Anna Maria Rentals
From $1043 per night (USD)VRBO
Cottage with Private Pool, Tropical Landscaped Backyard, Near Beach
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 7
Highlights • 7-minute walk to the beach • Private Pool • 1-minute walk to Pine Ave • Outdoor shower Covey Cottage 418 ...
From $1043 per night (USD)VRBO
From $280 per night (USD)Expedia
Heated Pool! 200 Steps to Gulf Beach!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Blue Lagoon 1 by Anna Maria Island Accommodations Home in Holmes Beach, FL 1.5 Blocks to Beach Highlights: • Complex ...
From $280 per night (USD)Expedia
From $549 per night (USD)VRBO
Private Home with Pool and Spa, 2 Blocks to Beach and Guest Suite!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Little Pink Houses by Anna Maria Island Accommodations Anna Maria, FL 34216 VR18-000136 Welcome to Little Pink Houses, ...
From $549 per night (USD)VRBO
From $888 per night (USD)Expedia
Canal Front Home with Private Pool and Spa, 2 Blocks to Beach!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Triple Play by Anna Maria Island Accommodations 313 Iris St Anna Maria, FL 34216 VR16-000416 Looking for that place ...
From $888 per night (USD)Expedia
From $598 per night (USD)VRBO
Ground Level Home with Saltwater Pool, 2 Blocks to Beach! - Pink Palm Bungalow
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Pink Palm Bungalow by Anna Maria Island Accommodations Home in Anna Maria, FL 34217 VR16-000353 Welcome to Pink Palm ...
From $598 per night (USD)VRBO
From $790 per night (USD)Expedia
Private Home with Pool and Game Room, 1 Block to Beach! - Dolphin Pointe
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Dolphin Pointe by Anna Maria Island Accommodations Home in Anna Maria, FL 34216 VR16-000318 Welcome to Dolphin Poi ...
From $790 per night (USD)Expedia
From $1025 per night (USD)VRBO
Beautiful Condo on Pine Ave, 2 Blocks to Beach
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
High Tide Haven by Anna Maria Island Accommodations 306 Pine Ave Anna Maria, FL 34216 Welcome to High Tide Haven where ...
From $1025 per night (USD)VRBO
From $560 per night (USD)Expedia
Adorable Cottage with Covered Balconies and Private Pool
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Social Nest by Anna Maria Island Accommodations Home in Anna Maria, FL 34216 Welcome to Social Nest, a second-level ho ...
From $560 per night (USD)Expedia
From $733 per night (USD)VRBO
Located Near Bay Beaches and Pine Ave! Family-Friendly with Pool and Games!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Highlights • Less than a 5-minute drive to the beach • Private pool and outdoor shower • Less than a 5-minute walk to ...
From $733 per night (USD)VRBO
From $669 per night (USD)Expedia
Spacious Canal Home Perfect For Family Vacations!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Highlights • Canal Front • 1-mile from the Beach • Private Pool and Hot Tub • Ping pong table Gypsy Sol by ...
From $669 per night (USD)Expedia
From $922 per night (USD)VRBO
Family Fun Anna Maria Vacation Home, Just Steps from Bean Point - Called In Sic
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
Called In Sic by Anna Maria Island Accommodations Home in Anna Maria, Florida Welcome to Called In Sic, your luxurious ...
From $922 per night (USD)VRBO
From $378 per night (USD)Expedia
Shared Pool, Private Patio, Only 2 Houses to the Beach - Sand and Sea 113 B
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Sand and Sea 113 B by Anna Maria Island Accommodations Condo in Anna Maria, FL 34216 VR16-000423 Welcome to Sand and Se ...
From $378 per night (USD)Expedia
From $1591 per night (USD)VRBO
Anna Maria Island Home with Pool, Spa, 1-minute to the Beach - Water Colors
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Water Colors by Anna Maria Island Accommodations Home in Anna Maria, FL 34216 VR18-000060 Welcome to Water Colors! T ...
From $1591 per night (USD)VRBO
From $567 per night (USD)Expedia
Private Home 1 Block to Beach with Pool and Hot Tub!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Highlights • 3-minute walk from Beach • Private pool and hot Tub • Outdoor shower • Washer and dryer Beach You To I ...
