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Holmes Beach House Rentals

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    Travellers to Holmes Beach are booking May dates now. Secure your holiday rental today, and have the perfect trip.
    314 Matching Rentals in Holmes BeachView all 502 rentals
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    A Pearl of a Beach Home - with luxury private heated pool and hot tub1 / 32
    (22)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Happy Island Cottage with heated private Pool1 / 52
    (28)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Ohana Hale North  2  Bedroom on Anna Maria1 / 17
    (23)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    North Beach Village, unit 59  - Great Townhouse!1 / 28
    (14)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Balcony
    • Patio
    • DVD Player
    • Grill
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 February 2018
    We've stayed at a number of places on Anna Maria Isl. and this beautiful house is one the best. You can see the new heated pool from the kids bedroom. Holmes Beach is only a 5-6...
    Reviewed 8 August 2017
    Tranquil and friendly people good beaches. Very family friendly,good neighbor Doddy, Very close to markets and restaurants.
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    About this property
    Grab your flip-flops and beach chairs! This family-friendly 3-bedroom, 2 1/2 -bath townhouse is just two quick blocks to the pristine, white sandy beaches of Anna Maria's gorgeous blue waters of the Gulf Coast. And after a relaxing day of sand and sun, come back for a refreshing dip in the heated...
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    Holmes Beach, Anna Maria Island 32417
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Spectacular Beach House With GulfView Only Steps to a Pristine Beach1 / 13
    (4)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Secure Parking
    • Cable/satellite TV
    • Private Garden
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 August 2017
    House is literally steps to the beach. Get to AMI's hot spots within minutes from this central location. Plenty of beach stuff - tents, chairs, boogie boards, floats, etc as...
    Reviewed 11 April 2015
    This house is lovely. It is well maintained and clean and has good sized rooms. The description is accurate.It is in an excellent location if you are looking for a beach week...
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    About this property
    Spacious 3-level House with 2 large decks overlooking the beautiful Gulf of Mexico. House is fully furnished with a large flat screen TV and Bose Stereo System. Great Gulf views from living room and Master Bedroom. One Guest room also has a gulf view. Large garage is fully equipped with beach...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    405 Bay Palms1 / 31
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Internet Access
    • Grill
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 April 2014
    This is the second time we stayed at the home. The home is located about a 5 min walk to the beach. The home is in a residential area so it is very quiet. The pool in the...
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    About this property
    405 Bay Palms - Private home 2 Bedroom/ 2 Bath with private pool , maximum occupancy of 4 people. VRC16-000053 If privacy is calling, quit stalling and come and play at 405 bay!~Distance to the Beach: 2 blocks Home in a very private tropical setting with lush landscaping. Large, open and airy...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Stunning 5 bedroom Pool Home just steps from the beach!1 / 49
    (4)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Patio
    • Air Conditioning
    • Ocean Views
    • Washer
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 October 2017
    This wonderful house is located about in the middle of the island, close to Walgreens (if you forgot something) and a couple of minutes from Publix (for your culinary needs...
    Reviewed 3 March 2013
    We had the most wonderful four days in this house with our baby son. The house is just two blocks from the beach and comes with basic gear (towels, umbrella, chairs, wagon...
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    About this property
    Beautiful 5 bedroom 4 bathroom vacation home in Holmes Beach, just steps from the beach with fantastic Gulf views. This home is the perfect beach getaway with everything you could want while enjoying Anna Maria Island. Just imagine waking up to the sound of the surf rolling in. Enjoy a cup of...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    Anthony Beach Cottages Island Retreat1 / 26
    (4)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Grill
    • Washer
    • Balcony
    • DVD Player
    • Air Conditioning
    • Patio
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 August 2015
    The house is spacious, close to the beach, convenient to numerous stores and the main road of Anna Marie Island. The Anthony beach cottage also has plenty of parking space and...
    Reviewed 9 February 2015
    First I want to thank the manager, April, for being helpful in arranging for my family and I to stay at this property at the last minute. She was really amazing to work with...
