Anna Maria, Florida

Vacation Rentals in Anna Maria, Florida

Discover 386 vacation rental properties in Anna Maria. From 1 to 7 bedrooms. Average $445/night. 100% have pools.

386 verified listings Book securely on VRBO Prices updated March 2026

386 properties available

Newly Renovated Vintage AMI Cottage. Heated Pool! North End! 2 Blocks to Beach!

Newly Renovated Vintage AMI Cottage. Heated Pool! North End! 2 Blocks to Beach!

2 beds 1 bath
PoolA/CWiFiBalcony
$300/night
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"Walk On The Beach " house~3 bed, heated pool, 3min walk to the Bean Point Beach

"Walk On The Beach " house~3 bed, heated pool, 3min walk to the Bean Point Beach

3 beds 2 baths
PoolA/CWiFiBalcony
$540/night
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Charming Beach Home-w/large Pool - Only 3 Houses from the Beach, Near Pine Ave!!

Charming Beach Home-w/large Pool - Only 3 Houses from the Beach, Near Pine Ave!!

4 beds 2 baths
PoolA/CWiFiBalcony
$476/night
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Sea Spray 3: *Steps to the beach *Close to shops, restaurants *Quiet street

Sea Spray 3: *Steps to the beach *Close to shops, restaurants *Quiet street

2 beds 1 bath
PoolA/CWiFiBalcony
$204/night
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Upscale waterfront home, private pool, beautiful views!

Upscale waterfront home, private pool, beautiful views!

4 beds 3 baths
PoolA/CWiFiBalcony
$570/night
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Incredible Beach Condo w/Free WiFi, TV, Shared Pool and Washer/Dryer

Incredible Beach Condo w/Free WiFi, TV, Shared Pool and Washer/Dryer

1 bed 1 bath
PoolA/CWiFiBalcony
$203/night
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New Home with Pool, Spa, and Rooftop Deck Views!

New Home with Pool, Spa, and Rooftop Deck Views!

4 beds 4 baths
PoolA/CWiFiBalcony
$660/night
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Canal Home with Private Pool and Dock - North End Zen

Canal Home with Private Pool and Dock - North End Zen

3 beds 3 baths
PoolA/CWiFiBalcony
$361/night
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Banyan Beach: Steps to Beach, Pool, Game Room, Putting Green

Banyan Beach: Steps to Beach, Pool, Game Room, Putting Green

5 beds 3 baths
PoolA/CWiFiBalcony
$921/night
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Beautiful Bay Front Home with Panoramic Views and Open Balcony!

Beautiful Bay Front Home with Panoramic Views and Open Balcony!

3 beds 2 baths
PoolA/CWiFiBalcony
$282/night
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Waterfront dog-friendly home with heated private pool, dock, views, and lanai

Waterfront dog-friendly home with heated private pool, dock, views, and lanai

3 beds 3 baths
PoolA/CWiFiBalcony
$428/night
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Hawaiian Punch -3 Blocks to Beach, Pool, Dock on Canal, Dog Friendly by Anna Maria Life

Hawaiian Punch -3 Blocks to Beach, Pool, Dock on Canal, Dog Friendly by Anna Maria Life

4 beds 2 baths
PoolA/CWiFiBalcony
$456/night
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Bikini Bottom: One Block to Pine,3 Blocks to Beach, Dog Friendly, Pool, by Anna Maria Life

Bikini Bottom: One Block to Pine,3 Blocks to Beach, Dog Friendly, Pool, by Anna Maria Life

4 beds 4 baths
PoolA/CWiFiBalcony
$1,011/night
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Sea Mist by Beach Boutique Rentals

Sea Mist by Beach Boutique Rentals

3 beds 2 baths
PoolA/CWiFiBalcony
$442/night
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Private Home with Heated Pool, Only 3 Blocks to Bean Point

Private Home with Heated Pool, Only 3 Blocks to Bean Point

3 beds 2 baths
PoolA/CWiFiBalcony
$260/night
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Island Oasis: Ground level canal front pool home

Island Oasis: Ground level canal front pool home

2 beds 2 baths
PoolA/CWiFiBalcony
$318/night
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Tucked Away in Anna Maria

