Anna Maria Island Vacation Rentals

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Vacation Rentals in Anna Maria Island

On the beach, white sand, beach towels
Anna Maria Beach Resort
3.5 star property
9.4 out of 10, Exceptional, (155)
"Had an amazing stay. Will definitely be back!"
The price is $683
$857 total
includes taxes & fees
May 23 - May 24
Anna Maria Beach Resort
A heated pool
Perfectly Located Home with Pool and Spa
9.6 out of 10, Exceptional, (20)
"The house is great, with the ease of having a pool and the beach being only 2 blocks away. This was our first time visiting Anna Maria. We have been finding other options the last couple years since we used to go to Captiva and that was destroyed in the hurricane almost 2 years ago. The island is pretty small but has different sections to explore. We enjoyed Coquina beach for a coupem hours one day, the restaurants were good very vactiony normal island grub type places. We did enjoy a great meal...
Perfectly Located Home with Pool and Spa
Garden
Pelican Post at Anna Maria Island Inn
3.0 star property
9.0 out of 10, Wonderful, (186)
"Very nice rooms. Lots of space. Newly renovated. Walking distance to everything and great pool. "
The price is $347
$435 total
includes taxes & fees
May 23 - May 24
Pelican Post at Anna Maria Island Inn
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Outdoor pool, pool umbrellas, sun loungers
Queen's Gate Resort
2.5 star property
9.0 out of 10, Wonderful, (376)
"Suite is a little small but has everything what you need, they have a laundry with soap, grill and pool. Very clean and close to the beach. They even provided free beach chairs, umbrellas and beach towels. They also has an ice machine. Close restaurants and shopping stores. "
Queen's Gate Resort
Private beach nearby, sun loungers, beach towels
Tradewinds Beach Resort
2.5 star property
9.2 out of 10, Wonderful, (353)
"Only good things to say about the Tradewinds. We have stayed at the Tortuga twice and loved it. Tradewinds was equally as awesome. Loved the pool location, communication was great by staff. "
The price is $260
$409 total
includes taxes & fees
May 29 - May 30
Tradewinds Beach Resort
Beach nearby, white sand, sun loungers, beach towels
Haley's at The Anna Maria Island Inn
3.0 star property
8.6 out of 10, Excellent, (344)
"Quick little walk to beach. Great beach chairs. Best location on the beach. They were easily and quick to get in touch with for questions and the location was perfect. "
The price is $286
$359 total
includes taxes & fees
May 27 - May 28
Haley's at The Anna Maria Island Inn
Sun loungers, beach towels
Anna Maria Sunsets - studio
9.4 out of 10, Exceptional, (185)
"Nice room, a little small but adequate, although an outside area for sitting (private) would have been nice. Excellent location across a busy street from a beautiful beach with a shady gazebo to sit in and next to a jet ski rental! Anna Maria Free Shuttle takes you up and down the island and runs every 20 minutes, with a stop very close by. Walking distance to the "Bridge Street" shopping and dining block!"
The price is $80
$196 total
includes taxes & fees
Jun 7 - Jun 8
Anna Maria Sunsets - studio
View from property
The Pink House Unit B: A Cozy Retreat Steps from the Beach
9.8 out of 10, Exceptional, (65)
"The Pink House Unit B was one of the best units I have stayed using VRBO for years now. The pictures do it perfect justice. It’s a nice quaint space with a 1 min walk to beach. The unit is literally across the street from the beach which was quiet, not crowded at all. The only tiny drawback was the bathroom. The shower and toilet do need updates but don’t let that detour you one bit. Great place and location! I would rent again for sure!!!"
The Pink House Unit B: A Cozy Retreat Steps from the Beach
Exterior
Beachfront Paradise w/ Totally PRIVATE BEACH ON THE WATERFRONT , Bring your dog
9.6 out of 10, Exceptional, (157)
"The location and views were incredible! It was so great being right on the beach and it was easy to walk everywhere. Unfortunately the house is a little tired, the refrigerator should be replaced as the door doesn’t close well, the shower head in the primary bathroom should be replaced and the pillows/mattresses need updating. Again, the location and views are stunning and we had the best time playing on the beach and in the water all day, but for the expensive cost per night, we were...
The price is $350
$821 total
includes taxes & fees
Jun 2 - Jun 3
Beachfront Paradise w/ Totally PRIVATE BEACH ON THE WATERFRONT , Bring your dog
On the beach, sun loungers, beach towels
Completely remodeled beach front condo with full ocean views, steps to the water
9.8 out of 10, Exceptional, (190)
"This is a lovely modern condo with excellent furnishings. This was an effortless vacation."
The price is $299
$503 total
includes taxes & fees
May 23 - May 24
Completely remodeled beach front condo with full ocean views, steps to the water
Exterior