From $567 per night (USD)Expedia
From $890 per night (USD)VRBO
Anna Maria Friends Getaway: Private Pool Close to the Beach - Coral Kai
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Coral Kai by Anna Maria Island Accommodations Home in Anna Maria, Florida VR20-000067 Welcome to Coral Kai, your ide ...
From $890 per night (USD)VRBO
From $1966 per night (USD)Expedia
Private pool, 1 Block to beach, Putting Green - Lady from the Sea
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Highlights • Less than a 10-minute walk from the beach • Private pool • Putting Green • Outdoor living space • Nea ...
From $1966 per night (USD)Expedia
From $584 per night (USD)VRBO
Private Home with Caged Pool, 1 Block to Beach, Great for Family!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Highlights • Less than a 5-minute walk to the beach • Private pool • Separate guest suite • Hammock • Washer and d ...
From $584 per night (USD)VRBO
From $344 per night (USD)Expedia
Beach Condo with Shared Pool, Only 2 Houses to the Beach - Sand And Sea 113 A
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Sand And Sea 113 A by Anna Maria Island Accommodations Condo in Anna Maria, FL 34216 VR16-000423 Welcome to Sand and Se ...
From $344 per night (USD)Expedia
From $711 per night (USD)VRBO
Casa Allegria: Remodeled Home with Private Pool, Just Over a Block to Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Casa Allegria by Anna Maria Island Accommodations 209 Archer Way Anna Maria, FL 34216 VR16-000015 Welcome to Casa Alle ...
From $711 per night (USD)VRBO
From $1410 per night (USD)Expedia
Private Home with Heated Pool, Just 5 Houses to Beach
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
Palm Paradise by Anna Maria Island Accommodations Anna Maria, FL 34216 VR16-000358 Welcome to Palm Paradise, an invi ...
From $1410 per night (USD)Expedia
From $349 per night (USD)VRBO
Quaint Condo with Shared Pool, Only 2 Houses to the Beach - Sand And Sea 109 A
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Sand And Sea 109 A by Anna Maria Island Accommodations Condo in Anna Maria, FL 34216 VR16-000422 Welcome to Sand and Se ...
From $349 per night (USD)VRBO
From $759 per night (USD)Expedia
Canal Home with Private Pool and Dock - North End Zen
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
North End Zen by Anna Maria Island Accommodations Home in Anna Maria, FL 34216 VR16-000360 Recharge your batteries N ...
From $759 per night (USD)Expedia
From $637 per night (USD)VRBO
Private Home Situated Near Bean Point with Spacious Heated Pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Absolutely Anna by Anna Maria Island Accommodations Home in Anna Maria, FL 34216 VR16-000095 Escape to paradise at ...
From $637 per night (USD)VRBO
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Beautiful Bay Front Home with Panoramic Views and Open Balcony!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Dolphin Watch by Anna Maria Island Accommodations Bayfront home in Anna Maria, FL 34216 VR16-000325 Your dream bayfront ...
Click For PricingExpedia
From $555 per night (USD)VRBO
Adorable Remodeled Duplex with Heated Pool, Just 2 Blocks to Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Turtle Crawl by Anna Maria Island Accommodations Duplex in Anna Maria, FL 34216 VR16-000350 Welcome to Turtle Crawl, a ...
From $555 per night (USD)VRBO
From $575 per night (USD)Expedia
Quiet North End Home Only 2 Blocks to Beach with Private Pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Our Place By The Sea Anna Maria, FL 34216 VR16-000359 Welcome to Our Place By The Sea, an inviting vacation home with a ...
From $575 per night (USD)Expedia
From $517 per night (USD)VRBO
Adorable Remodeled Duplex with Heated Pool, Just 2 Blocks to the Beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Highlights • Less than a 5-minute walk from the beach • Shared Pool • Less than 1 mile from Pine Ave restaurants and s ...
From $517 per night (USD)VRBO
From $649 per night (USD)Expedia
Beautiful Home with Pool, Outside Living Area, Near the Beach! - Coconut Lagoon
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Coconut Lagoon by Anna Maria Island Accommodations Home in Anna Maria, FL 34216 VR16-000285 Welcome to Coconut Lagoo ...
