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Compare 852 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 AED 1,561
AED 3,121 total
includes taxes & fees
1 Apr - 2 Apr
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, (41)
"Great location, well kept, clean, beds/mattresses were awesome. Supplies provided (towels for kitchen, bathroom, beach, paper towel, kitchen, laundry, bath soaps) were perfect for the two of us. Kitchen was well stocked with dishes & utensils. Definitely planning on renting again. "
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, (41)
"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)
"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, (112)
"We were the 1st guests after the hurricane and Jenny the owner did an amazing job. The place is off the beaten path of all the people which was wonderful! The island is a must stay at for a beautiful vacation. We willbeback"
The price is AED 1,282
AED 2,621 total
includes taxes & fees
22 Apr - 23 Apr
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, (60)
"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

8.6 out of 10, Excellent, (14)
"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, (110)
"Great location. Great stay, love the front porch excellent communication. Already missing it can’t wait return "
Escape to an island adventure!

The TipSea Turtle managed by Beach Retreats FL Anna Maria Island

10.0 out of 10, Exceptional, (15)
"A few of us missed connecting flights thanks to “ Tropical storm/ Hurricane Debby” but once we arrived it made all the travel stress worth it. Beautiful home, kids loved the pool and the beach was amazing. This might be our new annual family destination. "
The TipSea Turtle managed by Beach Retreats FL Anna Maria Island

Golf Cart, Stonehenge by SeaBreeze Vacation

10.0 out of 10, Exceptional, (17)
"We came stayed at Stonehenge over Spring vacation and enjoyed every minute here. The layout was perfect for family time, cooking together, big dinners and watching movies together. My husband and I enjoyed the den when we wanted a little quiet time to end the day together. It was a great combination of plenty of privacy and also a great family area. Location for us was perfect. Quiet neighborhood but just minutes from the most beautiful beach. We walked there in 5 minutes. Also, just blocks from...
Golf Cart, Stonehenge by SeaBreeze Vacation

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!"
BEACHFRONT, PRIVATE BEACH ON THE WATERFRONT, Bring your dog

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

10.0 out of 10, Exceptional, (213)
"Our family loved our stay in this sweet costal cottage! The home was so inviting, warm and comfortable! We had front row seats to the most AMAZING sunsets EVERY evening! The weather was not as warm and friendly as we had hoped but being right on the beach gave us every opportunity to grab some beach time whenever possible! We would love to stay here again and highly recommend this coastal cottage to all beach lovers!! "
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, (17)
"We loved this house. Very clean. Close to the beach. Will definitely stay there again."
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! December and Jan dates available NOW!!

9.8 out of 10, Exceptional, (189)
"We have stayed on Anna Maria yearly for the past 6 years and this house has truly been on of the most family friendly. There was plenty of space for all to sleep. The game room kept everyone in good spirits rain or shine or wind. It was such an easy walk out to the beach. This was the best stocked property I have stayed with tissues. Toiletries, a welcome basket, toys, bikes, beach and pool toys! We had a wonderful time. "
OPEN for booking after Helene & Milton! December and Jan dates available NOW!!

Bay Breeze Cottages #3

9.8 out of 10, Exceptional, (106)
"The cottage was very nicely decorated, had a heated pool which the kids loved, and was a very short walk to Bean point. "
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, (49)
"Enjoyed our stay very much, Cannot wait to go back!!"
The price is AED 2,120
AED 4,594 total
includes taxes & fees
6 Apr - 7 Apr
Adorable Beach cottage just steps Bean Point beach!

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 AED 1,561
AED 3,121 total
includes taxes & fees
1 Apr - 2 Apr
Waterfront dog-friendly home with heated private pool, dock, views, and lanai
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.