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Anna Maria Island Villas

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    AU$395 Average
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    Travellers to Anna Maria Island are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    22 Matching Rentals in Anna Maria IslandView all 796 rentals
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    Cozy Cabana West - Private Pool - Close to Beach1 / 22
    (6)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    1 Bedroom, 2 Bathrooms, Sleeps 8 Quick View
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    3B Villas on Anna Maria Island Two Bedroom1 / 12
    (5)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    This lovely property features a tropical setting surrounding a heated swimming pool. The six unit complex is located one block from the beach. Great for family reunions or wedding parties. This unit is a one bedroom one bath full size apartment. King bed in bedroom and a sofa sleeper in the living...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Beach Dreams ' Sweet Dreams Villa'1 / 33
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Pet friendly
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    Reviewed 15 September 2017
    We booked this unit literally last minute after Hurricane Irma had gone through. Wendy (the owner) allowed us to arrive in less than 24 hrs, and this very recently remodeled...
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    About this property
    This is the last property on COQUINA BEACH, GULFSIDE, after historic Bridge Street, before the new pier. This means the pier on Coquina Beach could literally be YOUR backyard for a night, a week or even Spring Break. It doesn't get any better than this. We are booking now for our Grand Opening in...
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    Anna Maria Island, Florida 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Beach House on Anna Maria Island-Rental Openings1 / 16
    (7)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • DVD Player
    • Washer
    • Wi-Fi
    • Cable/satellite TV
    • Waterfront
    • Ocean Views
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 July 2017
    Had another great stay close to the beach and all the extras. Great weather over the July 4th. Very pet friendly.
    Reviewed 22 December 2016
    We spent only a family wedding weekend at this rental, but it was wonderful and we hated to leave. We couldn't possibly take full advantage of the Island shuttle, the beach, the...
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    About this property
    This 3 bedroom 2.5 bath villa with 2 car garage accommodates 6 guests and is 150 feet from the pristine white sandy beaches with easy access. It has a heated 16 by 34 foot pool shared with the identical rental house next door. This unit is fully furnished in tropical decor and has all the luxuries...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    1A Villas on Anna Maria Island  One bedroom1 / 11
    (4)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
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    • Internet Access
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 April 2019
    The best week ever. Everyone was hospitable and friendly. The Villa we stayed in was clean and updated. The weather was perfect with beach fun and bike riding.
    Reviewed 9 July 2016
    Location is wonderful, villa is clean and nice pool. A little outdated, but had necessities. We have 2 adults and two teens. Would be much better suited for just two adults, as...
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    About this property
    This lovely property features a tropical setting surrounding a heated swimming pool. The six unit complex is located one block from the beach. Great for family reunions or wedding parties. This unit is a one bedroom one bath full size apartment. King bed in bedroom and a sofa sleeper in the living...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Stunning luxury newly constructed beachfront villa1 / 22
    (22)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Hot Tub
    • Washer
    • Cable/satellite TV
    • Internet Access
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Patio
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 July 2017
    Beautiful three level beach house on the northern end of Anna Maria Island. Relaxing and very comfortable home where our family enjoyed reconnecting during our vacation after a...
    Reviewed 2 May 2017
    If you are looking for a property to relax by the beach or a swimming pool, this is about as good as it gets. There is nothing the owner's have not thought about. Great ocean...
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    About this property
    4 Bedroom 5 bath luxury beach front house sleeping 8 with heated pool separate spa numerous decks and stunning beach views from every room. We are located on the desirable family friendly island of Anna Maria. The house is direct beach front on the quiet upmarket north end of the island. Recently...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
    BEACH WALK #1 BEACH SIDE VILLA1 / 15
    (1)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Air Conditioning
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 June 2019
    This house is one block from the beach on a very quiet street. When we stayed here, the upper unit was vacant, so I can't speak to the noise level related to other people...
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    About this property
    Beach Walk 1 is a ground level 2 bedroom, 2 bathl villa, just steps from the beach and includes a shared heated pool. Unit accommodates up to 8 people. The property consists of 3 units and sits west of Gulf Drive which is the beach side of the main road, a mere stones throw away from the beautiful...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Unheated)
    • Grill
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautiful villa has two bedrooms and two bathrooms, lots of storage space, laundry room, spacious kitchen and open and light living room. In the living room there is a sleepers sofa. The unit is bright and light, is fully furnished and gives its guests the feel of home. Kitchen is fully...
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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, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
    • Internet Access
    • Air Conditioning
    • Patio
    • DVD Player
    • Grill
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lush tropical landscaped setting. Beautifully maintained two bedroom vacation rental on gorgeous Anna Maria Island. Secluded beaches, shopping, restaurants, golf, fishing and relaxation. Apartment includes full kitchen, 50' flat screen TV in living room, flat screen TV also in one of the two...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    • Ocean Views
    • DVD Player
    • Washer
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ALECASSANDRA VACATION VILLAS are an ideal location on Anna Maria Island, for your family vacations, family staycations, family Spring Break trips, holiday beach vacations, or winter snowbirds . Please note when booking this listing it is only Villa #4, a 2 bedroom 2 bath villa that will sleep...
