Anna Maria Rentals
From $1081 per night (USD)VRBO
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 $1081 per night (USD)VRBO
From $737 per night (USD)Expedia
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 $737 per night (USD)Expedia
From $964 per night (USD)VRBO
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 $964 per night (USD)VRBO
From $1474 per night (USD)Expedia
Beautiful, Gulf-Front Home on Bean Point--Halcyon House
- Bedrooms:
- 3
- 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 $1474 per night (USD)Expedia
From $792 per night (USD)VRBO
Upscale waterfront home, private pool, beautiful views!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Paradise on Pine by AMI Locals Vacation Rental License #VR20-000052 Welcome to Paradise on Pine, a spectacular four b ...
From $792 per night (USD)VRBO
From $517 per night (USD)Expedia
Coquina Cottage A by Duncan Real Estate
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Coquina Cottage A! Family friendly Coquina Cottage A is exceptionally located at the northern end of Anna Mar ...
From $517 per night (USD)Expedia
From $560 per night (USD)VRBO
Spacious, Comfortable, Clean North-End Gem on Canal with Dock & Heated Pool.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to paradise! Pelican Perch is a recently updated, three-bedroom, two-bath house, located on a canal and a quiet ...
From $560 per night (USD)VRBO
From $616 per night (USD)Expedia
Moondance- 2 bedrooms- Breathtaking views and beachfront with steps from the bea
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Moondance 206 Spring Lane, Anna Maria, FL 34216 What you will love about this property: • Beachfront with direct access ...
From $616 per night (USD)Expedia
From $994 per night (USD)VRBO
White Pearl-Premier Anna Maria Home with Amazing Sunset Views and Great Reviews
- Bedrooms:
- 5
- 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 $994 per night (USD)VRBO
From $559 per night (USD)Expedia
Dog friendly cottage - One block to the Bay!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Slo M’Ocean by AMI Locals VR21-000011 Welcome to Slo M’Ocean, a recently refreshed 2-bedroom, 1-bath beach-style cott ...
From $559 per night (USD)Expedia
From $544 per night (USD)VRBO
Hook Wine & Sinker by Beach Boutique Rentals
- Bedrooms:
- 2
- 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 $544 per night (USD)VRBO
From $948 per night (USD)Expedia
Mangroves and Magnolias- Tropical island pool home on North end.
- Bedrooms:
- 3
- 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 $948 per night (USD)Expedia
From $880 per night (USD)VRBO
Beach Bliss: Perfect location, pool, views, steps to beach
- Bedrooms:
- 2
- 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 $880 per night (USD)VRBO
From $755 per night (USD)Expedia
Island Oasis: Ground level canal front pool home
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Looking to escape to a beautiful tropical oasis? This is the place for you! Refreshed with gorgeous coastal decor in the ...
From $755 per night (USD)Expedia
From $515 per night (USD)VRBO
Sharks Eye- Original island cottage on historic Pine Ave.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
<p>Close to a water park, sailing, and more, this smoke-free vacation home brings it all within reach. Anna Maria Island ...
From $515 per night (USD)VRBO
From $480 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 $480 per night (USD)Expedia
From $702 per night (USD)VRBO
Close to Beach! 1/2 Block from Beach- Private Boat Dock & 30' Pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Escape the Traffic: Private Waterfront Oasis on AMI’s Historic North End. Welcome to Sunshine Cottage, a beautifull ...
From $702 per night (USD)VRBO
From $389 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 $389 per night (USD)Expedia
From $457 per night (USD)VRBO
Canal Front - Going Coastal by SeaBreeze Vacation
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
NEWLY RENOVATED! Going Coastal is a 2 bedroom/2 bathroom home located on the north end of Anna Maria Island. This ground ...
From $457 per night (USD)VRBO
From $954 per night (USD)Expedia
Gulf Front Vacation Rental- Anna Maria Island, Florida
- Bedrooms:
- 1
- 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 $954 per night (USD)Expedia
From $571 per night (USD)VRBO
The Veranda on Jacaranda by Beach Boutique Rentals
- Bedrooms:
- 3
- Bathrooms:
- 4
- 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 $571 per night (USD)VRBO
From $1058 per night (USD)Expedia
Luxury Beach Home! Pool, Spa and Gourmet Kitchen!
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 8
Fortunate Sol by AMI Locals VR22-000005 Welcome to Fortunate Sol, a beautifully remodeled six-bedroom, four and a hal ...
