Search Vacation Homes in Anna Maria

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Compare 728 Vacation Homes in Anna Maria with updated reviews, rates, and availability.

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

Naut 2 Shabby Cottage Next-Level Pool Area, Darling FL Cottage - Best of Both!

9.8 out of 10, Exceptional, (68)
"We stopped in Anna Maria Island for three days on our road trip visiting Florida beaches. We loved Anna Maria Island. The Naut 2 Shabby Cottage was the perfect location for exploring the island. We loved the quaint charm of the cottage. "
Naut 2 Shabby Cottage Next-Level Pool Area, Darling FL Cottage - Best of Both!

Waterfront home with beautiful views

8.8 out of 10, Excellent, (23)
"Great location. Property smelled like cat urine but we understand that this is a pet friendly location. We bought new plugins to manage the smell. A few ants in the kitchen but mostly clean. Shower curtain needs to be replaced in guest bathroom (moldy). The lock was tricky but we replaced the batteries after calling help desk. Overall, we would recommend to others."
Waterfront home with beautiful views

The TipSea Turtle managed by Beach Retreats

10.0 out of 10, Exceptional, (15)
"A few of us missed connecting flights thanks to ā€œ Tropical storm/ Hurricane Debbyā€ 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

AMI Retreat: No Storm Damage! Pool Open! 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 Iā€™m...
AMI Retreat: No Storm Damage! Pool Open! by Anna Maria Life Vacation Rentals

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.

Once Upon A Tide managed by Beach Retreats

10.0 out of 10, Exceptional, (6)
"We had a two family stay at this home and it was very well stocked with kitchen items and beach accessories. Pool was wonderful and great location on the island!"
Once Upon A Tide managed by Beach Retreats

Aloha Beaches! Newly Renovated 4 Bedroom 3 Bath Home w/ Private Pool!

10.0 out of 10, Exceptional, (21)
"A great place for a quick trip with friends!! Well equipped for eating in. Everything you need for the beach"
Aloha Beaches! Newly Renovated 4 Bedroom 3 Bath Home w/ Private Pool!

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

9.6 out of 10, Exceptional, (15)
"Very nice walkable neighborhood. Walk to beach and restaurants. "
Dog-friendly home with amazing backyard, pool, spa, putting green & game room

*NEW LISTING* Boutique Spanish-Style Villa - perfect for family/couple getaway

10.0 out of 10, Exceptional, (18)
"Nice residential part of AMI. Fantastic job on the remodeling both inside (especially) and out. Very comfortable for the four of us adults. I imagine kids would really like the "Surf Room" addition. Host was very responsive to the couple of questions we had. Great place to idle away some Island Time. Would return."
*NEW LISTING* Boutique Spanish-Style Villa - perfect for family/couple getaway

"La Casita" Beautiful, Elegant Florida Cottage, 1 Minute Walk to the Beach!

9.6 out of 10, Exceptional, (33)
"Great house with a quick walk to the beach. It was perfect for our weekend getaway. The house was very clean and came with beach accessories which made for relaxing days on the sand. "
"La Casita" Beautiful, Elegant Florida Cottage, 1 Minute Walk to the Beach!

Tropical Island Sea-Cret. Now Remodeled. New floors and paint. New pictures.

9.8 out of 10, Exceptional, (37)
"Property is beautiful with an amazing view of the bay! My children LOVED the pool and hot tub! So quiet and peaceful and very relaxing and just minutes from the best beaches! Will definitely be back!"
Tropical Island Sea-Cret. Now Remodeled. New floors and paint. New pictures.

Canalfront Anna Maria Cottage w/ Pool & Hot Tub!

9.8 out of 10, Exceptional, (72)
"House was very clean and within walking distance from the local shops and restaurants. Kids love the pool and walking to the beach."
Canalfront Anna Maria Cottage w/ Pool & Hot Tub!

Pier Pleasure - Anna Maria at it's finest! Pool, hot tub, beach, putting green

10.0 out of 10, Exceptional, (4)
"This is an amazing home right across from the beach! We loved the architectural design and the floor to ceiling windows. This home is beautifully decorated and many places to hang out and socialize. The house was impeccably clean and incredibly spacious. The kitchen is definitely a chefs dream! The kitchen is stocked with everything that you need. The pool was perfect for gathering after spending the day at the beach! It gives plenty of shade to give you a break from the sun. The beach...
Pier Pleasure - Anna Maria at it's finest! Pool, hot tub, beach, putting green

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!

Steps away to beaches and the Gulf, snowbird friendly, AC, free WIFI and parking

2.0 star property
Steps away to beaches and the Gulf, snowbird friendly, AC, free WIFI and parking

Fun in the Sun šŸ˜Ž | Gulf front, steps to the sand, 4-bed with spectacular views!

9.2 out of 10, Wonderful, (20)
"This is an awesome house. A blend of remodeled with modern amenities and old Florida style, especially in the upper level. Beds were comfy. The views from the large windows in the upstairs bedroom and the downstairs living room are amazing! Walk out your door and across a tiny, sparsely trafficked street, and you are on the beach! Would definitely stay here again!"
Fun in the Sun šŸ˜Ž | Gulf front, steps to the sand, 4-bed with spectacular views!

Anna Maria Guest House 401- 3 bedrooms in the middle of everything

10.0 out of 10, Exceptional, (15)
"The property was just as described. Location was great, walking distance to the beautiful beach. Loved the high ceilings in the unit. Only recommendation I would make is to put lights on the front deck as we wouldā€™ve love to stay out however it was too dark. Great place to stay to enjoy Anna Maria Island."
Anna Maria Guest House 401- 3 bedrooms in the middle of everything

Near Bean Point!! Short stays available! Heated Pool

9.4 out of 10, Exceptional, (38)
"Great location, walking distance to beach. Quiet and relaxing. "
Near Bean Point!! Short stays available! Heated Pool

Waterfront home near beaches with private heated pool, spa, and more

9.4 out of 10, Exceptional, (66)
"The location and lay of the house was very nice and quiet. "
Waterfront home near beaches with private heated pool, spa, and more
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

Canalfront Anna Maria Cottage w/ Pool & Hot Tub!

9.8 out of 10, Exceptional, (72)
"House was very clean and within walking distance from the local shops and restaurants. Kids love the pool and walking to the beach."
Canalfront Anna Maria Cottage w/ Pool & Hot Tub!

Stylish bayside condo with WiFi & pool - close to the beach & restaurants

9.6 out of 10, Exceptional, (88)
"Couple small items need maintenance but otherwise up to date, modern and met our needs"
Stylish bayside condo with WiFi & pool - close to the beach & restaurants

180-degree water views! Shared pool and laundry - Bay Vista at Bayside Bungalow

9.6 out of 10, Exceptional, (89)
"The property is just as described! It was incredible. The beach and stores were all walking distance. Definitely would stay there again."
The price is SARĀ 1,641
SARĀ 3,755 total
includes taxes & fees
14 Jan - 15 January 2025
180-degree water views! Shared pool and laundry - Bay Vista at Bayside Bungalow
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.