Tucked Away in Anna Maria

3 beds 2 baths
PoolA/CWiFiBalcony
$452/night
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Colorful beach cottage w/ heated private pool & grill area - dog-friendly

Colorful beach cottage w/ heated private pool & grill area - dog-friendly

2 beds 2 baths
PoolA/CWiFiBalcony
$530/night
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Exclusive North End of AMI One Level Saltwater Heated Pool Canal Front Boat Dock

Exclusive North End of AMI One Level Saltwater Heated Pool Canal Front Boat Dock

3 beds 3 baths
PoolA/CWiFiBalcony
$602/night
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Beachology: 1 Block to Bean Point Beach, Pool, Game Room by Anna Maria Life Vacation Rentals

Beachology: 1 Block to Bean Point Beach, Pool, Game Room by Anna Maria Life Vacation Rentals

5 beds 3 baths
PoolA/CWiFiBalcony
$672/night
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Charming Bungalow with Fabulous Location and Private Pool!

Charming Bungalow with Fabulous Location and Private Pool!

2 beds 2 baths
PoolA/CWiFiBalcony
$386/night
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Sirenia Cove - Canal /Hot Tub/Htd Pool/ Dock/Backyard Beach - prime location

Sirenia Cove - Canal /Hot Tub/Htd Pool/ Dock/Backyard Beach - prime location

4 beds 3 baths
PoolA/CWiFiBalcony
$385/night
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BEAUTIFUL DIRECT BAY FRONT, Steps to Village, FREE WiFi/Trolley, Dog*(See...

BEAUTIFUL DIRECT BAY FRONT, Steps to Village, FREE WiFi/Trolley, Dog*(See...

3 beds 2 baths
PoolA/CWiFiBalcony
$324/night
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Lazy Lagoon: On Canal, Pool, Boat Dock, 2 blocks to Beach by Anna Maria Life Vacation Rentals

Lazy Lagoon: On Canal, Pool, Boat Dock, 2 blocks to Beach by Anna Maria Life Vacation Rentals

4 beds 3 baths
PoolA/CWiFiBalcony
$716/night
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Stunning 5 bedroom Luxury home, Pool and Spa, Rooftop Deck beach VIEWS!

Stunning 5 bedroom Luxury home, Pool and Spa, Rooftop Deck beach VIEWS!

5 beds 4 baths
PoolA/CWiFiBalcony
$657/night
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Bimini Bay Breeze: Canal Front | Close to Beach and Pine St. | Pool/Spa |

Bimini Bay Breeze: Canal Front | Close to Beach and Pine St. | Pool/Spa |

4 beds 3 baths
PoolA/CWiFiBalcony
$838/night
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Canal Front Home with Private Pool and Spa, 2 Blocks to Beach!

Canal Front Home with Private Pool and Spa, 2 Blocks to Beach!

3 beds 3 baths
PoolA/CWiFiBalcony
$370/night
View Details → Book on VRBO
Beautiful, well-maintained home w/ heated private pool - walk to beach & dining

Beautiful, well-maintained home w/ heated private pool - walk to beach & dining

3 beds 2 baths
PoolA/CWiFiBalcony
$829/night
View Details → Book on VRBO
Sea Spray 5: *Heated Pool *Steps to beach *Close to shops and dining

Sea Spray 5: *Heated Pool *Steps to beach *Close to shops and dining

3 beds 2 baths
PoolA/CWiFiBalcony
$371/night
View Details → Book on VRBO
New Home Steps from the Beach! Walk to Bean Point! Pool/spa! Golf Cart!!

New Home Steps from the Beach! Walk to Bean Point! Pool/spa! Golf Cart!!

4 beds 4 baths
PoolA/CWiFiBalcony
$1,398/night
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Bean Point Bliss: Pool Spa Putting Green

Bean Point Bliss: Pool Spa Putting Green

4 beds 4 baths
PoolA/CWiFiBalcony
$669/night
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North end canal front home ,tiki hut, dock, heated pool, spa,beaches....

