cottage resort located on the quiet Cyprus Avenue behind the Chapel By The Sea Church on Clearwater Beach. Email now for best selection. These beautiful homes are landscaped together in a tropical garden setting with palm trees,...
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    Location Information
    Clearwater, Florida 33767
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Taylor's Tavern: 2 Blocks off Main Street!1 / 13
    (8)Excellent
    Safety Harbor
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Parking
    • Grill
    • Private Garden
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 February 2018
    Great spot, private and very clean. This adorable efficiency had just what we needed for our stay. You are a 2 minute walk from the cutest variety of shops & restaurants...
    Reviewed 1 February 2018
    Very quaint, cute, clean and perfect location. Convenience to lots of awesome restaurants and shopping.
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    About this property
    In the HEART of Safety Harbor, Florida, “Taylor's Tavern” is a charming 1 bedroom / 1 bath cottage, located on the grounds of a 1926 historical bungalow in the redevelopment district of downtown. It is decorated with romantic elegance and just 2 blocks from Main Street! It's a perfect get-a-way to...
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    Location Information
    Safety Harbor, Florida 34695
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Clearwater
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Parking
    • Patio
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ** Please note that there is another vacation rental unit on the premises, and there may be other travelers present during your stay ** All the sun and surf of Clearwater Beach awaits at this charming 3-bedroom, 2-bath vacation rental cottage - perfect for a family of 6. Just across the street...
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    Location Information
    Clearwater, Florida 33767
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Clearwater
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Private Garden
    • Cable/satellite TV
    • Wi-Fi
    • Grill
    • Air Conditioning
    • Patio
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Turned off by noisy concrete condos with stairs and bad parking? If so, this single-story cottage complete with a large outdoor space is ideal for you! Nestled in a quaint and quiet, residential neighborhood, Bertie's Nest is completely new inside and is the perfect place for turn-key, comfortable...
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    Location Information
    Clearwater, Florida 33755
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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