From $649 per night (USD)Expedia
From $349 per night (USD)VRBO
Quaint Condo with Shared Pool, Only 2 Houses to the Beach - Sand And Sea 109 B
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Sand And Sea 109 B by Anna Maria Island Accommodations Condo in Anna Maria, FL 34216 VR16-000422 Welcome to Sand and S ...
From $349 per night (USD)VRBO
From $389 per night (USD)Expedia
Quaint Condo with Heated Pool, Only 2 Houses to the Beach - Sand and Sea 111 B
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Sand and Sea 111 B by Anna Maria Island Accommodations Condo in Anna Maria, FL 34216 VR16-000423 Welcome to Sand and Se ...
From $389 per night (USD)Expedia
From $1058 per night (USD)VRBO
Private Home with Heated Pool and Screened Lanai, 2 Houses to Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
Mermaid's Purse 107 Palm Ave Anna Maria, FL 34216 VR16-000364 Welcome to Mermaid’s Purse, a perfectly located north-en ...
From $1058 per night (USD)VRBO
From $735 per night (USD)Expedia
Luxury home near the beach and shopping! Private backyard and pool!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Highlights • 2-minute walk from the beach • Private Pool • Near free Anna Maria Island Trolley stop • Outdoor living spa ...
From $735 per night (USD)Expedia
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Private Home 1 House From Beach with Heated Pool!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Highlights • 1-minute walk to the Beach • Private Pool • Outdoor Shower Blue Mermaid by Anna Maria Island Accommoda ...
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From $1108 per night (USD)Expedia
Sea La Vie Beach House - Luxurious 4BR Home W\/ Pool, Spa, Dock, & Canal Access on Anna Maria Island
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Sea La Vie Beach House! On Anna Maria Island (Anna Maria, FL) Luxurious 2,825 Sq. Ft. Canal-Front Home With ...
From $1108 per night (USD)Expedia
From $543 per night (USD)VRBO
Anna Maria Island, NORTH END 3 bedroom, pet friendly, private pool home!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Paradise found in this 3 bedroom, 2 bath pet friendly, home on Anna Maria Island! This family home is just 1 block from ...
From $543 per night (USD)VRBO
From $719 per night (USD)Expedia
Bella Vita: Canal front, pool, perfect location!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
SECURITY CAMERAS IN USE LIFE IS BEAUTIFUL AND ALWAYS BETTER AT THE BEACH! BELLA VITA. YOUR NEW CORNER OF PARADISE! THI ...
From $719 per night (USD)Expedia
From $1549 per night (USD)VRBO
Once Upon a Tiki: Canal, Dock, Backyard Paradise, Games, Pool by Anna Maria Life Vacation Rentals
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 14
211 Chilson Ave, Anna Maria, FL 34216 What You'll Love About This Home: Location! One Block to the Beach! On a Canal! 5 ...
From $1549 per night (USD)VRBO
From $1245 per night (USD)Expedia
Precious Memories: North End! Quick Walk to Beach! Elevator,Pool,Ping Pong & Pool by Anna Maria Life
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Precious Memories by Anna Maria Life Vacation Rentals 753 Jacaranda, Anna Maria, FL 34216 What You'll Love About This H ...
From $1245 per night (USD)Expedia
From $768 per night (USD)VRBO
Luxury Home with Pool, Spa, and Deck! - AMI Breeze
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
AMI Breeze by AMI Locals Home in Anna Maria VR20-000022 Welcome to AMI Breeze, a beautiful two bedroom and two bathroo ...
From $768 per night (USD)VRBO
From $1501 per night (USD)Expedia
Beautiful, Gulf-Front Home on Bean Point--Halcyon House
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
As seen in Coastal Living Magazine, this is a quintessential, beachfront home on desirable Bean Point with with direct a ...
From $1501 per night (USD)Expedia
From $852 per night (USD)VRBO
Upscale waterfront home, private pool, beautiful views!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
The heart of Anna Maria Island is captured in Paradise on Pine! Highlights • Waterfront home with a private dock accomm ...
