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 CA $918
CA $1,152 total
includes taxes & fees
Jun 2 - Jun 3
Anna Maria Beach Resort
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
Garden
Pelican Post at Anna Maria Island Inn
3.0 star property
9.2 out of 10, Wonderful, (188)
"My favorite hotel to stay! Super clean and peaceful! My kids love the pool and beach is two minute walk. Stores and food are walking distance. "
The price is CA $474
CA $594 total
includes taxes & fees
May 29 - May 30
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, (379)
"Amazing property and super friendly staff. We had the best time and our room was perfect. Full kitchen with everything we needed to make any meal. Washer/dryer that we could use plus so many little extras in the supply house we could use if needed! Pool was clean and beautiful. Beach was super close, just about a minutes walk away. Will definitely be returning in the future! "
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)
"Friendly staff. Diane was very helpful."
The price is CA $355
CA $559 total
includes taxes & fees
Jun 3 - Jun 4
Tradewinds Beach Resort
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 CA $109
CA $267 total
includes taxes & fees
Jun 7 - Jun 8
Anna Maria Sunsets - studio
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, (346)
"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 CA $402
CA $504 total
includes taxes & fees
May 28 - May 29
Haley's at The Anna Maria Island Inn
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
The Sailor Park
3.0 star property
3.4 out of 10, (12)
"This was a very welcome get away. Absolutely beautiful views. The owner is great. I definitely will come back. "
The price is CA $80
CA $233 total
includes taxes & fees
Jun 10 - Jun 11
The Sailor Park
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!!!!
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 CA $409
CA $687 total
includes taxes & fees
May 29 - May 30
Completely remodeled beach front condo with full ocean views, steps to the water
Exterior
Beachfront Paradise w/ Totally PRIVATE BEACH ON THE WATERFRONT , Bring your dog
9.6 out of 10, Exceptional, (158)
"This property was true to pictures, very beautiful private beach, and the surrounding areas were very well maintained. Our host was exceptional, and our gorgeous rental was spotless.I would absolutely recommend this rental!!"
The price is CA $478
CA $1,122 total
includes taxes & fees
Jun 2 - Jun 3
Beachfront Paradise w/ Totally PRIVATE BEACH ON THE WATERFRONT , Bring your dog
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
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
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
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.
Pool
DISCOUNT OFFER! Rum Cove-Magical Tropical Oasis: Pool/Hot Tub, Golf Cart, Kayak
10.0 out of 10, Exceptional, (97)
"This was our 2nd year staying at Rum Cove and we would definitely book this house again. The property managers were very responsive to one minor issue that we had on check in. The house is in walking distance to the beach, the pier and many restaurants and shops."
DISCOUNT OFFER! Rum Cove-Magical Tropical Oasis: Pool/Hot Tub, Golf Cart, Kayak
Beach
Anna Maria Beach Condo 1/1
9.8 out of 10, Exceptional, (177)
"Beautiful area, condo was very clean and beautifully decorated. Plenty of room for 2 people (my sister and me..) Huge, comfortable king sized bed. Nice roomy closets. Excellent bathroom with privacy door between double sink vanity area and shower /toilet. Fully equipped cheery kitchen. Private, roomy screened in balcony . And the beach was magnificent......"
The price is CA $191
CA $456 total
includes taxes & fees
Jun 7 - Jun 8
Anna Maria Beach Condo 1/1
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 CA $184
CA $362 total
includes taxes & fees
Jun 9 - Jun 10
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, (132)
"Loved the convenience of the location. The manager was very helpful when needed"
The price is CA $266
CA $553 total
includes taxes & fees
Jun 3 - Jun 4
Gulf & Sunset Views!!! 1BR Apt. B is a Centrally Located, walk to all location
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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, (1002)
"We had an amazing experience at the Silver Surf Resort. Top 5 why you should stay here: 1. Super friendly staff 2.Complentary breakfast is a plus 3. Walk to the beach 4. You don’t have to bring beach umbrella or chairs they provide it for you. 5.Super clean rooms , beds are comfortable"
The price is CA $304
CA $341 total
includes taxes & fees
May 29 - May 30
Silver Surf Gulf Beach Resort
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
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, (449)
"The staff was amazing! Mike the bartender is great! The manager was so kind. Front desk staff super helpful. Great place. We loved it so much, we WILL be coming back!"
The price is CA $546
CA $686 total
includes taxes & fees
Jun 9 - Jun 10
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, cottages, cabins, villas... 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Anna Maria Island vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Anna Maria Island vacation rentals we have selected for you start as low as CA $80 per night. Entering your travel dates in the search wizard 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

Tropic Isle at Anna Maria Island Inn

Tropic Isle at Anna Maria Island Inn

5/5 Excellent
"Espectacular, súper bien ubicado. Habitación limpia, trato amable. La comida riquísima, en fin no tengo ninguna queja, y recomendé a todos mis amigos!"
A verified traveller stayed at Tropic Isle at Anna Maria Island Inn
Posted 22 hours ago
Tropic Isle at Anna Maria Island Inn