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Compare 858 Vacation Homes in Anna Maria with updated reviews, rates, and availability.

Waterfront dog-friendly home with heated private pool, dock, views, and lanai

8.0 out of 10, Very Good, (68)
"walk to sunset bar with great food, monkey bus will take you anywhere on island quickly!!"
The price is AED 2,681
AED 4,763 total
includes taxes & fees
28 May - 29 May
Waterfront dog-friendly home with heated private pool, dock, views, and lanai

Near Bean Point!! Short stays available! Heated Pool

9.4 out of 10, Exceptional, (43)
"Great location, walking distance to beach. Quiet and relaxing. "
Near Bean Point!! Short stays available! Heated Pool

Quiet North End Home Only 2 Blocks to Beach with Private Pool

9.0 out of 10, Wonderful, (44)
"Clean property and cute inside. The location was fantastic and very quiet area. The pool was lovely and the sound of the waterfall was a nice surprise. I would definitely recommend this property. "
Quiet North End Home Only 2 Blocks to Beach with Private Pool

Sandy Cheeks: Ground-level home with plunge pool. Close to pier, park, & Bay!

9.6 out of 10, Exceptional, (11)
"Great location, well appointed!"
Sandy Cheeks: Ground-level home with plunge pool. Close to pier, park, & Bay!

Bella Vista: Bay front with gorgeous views and outdoor living space.

9.6 out of 10, Exceptional, (11)
"It’s the perfect getaway right on the bay, beautiful home with a amazing view. This house has everything we wanted and needed for a wonderful vacation"
Bella Vista: Bay front with gorgeous views and outdoor living space.

Water Front Sea Waves Cottage With Private Dock, Access To Bimini Bay

9.8 out of 10, Exceptional, (116)
"The house was perfect. Great location and the outdoor space is phenomenal!"
Water Front Sea Waves Cottage With Private Dock, Access To Bimini Bay

Anna Maria Northshore beauty W/ Private Pool. 1 block from Anna Maria Beach!!!

9.2 out of 10, Wonderful, (61)
"Fun and convenient location. Nice property. Had a blast."
Anna Maria Northshore beauty W/ Private Pool. 1 block from Anna Maria Beach!!!

The Wee Cottage | House in Anna Maria

8.4 out of 10, Very Good, (15)
"Easy and close beach access. Location nearby all amenities and necessities. Did not see that the a/c units were window units, the bedroom unit is AMAZING, however the main room unit was mediocre. The Wee Cottage is adorable!!!"
The Wee Cottage | House in Anna Maria

Escape to an island adventure!

10.0 out of 10, Exceptional, (113)
"We LOVED our stay here!! It was perfect. Great location and the game room downstairs is so cute.Also, don’t forget they have BIKES!!! Loved!"
Escape to an island adventure!

The TipSea Turtle managed by Beach Retreats FL Anna Maria Island

10.0 out of 10, Exceptional, (16)
"Wonderful time at The TipSea Turtle. The kids had a blast at the pool and playing mini golf!! The beach was close by Thank you"
The TipSea Turtle managed by Beach Retreats FL Anna Maria Island

Golf Cart, Stonehenge by SeaBreeze Vacation

10.0 out of 10, Exceptional, (19)
"Amazing Stay!"
Golf Cart, Stonehenge by SeaBreeze Vacation

MAY SPECIALS, BEACHFRONT, PRIVATE BEACH ON THE WATERFRONT, Bring your dog

9.6 out of 10, Exceptional, (177)
"Great location and very cute house with fantastic views. Just wish it was stocked slightly better. One beach chair, one seater kayak. No cooking spray or oil. Only salt and pepper. Deck of cards or other family games? With just a few more items to make this house comfortable for a family, this place would be awesome. For the price, it is a reasonable idea. Oh and the TV didn’t work in the master bedroom."
The price is AED 1,561
AED 3,358 total
includes taxes & fees
20 May - 21 May
MAY SPECIALS, BEACHFRONT, PRIVATE BEACH ON THE WATERFRONT, Bring your dog