From $852 per night (USD)VRBO
From $393 per night (USD)Expedia
Coquina Cottage A by Duncan Real Estate
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Coquina Cottage! Relax stress-free in this two-bedroom ground level duplex accommodation with water views, ac ...
From $393 per night (USD)Expedia
From $517 per night (USD)VRBO
Desirable North-End Gem on Canal with Dock, Heated Pool. Clean and Spacious.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Welcome to paradise! Pelican Perch is a spacious, three-bedroom, two-bath house, located on a canal and a quiet cul-de- ...
From $517 per night (USD)VRBO
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Hunt's Hideaway: *Putting Green *Pool *Hot Tub *5 min walk to Beach!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Escape to Hunt's Hideaway, a luxurious vacation rental that promises an unforgettable retreat. With four bedrooms and th ...
Click For PricingExpedia
From $458 per night (USD)VRBO
Moondance- Breathtaking views and beachfront with steps from the beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
At A Glance Gulf-front elevated home Washer and dryer in-unit Smart TV in the living room Part of our Professional Linen ...
From $458 per night (USD)VRBO
From $1024 per night (USD)Expedia
White Pearl-Premier AMI Home with Amazing Sunset Views and Great Reviews
- Bedrooms:
- 6
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to White Pearl. This brand new elevated custom home (2019) on Anna Maria Island located within AMI city limits ...
From $1024 per night (USD)Expedia
From $338 per night (USD)VRBO
Dog friendly cottage - One block to the Bay!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Slo M'Ocean by Anna Maria Island Locals Home in Anna Maria, FL 1 easy block to the Bay Highlights: - Recently refresh ...
From $338 per night (USD)VRBO
From $1504 per night (USD)Expedia
Paradise Point-5 bedroom luxury with private pool across the street from beach
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
At A Glance Private pool- Pool heat must be requested! Just across the street from the beachElevator accessMultiple Balc ...
From $1504 per night (USD)Expedia
From $926 per night (USD)VRBO
Hook Wine & Sinker by Beach Boutique Rentals
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Hook Wine and Sinker, a gorgeous 2000 square foot canal-front home situated in the coveted North end of Anna ...
From $926 per night (USD)VRBO
From $679 per night (USD)Expedia
Mangroves and Magnolias- Tropical island pool home on North end.
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Vacation in luxury at the most desirable location on the north end of Anna Maria Island. The perfect home to unite and u ...
From $679 per night (USD)Expedia
From $971 per night (USD)VRBO
Beach Bliss: Perfect location, pool, views, steps to beach
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Beach Bliss offers something special for everyone in the family! Come enjoy this beautiful 3 bedroom 2 bath home just st ...
From $971 per night (USD)VRBO
From $477 per night (USD)Expedia
Island Oasis: Ground level canal front pool home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Looking to escape to a beautiful tropical oasis? This is the place for you! Refreshed with gorgeous coastal decor in the ...
From $477 per night (USD)Expedia
From $534 per night (USD)VRBO
Sharks Eye- Original island cottage on historic Pine Ave.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
Cozy and quaint and perfectly nestled in the hustle and bustle of Anna Maria’s Pine Avenue, you’ll fall in love with Sha ...
From $534 per night (USD)VRBO
From $314 per night (USD)Expedia
Ground-Floor Suite w\/Full Kitchen, Free WiFi, Shared Pool & Washer\/Dryer
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Sunrise Garden #1 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $314 per night (USD)Expedia
From $353 per night (USD)VRBO
Perfect Family Vacation home just off the beach! Private Pool!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Island Hideaway by AMI Locals Home in Holmes Beach, FL Features: • Private heated pool • Ground-level home, very access ...
From $353 per night (USD)VRBO
From $1069 per night (USD)Expedia
Villa Marianne: AMI North End, Steps to Beach, West of Gulf, Pool by Anna Maria Life
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
Villa Marianne by Anna Maria Life Vacation Rentals 111 Maple Ave, Anna Maria, FL 34216 What You'll Love About This Home ...
From $1069 per night (USD)Expedia
From $737 per night (USD)VRBO
Discounted April 26th thru May 17th stays w\/ Private Pool & Dock!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
DESCRIPTION: It doesn't get much better than being right on the water, located on a wide canal, and ½ block from the ...