From $1058 per night (USD)Expedia
From $569 per night (USD)VRBO
BGs Bungalow - by Island Real Estate Vacations
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
BG’s Bungalow is your perfect island getaway! Spectacular proximity to the amazing beaches of Bean Point, meticulously d ...
From $569 per night (USD)VRBO
From $657 per night (USD)Expedia
Willow Cottage: Steps to the beach, heated pool, perfect location!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
***Photos Updated April 2025*** Welcome to Willow Cottage, a charming sunny cottage just steps to the white sandy beache ...
From $657 per night (USD)Expedia
From $821 per night (USD)VRBO
Sunset Shores: Stunning sunset views over the beach!
- Bedrooms:
- 2
- 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 $821 per night (USD)VRBO
From $536 per night (USD)Expedia
Pelican Bay | Private Waterfront Pool Home | Near Bean Point | Dog Friendly See Note!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
**ASK ABOUT LAST MINUTE DEALS! Escape to Pelican Bay, a beautifully updated waterfront home on the highly sought-after ...
From $536 per night (USD)Expedia
From $543 per night (USD)VRBO
Welcome to Beach Basket – Your Seaside Retreat!\"
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Step back in time and into paradise at this charming 1920s Florida beach cottage, just steps from the pristine, sugar-wh ...
From $543 per night (USD)VRBO
From $923 per night (USD)Expedia
Canal front Home with Private Dock, Pool, Games, and Water Adventures
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Castaway Cove by AMI Locals VR16-000471 Experience the ultimate island escape at Castaway Cove, a stunning canal fr ...
From $923 per night (USD)Expedia
From $836 per night (USD)VRBO
Spacious Island waterfront house w/ heated pool, steps to beach and dining
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Spacious Waterfront Home w/Pool, Steps to Beach Perfect for families and groups, this coastal retreat offers a private ...
From $836 per night (USD)VRBO
From $541 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 rent ...
From $541 per night (USD)Expedia
From $1046 per night (USD)VRBO
Waterfront -Canal, Heated Pool, Free Golf Cart Pro
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 14
Newly renovated December 2024, with state of the art finishes! 5 King BR, 1 also has a Daybed + 2 King Sleeper Sofas, 1. ...
From $1046 per night (USD)VRBO
From $978 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 $978 per night (USD)Expedia
From $1179 per night (USD)VRBO
Dragonfly - Southern charm on the North end of Anna Maria Island
- Bedrooms:
- 3
- 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 $1179 per night (USD)VRBO
From $700 per night (USD)Expedia
Isle Relax: Close to Gulf of Mexico and Pine Ave.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Isle Relax! This elevated beach home with three bedrooms, two bathrooms, and a private heated pool, is locat ...
From $700 per night (USD)Expedia
From $460 per night (USD)VRBO
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 $460 per night (USD)VRBO
From $394 per night (USD)Expedia
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 $394 per night (USD)Expedia
From $780 per night (USD)VRBO
EV Charger, Blue Lagoon by SeaBreeze Vacation
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Come enjoy this 4 bedroom/4 bath duplex that can sleep up to 8 people with the add-on of the sleeper sofas. Blue Lagoon ...
From $780 per night (USD)VRBO
From $713 per night (USD)Expedia
Pool/Spa - Anchor Splash by SeaBreeze Vacation
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
If you're looking for the perfect spot to drop anchor on Anna Maria Island— look no further than this spacious four-bedr ...
From $713 per night (USD)Expedia
From $904 per night (USD)VRBO
Ship Watch: Private Beach, North End, Dog Friendly by Anna Maria Life Vacation Rentals
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Ship Watch by Anna Maria Life Vacation Rentals 895 North Shore Dr., Anna Maria, FL 34216 What You'll Love About This Ho ...
From $904 per night (USD)VRBO
From $480 per night (USD)Expedia
Whispering Winds by Beach Boutique Rentals
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This custom crafted two bedroom/two bath bayside beauty is your perfect beach escape. *Features include* * Balcony w ...
From $480 per night (USD)Expedia
From $572 per night (USD)VRBO
Bay Bungalow by Beach Boutique Rentals
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Perfectly situated in the North end of the island, Bay Bungalow is just a short stroll away from Bay beaches and famous ...
From $572 per night (USD)VRBO
From $415 per night (USD)Expedia
Waterfront Charm! Walk to Bayfront Park!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Bay Haven by AMI Locals Vacation Rental License #VR16-000039 Welcome to Bay Haven, a relaxing 2-bedroom, 2-bathroom d ...
