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Check prices for these dates

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14 Saf. - 16 Saf.
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Compare 717 Vacation Homes in Anna Maria with updated reviews, rates, and availability.

The Wee Cottage | House in Anna Maria

The Wee Cottage | House in Anna Maria

8.4 out of 10, Very Good, (12)
"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-
Terrace/patio

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

9.8 out of 10, Exceptional, (78)
"We walked into the space and gasped at how beautiful it was! Everything (sadly because of hurricane helenne) was brand new. Such tasteful furnishings and touches! The two bedrooms were both spacious. The kitchen had everything, including a great coffee maker. For a small beach house, it felt spacious! A back porch and a beautiful yard. And the pool was much larger than we could have imagined! Hosts were totally attentive, but we didn’t need anything because they thought of everything! Definitely...
Beachy Boathouse Cottage, 2 BR,1BA, Private Pool, Steps to Beach and Bay-
Private Home 1 Block to Beach with Pool and Hot Tub!
Beach You To It by Anna Maria Island Accommodations

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!

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!
Upscale waterfront home, private pool, beautiful views!
Canal Front Home

Upscale waterfront home, private pool, beautiful views!

10.0 out of 10, Exceptional, (29)
"This property was beautiful and well laid out for our needs. It was located in the perfect spot for what we wanted. The dock and pool being so close let the guys enjoy fishing while being able to watch the kids enjoy the heated pool! The use of the elevator was a huge bonus for my dad since he has trouble with all the stairs. We will definitely be back! Thank you so much!"
Upscale waterfront home, private pool, beautiful views!
The Sunset Place- Unbeatable location. Gorgeous Sunsets. Updated Coastal Gem
Look how close to the beach!

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!!
Front Castaway Cove Jacaranda Rd Anna Maria

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

9.6 out of 10, Exceptional, (183)
"Spacious and well equipped house. Great location!"
OPEN for booking after Helene & Milton! December and Jan dates available NOW!!
Spacious beach house with a beautiful view of the gulf
Exterior

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

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!
Coastal Couture by AMI Locals

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!
Pool and Yard at twilight

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

The 19th Hole | Luxury AMI Beach Home - Private Pool & Spa, 7 Hole Putting Green!
Isle Relax: Close to Gulf of Mexico and Pine Ave.

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

9.4 out of 10, Exceptional, (23)
"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

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
Honeywood House - AMI Accommodations

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
JAN. SPECIALS Beachfront, PRIVATE BEACH ON THE WATERFRONT, Bring your dog
Rear of home from the edge of the water

JAN. SPECIALS Beachfront, PRIVATE BEACH ON THE WATERFRONT, Bring your dog

9.6 out of 10, Exceptional, (173)
"We loved this beachfront property, it was perfect for our family. The layout was nice, we had space for privacy and togetherness. The views were spectacular from the porch we got to see the sunrise and sunsets. The house is located in an upscale neighborhood within walking distance to Motte Marina. The kitchen had everything you might need to cook, also provided were linens and towels, as well as beach chairs. We hope to return soon."
JAN. SPECIALS Beachfront, PRIVATE BEACH ON THE WATERFRONT, Bring your dog
Bay -Canal Waterfront! Tiki Bar 5BR, 5BA Huge Pool, 2 Kayaks/Bikes Sleeps 16
Best Location! Water Views From Everywhere! Canal Fishing! Night Fishing! Best Views of Skyway Freeway Bridge at Night! Huge Pool.

Bay -Canal Waterfront! Tiki Bar 5BR, 5BA Huge Pool, 2 Kayaks/Bikes Sleeps 16

9.8 out of 10, Exceptional, (105)
"We had a wonderful time! This is a great location and Carolyn was an excellent host."
Bay -Canal Waterfront! Tiki Bar 5BR, 5BA Huge Pool, 2 Kayaks/Bikes Sleeps 16
Felicity: Luxury Bayfront Home, Heated Pool, Hot tub and more!

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.

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

BeachFront 4/3/ Amazing Views plus hot tub

9.4 out of 10, Exceptional, (24)
"This property and the owner/managers we communicated with were excellent. Be aware there is no direct beach access, but you do have a small sand beach area private to the house. Access to the beach is a short drive away. The listing states a golf cart is included, but note that this is dependent on length of stay and isn’t a given. As of writing this, you wouldn’t know differentlg, and I ended Up getting stuck with 500 in rental fees for a golf cart. I booked Because of all of the amenities for...
BeachFront 4/3/ Amazing Views plus hot tub
AMI Retreat: 200 Steps to Beach, Dog Friendly Pool Home by Anna Maria Life Vacation Rentals

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
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

The Wee Cottage | House in Anna Maria

The Wee Cottage | House in Anna Maria

8.4 out of 10, Very Good, (12)
"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-
Terrace/patio

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

9.8 out of 10, Exceptional, (78)
"We walked into the space and gasped at how beautiful it was! Everything (sadly because of hurricane helenne) was brand new. Such tasteful furnishings and touches! The two bedrooms were both spacious. The kitchen had everything, including a great coffee maker. For a small beach house, it felt spacious! A back porch and a beautiful yard. And the pool was much larger than we could have imagined! Hosts were totally attentive, but we didn’t need anything because they thought of everything! Definitely...
Beachy Boathouse Cottage, 2 BR,1BA, Private Pool, Steps to Beach and Bay-
Sandy Cheeks: Ground-level home with plunge pool. Close to pier, park, & Bay!

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!
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.