From $737 per night (USD)VRBO
From $525 per night (USD)Expedia
Bayside Cutie at Bayside Bungalow: Anna Maria Island Getaway Near Pine Avenue!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Bayside Cutie at Bayside Bungalow by AMI Locals Villa in Bradenton Beach, FL 34217 VR18-000088 Experience coastal ...
From $525 per night (USD)Expedia
From $908 per night (USD)VRBO
Condo Close to Shops, Beach, Restaurants! - Blissful Bay at Bayside Bungalow
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Blissful Bay at Bayside Bungalow by AMI Locals Condo in Bradenton Beach, FL 34217 VR18-000088 Welcome to Blissful Ba ...
From $908 per night (USD)VRBO
From $523 per night (USD)Expedia
Shared Pool, Bay Views! - Barefoot by the Bay at Bayside Bungalow
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Barefoot by the Bay at Bayside Bungalow by AMI Locals Condo in Anna Maria, FL 34217 VR18-000088 Welcome to Barefo ...
From $523 per night (USD)Expedia
From $1019 per night (USD)VRBO
Experience Family Fun at Blue Pearl: Steps from Beaches, Shops, and Dining!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Blue Pearl By AMI Locals Home in Anna Maria VR19-000007 Discover paradise at Blue Pearl! This beautiful three-bedroom, ...
From $1019 per night (USD)VRBO
From $587 per night (USD)Expedia
AMI Boathouse:Dog Friendly Canal Front Pool Home North End of AMI by Anna Maria Life
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
AMI Boathouse by Anna Maria Life Vacation Rentals 520 Loquat, Anna Maria, FL 34216 What You'll Love About This Home: Lo ...
From $587 per night (USD)Expedia
From $413 per night (USD)VRBO
Canal Front - Going Coastal by SeaBreeze Vacation
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Going Coastal is a 2 bedroom/2 bathroom home located on the north end of Anna Maria Island. This ground level canal fron ...
From $413 per night (USD)VRBO
From $828 per night (USD)Expedia
Gulf Front Vacation Rental- Anna Maria Island, Florida
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Our Gulf Front vacation home is located on Anna Maria's North Shore Drive with Magnificent Panoramic views of the Gulf o ...
From $828 per night (USD)Expedia
From $1240 per night (USD)VRBO
The Veranda on Jacaranda by Beach Boutique Rentals
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
Views, views, views! Experience the peace and beauty of the North end of Anna Maria from this sprawling home named for i ...
From $1240 per night (USD)VRBO
From $1338 per night (USD)Expedia
Private Home with Pool + Spa - One Block to Beach!
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 8
Fortunate Sol by AMI Locals Home in Anna Maria, FL One block to beach! Highlights: • Game room with Foosball and Pinb ...
From $1338 per night (USD)Expedia
From $928 per night (USD)VRBO
180-degree water views! Shared pool and laundry - Bay Vista at Bayside Bungalow
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Bay Vista at Bayside Bungalow by AMI Locals Home in Bradenton Beach, FL 34217 VR18-000088 Welcome to Bay Vista, a lu ...
From $928 per night (USD)VRBO
From $602 per night (USD)Expedia
Bay Breezes at Bayside Bungalow: Enjoy Resort-Style Pool Steps from Pine Ave!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Bay Breezes at Bayside Bungalow by AMI Locals Villa in Bradenton Beach, FL 34217 VR18-000088 Welcome to Bay Breezes ...
From $602 per night (USD)Expedia
From $947 per night (USD)VRBO
Anna Maria Island Private Waterfront Oasis on Bimini Bay | IG: AMIBlueHeron
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Imagine your own private oasis overlooking Bimini Bay on a quiet street on Anna Maria Island. Well, imagine no further. ...
From $947 per night (USD)VRBO
From $708 per night (USD)Expedia
BGs Bungalow - by Island Real Estate Vacations
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
BG’s Bungalow is your perfect island getaway! Spectacular proximity to the amazing beaches of Bean Point, meticulously d ...
From $708 per night (USD)Expedia
From $301 per night (USD)VRBO
Pet-Friendly - Rum Dog by SeaBreeze Vacation
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Perfect for a family vacation or a couple's retreat, this newly listed and newly updated, furnished 2 bedroom/2 bath dup ...