From $415 per night (USD)Expedia
From $477 per night (USD)VRBO
3 bedroom 2 bathroom canal front home with a heated pool located in Anna Maria
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Copacabana is a ground level 3-bedroom, 2-bath private home located directly on a tranquil canal in Anna Maria, nestled ...
From $477 per night (USD)VRBO
From $716 per night (USD)Expedia
Luxury waterfront home with a heated pool and spa!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
A beautifully furnished 4-bedroom, 3.5-bathroom home, this canal front property is in the heart of the Historic Anna Mar ...
From $716 per night (USD)Expedia
From $413 per night (USD)VRBO
Naut 2 Shabby Cottage-Awesome Pool Area, Pine Ave location close to everything
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Completely restored with all new kitchen and appliances, new flooring and all new furnishings just as cute! Welcome to ...
From $413 per night (USD)VRBO
Click For PricingExpedia
Tropical Island Sea-Cret. Now Remodeled. New floors and paint. New pictures.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Tropical and very private 3 bedroom canal home with heated pool on private drive. All 3 bedrooms have king sized beds. ...
Click For PricingExpedia
From $456 per night (USD)VRBO
Seabatical -Beachy Chic Canalfront Home with Large Pool with Spa & boat Dock!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Bring your boat or jetskis to this Anna Maria Canal Home with a large 40 ft Private Pool and Spa. Newly remodeled home ...
From $456 per night (USD)VRBO
From $997 per night (USD)Expedia
Willow Hideaway: Luxury Canal Front Home w/Pool and Spa
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Come enjoy this luxury canal home that is located only 2 short blocks to the world-famous beaches of Anna Maria Island. ...
From $997 per night (USD)Expedia
From $500 per night (USD)VRBO
Wave n Sea - Close to the Beach with Pool - Anna Maria Island - By Island Real E
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
“Wave N’Sea” is a premiere vacation home located in the city of Anna Maria on Anna Maria Island. Here you’ll find a perf ...
From $500 per night (USD)VRBO
From $719 per night (USD)VRBO
LOCATION! -Bean Point area w/pool. PANORAMIC WATER VIEW. Walk to Beach and town!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This is our much-loved AMI family home and we want you to have a wonderful visit. We are a midwestern family -we are ea ...
From $719 per night (USD)VRBO
From $867 per night (USD)VRBO
Luxe AMI Stay! Saltwater Pool and Rooftop Views
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
AM I Dreaming by AMI Locals VR19-000055 Welcome to AM I Dreaming, a luxurious three bedroom, three and a half bath can ...
From $867 per night (USD)VRBO
From $420 per night (USD)Expedia
AMI North End Private Heated Pool. 1.2 Block to Gulf Beach!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Diamond Surf – Your Private Slice of Paradise on Anna Maria Island What You’ll Love About This Home: • Ama ...
From $420 per night (USD)Expedia
From $1085 per night (USD)VRBO
Casa Amiga managed by Beach Retreats FL Anna Maria Island
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
🌊 Casa Amiga by Beach Retreats Vacation Rentals 144 Crescent Dr. Anna Maria, FL 34216 📍 City of Anna Maria | 4 ...
From $1085 per night (USD)VRBO
From $993 per night (USD)Expedia
North Shore Beach House: Tranquil 4BR Retreat with Pool, Spa, & Walk to Beach
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Escape to North Shore Beach House, your serene sanctuary on the North End of Anna Maria Island. This stunning 4-bedroom, ...
From $993 per night (USD)Expedia
From $802 per night (USD)VRBO
Bean Point Beach Cottage -North End of Anna Maria Island lovely sand & sunsets!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Anna Maria Bean Point Beach Cottage. Vacation at Anna Maria Island with the most beautiful white sands beach and crystal ...
From $802 per night (USD)VRBO
From $710 per night (USD)Expedia
A Hidden Key West Style Gem on Anna Maria Island
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Property Highlights • Beautiful Key West-style home with nearly 2,500 sq. ft. of living space • 3 Bedrooms | 3.5 Bathro ...
From $710 per night (USD)Expedia
From $988 per night (USD)VRBO
Our Great Escape by Duncan Real Estate
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
This beautiful, brand-new luxury pool home is one of a kind in a secluded prestigious North end location directly on the ...
