Anna Maria Vacation Homes

A marina with boats, a bridge, and high-rise buildings.

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Our top choices for Anna Maria holiday homes

The Hideaway - Less than a block from beach!

Anna Maria

JASON G.

Seaside Magnolia~1 Block to Pine Ave, Heated Pool!

Anna Maria

Aaron Z.

HK$14,443 total

includes taxes & fees

12 Jul - 13 Jul

Coast is Clear! Heated pool/spa~Close to shops

Anna Maria

HK$8,580 total

includes taxes & fees

12 Jul - 13 Jul

3 bedrooms, iron/ironing board, WiFi, bed sheets

Coconut Cottage~Private Heated Pool~Block to shops

Anna Maria

Jenny R.

HK$9,285 total

includes taxes & fees

12 Jul - 13 Jul

Mermaid’s Purse~Private Pool! 40 steps to beach!

Anna Maria

Magen S.

HK$14,904 total

includes taxes & fees

8 Aug - 9 Aug

Birdsong-Steps to Bean Point Beach Heated Pool!

Anna Maria

Aaron C.

HK$6,533 total

includes taxes & fees

26 Jul - 27 Jul

Flirty Flamingo Cottage Updated beach cottage, moments from the sand, w/pool!

Anna Maria

Kimberly R.

Private, Remodeled Home with Pool! 1 Block to Beach, Great for Families!

Anna Maria

Wilson

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Top Anna Maria Hotel Reviews

Newly Renovated w/Heated Pool/Spa/Bistro, Stunning Views, Minutes from the Beach

10/10 Excellent

"Wonderful stay! Clean home, awesome location, easy communication. Home was well stocked and we used the golf carts to get around every day! Beautiful backyard/pool and comfortable beds. Perfect place for our large group of 16. Highly recommend!"

Bean Point Bungalow! Pet Friendly Home with Pool and Walk to Beach

10/10 Excellent

"This beach house was the perfect family getaway. From the moment we walked in, everything felt fresh, spotless, and brand new, from the kitchen appliances to the beautifully kept rooms. The AC was cold, the master bedroom shower felt like a little luxury after a day in the sun, and the kids had plenty of space to settle in and enjoy themselves.The location could not have been better. The beach is literally right across the street, so our days were spent bouncing between the sand, the surf, and the backyard pool. The house also had great beach supplies, which made everything easy and stress-free. By day, it was perfect for relaxing by the pool or heading straight to the beach. By evening, it was just a short stroll to catch the sunset along the water.For a family of four or five, this place is a gem: clean, comfortable, beautifully maintained, and perfectly located for a relaxing beach escape."

JUNE, JULY SPECIALS ,BEACHFRONT, PRIVATE BEACH ON THE WATERFRONT, Bring your Dog

10/10 Excellent

"Great location walking distance to AMI pier. Excellent restaurants and ice cream shop also within walking distance. Home was clean and excellent for large families. Generous on site parking.Private beach right behind the house. Host was very friendly and helpful."

Naut 2 Shabby Bungalow - A sweet and cozy getaway on Pine Avenue!

8/10 Good

"The way the property is presented on-line you believe is a shared unit and it includes access to the pool and wash and dyer. You do not have access to the pool. It also miss leads you about parking and does not tell you that you must walk down a narrow path, that your suitcase will not easily fit down to get to the unit. Because I am a landlord myself, I read the lease cover to cover and it does not state anything about the pool usage. I was very disappointed in this portion of our rental."

Luxury Home with Pool, Rooftop Deck, and Gulf Views! 1.5 Blocks to Beach

10/10 Excellent

"We had an absolutely fantastic stay! The property exceeded our expectations in every way. The home was spotless, spacious, and beautifully maintained, with plenty of room for our entire group to relax and enjoy ourselves. The pool was a huge hit and quickly became everyone’s favorite spot.The location was perfect—close to restaurants, shops, and everything we needed, while still feeling private and peaceful. The host was incredibly responsive, helpful, and made the entire experience seamless from check-in to check-out.Every detail seemed thoughtfully considered, and it truly felt like a home away from home. We created amazing family memories here and would not hesitate to stay again. Highly recommend this property to anyone looking for a relaxing, comfortable, and memorable getaway. Five stars all around! "

Mermaid Cove: Updated Forida Cottage w/pool, hot tub

10/10 Excellent

"This home was absolutely amazing! The location was perfect, close to shopping, restaurants and the ocean. The pool was big with lots of room for the whole family. We walked for ice cream every evening as there are several ice cream shops really close to the house. The kids walked to the coffee shops every morning as they were close to the house too. The home was clean upon arrival and had everything we needed. Our family had the best vacation on Anna Maria Island! We will be back and stay here again!!"

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