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    About this property
    Situated 3 blocks from the beach and 2 blocks from the bay with a secluded yard surrounded by mangroves, this two-story pool home includes 3 bedrooms on the first floor and a regal master suite on the second floor. Comes equipped with Wifi, cable TV in all 4 bedrooms, washer/dryer, dishwasher,...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    5801 DePalmas - Private home 3 Bedroom / 2 Bath , maximum occupancy of 6 people. Comfy and Cozy Florida Living!~ Distance to the Beach: 1/2 block Cute cozy ground level home 3 Bedroom/ 2Bath close to the beach on a quiet dead end street. Fully furnished with linens towels, cooking utensils,...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Private Tropical Paradise in Holmes Beach!  Large home with Pool and fenced yard1 / 30
    (2)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Grill
    • Wi-Fi
    • Patio
    • Washer
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    We stayed at this house for 2 weeks. There’s a lot of room inside. House is well stocked with towels and any utensil you need. It is close to everything and the neighborhood is...
    Reviewed 4 weeks ago
    Anna Maria Island is a friendly, eclectic place to visit. This is a very nice home with a fenced in yard and pool. It worked very well for our dogs and us!
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    About this property
    Tropical Paradise on Holmes Beach and ONLY 3 blocks to the beach. Anna Maria Island, noted for its old Florida ambiance, offers this Key West styled home, where you may awaken to greet the dawn sipping coffee on the balcony or swimming in your private pool. The modern interior arrangements add to...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 7
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Grill
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Anna Cabana Beach House is an adorable two bedroom, two bath home located at 3709 Gulf Drive in Holmes Beach. This quaint home has a large open deck with a great view of the beach. Watch the sunsets or enjoy the tropical landscaping on the large deck facing the Gulf. Numerous fruit trees and...
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    Location Information
    Holmes Beach, Anna Maria Island 34218
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    PARADISAICAL ENCLAVE 5*WaterfrontCanal/Pool/Dock/Kayak/Bikes/Hammocks//FamilyFun1 / 45
    (3)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Patio
    • Air Conditioning
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Waterfront
    • Wi-Fi
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 May 2017
    My sisters and I had the best time. House in perfect area, great view. Very nice pool. Everything you need. We rented Golf Cart [AMI Golf Cart], and drove the Golf Cart...
    Reviewed 16 August 2016
    Beautiful location. Accurate description. Loved firm bedding in master bedroom. Kids complemented theirs. Nice entertainment ambiance. Confortable all around. Easy dealings with...
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    About this property
    Adriel's Place in Anna Maria... A two bedroom located in upscale private golf club neighborhood, a stone throw from pristine beaches, restaurants and island entertainment ( less than 1 mile ). An expansive backyard dotted with majestic palms, pavered terrace and pool overlooking sailboat water....
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Sandy Beach Access1 / 10
    (1)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Wi-Fi
    • Grill
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    • Air Conditioning
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sandy Beach Access Duplex, 2 bedrooms, 2 baths, 6 Places Newly renovated, fully furnished, 2 BR 2 Bath duplex. 202B 76th Street, Holmes Beach, FL 34217 New landscaping. 1 1/2 blocks (300 yards) to a beautiful sandy beach. Cable TV's, Wireless Internet, DVD Player. Laundry room. Anna Maria Island...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Anna Maria Island Private Tropical Garden Home1 / 20
    (98)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • Patio
    • Cable/satellite TV
    • DVD Player
    • Internet Access
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 August 2017
    Stayed here again in July 2017. We had just as much fun as we did the previous year. Kent and Pa take very good care of their home, and it is in perfect condition upon your...
    Reviewed 26 June 2017
    We just returned from another great anniversary week in this lovely home on Anna Maria Island. This was our 6th visit to this immaculate property which was recently enhanced...