From $301 per night (USD)VRBO
From $549 per night (USD)Expedia
Willow Cottage: Steps to the beach, heated pool, perfect location!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
***Photos Updated April 2025*** Welcome to Willow Cottage, a charming sunny cottage just steps to the white sandy beache ...
From $549 per night (USD)Expedia
From $503 per night (USD)VRBO
Great Villa! Just updated, private pool and 1 block to the beach!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
AMI Sunrise by AMI Locals Home in Holmes Beach VRC20-000165 Welcome to AMI Sunrise! This fantastic ground-level home i ...
From $503 per night (USD)VRBO
From $417 per night (USD)Expedia
Lovely 3 bd island cottage with a private pool + close to the beach!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
AMI Sunset by Anna Maria Island Locals Home in Holmes Beach, FL Only 75 yards to the beach! Highlights: • Private back ...
From $417 per night (USD)Expedia
From $713 per night (USD)VRBO
Newly-Renovated, Dog-Friendly Home w\/ Private Heated Pool & Streaming Services
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Beach to Bay Getaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $713 per night (USD)VRBO
From $585 per night (USD)Expedia
One Day More: Spectacular Oasis Backyard with Pool & Spa by Anna Maria Life Vacation Rentals
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
403 72nd St., Holmes Beach, FL 34217 What You'll Love About this Home: Location! 4 Blocks to the Beach! Centrally Locat ...
From $585 per night (USD)Expedia
From $573 per night (USD)VRBO
Sunset Shores: Stunning sunset views over the beach!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Dreaming of the perfect beach vacation home? Dreaming of sipping coffee on your choice of decks with views of the Gulf? ...
From $573 per night (USD)VRBO
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The Oasis at AMI: Walk to beach, heated pool, hot tub
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to The Oasis at AMI! This charming 4 Bedroom 3.5 Bath home is the perfect place to escape it all! With no busy s ...
Click For PricingExpedia
From $689 per night (USD)VRBO
Island Dream- 4 bedroom with private heated pool and great views
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Island Dream 157 Crescent Drive, Anna Maria What you will love about this property: • Exclusive North End location-Eas ...
From $689 per night (USD)VRBO
From $419 per night (USD)Expedia
Heated Pool, FREE WiFi, Close to Beach, Dock your Boat, Dog* Friendly (See...
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
**ASK ABOUT LAST MINUTE DEALS! A contemporary aesthetic combined with a top-notch location is sure to make ...
From $419 per night (USD)Expedia
From $658 per night (USD)VRBO
Beach Basket Cottage: Cute Old Florida Style Beach Cottage just steps to the Beach!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Beach Basket is a 1920's cottage located on Oak Ave which dead ends to the white sandy beaches and emerald waters of Ann ...
From $658 per night (USD)VRBO
From $1212 per night (USD)Expedia
1 block from the Beach w\/Pool, Spa, & Game Room -Castaway Cove
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
Castaway Cove by AMI Locals Home in Anna Maria, Florida VR16-000471 Welcome to Castaway Cove, a canal-front home with ...
From $1212 per night (USD)Expedia
From $645 per night (USD)VRBO
Lake La Vista Beach House: Canal front beauty in quiet neighborhood, pool
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Located north of Pine Avenue, in the heart of Anna Maria, you'll find the lovely Lake LaVista Beach House. This four be ...
From $645 per night (USD)VRBO
From $604 per night (USD)Expedia
Beach Don't Kill My Vibe by Beach Boutique Rentals
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Two bedroom apartment in the heart of Pine Avenue. One block to the beach! *Features include* * Modern vacation rental ...
From $604 per night (USD)Expedia
From $1151 per night (USD)VRBO
Pet Friendly Bay-Canal Waterfront! Tiki Bar 5BR, 5BA Huge Pool, 2 Kayaks\/Bikes
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 14
Newly renovated December 2024, with state of the art finishes! 5 BR + 2 King Sleep Sofas, 1.5 Chaise Lounger, 5 BA Duple ...
