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Compare 717 Vacation Homes in Anna Maria with updated reviews, rates, and availability.

The Wee Cottage | House in Anna Maria

8.6 out of 10, Excellent, (13)
"Found a little piece of paradise"
The Wee Cottage | House in Anna Maria

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

9.8 out of 10, Exceptional, (79)
"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-

Private Home 1 Block to Beach with Pool and Hot Tub!

9.8 out of 10, Exceptional, (39)
"House was great. Fantastic location, easy to beach, easy walk to the north end shops/restaurants. Pool was awesome. Hot tub was great especially with cooler weather!Amenities at the house are well stocked (eg. pans, utensils, coffee maker (Dual filter and Keurig!).Host is very responsive. Check in was easy."
Private Home 1 Block to Beach with Pool and Hot Tub!

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

9.4 out of 10, Exceptional, (9)
"House is just as pictured, beautiful and great location. Pool is small but perfect size for a few people to cool off in. Walking distance from the bay side and rod and reel pier. Highly recommend staying here!"
Sandy Cheeks: Ground-level home with plunge pool. Close to pier, park, & Bay!

The Sunset Place- Unbeatable location. Gorgeous Sunsets. Updated Coastal Gem

9.8 out of 10, Exceptional, (26)
"There's something for everyone at this home--steps to the beach, ping pong, pool table, resting on a hammock, sitting on the screened in porch or enjoying views from the spacious kitchen and living area. "
The Sunset Place- Unbeatable location. Gorgeous Sunsets. Updated Coastal Gem

OPEN for booking after Helene & Milton! December and Jan dates available NOW!!

9.6 out of 10, Exceptional, (185)
"SimonWe had a great time on AMLI and staying at your place. Accomodations were great . Loved the pool , games , beach chairs etc. Beach was so convenient and used it every day plus sunsets. The island made a great recovery. Everything was wonderful. Will definitely recommend your place to others."
OPEN for booking after Helene & Milton! December and Jan dates available NOW!!

Spacious beach house with a beautiful view of the gulf

9.8 out of 10, Exceptional, (69)
"I had the best time at A.M.I. everything was great. Will definitely come back next year."
Spacious beach house with a beautiful view of the gulf

Dog-friendly home with amazing backyard, pool, spa, putting green & game room

9.0 out of 10, Wonderful, (16)
"Very nice walkable neighborhood. Walk to beach and restaurants. "
Dog-friendly home with amazing backyard, pool, spa, putting green & game room

Pathway to the Beach! Secluded Pool and Spa!

10.0 out of 10, Exceptional, (2)
"We loved the house! Neighborhood was quiet and the beach was a very short distance away. The house is surrounded by vegetation and it had everything we needed it!"
Pathway to the Beach! Secluded Pool and Spa!

The 19th Hole | Luxury AMI Beach Home - Private Pool & Spa, 7 Hole Putting Green!

10.0 out of 10, Exceptional, (1)
The 19th Hole | Luxury AMI Beach Home - Private Pool & Spa, 7 Hole Putting Green!

Isle Relax: Close to Gulf of Mexico and Pine Ave.

9.4 out of 10, Exceptional, (24)
"The location was perfect! (would book again for the location alone) The neighborhood is nice. The pool and yard are the perfect size and although the neighbors are close, the landscaping makes it so quiet and private. The house is perfectly laid out and clean. The screened-in porch was great, we finished out every night just sitting out there listening to the breeze. The wagon and chairs for the beach were game-changers! Would definitely stay here again. If you are thinking you might want a golf...
Isle Relax: Close to Gulf of Mexico and Pine Ave.

Sandy Rose: Putting green, heated pool, outdoor living spaces

10.0 out of 10, Exceptional, (4)
"Beautiful home on a beautiful Island. We had an issue with a door alarm which was taken care of immediately by management. Top floor master bedroom took over 24 hours to cool down but was pleasant after that."
Sandy Rose: Putting green, heated pool, outdoor living spaces

Canal front with Dock and Pool -Honeywood House

9.2 out of 10, Wonderful, (9)
"We enjoyed our stay. The pool alarms were a bit cumbersome. We didn't need them. The kitchen is not open to the living space. The mattresses need to be changed, especially in the twin/trundle. Otherwise, it was very peaceful, and we enjoyed access to the canal and lounging in the pool!! "
Canal front with Dock and Pool -Honeywood House

BEACHFRONT, PRIVATE BEACH ON THE WATERFRONT, Bring your dog

9.6 out of 10, Exceptional, (174)
"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

Pet Friendly Bay-Canal Waterfront! Tiki Bar 5BR, 5BA Huge Pool, 2 Kayaks/Bikes

9.8 out of 10, Exceptional, (106)
"The property was great! The kids loved the pool and did not qant to leave. We had a great time. "
Pet Friendly Bay-Canal Waterfront! Tiki Bar 5BR, 5BA Huge Pool, 2 Kayaks/Bikes

Felicity: Luxury Bayfront Home, Heated Pool, Hot tub and more!

10.0 out of 10, Exceptional, (38)
"This house is so beautiful and has the most beautiful view. Everything you need is in the house to make a wonderful vacation with family. We cooked in most nights because the kitchen is so great and the house is so relaxing. We have rented this house two years in a row. Sad that we can't rent next year but the price is going up $3000!"
Felicity: Luxury Bayfront Home, Heated Pool, Hot tub and more!

Sharks Eye- Original island cottage on historic Pine Ave.

9.8 out of 10, Exceptional, (21)
"I would love to live there! "
Sharks Eye- Original island cottage on historic Pine Ave.

BeachFront 4/3/ Amazing Views plus hot tub

9.4 out of 10, Exceptional, (24)
"Absolutely best AMI location. Right on the beach and steps from miles of the best walking beach I’ve encountered. We did not want to leave this home with its 180 degree view out the wall of windows. Just imagine waking each morning to pelicans soaring and diving. It’s an exquisite natural wonderland. We enjoyed making meals in the well equipped kitchen and found the beds to be super comfy. The owners were completely available for any and all assistance. This was a great place for us to relax...
BeachFront 4/3/ Amazing Views plus hot tub

AMI Retreat: 200 Steps to Beach, Dog Friendly Pool Home by Anna Maria Life Vacation Rentals

8.8 out of 10, Excellent, (28)
"We picked this home because it had many things for kids to do,was assured by asking many times if the pool was going to be working by email we were told the pool was going to be working for our stay nov23-dec5 pool was not in working order,very cloudy asked if it was safe to swim in was told yes pump was not working had someone out to fix that daily heater was not working had been replaced 5 days into our stay,4 of the people got chemical burns from the water,I would of rather them tell me I’m...
AMI Retreat: 200 Steps to Beach, Dog Friendly Pool Home by Anna Maria Life Vacation Rentals

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
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

Charming cottage in quiet area, close to beach & bay.

9.8 out of 10, Exceptional, (254)
"Always wonder what the placees lookes like veerry small but cute places . My only sugggestion, whhsjcj make at mosdtcprlces ie stay is a ccoi"
Charming cottage in quiet area, close to beach & bay.

The Wee Cottage | House in Anna Maria

8.6 out of 10, Excellent, (13)
"Found a little piece of paradise"
The Wee Cottage | House in Anna Maria

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!!"
Adorable Beach cottage just steps Bean Point beach!
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.