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    About this property
    PRIVATE ISLAND PARADISE - This unique custom home is hidden on a huge garden lot surrounded by palms, birds of paradise, tropical plants and a 6 ft fence. Few island homes offer this degree of privacy. SPACIOUS ELEGANCE - The home has 2,600 sq ft (240 sq m.) of ground level indoor living space with...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Chic Mid-Century Beach Cottage with a private dock1 / 24
    (1)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Air Conditioning
    • DVD Player
    • Grill
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    • Patio
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    Great House access to all beaches and restaurants, very comfortable and clean and everything we wanted.We did not want to leave.
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    About this property
    Authentic spacious beach cottage charm in a mid-century shell. Located a couple blocks from Florida's best powder sand beach and situated across from Bimini Bay with use of our dock. Explore the quiet paradise where the locals live. The Pine Ave shops and famous Beach Bistro Restaurant are less...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Shared Outdoor Pool (Unheated)
    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    8201 Gulf Drive - Private home 3 Bedroom/ 3 Bath with private pool, maximum occupancy of 6 people. Distance to the Beach:1 short block Welcome to 8201 Gulf Drive located on a spacious corner lot that is just a short stroll to the beach. Tastefully decorated, this beautiful residence was designed...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Gulf Sound is a gulf side, ground level tri-plex located at 2814 Gulf Drive in the southern end of Holmes Beach. This two bedroom one bath unit is fully equipped with everything you need for your stay. Each unit has been updated and is comfortably furnished. It's quiet, yet close to shopping,...
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    Location Information
    Holmes Beach, Anna Maria Island 34218
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    ISLAND TOWNHOUSE - 200 Steps to the BEACH1 / 18
    (26)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
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    • Grill
    • Patio
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 October 2017
    The unit is in great condition with everything you need for an excellent vacation. The location is perfect, located in Holmes Beach close to the middle of Anna Maria Island...
    Reviewed 18 August 2016
    This is a very clean, cozy, and serene townhouse located in a very quiet street. Very updated with all of the essential amenities necessary to cook (inside as well as outside...
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    About this property
    Fantastic 2 bedroom / 1.5 bath townhome just 200 steps to the beach. Relax in Paradise at #116 52nd Street in Holmes Beach on Anna Maria Island and enjoy all the comforts that this beautifully furnished townhome has to offer. Newly decorated with granite countertops, stainless steel appliances,...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Shady Palms - Real Beachfront on the Gulf of Mexico1 / 15
    (3)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Washer
    • Grill
    • Cable/satellite TV
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 November 2017
    This rental is fabulous! Spacious, and with old world charm, this home has all the comfort and amenities you could want, including a washer and dryer, dishwasher, range and...
    Reviewed 11 September 2015
    Shady Palms brings you back to old style Florida, before condos and high rises took over the beaches. This 50's ranch house is surprisingly spacious, with multiple living areas...
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    About this property
    Perhaps Shady Palms will become 'your place on the beach.' Walk into a charming, Old Florida style beach cottage with a view of the beautiful Gulf of Mexico from every room in the house. Continue through the back door, and into the yard and you are one step from the wide, white, sugar-sand beach...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Terrace
    • Internet Access
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    • Air Conditioning
    • Grill
    • Washer
    • DVD Player
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Find cool island comfort at this two-bedroom Holmes Beach escape, a bright, spacious home with a dog-friendly interior, a screened-in balcony, free WiFi, and a perfectly walkable location close to the beach and the free island trolley. You'll find this home in the northern reaches of Holmes Beach,...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Make this Mediterranean-style home with a private lagoon-shaped pool, jetted tub, and easy beach access your home away from home when you come to Anna Maria Island. Come revel in luxury and local flavor! Located in the heart of Holmes Beach, yet tucked away from the hustle and bustle, this home...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Let the 'Good Times' roll at this original and fun Anna Maria Island vacation home! The location is excellent, just a few blocks to the white sand beaches of the Gulf of Mexico! This fantastic, three-bedroom, two-bath vacation rental offers everything you need for a relaxing getaway. There are two...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    • Internet Access
    • Central Heating
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Cast Away located at 4101 Gulf Drive in Holmes Beach is a delightful condo situated conveniently across from the Manatee Public Beach and the shimmering Gulf of Mexico. These two bedroom and one bath units sleeps six each with a queen size bed, two twin beds and a sofa bed. A full size kitchen and...