North end canal front home ,tiki hut, dock, heated pool, spa,beaches....

3 beds 2 baths
PoolA/CWiFiBalcony
$649/night
View Details → Book on VRBO
Stunning Canal front Luxury home! Beautiful tropical backyard Pool and Spa!

Stunning Canal front Luxury home! Beautiful tropical backyard Pool and Spa!

4 beds 3 baths
PoolA/CWiFiBalcony
$555/night
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707 N Bay The Shell House

707 N Bay The Shell House

3 beds 2 baths
PoolA/CWiFiBalcony
$396/night
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Coconut Hut: Pool & Spa, Pool Table, Putting Green by Anna Maria Life Vacation Rentals

Coconut Hut: Pool & Spa, Pool Table, Putting Green by Anna Maria Life Vacation Rentals

3 beds 3 baths
PoolA/CWiFiBalcony
$605/night
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Beach Don't Kill My Vibe by Beach Boutique Rentals

Beach Don't Kill My Vibe by Beach Boutique Rentals

2 beds 1 bath
PoolA/CWiFiBalcony
$362/night
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Summer Strand: Resort like pool, close to beach, kayak w/ manatees, Rooftop Deck

Summer Strand: Resort like pool, close to beach, kayak w/ manatees, Rooftop Deck

4 beds 4 baths
PoolA/CWiFiBalcony
$1,175/night
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Willow Cottage: 3 BR, 2 BA House in Anna Maria, Sleeps 8

Willow Cottage: 3 BR, 2 BA House in Anna Maria, Sleeps 8

3 beds 2 baths
PoolA/CWiFiBalcony
$438/night
View Details → Book on VRBO
New Luxury-Professionally Decorated Home Pool/Spa 5 Minutes walk to beach

New Luxury-Professionally Decorated Home Pool/Spa 5 Minutes walk to beach

3 beds 3 baths
PoolA/CWiFiBalcony
$568/night
View Details → Book on VRBO
🏝AMI’s local LANDMARK🏖The BLUE HOUSE on PINE 🐬Casa Calienta🐬

🏝AMI’s local LANDMARK🏖The BLUE HOUSE on PINE 🐬Casa Calienta🐬

2 beds 2 baths
PoolA/CWiFiBalcony
$525/night
View Details → Book on VRBO
Charming Canal front Luxury home with brand-new Pool!

Charming Canal front Luxury home with brand-new Pool!

2 beds 2 baths
PoolA/CWiFiBalcony
$315/night
View Details → Book on VRBO
Direct Beachfront Home, Steps to the Sand! Private Pool, Amenities for All!

Direct Beachfront Home, Steps to the Sand! Private Pool, Amenities for All!

5 beds 4 baths
PoolA/CWiFiBalcony
$993/night
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Beach N Bay 204 by Duncan Real Estate

Beach N Bay 204 by Duncan Real Estate

2 beds 1 bath
PoolA/CWiFiBalcony
$199/night
View Details → Book on VRBO
4 Bed 4.5 Bath Family Friendly, 3 Blocks to Gulf

4 Bed 4.5 Bath Family Friendly, 3 Blocks to Gulf

4 beds 4 baths
PoolA/CWiFiBalcony
$749/night
View Details → Book on VRBO
BEACH NEST! Free bikes+2 tandem kayaks+beach cart+hot tub+dock+heated pool

BEACH NEST! Free bikes+2 tandem kayaks+beach cart+hot tub+dock+heated pool

4 beds 3 baths
PoolA/CWiFiBalcony
$616/night
View Details → Book on VRBO
Tropical Island Sea-Cret. Now Remodeled. New floors and paint. New pictures.

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

3 beds 2 baths
PoolA/CWiFiBalcony
$469/night
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luxury beachfront/ heated pool

luxury beachfront/ heated pool

4 beds 5 baths
PoolA/CWiFiBalcony
$1,693/night
View Details → Book on VRBO
313 Palm Ave in Anna Maria

313 Palm Ave in Anna Maria

2 beds 1 bath
PoolA/CWiFiBalcony
$178/night
View Details → Book on VRBO

Showing 48 of 386 properties

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