The Sailor Park
3.0 star property
3.6 out of 10, (10)
"This was a very welcome get away. Absolutely beautiful views. The owner is great. I definitely will come back. "
The price is $52
$160 total
includes taxes & fees
May 23 - May 24
The Sailor Park
Property grounds
Anna Maria Sunsets - studio
9.2 out of 10, Wonderful, (173)
"I had no idea that a unit on the second floor was actually on the third floor above the garage and we had to take the steps because the elevator was broken. It was very hard to find and has a weird one way driveway that you have to see to believe. Once we finally got into the unit it was fine. Thought I might have a heart attack lugging suitcase up but I lived. My husband’s recent knee replacement didn’t like the two flights of stairs either. But would it kill you to include a coffee maker and a...
The price is $135
$265 total
includes taxes & fees
Jun 2 - Jun 3
Anna Maria Sunsets - studio
Beach nearby, sun loungers, beach towels
Gulf & Sunset Views!!! 1BR Apt. B is a Centrally Located, walk to all location
9.8 out of 10, Exceptional, (131)
"Property location was great. Clean and spacious. Parking space was a plus for us. We stayed for a short stay but would return and stay here. Communication w/ PM was easy and accessible."
The price is $148
$345 total
includes taxes & fees
May 23 - May 24
Gulf & Sunset Views!!! 1BR Apt. B is a Centrally Located, walk to all location
Beach nearby, sun loungers, beach towels
Charming cottage in quiet area, close to beach & bay.
10.0 out of 10, Exceptional, (233)
"This charming 2 bed, 1 bath cottage is in the perfect location. It is in walking distance to coffee shops, breakfast spots and dinner restaurants. Close to the beach one direction and city pier the other. It is well stocked with all you would need and exceptionally clean. The screened porch in back with solar lighting in the back yard is ideal for your evening glass of wine! Definitely recommend!"
Charming cottage in quiet area, close to beach & bay.
Outdoor pool, a heated pool
COZY APT IN QUAINT QUADRAPLEX HOME. STEPS TO BEACH! 1 BR/1BA. SLEEPS 2. POOL
9.8 out of 10, Exceptional, (156)
"PROPERTY WAS IN A PERFECT LOCATION ON THE ISLAND Had a fantastic week."
COZY APT IN QUAINT QUADRAPLEX HOME. STEPS TO BEACH! 1 BR/1BA. SLEEPS 2. POOL
Beach nearby
Villa by the Sea #3; Heated Pool, Walk to Beach & Shops- Perfect Location!
9.8 out of 10, Exceptional, (58)
"We had a wonderful week at Villa By The Sea #3! You can walk to the beach and lots ofshops and restaurants. Condo is small but nice for a couple."
Villa by the Sea #3; Heated Pool, Walk to Beach & Shops- Perfect Location!
Beach nearby, sun loungers, beach towels
Heated pool with private outdoor "kitchenette", hot tub, and fire pit!!!!
9.8 out of 10, Exceptional, (257)
"I rented this entire house for my sons wedding on Anna Maria Island. Giving 5 stars for this place feels like an injustice. The location is perfect-a short walk to watch the sunrise on the bay or the sunset from the beach. Plenty of parking, but who needs a car when there’s a free trolley right out your door to take you anywhere on the island. No need to pack for the beach. This property provides anything you would ever need, from chairs to towels to beach toys, and a wagon to load it all in....
Heated pool with private outdoor "kitchenette", hot tub, and fire pit!!!!
A heated pool
Bay -Canal Waterfront! Tiki Bar 5BR, 5BA Heated Pool 2 Kitchens, Golf Cart
9.8 out of 10, Exceptional, (100)
"We enjoyed our stay at Bay - Canal Waterfront! We enjoyed the amenities - the pool is beautiful, large and in the sun all day but plenty of shady areas if you want that too. The kayaks were enjoyed as well and we did have some manatee sightings! We enjoyed the golf cart as well! The layout of the house is 2 separate areas with a full unit on top and on bottom. The only complaint we had which cannot be controlled by the owner is the smell of the muck that congregates at the end of the canal which...
Bay -Canal Waterfront! Tiki Bar 5BR, 5BA Heated Pool 2 Kitchens, Golf Cart
Interior
Family Beachfront condo boasting 180-degree views. Steps from sand!
9.8 out of 10, Exceptional, (169)
"So close to the beach and walkable to the restaurants and shops."
Family Beachfront condo boasting 180-degree views. Steps from sand!
On the beach
Club Bamboo South 122 Studio
9.2 out of 10, Wonderful, (70)
"This is our second stay at Club Bamboo South. We really enjoyed our time. It’s a small space but doesn’t seem as small because of your view of the gulf. We love the location and walked to bridge street and several restaurants near by. We had no issues and everything was perfect!!"
The price is $284
$632 total
includes taxes & fees
Jun 9 - Jun 10
Club Bamboo South 122 Studio
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See all available properties in Anna Maria Island
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other types of properties in Anna Maria Island you may be interested in