Beautiful, Gulf-Front Home on Bean Point--Halcyon House

10.0 out of 10, Exceptional, (219)
"This was a beautiful house with an amazing location! We loved our stay!"
Beautiful, Gulf-Front Home on Bean Point--Halcyon House

Beautiful cottage w/ heated private pool - walk to beach, dining, Bayfront Park

9.8 out of 10, Exceptional, (84)
"We love this house. Great location. The house was clean and the kitchen is well e"
Beautiful cottage w/ heated private pool - walk to beach, dining, Bayfront Park

Short stays available! Located on North End of Island.

9.2 out of 10, Wonderful, (49)
"walking distance to beach and Rod Reel Pier was perfect!"
Short stays available! Located on North End of Island.

On Point: Across Street from Bean Point Beach, Outdoor Games & Pool by Anna Maria Life

9.6 out of 10, Exceptional, (19)
"This was the perfect place for our family vacation to AMI!"
On Point: Across Street from Bean Point Beach, Outdoor Games & Pool by Anna Maria Life

Reef Romance managed by Beach Retreats FL Anna Maria Island

10.0 out of 10, Exceptional, (17)
"What a beautiful place with anything you could need for the comfort of home. Quick walk to the beach and only a block or so to the coffee shop and shopping. "
Reef Romance managed by Beach Retreats FL Anna Maria Island

Gulf Views 🌊 | Elevator 🏡 | 50 Yards to Beach 🌴| Heated Pool & Spa 🌅Sunsets

10.0 out of 10, Exceptional, (3)
"We were absolutely thrilled with our stay at Shore to Please! The house was impeccably clean, beautifully decorated, and had everything we needed for a comfortable vacation. The location was perfect, close to the beach and local shops, and the hosts were incredibly responsive to any questions we had. We felt truly welcomed and would definitely return for another stay."
Gulf Views 🌊 | Elevator 🏡 | 50 Yards to Beach 🌴| Heated Pool & Spa 🌅Sunsets

OPEN for booking after Helene & Milton! for 2025 limited dates available NOW!!

9.8 out of 10, Exceptional, (193)
"We had a wonderful stay. The house offers every comfort and is absolutely gorgeous, with thoughtful details that enhance both convenience and aesthetics. The kids loved the playroom with games, the pool was heated, and there was a beautiful outdoor seating area. It’s a place we’d love to return to again and again—more than just a house, it truly feels like a home."
OPEN for booking after Helene & Milton! for 2025 limited dates available NOW!!

Bay Breeze Cottages #3

9.8 out of 10, Exceptional, (111)
"Really enjoyed my stay. Beautiful cottage and scenery."
Bay Breeze Cottages #3
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.
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Other property types in Anna Maria

Sandy Cheeks: Ground-level home with plunge pool. Close to pier, park, & Bay!

9.6 out of 10, Exceptional, (11)
"Great location, well appointed!"
Sandy Cheeks: Ground-level home with plunge pool. Close to pier, park, & Bay!

Updated bayside condo with heated pool - across the street from the beach

9.2 out of 10, Wonderful, (86)
"Had a great stay. Highly recommend "
The price is AED 569
AED 1,490 total
includes taxes & fees
8 Jun - 9 Jun
Updated bayside condo with heated pool - across the street from the beach

Beachy Boathouse Cottage, 2 BR,1BA, Private Pool, Steps to Beach and Bay-

9.8 out of 10, Exceptional, (85)
"We had a great vacation at this rental property and will definitely stay here again when we return to Anna Maria island. House is beautiful, location is perfect, and it had everything we needed to make our week in Anna Maria island fun and relaxing. The pool was great, heated to the perfect temperature. Thank you to our great hosts for making our stay a great one! "
Beachy Boathouse Cottage, 2 BR,1BA, Private Pool, Steps to Beach and Bay-
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.