Anna Maria Island House Rentals
Discover the ultimate vacation retreat with an luxury Anna Maria Island vacation home! Unwind in the lap of luxury as Island Real Estate presents a diverse selection of exquisite Anna Maria Island vacation homes, ranging from intimate one-bedroom escapes to spacious Anna Maria Island large group rentals. Ideal for couples, families, and larger groups, our Anna Maria Island rentals redefine comfort and relaxation..
Guests can enjoy beach access with our Anna Maria Island Beachfront rentals, where they can sunbathe, swim, and engage in water sports. There are also plenty of activities to do on the island, including bike rentals, kayaking, and fishing. The island is a tranquil escape from the hustle and bustle of city life. Guests can relax on the beach and take in the beautiful surroundings, enjoying the fresh air and stunning sunsets.
The island also boasts a variety of restaurants, shops, and galleries, offering guests a taste of local cuisine and art. We offer vacation rental homes throughout Anna Maria Island, so there's always something to do! Want to bring your furry friend along? Browse our Anna Maria Island dog friendly rentals and bring your pet along for the adventure!
Whether you're looking for a romantic getaway, a family vacation, or a trip with friends, our vacation home rentals on Anna Maria Island offer the perfect home away from home.
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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
- 9 Views
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A comfortable stay with a peekaboo view of the Gulf of Mexico, private pool, and rooftop deck included!With a recently updated kitchen, this Holmes Beach property is decorated with a beach cottage style, giving it a relaxing vibe that you’re sure to enjoy. This island getaway is only a few steps away from the beach, just a little jaunt across Gulf
Heron Heaven
Home- 3
- 2
- Pool
- No Pets
- Sleeps 8
- 28 Views
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Newly Updated - New bathrooms and updates completed in February of 2023!! Four minutes from the beach, located in the heart of Holmes Beach, and a private oasis on Anna Maria Island. All this and more makes “Forget Me Knot” the ideal place to stay during your island vacation. From the secluded and private placement to its closeness to the beach as
Forget Me Knot
Home- 3
- 3
- Pool
- No Pets
- Sleeps 6
- 9 Views
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Searching for a suitable home to enjoy your luxury island vacation? Flip Flop Inn certainly makes the list, a Mediterranean-style townhouse tucked away on one of Anna Maria Island’s peaceful streets. When you enter the home, you’ll be greeted with a bright and airy main level, just upstairs you’ll find a dining area and open living space beneath th
Flip Flop Inn
Home- 3
- 3
- Pool
- Dogs Allowed
- Sleeps 6
- 81 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
- 46 Views
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“Summer Breeze” is one of the premier homes on the island. The perfect home for an Anna Maria Island getaway. With tropical landscaping, updated inside and out, and this rental home is stunning on all fronts. Elevated, high-end tropical décor, and pristine floors, “Summer Breeze” is love at first sight. Five large bedrooms, a spacious layout, this
Summer Breeze
Home- 5
- 4
- Pool
- Dogs Allowed
- Sleeps 14
- 14 Views
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Fun and tastefully decorated recently remodeled, “Aquarius” is the ideal place for a fabulous Anna Maria Island vacation getaway for up to eight guests. Situated just a short walk from beautiful gulf beaches, when you visit this vibrant vacation rental you’ll leave with memories that last a lifetime.Offering four bedrooms and two and a half bathroo
Aquarius
Home- 4
- 3
- Pool
- Dogs Allowed
- Sleeps 8
- 30 Views
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Discover unparalleled comfort on Anna Maria Island with "Mambo Italiano." This Mediterranean-style retreat caters to your every need, accommodating up to 8 guests across its 4 bedrooms and 4 bathrooms. From the moment you arrive, the striking white facade and elegant black gates welcome you.Step inside to find a haven of solitude, where every detai
Mambo Italiano
Home- 4
- 4
- Pool
- Dogs Allowed
- Sleeps 8
- 18 Views
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Welcome to your newly updated tropical retreat at “Jacaranda Beach House” located just steps away from the serene beaches of Anna Maria Island's Northend. This exquisite 3-bedroom, 3-bath home promises a deluxe island living experience, suited perfectly for family vacations or a peaceful getaway.Step inside “Jacaranda Beach House” to discover a spa
Jacaranda Beach House
Home- 3
- 3
- Pool
- No Pets
- Sleeps 6
- 16 Views
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Ready to find your piece of island paradise? Look no further than “Wave N’ Sea”. This beautiful, sunny Anna Maria home is a spacious three-bedroom two-bathroom rental that can accommodate up to six guests. With a new, and private, heated pool, an oversized yard with tropical landscaping, and less that two blocks from the beach, “Wave N’ Sea” is tru
Wave N Sea
Home- 3
- 2
- Pool
- Dogs Allowed
- Sleeps 6
- 23 Views
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“dreAMI” 12 Palm Harbor Drive is perfect for a fun and memorable vacation, one of the best rental homes that Anna Maria Island has to offer. “dreAMI” 12 Palm Harbor Drive is a gorgeous home, with three bedrooms three and a half baths this home sports two king beds, and two twin beds and is able to accommodate up to 6 guests. Only monthly stays are
DreAMI
Home- 3
- 3 Full Baths , 1 Half Baths
- Pool
- Dogs Allowed
- Sleeps 6
- 18 Views
Are there any splash parks or places to cool off other than the beach on Anna Maria Island?
Yes, GT Bray in Northwest Bradenton has a wonderful splash park only a few minutes from Anna Maria Island. Perfect for those in the family looking for some water fun on their Anna Maria Island Vacation.
What are the closest major water parks to Anna Maria Island?
The largest major waterpark close to Anna Maria Island can be found in Tampa at Busch Gardens, about 1 hour and 20 minutes from Anna Maria Island. Lego Land is in Winter Haven and has a wave pool and lazy river. Lego Land is in close proximity to Orlando and about 2 hours and 30 minutes from Anna Maria Island. Of course Disney World as well as Universal are all in Orlando as well and plenty of waterparks to choose from!
How far are vacation rental properties from the beach?
At the widest section of Anna Maria Island the distance to the beach is just two miles which is in Key Royale. There are sections of Anna Maria Island that are too far to walk every day to the beach. Be sure to google your location and attempt to count the number of homes to the beach as a good indication of how far the walk is. Some vacation rentals offer golf carts to get to the beach easier. Many vendors provide golf cart rentals on Anna Maria Island.
Can I visit Anna Maria Island without a car?
Yes. The island provides a free trolley along with a service that provides transportation for tips only. In addition it is easy to rent bicycles and bring bikes on the free trolley if you wish to visit a portion of the island farther than you would like to. Anna Maria Island is only 7 miles long so relatively easy to bike the entire length of the island!
Where is the nearest major medical facility?
Our closest hospital is a short 15 minute drive along Manatee Avenue to Blake Hospital. We also have a second hospital about 25 minutes from Anna Maria Island which is Manatee Memorial. Note, both hospitals do have estimated waiting times that are updated on their websites.
Are there doctor’s offices on Anna Maria Island?
Yes, we have several medical doctors on Anna Maria Island. Fifteen minutes off Anna Maria Island is a fairly large urgent care facility, Pinnacle. If the “Doctor is not in the house” then perhaps a visit to a local beverage establishment is in order? Maybe just a cocktail is what the doctor ordered? If YES! Then a visit to “The Doctor’s Office” might be just what is needed?
What Our Clients Have To Say On Google!
"Enormous house. It boasts 5 bedrooms and 5 bathrooms. Kitchen is on third floor, with beautiful scenic views. The pool is a nice resort like swim. Bring your families, all within one block of the beach."
Nauti M. 