From $988 per night (USD)VRBO
From $2191 per night (USD)Expedia
Luxury Beachfront on the Sand of Gulf of Mexico
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Photos Updated January 2025! Sunnyside Escape is a newly built luxury home situated on the famous white sand gulf beach ...
From $2191 per night (USD)Expedia
From $1231 per night (USD)VRBO
Serendipity | Beachfront | Hot Tub | Golf Cart | Elevator
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Escape to Serendipity, a luxurious beachfront haven on Anna Maria Island! This stunning 4-bedroom home offers ...
From $1231 per night (USD)VRBO
From $387 per night (USD)Expedia
Angel Fish Cottage, Sweet 2 BR 1 B, Private Pool, Steps to Gulf and Bay
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Newly Renovated Angel Fish Cottage with new flooring, beds and furniture. Located on the north, quiet end of Anna Maria ...
From $387 per night (USD)Expedia
From $602 per night (USD)VRBO
Canalfront Home, Saltwater Pool, Near Beaches and Shopping - Sunrise Shore
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 11
Sunrise Shore by AMI Locals VPR16-000431 Welcome to Sunrise Shore, your ideal Anna Maria Island vacation home! Thi ...
From $602 per night (USD)VRBO
From $429 per night (USD)Expedia
Hav'Anna Holiday: 2 Blocks to Beach! North End! Private Pool by Anna Maria Life Vacation Rentals
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Hav'Anna Holiday by Anna Maria Life Vacation Rentals 211 Periwinkle, Anna Maria, FL 34217 What You'll Love About This H ...
From $429 per night (USD)Expedia
From $1109 per night (USD)VRBO
Park n Chill: North End, Steps to Beach, West of Gulf, Pool by Anna Maria Life Vacation Rentals
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Park n Chill by Anna Maria Life Vacation Rentals 117 Park Ave, Anna Maria, FL 34216 What You'll Love About This Home: L ...
From $1109 per night (USD)VRBO
From $1027 per night (USD)Expedia
Brand New Putting Green! Close to beach!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Blue Marlin by AMI Locals VR18-000106 Welcome to Blue Marlin by AMI Locals, a stunning four bedroom, four and a half ...
From $1027 per night (USD)Expedia
From $387 per night (USD)VRBO
Beachy Boathouse Cottage, 2 BR,1BA, Private Pool, Steps to Beach and Bay-
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Newly Renovated Boathouse Cottage is ready to welcome guests. New flooring, new beds, new furniture. Located on the we ...
From $387 per night (USD)VRBO
From $672 per night (USD)Expedia
Beachside Duplex in Anna Maria – Steps to Gulf Beaches | FREE WIFI | 4BR Parking for 4
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
**ASK ABOUT LAST-MINUTE DEALS! Welcome to Big Seader, a spacious vacation rental in Anna Maria Island just steps from t ...
From $672 per night (USD)Expedia
From $1334 per night (USD)VRBO
Steps from the Beach! Walk to Bean Point! Pool/spa! Golf Cart
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Have the best of both worlds with the bay & the gulf beaches at this new 4 bed/3.5 bath luxury home. Enjoy the quiet, l ...
From $1334 per night (USD)VRBO
From $1442 per night (USD)Expedia
Three Little Birds - Luxury Gulf-View Home w/ Heated Pool & Steps to Bean Point
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Three Little Birds! On Anna Maria Island (Anna Maria, FL) The Space Step into Three Little Birds — a bright, ...
From $1442 per night (USD)Expedia
From $585 per night (USD)VRBO
Poolside Comfort Just Steps from the AMI Beaches
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Property Highlights • Walk to the beach, Pine Avenue, shops & restaurants • Private fenced pool with gas grill • 3 B ...
From $585 per night (USD)VRBO
From $939 per night (USD)Expedia
Paradise Blu by Beach Boutique Rentals
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Paradise Blu! Your luxury vacation awaits in this newly built 4 bedroom, 4.5 bath treasure. Perched in the mo ...
From $939 per night (USD)Expedia
From $1197 per night (USD)VRBO
Beach Escape! Luxury Home with Pool, Spa, Rooftop Deck and Walk to Beach
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Beach Escape by AMI Locals VR18-000090 Welcome to Beach Escape, a stunning five-bedroom, four-bath luxury home just o ...