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    Holmes Beach, Anna Maria Island 34218
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 12
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Grill
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    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sun-Day West is the picture-perfect name for this two-bedroom, two-bath, elevated duplex. Located in Holmes Beach on Anna Maria Island, this vacation rental features a large, west-facing balcony that allows for plenty of sunshine in the afternoon and shade in the morning for that early cup of...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Aloha and welcome to our Island Home. Ohana is Hawaiian for family and that is who you are when you stay with us. Our retreat is nestled on Anna Maria Island, Florida and is a short 5 minute walk to the white sand beaches and turquoise waters of the Gulf of Mexico. We offer three locations on Anna...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Experience casual island luxury at this Holmes Beach getaway. Boasting plenty of room for the whole crew and even the family dog (for a small nightly fee), this getaway has it all. Stay in the heart of the island and enjoy a tropical shared pool with a 10-foot waterfall, a Tiki hut, and a communal...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Coquina Sands, view beach from balcony, priv pool1 / 12
    (8)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
    • Cable/satellite TV
    • Internet Access
    • Hot Tub
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    We rented this house for spring break and it couldn’t have been better! Great location- walking to restaurants and bars; 1/2 block to the beach with a nice view; and perfect...
    Reviewed 11 July 2017
    We were a family of 6 and stayed for a week. With the pull out bed in the living room we had space for everyone to sleep. The place was very clean and tidy, well stocked with...
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    About this property
    This is a gorgeous home, just 1/4 block from the beach which you can see from the balcony. Private elevator to all floors, relaxing living room with flat screen TV. Impressive Kitchen with granite counter tops, Stainless steel appliances, wood floors, bar sitting area, large dining room....
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    217 84th - Private home 3 Bedroom/ 2 Bath with private pool , maximum occupancy of 6 people. Distance to the Beach: 3 Blocks Old Florida with all the comforts! of home~ 217 84th. Street 3 bedroom 2 bath home in quiet residential area of Holmes Beach. Private, screened-in, solar heated pool. 3...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    510 Bayview1 / 20
    (3)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Terrace
    • Balcony
    • Grill
    • DVD Player
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 April 2016
    Had a fantastic week here nine adults and we did not bump into one another once 4double rooms and 1 twin all with their own bathrooms pool area great pity that the water...
    Reviewed 30 December 2015
    I recently stayed at this beautiful house and it was the best decision I made for the holiday. First, the rental company was so easy to work with. There was no stress at all...
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    About this property
    510 Bayview - Private canal home 5 Bedroom / 5 Bath with private pool , maximum occupancy of 10 people. Island Elegance for the whole family!~ Distance to the Beach: 2 blocks Come to Anna Maria Island, bring family, friends and your boat to enjoy the simple pleasures of life: sun, sand, and...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    SUMMER BOOKING SPECIAL! Book now and stay June 1st to June 30, 2018 for a 20% discounted rate! Get your beach on at Beach n It -- the place to spend your fantastic sunny Florida vacation on Anna Maria Island!! This fabulously remodeled and updated, new pool home is located in the heart of Holmes...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Make this beautiful 3-bedroom, 2.5-bath vacation rental house your new home-away-from-home in Holmes Beach! Up to 6 travelers will have the luxury of swimming in the private pool or hot tub after kayaking in Palma Sola Bay. Take the provided wagon to the Gulf Beach a mere 2-minute walk away or...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Starfish Villa: 2BR Pool Home w/Elevator1 / 23
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 April 2016
    We had a wonderful time here and the house itself is lovely. Plenty of towels in the bathrooms and the kitchen is well stocked. The upstairs shower is so tiny/short in height...
    Reviewed 8 November 2015
    Great house in a great location. It was even better than it looks in the photos. Decor was really nice and it looks like the property has recently been built. The balconies...