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Air Conditioning
    • Parking
    • DVD Player
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This quaint 2 bedroom, 1 bath grond level villa is just a short half block from the white sand beaches of Anna Maria Island. Quiet neighborhood on the beach side of Gulf Drive! Amenities include: Full kitchen with all your utensils and supplies needed, microwave, coffee maker, toaster, oven,...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beach Walk 3 is a 1 bedroom, 1 bath suite on the 2nd level, just steps from the beach and includes a heated pool. Unit accommodates up to 6 people. Amenities include: Full kitchen with all your utensils and supplies needed, microwave, coffee maker, toaster, oven, linens, cable TV, dvd player,...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 6
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Air Conditioning
    • Wi-Fi
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 2 bedroom, 2 bath villa is in the heart of Anna Maria Island. It is located 300 feet to the beach in a residential neighborhood, west of Gulf Drive, which is the beach side of the main road. Decorated with simplicity, yet fully equipped this ground level villa is conveniently located in the...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Mintfish, beautiful views across Bimini Bay! 4-Bed1 / 16
    (22)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Waterfront
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    • Grill
    • Patio
    • Private Outdoor Pool (Heated)
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 March 2019
    We stayed here for one week with extended family. We have a great time - house was spacious enough and well equipped in the kitchen. Pool was wonderful. The view of the bay was...
    Reviewed 28 March 2019
    Mint fish was VERY comfortable for us, with 3 generations staying together for the week. Spacious common area, private bedrooms, and gorgeous patio and dock area overlooking...
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    About this property
    Mintfish is a fantastic 4-bedroom waterfront rental home on Anna Maria Island from Pineapplefish Villas. Our latest and one of our most exclusive offerings: this home enjoys and incredible waterfront location with spectacular views across Bimini Bay. A single-storey, spacious rental, with open...
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    Location Information
    Anna Maria Island, Florida 34216
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beach Walk 2 is a 1 bedroom, 1 bath second level villa, just steps from the beach and includes a heated pool. Unit accommodates sleeping for up to 4 people. Amenities include: Full kitchen with all your utensils and supplies needed, microwave, coffee maker, toaster, oven, linens, cable TV, dvd...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Honeyfish, stunning views across Bimimi Bay!1 / 15
    (36)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Air Conditioning
    • Grill
    • Patio
    • Internet Access
    • Waterfront
    • Washer
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 June 2019
    This was our second visit to Honeyfish. The villa is beautiful and has very colourful interior. The kitchen is huge and master bedroom overlooks the bay so you can wake up to...
    Reviewed 28 March 2019
    I would absolutely recommend the Pineapplefish rentals. They are what a beach house should look like, airy, happy colors, simple but beautifully decorated. I've stayed at...
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    About this property
    Honeyfish is a fabulous, single storey vacation rental from Pineapplefish. Its location, on the edge of Bimini Bay, its nautically themed complete with boating artefacts, makes Honeyfish a water lover's dream luxury home on Anna Maria Island. Honeyfish is surrounded by the water and is perfect...
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    Location Information
    Anna Maria Island, Florida FL 34216
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    Lemonfish, stunning and spacious 4-bed rental!1 / 14
    (33)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Internet Access
    • Waterfront
    • Grill
    • Washer
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 July 2019
    We live in town and needed a place for the weekend to celebrate a birthday. Very clean house and well taken care of. Nice open floor plan and good sized bedrooms. Dock was...
    Reviewed 27 March 2019
    We loved our week on Anna Maria Island at Lemonfish! We were a family of 7, including- 3 older teens and 2 grandmas. We utilized every inch of the house, the lovely pool and...
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    About this property
    Lemonfish is a large, southern style rental property from unique designers Pineapplefish. Perched on a canal leading to Bimini Bay and minutes from the gorgeous beaches of Anna Maria Island, Lemonfish is a 3 storey sumptuous home that will accommodate up to 8 guests. The spacious open plan living...
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    Location Information
    Anna Maria Island, Florida 34216
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    1 Bedroom, 2 Bathrooms, Sleeps 5 Quick View
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    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape from your daily routine to this oceanfront 1-bedroom, 2-bath vacation rental villa in Longboat Key! With enough space to sleep 5, this expansive 2,000-square-foot unit boasts beach-themed decor, a screened-in porch, garden patio with a grill, and access to all of the Whitney Beach amenities...
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    Location Information
    Bradenton Beach, Anna Maria Island 34228
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 5
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    Limefish, spectacular beachfront location!1 / 22
    (33)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Grill
    • Internet Access
    • Cable/satellite TV
    • Patio
    • Washer
    • Private Outdoor Pool (Heated)
    • Ocean Views
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 July 2019
    Lovely three bedroom, 3 bathroom home right on the beach but still very private.Enjoyed the sunsets, sunrises and coffee on the back porch,Not to mention the fantastic pool when...
    Reviewed 14 April 2019
    Step out of the back door and you are directly on the beach. Just a few yards to the sea.No need for beach cart to carry your chair, umbrella or cooler. This part of the beach...
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    About this property
    Limefish, from Pineapplefish is one of the most stunning beachfront holiday rentals on Anna Maria Island, with direct access to a beautiful, almost private beach. With spectacular views across the Gulf, Limefish has a wonderful and spacious decked area across the whole of the property, where you...
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    Location Information
    Anna Maria Island, Florida 34217
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Cherryfish, a spectacular spacious 4-bed home!1 / 29
    (10)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Washer
    • Balcony
    • Porch
    • Cable/satellite TV
    • Internet Access
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 March 2019
    This is house is big and beautiful, but...on arrival we relalized many high points in the advertised video were not working. Ice maker, wine refrigerator, staircase to viewing...
    Reviewed 1 November 2017
    Cherryfish is the ultimate vacation home. We have vacationed in Anna Maria numerous times and have stayed at Cherryfish twice it is our favorite home and we will stay there...
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    About this property
    Cherryfish is the latest addition to the Pineapplefish collection of houses on Anna Maria Island. It is a spectacular 4 bedroom house, in a fantastic location, just one block from Tampa Bay Beach, the amazing Waterfront Restaurant and the island's most popular tourist destination - City Pier....
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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