Anna Maria Island Platinum Vacation Rentals
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*Please Note: Exterior painting and roofing projects are scheduled between Sept 22–Dec 31, 2025. Work may cause noise or limited access to decks. Schedule may vary due to weather.*With stunning direct gulf front views, the stylish “Water's Edge 209S” is a fine example of a luxury island vacation getaway. Comfortably rooming up to 4 guests this 2 be
Waters Edge 209S
Condominium- 2
- 2
- Pool
- No Pets
- Sleeps 4
- 34 Views
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Welcome to a relaxing tropical Island getaway when you stay at Anna Maria Island vacation rental "TipSea Turtle at Palm Isle Village 3201" ! This peaceful condo nestled just across the street from the beach, and sleeps up to six guests with 2 bedrooms and 2 bathrooms. Find everything you’ll need for the perfect vacation right at your flip flopped f
Palm Isle Village 3201 - TipSea Turtle
Condominium- 2
- 2
- Pool
- No Pets
- Sleeps 6
- 25 Views
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Experience Island Living at Waters Edge 208S, an exquisite, newly remodeled condo located just a short stroll from the serene shores of Anna Maria Island. Whether you're drawn to the beach for sunbathing, water sports, or peaceful relaxation, this charming property has it all. With easy beach access, a shared heated pool, and local shops and restau
Waters Edge 208S
Condominium- 2
- 2
- Pool
- No Pets
- Sleeps 6
- 27 Views
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Harrington Cottage is an adorable Anna Maria beach cottage that’s so close to the Gulf of Mexico you can practically smell the sea salt air! Less than a block away you’ll find the white sand beaches of Anna Maria Island, all while staying in this cute 4 bedroom, 3 bath cottage. Enjoy the peace and quiet afforded by the city of Holmes Beach. Harring
Harrington Cottage
Home- 4
- 3
- Pool
- No Pets
- Sleeps 8
- 59 Views
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Relax and unwind in the luxurious Anna Maria Island vacation rental home “Beach Pearl”. This five star rental has everything experienced vacationers look for in a home from the perfect location to well-appointed amenities. Just a block and a half from the powder sand beaches of Anna Maria City, “Beach Pearl” is the quintessential Anna Maria Island
Beach Pearl
Home- 3
- 2
- Pool
- No Pets
- Sleeps 6
- 26 Views
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This three bedroom three and a half bath villa is located just a few blocks from the white sandy beaches of Anna Maria Island. This spacious vacation home offers an open floor plan, perfect for all family and friends to gather for laughter and wonderful memories. This dreamy vacation home has a remodeled kitchen features such as granite countertops
Blue Lagoon 4
Condominium- 3
- 3 Full Baths , 1 Half Baths
- Pool
- No Pets
- Sleeps 6
- 16 Views
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*Current construction on the premises, may hear construction noise 7am-7pm*The cottages at Palm Isle Village are some of the finest and most favored vacation properties on Anna Maria Island. We are always very proud to recommend to our vacationers, and no one can say it isn't a special place to spend quality time with friends and family. With so ma
Palm Isle Village 3203 - Pink Flamingo
Condominium- 2
- 2
- Pool
- No Pets
- Sleeps 6
- 20 Views
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This perfect vacation rental villa “Harrington Bungalow 5” is located just a short walk from the beautiful beaches of Anna Maria Island. This bungalow is in a great group of six vacation rentals previously managed by the Harrington House Bed and Breakfast. Owner just added a private heated pool!<br /><br />It offers two bedrooms, two bathrooms and
Bungalow on Guava
Home- 2
- 2
- Pool
- Dogs Allowed
- Sleeps 6
- 23 Views
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Located on beautiful canal front property in Anna Maria City, 230 Chilson Avenue "Sand Dollar Dream" is the perfect spot for a Florida vacation with a brand new, private, heated pool and spa. Relax in spacious back yard swaying the hammock amongst the lush tropical landscaping, or roast s'mores in the fire pit seating area. This lovely renovated ho
Sand Dollar Dream
Home- 4
- 2
- Pool
- Dogs Allowed
- Sleeps 8
- 54 Views
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Looking for a vacation spot that offers all the comforts of home with the perks of a beachside getaway? Welcome to Palm Isle Village 3208, a bright and inviting condo in the charming and well-loved Palm Isle Village community. Enjoy Gulf views from your balcony, a shared pool, and a prime location just steps from the soft, white sands of Holmes Bea
Palm Isle Village 3208
Condominium- 2
- 1
- Pool
- No Pets
- Sleeps 4
- 10 Views
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Luxury Anna Maria vacation rental "Sunset at 714" is a casually sophisticated four-bedroom three-bathroom home nestled a short walk away from Anna Maria’s best gulf beaches with one small road to cross. Accommodating up to 8 guests, "Sunset at 714" offers three king beds and set of twinsThe North Shore beach access for Bean Point is a favorite amon
Sunset at 714
Home- 4
- 3
- Pool
- No Pets
- Sleeps 8
- 41 Views