Private beach nearby, beach umbrellas, beach towels, beach massages
Silver Surf Gulf Beach Resort
3.0 star property
9.4 out of 10, Exceptional, (1000)
"Right across the street from the beach, super easy access with free umbrellas and chairs.Free trolley stop at the hotel. Noah was super friendly and helpful. Very nice rooms with fridge and microwave. Breakfast was light but plentiful."
The price is $228
$256 total
includes taxes & fees
Jun 16 - Jun 17
Silver Surf Gulf Beach Resort
A heated pool
Perfectly Located Home with Pool and Spa
9.6 out of 10, Exceptional, (20)
"The house is great, with the ease of having a pool and the beach being only 2 blocks away. This was our first time visiting Anna Maria. We have been finding other options the last couple years since we used to go to Captiva and that was destroyed in the hurricane almost 2 years ago. The island is pretty small but has different sections to explore. We enjoyed Coquina beach for a coupem hours one day, the restaurants were good very vactiony normal island grub type places. We did enjoy a great meal...
Perfectly Located Home with Pool and Spa
On the beach, white sand, sun loungers, beach umbrellas
Bali Hai Beachfront Resort and Spa
3.5 star property
8.6 out of 10, Excellent, (447)
"The location right on the beach. "
The price is $364
$457 total
includes taxes & fees
May 23 - May 24
Bali Hai Beachfront Resort and Spa
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Everything you need to know about Anna Maria Island vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Anna Maria Island vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Anna Maria Island vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Anna Maria Island vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Anna Maria Island. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Anna Maria Island in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $52 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Anna Maria Island rentals

At Expedia, we put the best Anna Maria Island vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Anna Maria Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Anna Maria Island vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Anna Maria Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Recent reviews of Anna Maria Island properties
Expedia verified reviews

Anna Maria Beach Resort

Anna Maria Beach Resort

5/5 Excellent
"Had an amazing stay. Will definitely be back!"
A verified traveler stayed at Anna Maria Beach Resort
Posted 1 day ago
Anna Maria Beach Resort