Anna Maria Island Vacation Rentals

Vacation Rentals in Anna Maria Island

Anna Maria Beach Resort
On the beach, white sand, beach towels
Anna Maria Beach Resort
3.5 star property
9.4 out of 10, Exceptional, (157)
"the location was just perfect - beach, pool were wonderful "
The price is $730
$916 total
includes taxes & fees
Jun 24 - Jun 25
Anna Maria Beach Resort
Perfectly Located Home with Pool and Spa
A heated pool
Perfectly Located Home with Pool and Spa
9.8 out of 10, Exceptional, (21)
"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
Pelican Post at Anna Maria Island Inn
Garden
Pelican Post at Anna Maria Island Inn
3.0 star property
9.2 out of 10, Wonderful, (190)
"This place is so beautiful I do not want to leave. The only improvement I would suggest would be a USB port for charging devices. Other than that the place is clean,comfortable and about perfect. "
The price is $229
$288 total
includes taxes & fees
Jun 13 - Jun 14
Pelican Post at Anna Maria Island Inn
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Tradewinds Beach Resort
Private beach nearby, sun loungers, beach towels
Tradewinds Beach Resort
2.5 star property
9.2 out of 10, Wonderful, (353)
"Friendly staff. Diane was very helpful."
The price is $260
$409 total
includes taxes & fees
Jun 16 - Jun 17
Tradewinds Beach Resort
Queen's Gate Resort
Outdoor pool, pool umbrellas, sun loungers
Queen's Gate Resort
2.5 star property
9.0 out of 10, Wonderful, (381)
"The Location 100 steps to the beach ! Property manager Kathy and assistant manager Pete were amazing they attended to every need we had , gave us a tour of the property and followed up every day on how our stay was ."
Queen's Gate Resort
Haley's at The Anna Maria Island Inn
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, (347)
"Peaceful "
The price is $189
$238 total
includes taxes & fees
Jun 9 - Jun 10
Haley's at The Anna Maria Island Inn
The Sailor Park
Exterior
The Sailor Park
3.0 star property
3.2 out of 10, (15)
"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
Jun 8 - Jun 9
The Sailor Park
Anna Maria Sunsets - studio
Property grounds
Anna Maria Sunsets - studio
9.2 out of 10, Wonderful, (175)
"This was our second time staying here and once again it did not disappoint! We will be back again next year!"
Anna Maria Sunsets - studio
Anna Maria Sunsets - studio
Sun loungers, beach towels
Anna Maria Sunsets - studio
9.4 out of 10, Exceptional, (186)
"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 $150
$281 total
includes taxes & fees
Jul 7 - Jul 8
Anna Maria Sunsets - studio
Completely remodeled beach front condo with full ocean views, steps to the water
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, (191)
"My wife and I stayed here for a long weekend. The condo was immaculate and the views of the ocean couldn't have been better. Bernard was an excellent host and was very responsive. We have already booked our return visit!"
The price is $333
$546 total
includes taxes & fees
Jun 11 - Jun 12
Completely remodeled beach front condo with full ocean views, steps to the water
COZY APT IN QUAINT QUADRAPLEX HOME. STEPS TO BEACH! 1 BR/1BA. SLEEPS 2. POOL
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
The Pink House Unit B: A Cozy Retreat Steps from the Beach
View from property
The Pink House Unit B: A Cozy Retreat Steps from the Beach
9.8 out of 10, Exceptional, (69)
"My husband and I enjoyed this amazing property for our anniversary! We loved the proximity to the beach and walkable to bridge street. We had a car, and went to the north end of the island, but also took the trolley which was super easy. This home is so comfortable, cozy, sweetly decorated and clean. We definitely want to go back again!"
The Pink House Unit B: A Cozy Retreat Steps from the Beach
The Pink House Unit A: A Cozy Retreat Steps from the Beach
Smart TV
The Pink House Unit A: A Cozy Retreat Steps from the Beach
9.4 out of 10, Exceptional, (58)
"house was perfect as we just needed a place to sleep since we were visiting friends who live on the island. as it turned out the house was close to the beach, shopping, bars and restaurants so it was a plus for us! plenty of room for the four of us"
The Pink House Unit A: A Cozy Retreat Steps from the Beach
Anna Maria Beach Condo 1/1
Beach
Anna Maria Beach Condo 1/1
9.8 out of 10, Exceptional, (178)
"Property was as advertised. Location was good and quiet. Close to ocean and walking distance to several reasonable restaurants"
The price is $140
$335 total
includes taxes & fees
Jun 14 - Jun 15
Anna Maria Beach Condo 1/1
Gulf & Sunset Views!!! 1BR Apt. B is a Centrally Located, walk to all location
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, (133)
"Everything was great! Just as explained…"
The price is $167
$369 total
includes taxes & fees
Jun 19 - Jun 20
Gulf & Sunset Views!!! 1BR Apt. B is a Centrally Located, walk to all location
Vibrant Island Home w/ Pool, 1 Block to Beach
Property grounds
Vibrant Island Home w/ Pool, 1 Block to Beach
9.6 out of 10, Exceptional, (28)
"Home close to beach and restaurants."
Vibrant Island Home w/ Pool, 1 Block to Beach
Naut 2 Shabby Bungalow 🤗 A sweet and cozy getaway on Pine Avenue!
Aerial view
Naut 2 Shabby Bungalow 🤗 A sweet and cozy getaway on Pine Avenue!
10.0 out of 10, Exceptional, (168)
"Very comfortable dwelling. Close to Pier, shops, restaurants, and island trolley pickups. Extremely clean and neat. Owner easy to contact. Would definitely stay here again!"
Naut 2 Shabby Bungalow 🤗 A sweet and cozy getaway on Pine Avenue!
Adorable luxury Resort Unit in a perfect location! Great Pool area!
Beach nearby
Adorable luxury Resort Unit in a perfect location! Great Pool area!
9.6 out of 10, Exceptional, (49)
"Nice unit, but a bit difficult without a washer and dryer in the unit and one can easily be put in in the closet of the main bedroom. We asked for more towels and were told they would be coming, but none were delivered. The kitchen was nicely equipped with what we needed and we liked the pool, outdoor patio, and proximity to the pier. Thank you for a lovely stay."
The price is $350
$768 total
includes taxes & fees
Jun 18 - Jun 19
Adorable luxury Resort Unit in a perfect location! Great Pool area!
HEATED POOL... A private outdoor living area with grill, fire pit, and hot tub!
Beach nearby, sun loungers, beach towels
HEATED POOL... A private outdoor living area with grill, fire pit, and hot tub!
9.8 out of 10, Exceptional, (258)
"Absolutely beautiful property & location was amazing!!! We had an absolutely wonderful time!! The house has a wonderful lanai and pool area that accommodates many people …. This home has a lot of steps that was the only downfall so if you have somebody in your party, that can’t handle steps. This wouldn’t be a good location for them but other than that everything was great."
HEATED POOL... A private outdoor living area with grill, fire pit, and hot tub!
Bay -Canal Waterfront! Tiki Bar 5BR, 5BA Heated Pool 2 Kitchens, Golf Cart
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
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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