From $1197 per night (USD)VRBO
From $336 per night (USD)Expedia
Hidden Oasis - DIRECT BEACHFRONT DUPLEX - 1BR/1BA Anna Maria - By Island Real Es
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Hidden Oasis is beautiful 1-bedroom 1-bathroom duplex that’s perfect for an island stay. The décor will make you feel ri ...
From $336 per night (USD)Expedia
From $587 per night (USD)VRBO
BEST LOCATION! NORTH END OF ANNA MARIA, FL , STEPS TO BEACH & DINING - UNIT A
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Green Jacaranda Unit A (Downstairs Unit) - 2 bedroom/1 bath Duplex on the North End of Anna Maria , Bean Point Beach les ...
From $587 per night (USD)VRBO
From $599 per night (USD)Expedia
The Salty Beach Cottage: North end canal front pool home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to The Salty Beach Cottage, a comfortable and inviting family vacation home. Decorated with a refreshing palette ...
From $599 per night (USD)Expedia
From $413 per night (USD)VRBO
Briney Breezes - Old Florida living with modern comforts
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
308 TARPON ST. BRINEY BREEZES This three bedroom, three bath dream home is the perfect way to experience all that Anna M ...
From $413 per night (USD)VRBO
From $536 per night (USD)Expedia
Eclectic North end AMI home with Private pool on Canal!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Top Reasons to Book Crazy Mermaid • Waterfront canal views throughout the home • Private pool (heated upon request for a ...
From $536 per night (USD)Expedia
From $820 per night (USD)VRBO
Blue Heron Beach House: Canal-front pool home near Pine Ave.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Blue Heron Beach House! This beautiful, newly renovated home is located in the heart of Anna Maria on a deep ...
From $820 per night (USD)VRBO
From $825 per night (USD)Expedia
Funky Beach Farmhouse: Beautiful Bay views, heated pool, hot tub, lounge area
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
We invite you to come enjoy your vacation at the Funky Beach Farmhouse! This professionally decorated beach house is sur ...
From $825 per night (USD)Expedia
From $743 per night (USD)VRBO
Coconut Cottage by Duncan Real Estate
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Coconut Cottage! This beautiful 3-bedroom, 2-bathroom cottage has 1,620 square feet of elevated living space ...
From $743 per night (USD)VRBO
From $955 per night (USD)Expedia
Spectacular Northshore Anna Maria Home w/ Private Pool – 1 Block to Beach
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
WELCOME TO YOUR ANNA MARIA ISLAND GETAWAY just one block from Anna Maria beach. Enjoy the good life at our inviting AMI ...
From $955 per night (USD)Expedia
From $742 per night (USD)VRBO
Anna Maria Beach Cottage 110 Traditional beach cottage, moments from the sand!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
PLEASE NOTE THE POOL WILL BE CLOSED SEPTEMBER 14 - OCTOBER 5, 2026 FOR RESURFACING. Special rates are being offered dur ...
From $742 per night (USD)VRBO
From $475 per night (USD)Expedia
Anna Maria Beach Cottage 109G Old-Florida beach cottage,moments from the sand!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
PLEASE NOTE THE POOL WILL BE CLOSED SEPTEMBER 14 - OCTOBER 5, 2026 FOR RESURFACING. Special rates are being offered dur ...
From $475 per night (USD)Expedia
From $664 per night (USD)VRBO
Adorable Updated Cottage steps to the beach with pool, beach gear, bikes & grill
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
PLEASE NOTE THE POOL WILL BE CLOSED SEPTEMBER 14 - OCTOBER 5, 2026 FOR RESURFACING. Special rates are being offered dur ...
From $664 per night (USD)VRBO
From $458 per night (USD)Expedia
Anna Maria Beach Cottage 110B Updated studio beach cottage, steps to the sand!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
PLEASE NOTE THE POOL WILL BE CLOSED SEPTEMBER 14 - OCTOBER 5, 2026 FOR RESURFACING. Special rates are being offered dur ...
From $458 per night (USD)Expedia
From $662 per night (USD)VRBO
Sassy Seagull -Classic beach cottage, moments from the sand, beautiful pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
PLEASE NOTE THE POOL WILL BE CLOSED SEPTEMBER 14 - OCTOBER 5, 2026 FOR RESURFACING. Special rates are being offered dur ...
From $662 per night (USD)VRBO
From $485 per night (USD)Expedia
Anna Maria Beach Cottage 107A Pool, bikes, beach gear, moments from the sand!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
PLEASE NOTE THE POOL WILL BE CLOSED SEPTEMBER 14- OCTOBER 5, 2026 FOR RESURFACING. Special rates are being offered duri ...
