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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, (67)
"Overall this worked great for us. About 2 blocks from the gulf coast. Fishing access on an inlet behind the house and pool was great for us and kids. Out of the way for major island traffic but close enough to the coast to walk and enjoy it"
The price is SAR 1,125
SAR 2,524 total
includes taxes & fees
4 May - 5 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)
"Wonderful place"
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)
"Loved this spacious ranch. Liked being on the quiet north end. "
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)
"The interior was all new. Furnishings, decor, kitchen supplies, and everything fresh and tastefully done. Quiet neighborhood just a couple blocks from beach. Exterior privacy will improve as landscape recovers. Parking and access easy. "
Sandy Cheeks: Ground-level home with plunge pool. Close to pier, park, & Bay!

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

9.4 out of 10, Exceptional, (9)
"We had an absolutely wonderful time! The house is gorgeous, the view is amazing and the whole area is so nice! We couldn’t have asked for a better experience!!!"
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, (113)
"Property was excellent, comfortable and well appointed. The Owner was very proactive in providing guidance. The outlook from our deck over the waters of Bimini Bay was superb."
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)
"We stayed with my family, my brother's family and my parents and everyone had a wonderful time. There was plenty of beds, the pool was great and the location was perfect."
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)
"Cute, quaint cottage. Loved the old Florida style decor. House inside was clean. Window air conditioner units kept house cool. The one in the bedroom was noisy though and kicked on often. Shower is a good size but the bathroom is very small. Pool was warm and great! Loved the putting green. Would've been nice to have a couple other putters though. Screened porch with table and chairs was very nice. Landscaping and the outside area needed some TLC and clean up. Hose to fill the...
The Wee Cottage | House in Anna Maria

Escape to an island adventure!

10.0 out of 10, Exceptional, (112)
"We had a lovely visit at this VRBO. Jeff was communicative and responsive. This VRBO has SO many extras!!! It's the little things that you don't realize you need till you're away from home and need it, well, they've likely got it there for you. Great location and would absolutely stay there again! "
Escape to an island adventure!

The TipSea Turtle managed by Beach Retreats FL Anna Maria Island

10.0 out of 10, Exceptional, (16)
"Our second trip to AMI but first time at this home. It was perfect for 4 couples just enjoying some sun and time away. Weather was incredibly windy but the outdoor space was covered/sheltered enough that we could still enjoy time outdoors and in the hot tub. Roof top deck was amazing before the winds came in.Home is very comfortable and fairly well stocked. Location is fine- close to get around the island but out enough to not be too busy.Devastating to see so much storm damage since last year-...
The TipSea Turtle managed by Beach Retreats FL Anna Maria Island

Golf Cart, Stonehenge by SeaBreeze Vacation

10.0 out of 10, Exceptional, (18)
"Great location, lovely neighborhood, walk to the beach. Enjoyed the open kitchen, living, and dining area. Wonderful private pool, and had all of the beach chairs and wagons for the beach. Super clean. "
Golf Cart, Stonehenge by SeaBreeze Vacation

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

9.6 out of 10, Exceptional, (175)
"Although we had not so nice weather we managed to sit and enjoy the view! Lots of fun moments with friends and family. Enjoyed local eateries and shopping. Thanks again!"
The price is SAR 1,872
SAR 3,770 total
includes taxes & fees
4 May - 5 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, (217)
"Over the years, our family has rented a great number of beach houses. This is #1 of all times."
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 have been going to Anna Maria for three years now and each year it gets better. The house was super comfortable with everything we needed and worth more space than what we expected. Walking to the beach was super easy with the kids and the pool though small was enough. The only “but” of our stay was the pool temperature that by no means was as warm as promised and the alarm that leads outside from the back covered porch that is super annoying because you can’t stop it from going on from the...
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)
"I brought my daughter down for the weekend to celebrate her 16th birthday and the accommodations were perfect! 10/10 would highly recommend."
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, (18)
"Great location, nice house , very clean , easy to deal with "
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, (16)
"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)
"Our stay in Anna Maria, FL, was nothing short of spectacular! The crystal-clear, calm waters made for some of the best swimming we’ve ever experienced. The beach was pristine, with gentle waves and soft, powdery sand, making it perfect for both kids and adults. We felt completely safe and relaxed every time we stepped into the water.The house itself was an absolute dream! From the moment we walked in, we were blown away by the gorgeous Gulf views, luxurious furnishings, and top-of-the-line...
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, (191)
"Simon and his family have a beautiful well-kept home and it was perfect for our long wedding weekend because of the location and outdoor entertaining area. We rented this home for our family traveling in for the wedding and hosted our rehearsal here for our wedding party. When I had concerns Simon was very responsive and unfortunately had to rely on others to address them since he is not local which was not always successful (i.e. the broken grill and outdoor fridge used for outdoor...
OPEN for booking after Helene & Milton! for 2025 limited dates available NOW!!

Bay Breeze Cottages #3

9.8 out of 10, Exceptional, (110)
"Very nice little place with a great pool and even better location. Will definitely be booking again in the future. "
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)
"The interior was all new. Furnishings, decor, kitchen supplies, and everything fresh and tastefully done. Quiet neighborhood just a couple blocks from beach. Exterior privacy will improve as landscape recovers. Parking and access easy. "
Sandy Cheeks: Ground-level home with plunge pool. Close to pier, park, & Bay!

Adorable Beach cottage just steps Bean Point beach!

9.8 out of 10, Exceptional, (53)
"Our family of 6enjoyed our stay!"
The price is SAR 1,346
SAR 3,517 total
includes taxes & fees
29 Apr - 30 Apr
Adorable Beach cottage just steps Bean Point beach!

Anna Maria Home with Saltwater Pool Near Beaches & Shopping - Sunrise Shore

9.4 out of 10, Exceptional, (47)
"We really enjoyed our stay. The location was perfect to walk to the beach or to walk to shops and restaurants. Very clean with comfortable beds. "
Anna Maria Home with Saltwater Pool Near Beaches & Shopping - Sunrise Shore
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.