Silver Surf Gulf Beach Resort
Private beach nearby, beach umbrellas, beach towels, beach massages
Silver Surf Gulf Beach Resort
3.0 star property
9.4 out of 10, Exceptional, (1013)
"Older hotel/motel. Ample parking, friendly staff, clean room, plenty of space, an overall good value. Beach steps away across the street, free beach chairs and umbrella. Jet ski and hobie cat rental available."
The price is $228
$256 total
includes taxes & fees
Jun 16 - Jun 17
Silver Surf Gulf Beach Resort
Bali Hai Beachfront Resort 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, (453)
"Most beautiful beach!!!! We were comfortable and had all we needed. Bali Hai made us feel welcomed and took great care of us. "
The price is $349
$438 total
includes taxes & fees
Jun 25 - Jun 26
Bali Hai Beachfront Resort and Spa
Perfectly Located Home with Pool and Spa
A heated pool
Perfectly Located Home with Pool and Spa
9.8 out of 10, Exceptional, (21)
"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
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

Bali Hai Beachfront Resort and Spa

Bali Hai Beachfront Resort and Spa

5/5 Excellent
"Most beautiful beach!!!! We were comfortable and had all we needed. Bali Hai made us feel welcomed and took great care of us. "
A verified traveler stayed at Bali Hai Beachfront Resort and Spa
Posted 2 days ago
Bali Hai Beachfront Resort and Spa