BEST Anna Maria Vacation 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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GONE COASTAL at FOUNTAINHEAD CONDOMINIUMS - Accommodating up to four guests for a fun laid back beach vacation, Fountainhead Unit 2 offers the perfect two bedroom, two bathroom getaway for you and your family. Centrally located on Anna Maria Island, Fountainhead Unit 2 is near everything for an entertaining stay including gulf beaches, free trolley
Fountainhead 2 - Gone Coastal
Condominium- 2
- 2
- Pool
- No Pets
- Sleeps 4
- 10 Views
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“Pirate’s Cove” is a great island oasis to enjoy during your stay, the perfect cove for your vacation getaway. One of the only "Any Day" arrival properties on the island.This elevated home is built for family vacations, as it has the room to allow for a relaxing vacation giving everyone their space. “Pirate’s Cove” has an extensive layout, with mul
Pirates Cove
Home- 7
- 7 Full Baths , 1 Half Baths
- Pool
- No Pets
- Sleeps 16
- 16 Views
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“Martinique” is directly on the coast providing the quintessential beach experience complete with powder white sand, blue water, fresh gulf breezes and amazing sunsets. You’ll want to spend all day soaking up the sun and salt water! Relax with a good book, cool drink or chat with friends around the heated community pool. Enjoy premium linen service
Martinique404N
Condominium- 2
- 2
- Pool
- Dogs Allowed
- Sleeps 6
- 12 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
- 42 Views
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“Sea Glass” is a lovely ground level 3 bedroom 2 bathroom duplex style Holmes Beach vacation rental home suited for up to 6 vacationers. Plenty of space for everyone, this rental home has 1 king bed, 1 queen bed, a Twin over Full Bunk, a Twin bed, and a queen sleeper sofa. Spacious, but not too big, “Sea Glass” is sophistication without pretension.
Sea Glass
Multi-Family- 3
- 2
- Pool
- No Pets
- Sleeps 6
- 35 Views
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"Flip Flop Oasis" Two Single Family Homes with Adjoining Yards and TWO Heated PoolsFirst Home 201 57th Street "Flip Flop Inn" If you are searching for luxury on your Island vacation, this home is your dream come true. Tucked away on a quiet street on Anna Maria Island, this Mediterranean-style Townhouse is your perfect family vacation destination.T
Flip Flop Oasis
Multi-Family- 6
- 6
- Pool
- No Pets
- Sleeps 12
- 12 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
- 6 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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"Yacht Rock Ranch" is a single-story ranch-style home featuring 4 bedrooms and three bathrooms. Originally constructed as a duplex, this property ensures excellent privacy. The centrally located bunk bedroom is ideal for children, as it is isolated from the pool area, and all pool doors are equipped with alarms.We provide various amenities to enhan
Yacht Rock Ranch
Home- 4
- 3
- Pool
- No Pets
- Sleeps 10
- 19 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
- 25 Views
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North Beach Village 6301 is a lovely three-bedroom rental located in the island city of Holmes Beach. This home is within the peaceful North Beach Village community, hence the name, where you’ll find great comfort and relaxation in island style. The foliage that surrounds you has a beautiful, tropical feel, there’s even a community pool for you to
North Beach Village 6301
Condominium- 3
- 2
- Pool
- No Pets
- Sleeps 6
- 19 Views
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When looking to accommodate a large group during you paradise Anna Maria Island vacation look no further than “Tina’s Piece of Paradise”. This fun four bedroom, three bathroom Holmes Beach vacation rental spaciously sleeps up to 8 guests in comfort and style. After spending a week at this fabulous Holmes Beach vacation rental home within walking di
Tinas Piece of Paradise
Home- 4
- 3
- Pool
- No Pets
- Sleeps 8
- 10 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.