From $1151 per night (USD)VRBO
From $469 per night (USD)Expedia
GULF FRONT Beautiful Condo w\/Heated Pool, FREE WiFi & Trolley, Great Sunsets!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
**ASK ABOUT LAST MINUTE DEALS! Enjoy a fabulous stay at the beach in this beautifully remodeled two bedroom ...
From $469 per night (USD)Expedia
From $511 per night (USD)VRBO
Large Private Pool Home with Spa - 150 yards to the Beach - By Island Real Estat
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
“Catchin’ Rays” is an excellent choice for your next Anna Maria Island vacation! This centrally located home offers ever ...
From $511 per night (USD)VRBO
From $926 per night (USD)Expedia
Knot 4 Reel: Gorgeous canal front w\/pool, hot tub, dock and steps to the Bay!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This stunning, custom, canal home is 4 bedroom, 3 bathroom on desirable North End of Anna Maria Island. Conveniently loc ...
From $926 per night (USD)Expedia
From $372 per night (USD)VRBO
Sam's Cove! Second Floor Condo Overlooking Water
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
IMPORTANT: Per homeowner's association, a minimum monthly stay is required, as well as an application. Please allow at l ...
From $372 per night (USD)VRBO
From $1652 per night (USD)Expedia
Dragonfly - Southern charm on the North end of Anna Maria Island
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
Dragonfly is a private retreat located right across the street from the sugary white sands of famous Bean Point Beach in ...
From $1652 per night (USD)Expedia
From $648 per night (USD)VRBO
Isle Relax: Close to Gulf of Mexico and Pine Ave.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Isle Relax! This elevated beach home with three bedrooms, two bathrooms, and a private heated pool, is locat ...
From $648 per night (USD)VRBO
From $397 per night (USD)Expedia
EV Charger, Blue Lagoon South by SeaBreeze Vacation
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Come enjoy this 2 bedroom/2 bath duplex that can sleep up to 6 people with the add-on of the sleeper sofa. Blue Lagoon i ...
From $397 per night (USD)Expedia
From $405 per night (USD)VRBO
Blue Lagoon North by SeaBreeze Vacation
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Come enjoy this 2 bedroom/2 bath duplex that can sleep up to 6 people with the add-on of the sleeper sofa. Blue Lagoon i ...
From $405 per night (USD)VRBO
From $760 per night (USD)Expedia
EV Charger, Blue Lagoon by SeaBreeze Vacation
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Come enjoy this 4 bedroom/4 bath duplex that can sleep up to 12 people with the add-on of the sleeper sofas. Blue Lagoon ...
From $760 per night (USD)Expedia
From $770 per night (USD)VRBO
Pool\/Spa - Anchor Splash by SeaBreeze Vacation
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
If you're looking for the perfect spot to drop anchor on Anna Maria Island— look no further than this spacious four-bedr ...
From $770 per night (USD)VRBO
From $964 per night (USD)Expedia
Ship Watch: Private Beach, North End, Dog Friendly by Anna Maria Life Vacation Rentals
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
895 North Shore Dr., Anna Maria, FL 34216 What You'll Love About This Home: Location! Relax on your own Private Beach ...
From $964 per night (USD)Expedia
From $812 per night (USD)VRBO
Blue Palm Paradise: Dog friendly, Pool, 3 Minute Walk to Beach by Anna Maria Life Vacation Rentals
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Blue Palm Paradise by Anna Maria Life Vacation Rentals 205 65th St, Holmes Beach, FL 34217 What You'll Love About This ...
From $812 per night (USD)VRBO
From $642 per night (USD)Expedia
Whispering Winds by Beach Boutique Rentals
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This custom crafted two bedroom/two bath bayside beauty is your perfect beach escape. *Features include* * Balcony w ...
From $642 per night (USD)Expedia
From $464 per night (USD)VRBO
Sea Breeze: Pool home in perfect central location
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This 3 bed 2 bath island oasis will take you back to the days of old Florida charm, but in a modern and well appointed s ...
From $464 per night (USD)VRBO
From $724 per night (USD)Expedia
Bay Bungalow by Beach Boutique Rentals
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Perfectly situated in the North end of the island, Bay Bungalow is just a short stroll away from the Bay beaches, and fa ...
From $724 per night (USD)Expedia