From $485 per night (USD)Expedia
From $494 per night (USD)VRBO
Charming beach cottage close to the beach with Pool, Bikes, Beach gear and Grill
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
PLEASE NOTE THE POOL WILL BE CLOSED SEPTEMBER 14 - OCTOBER 5, 2026 FOR RESURFACING. Special rates are being offered dur ...
From $494 per night (USD)VRBO
From $472 per night (USD)Expedia
Anna Maria Updated Studio moments from the sand w/ Pool, Beach Gear & Bikes
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
PLEASE NOTE THE POOL WILL BE CLOSED SEPTEMBER 14 - OCTOBER 5, 2026 FOR RESURFACING. Special rates are being offered dur ...
From $472 per night (USD)Expedia
From $581 per night (USD)VRBO
Charming Cottage with modern amenities close to beach w/ pool, beach gear, bikes
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
PLEASE NOTE THE POOL WILL BE CLOSED SEPTEMBER 14 - OCTOBER 5, 2026 FOR RESURFACING. Special rates are being offered dur ...
From $581 per night (USD)VRBO
From $835 per night (USD)Expedia
Flirty Flamingo Cottage Updated beach cottage, moments from the sand, w/pool!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
PLEASE NOTE THE POOL WILL BE CLOSED SEPTEMBER 14 - OCTOBER 5, 2026 FOR RESURFACING. Special rates are being offered dur ...
From $835 per night (USD)Expedia
From $494 per night (USD)VRBO
Anna Maria Beach Cottage 110G Updated beach cottage, with pool and beach gear!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
PLEASE NOTE THE POOL WILL BE CLOSED SEPTEMBER 14 - OCTOBER 5, 2026 FOR RESURFACING. Special rates are being offered dur ...
From $494 per night (USD)VRBO
From $8594 per night (USD)Expedia
Charming cottage with heated pool, tropical landscaping in prime location.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Starfish Cottage has been recently renovated while maintaining all the charm of an old Florida Key West style bungal ...
From $8594 per night (USD)Expedia
From $1792 per night (USD)VRBO
Impressive Luxury Home steps to the Beach! Great Pool and Spa! - Grande Haven
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 18
Grande Haven by AMI Locals VR18-000049 *Grande Haven is currently undergoing major renovations, bringing fresh upgrade ...
From $1792 per night (USD)VRBO
From $311 per night (USD)Expedia
Coconut Bayou by Duncan Real Estate
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to The Bayou 5C! With a prime location the north side of Pine Avenue on Anna Maria Island. The Bayou 5C is the ...
From $311 per night (USD)Expedia
From $499 per night (USD)VRBO
Beach Pearl - Private Pool Home - By Island Real Estate Vacations
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Just a short stroll from Gulf of Mexico beaches, Anna Maria vacation rental “Beach Pearl” offers a luxurious getaway exp ...
From $499 per night (USD)VRBO
From $1316 per night (USD)Expedia
Tern Key - Luxury Canal-Front Home w/ Heated Pool, Spa, Dock & Near Bean Point
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Tern Key! On Anna Maria Island (Anna Maria, FL) The Space Tern Key is a home that feels both artful and effo ...
From $1316 per night (USD)Expedia
From $1007 per night (USD)VRBO
Modern Beach House with excellent location
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Direct Beach Access, fully renovated beach house. Brand new pool renovated in 2026, Main floor master suite that walks o ...
From $1007 per night (USD)VRBO
From $1062 per night (USD)Expedia
Pink Palm: Dog-friendly, 6-bedroom, 3-min walk to beach!
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 14
Pink Palm is one of the most impressive vacation rentals on Anna Maria Island! The home is located just a half a block a ...
From $1062 per night (USD)Expedia
From $1424 per night (USD)VRBO
Still Waters Beach House- A north end tropical getaway.
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 14
Welcome to Still Waters Beach House! Come rest and be refreshed in one of the most family friendly and spacious (3600+ S ...
From $1424 per night (USD)VRBO
From $558 per night (USD)Expedia
BEST LOCATION! NORTH END OF ANNA MARIA, FL , STEPS TO BEACH & DINING , UNIT B
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Green Jacaranda Unit B (Upstairs Unit) - 2 bedroom/1 bath Duplex on the North End of Anna Maria , Bean Point Beach less ...
From $558 per night (USD)Expedia