Anna Maria Island Vacation Rentals

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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, (155)
"Had an amazing stay. Will definitely be back!"
The price is CA $939
CA $1,179 total
includes taxes & fees
Jun 9 - Jun 10
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, (188)
"Great property, it’s close to the beach, restaurants, checking in and out very easy (all done via text and phone). The beach across the street is beautiful. Definitely coming back."
The price is CA $627
CA $787 total
includes taxes & fees
Jun 2 - Jun 3
Pelican Post at Anna Maria Island Inn
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Queen's Gate Resort
Outdoor pool, pool umbrellas, sun loungers
Queen's Gate Resort
2.5 star property
9.0 out of 10, Wonderful, (380)
"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
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 CA $355
CA $558 total
includes taxes & fees
Jun 4 - Jun 5
Tradewinds Beach Resort
Anna Maria Sunsets - studio
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!"
Anna Maria Sunsets - studio
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, (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 $555
CA $696 total
includes taxes & fees
Jun 2 - Jun 3
Haley's at The Anna Maria Island Inn
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, (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
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 CA $89
CA $246 total
includes taxes & fees
May 30 - May 31
The Sailor Park
Heated pool with private outdoor "kitchenette", hot tub, and fire pit!!!!
Beach nearby, sun loungers, beach towels
Heated pool with private outdoor "kitchenette", hot tub, and fire pit!!!!
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 with private outdoor "kitchenette", hot tub, and fire pit!!!!
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, (190)
"This is a lovely modern condo with excellent furnishings. This was an effortless vacation."
The price is CA $408
CA $685 total
includes taxes & fees
May 30 - May 31
Completely remodeled beach front condo with full ocean views, steps to the water
Beachfront Paradise w/ Totally PRIVATE BEACH ON THE WATERFRONT , Bring your dog
Exterior
Beachfront Paradise w/ Totally PRIVATE BEACH ON THE WATERFRONT , Bring your dog
9.6 out of 10, Exceptional, (159)
"This property checked off the boxes for a wonderful generational trip for the girls. It was clean, beach access was so private, and the deck furniture worked well for our needs. Baby gate was helpful. All equipment was working and the air conditioning unit was very good and kept us cool on the warmer days. Location was great! The pier was a close walk and instacart delivers to the address so no leaving for groceries!"
The price is CA $477
CA $1,119 total
includes taxes & fees
Jun 2 - Jun 3
Beachfront Paradise w/ Totally PRIVATE BEACH ON THE WATERFRONT , Bring your dog
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
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
Villa by the Sea #3; Heated Pool, Walk to Beach & Shops- Perfect Location!
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!
Charming cottage in quiet area, close to beach & bay.
Terrace/patio
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.
DISCOUNT OFFER! Rum Cove-Magical Tropical Oasis: Pool/Hot Tub, Golf Cart, Kayak
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
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 CA $191
CA $457 total
includes taxes & fees
Jun 14 - Jun 15
Anna Maria Beach Condo 1/1
Anna Maria Sunsets - studio
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
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, (132)
"Loved the convenience of the location. The manager was very helpful when needed"
The price is CA $266
CA $552 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

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, (1001)
"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
Jun 16 - Jun 17
Silver Surf Gulf 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
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, (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 $547
CA $687 total
includes taxes & fees
Jun 4 - Jun 5
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 $89 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

Queen's Gate Resort

Queen's Gate Resort

5/5 Excellent
"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 ."
A verified traveller stayed at Queen's Gate Resort
Posted 22 hours ago
Queen's Gate Resort