Anna Maria Island Rentals
Book a stay at one of our stunning Anna Maria Island vacation rentals. Known around the world for its pristine turquoise waters and white, sandy beaches, Anna Maria Island is the BEST destination for your island vacation. Island Real has 80+ Anna Maria Island vacation rentals in Anna Maria City, Holmes Beach, and Bradenton Beach.
Our Anna Maria Island vacation rentals feature a wide range of amenities, including hot tubs, pools, updated designs, outdoor lounge areas, multiple bedrooms, and more!
Popular Anna Maria Island Rental Searches
Everyone has specific needs and desires when it comes to choosing the perfect Anna Maria Island vacation rental property. Check out some of our most popular searches and get the best rate on your Anna Maria Island rental! From pet-friendly homes to oceanfront rentals with private pools, we have an Anna Maria Island vacation rental perfect to suit everyone's needs at Island Real Estate.
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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
- 51 Views
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Enjoy a week in tropical island luxury when you visit the beautiful “Gulfview Townhomes Unit 4"! The perfect Anna Maria Island vacation rental condominium, “Gulfview Townhomes Unit 4" is a refreshing departure from the ordinary Florida holiday. Sleeping up to six guests just a short walk to pristine gulf beaches, this Holmes Beach vacation rental i
Gulfview Townhomes 4
Condominium- 2
- 2 Full Baths , 1 Half Baths
- Pool
- No Pets
- Sleeps 6
- 49 Views
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Experience the Tropical beach paradise vacation of a lifetime when you stay at Holmes Beach vacation rental condominium “Vista Grande Sul Mar”. This gorgeous beach front condo, located within the Vista Grande complex, rooms up to 6 guests with 1 king bed, 1 queen bed and 2 twin beds in this 3 bedroom 3 bathroom spacious vacation destination.<br /><
Vista Grande 1 Sul Mare
Condominium- 3
- 3
- Pool
- No Pets
- Sleeps 6
- 65 Views
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Discover your slice of paradise in this charming Holmes Beach rental, where coastal living meets comfort and convenience. This delightful three-bedroom, den and two-and-a-half-bathroom house is your ticket to the ultimate Florida getaway.Step outside and embrace the allure of outdoor living. Bask in the warm sunshine on your private patio, perfect
Rest Assured
Home- 3
- 2 Full Baths , 1 Half Baths
- Pool
- No Pets
- Sleeps 8
- 53 Views
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This Poolside condo offers direct access to the Pool Area, creating a dreamy atmosphere reminiscent of living atop the beautiful blue waters of the Gulf of Mexico. Memorable sunsets and the soothing sound of calm waves will leave you feeling refreshed and rejuvenated during your stay on Anna Maria Island. The kitchen, living, and dining areas boast
Coconuts 119
Condominium- 1
- 1
- Pool
- No Pets
- Sleeps 4
- 23 Views
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The North Beach Village community offers a quiet and peaceful slice of the Holmes Beach island life. Just a short walk to pristine Gulf of Mexico beaches makes spending time at this home a real treat. Just grab your swimsuit, sunblock and a cold drink and relax the day away on powder sand beaches. You will love spending time with friends and family
North Beach Village 45
Condominium- 2
- 2 Full Baths , 1 Half Baths
- Pool
- No Pets
- Sleeps 6
- 22 Views
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Fall in love with Anna Maria Island paradise when you vacation at “Over the Moonl”! This gorgeous three bedroom, private heated pool getaway accommodates up to six guests with 2 kings beds and two twin beds in this ground level single family home located in the coveted north end of Anna Maria. <br /><br />The city of Anna Maria boasts some of the i
Over the Moon
Home- 3
- 2
- Pool
- No Pets
- Sleeps 6
- 47 Views
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Inside Casa Sierra 203 B you’ll enjoy an updated and laid back beach style. Relax in the living room with television and wireless internet after a long day of fun in the sun. The Kitchen has stainless steel appliances and everything you’ll want for your stay. Equipped with two bathrooms, both offer a walk-in shower.Casa Sierra Resort is a private
Casa Sierra 203B
Condominium- 2
- 2
- Pool
- Dogs Allowed
- Sleeps 6
- 16 Views