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    About this property
    *SPECIAL* 20% OFF A WEEKLY STAY NOW THROUGH THE END OF THE YEAR (EXCLUDES HOLIDAYS)!! With breathtaking views of the Gulf of Mexico from almost every room and just steps to the beach, you may never want to leave the soothing and relaxing atmosphere of Starfish Villa. Located in Holmes Beach on...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Captain's Quarters Spinnakers: 3BR Pool Home1 / 23
    (2)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 June 2016
    We found the rental home on FlipKey.com and it worked out very well. The house is on the main road on Anna Maria Island. The directions say to use find a key, but it simply has...
    Reviewed 5 December 2015
    Stayed for Thanksgiving nice place has everything you need and great location. Love the pool area too.
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    About this property
    Spinnakers Vacation Cottages, Captain's Quarters is surrounded by lush tropical landscaping, close to everything but with a feeling of being tucked away! This lovely vacation rental is located in Holmes Beach and is just 250 steps to the beach! Spinnakers is made up of four cottage-style...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Sprawling 3 bed 2.5 bath LUXURY Single Family Home with HEATED pool and ELEVATOR Welcome to this luxury Key West style home by the sea! It is your place in the sun to make memories and unwind! Crosswinds Cottage is just a short five minute walk to Anna Maria Island's world renowned white sandy...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    617 Dundee Lane1 / 24
    (1)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Internet Access
    • Shared Outdoor Pool (Unheated)
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    • Terrace
    • Balcony
    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    617 Dundee - Private home 3 Bedroom / 3 Bath with private pool and boatdeck, maximum occupancy of 6 people. Distance to the Beach: 1/2 mile Hop out of the bed and into the pool! Lovely 3 bedroom, 3 bath home with newly remodeled kitchen. Screened pool on a canal with dock and davits. Enjoy the...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Escape to Serenity A: 2BR Pet-Friendly Pool Home1 / 23
    (6)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 March 2017
    We have stayed at Escape to Serenity a couple of times now. We absolutely love it and are already planning on when we can come back. The house is clean and the perfect get away...
    Reviewed 28 February 2017
    This house is in a great location on AMI, just 1 block from the beach and not at the busier south or north ends. The house was quite clean and comfortable. Despite being a...
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    About this property
    Escape to Serenity sums it up for this quaint and cozy duplex (with no shared walls). You will feel as if you have landed on your own personal island with this gem of a property. This fantastic, two-bedroom, one-bathroom vacation rental will help you find some serenity. This home boasts an all-new...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Secure Parking
    • Private Garden
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This Beautiful new 4 bedroom 3 bathroom home ideally located just down the street from the white sand beaches, restaurants and shops. After a day of fun in the sun relax by the heated pool in your own backyard oasis. This house has every luxury you could want, Flat screen TV’s, stainless steel...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • Private Outdoor Pool (Heated)
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    • Hot Tub
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    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    At 4 bedrooms and 3 full bathrooms, this is one of the most charming rentals on Anna Maria Island!! Located a few houses from the beach, it is only a two minute walk until white powdery sand is between your toes! Easy on the kids and even easier on you! Around the corner from restaurants, pubs &...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Ah this is it v2.0! Lemon Cottage w Pool!! Relax!!1 / 28
    (42)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    • Private Outdoor Pool (Heated)
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    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 July 2017
    The Lemon Cottage is such a cute and cozy house, not far from the beach. 5 of us stayed comfortably for the week and never felt like we were living on top of each other. My...
    Reviewed 7 June 2017
    Thank you Chris and his family for this really nice place.Well organised, quite, 5 minutes walk for the beach.A free Trolley to get to bean point is to try.
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    About this property
    From the same owners of A Lime Cottage (p277325), who've been recognized as TripAdvisor 'rated excellent' vacation rental, Flipkey 2012 and 2013 Top Vacation Rental, 2012 Top Rental Manager', we're delighted to now have Lemon Cottage. Nestled in a quiet residential boating community across from...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    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
    The Pool Party South side, located at 314 61st Street in Holmes Beach, is a beautiful two bedroom, two bath duplex with a pool area that is unsurpassed! This unit features a heated pool with a spa surrounded by mature, native plantings as well as a shaded hammock and an outdoor bar with charcoal...