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Perfect for a fun couple’s getaway, a casual vacation, or even a family escape. “The Villas 3A” is a one-bedroom villa that boasts a top tier location near shopping, dining, and beaches, as it’s located in the city of Holmes Beach. Able to sleep up to four guests, this unit has a welcoming and laid-back feel that’s synonymous with an island vacati
The Villas 3A
Condominium- 1
- 1
- Pool
- No Pets
- Sleeps 4
- 66 Views
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Stylishly decorated and spaciously accommodating, you’ll fall in love with Florida living when you stay at the gorgeous vacation rental 1107 Edgewater Circle in Perico Bay Club. Come for the sun, but stay for the view from this beautiful two bedroom, two bathroom condominium sleeping up to four guests!Perico Bay Club is a prestigious gated communit
Perico Bay Club 1107 Edgewater
Condominium- 2
- 2
- Pool
- No Pets
- Sleeps 4
- 36 Views
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Inside this Holmes Beach vacation rental you’ll find a well-appointed condominium to kick your feet up in island style. The living room offers a flat screen television, comfortable furniture and the dining area seating four. In the kitchen you’ll find all the basics including a dishwasher. Off the kitchen there is a private balcony.Accommodating up
Casa Sierra 205B
Condominium- 2
- 2
- Pool
- Dogs Allowed
- Sleeps 6
- 16 Views
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Everything you expect from a relaxing stay can be found at this Anna Maria Island vacation rental condominium. If you’ve never experienced Gulf of Mexico beaches you are in for a real treat. Enjoy powder white sand, crisp blue water, gorgeous sunsets and great beach combing all waiting right outside your door! If you visit in the winter months, enj
Buena Vista 3
Condominium- 4
- 3 Full Baths , 1 Half Baths
- Pool
- No Pets
- Sleeps 8
- 55 Views
Where can I find your BEST Anna Maria Island Vacation Rentals?
Our Anna Maria rental properties are spread across the island, giving our guests the power to choose where they want to stay on the island. For those traveling with their dogs, we offer pet-friendly vacation rentals that are perfect for the whole family. To be as close to the ocean as possible, be sure to check out our beachfront rentals.
My parents need help up and down the stairs - are any of your units one story or elevator accessible?
We have a number of Anna Maria Island elevator-equipped vacation rentals available - we also have some single story homes and ground-floor condos to make access easier for anyone who needs it. You can also haul luggage to bedrooms, groceries to the kitchen level, or just access rooms much more easily in these homes.
What are some fun things to do on Anna Maria Island?
While staying in an Anna Maria rental there are tons of activities available to you. The island is best known for its soft, sandy beaches and stunning turquoise water. With seven miles of beach to explore, there's plenty to keep the kids and parents entertained. If you want to shake things up on your stay in one of our Anna Maria Island Vacation Rentals, check out what the locals say are the best things to do on Anna Maria Island.
Where is Anna Maria Island located?
Anna Maria Island is 109 miles west of Florida as the crow flies, but it's just over 117 miles by car. It's about an hour and a half southwest of Tampa International Airport and 30 minutes northwest of the Sarasora-Bradenton International Airport. Anna Maria Island is also about 2 hours southwest of Orlando and Disney World.
What is the difference between Anna Maria and Anna Maria Island?
For sure this can be confusing. Anna Maria Island is made up of three cities. Bradenton Beach, the southernmost city. Holmes Beach is in the middle of the Island and the northernmost city is Anna Maria City. So when someone refers to Anna Maria it could be short for Anna Maria Island or it could be short for Anna Maria City. Most of the time when a local references Anna Maria means Anna Maria City.
Are there supermarkets on Anna Maria Island?
Yes, Publix located on Anna Maria Island is a major grocery store. It has a deli, bakery, and seafood along with all the normal amenities. The grocery store does get very busy Saturday afternoon as well as Sunday due to the high amount of vacation rental check-ins on Saturdays.
What sort of restaurants are on Anna Maria Island?
The island has a vast collection of unique eateries to choose from, offering everything from gourmet donuts to delectable sushi to mouthwatering seafood. The island is proud to offer a wide selection of restaurants that are not chain restaurants and are unique to the island. To see more of our restaurant selection check out the dining and nightlife page of our site.