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    Location Information
    Holmes Beach, Anna Maria Island 34218
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This cozy duplex with a shared pool and easy beach access is waiting for your upcoming Anna Maria Island vacation. You'll be in close proximity to dining and shopping, and you'll have space to park two cars. This rental is located two blocks from flour soft, sugar white beaches on the Gulf of...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Cable/satellite TV
    • Hot Tub
    • Private Outdoor Pool (Heated)
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    • Wi-Fi
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This brand new Stunning 3 bedroom 3.5 bathroom + den . This home is ideally located just down the street from the white sand beaches, restaurants and shops. After a day of fun in the sun relax by the heated pool in your own backyard oasis. This house has every luxury you could want, Flat screen...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Patio
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Experience the joys of island living at this five-bedroom Holmes Beach escape, a palm-lined duplex with two separate living spaces, an outdoor heated pool and terrace, and a wonderful location one block from the beach. You'll find this duplex on the west side of Holmes Beach, one block from the...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    Beautiful Villa by the Sea: 4BR Pet-Friendly Pool Home1 / 19
    (9)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 January 2017
    Anna Maria Island was the perfect place our teenage family's. The home was large, modern, comfortable. The 7 mile island with 7 miles of soft beach, no high rises, 25 mile per...
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    About this property
    White Sands Beach House is the latest property to join our vacation rental program! It is the epitomy of beachy chic, with its beautiful coastal decor throughout. Soothing turquoises and pastels invite you into its living area and open floor plan with a granite and stainless kitchen, large dining...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    To see a video tour of this home, click here. Experience luxury living at this three-bedroom seaside home with a fireplace, tropical accents, casually sophisticated decor, and updated amenities. Spend lazy days by the heated pool or stroll out to the adjacent Gulf-front beach, with its powdery...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Aqua Maria1 / 21
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 May 2017
    We love Anna Maria Island and this is the best place we have stayed. The location is walking distance to the beach, restaurants, ice cream and coffee places. The house was so...
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    About this property
    Located in Holmes Beach on Florida's beautiful Anna Maria Island, Aqua Maria is just steps to the beach. Newly decorated and updated, this two bedroom, two bath vacation rental is inviting and relaxing. Gorgeous furnishings from The Pamaro Shop gives this vacation rental an incredible beachy feel....
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
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    About this property
    Gulf Sound is a gulf side, ground level tri-plex located at 2814 Gulf Drive in the southern end of Holmes Beach. This five bedroom, three bath property is fully equipped with everything you need for your stay. Each unit has been updated and is comfortably furnished. It's quiet, yet close to...
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    Location Information
    Holmes Beach, Anna Maria Island 34218
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Grill
    • Central Heating
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Pool Party, located at 314 61st Street in Holmes Beach, is a beautiful duplex featuring two bedrooms and two baths on each side with a pool area that is unsurpassed! This property features a heated pool with a spa surrounded by mature, native plantings as well as a shaded hammock and an outdoor...
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    Location Information
    Holmes Beach, Anna Maria Island 34218
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Sea Spray, also known as Brady’s Beach House, a colorful, airy, updated island cottage! This single-family home is situated on a large grassy lot, conveniently located west of Gulf Drive only 1.5 blocks from the fine white sand beach of the Gulf of Mexico! No busy streets to cross to be...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Twin Villa by the Sea: 3BR Pet-Friendly Pool Home1 / 24
    (8)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 September 2016
    This was the first time we had visited Anna Maria, Island. We had no idea where to stay. We reserved this property because it fit the needs of our family. We were not...
    Reviewed 12 August 2016
    Exelent house, very clean, clouse to the beach, very confortable beds. Internet service, nice kitchen with all you need to fix your own meals, pool very clean, what more can I...
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    About this property
    This newer construction vacation rental has high ceilings, tile floors throughout, two screened lanais and a beautiful heated pool area with BBQ grill. Centrally located on Anna Maria Island, Twin Villa is a short two block walk to the beach. The well-appointed kitchen is equipped with a vegetable...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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