Anna Maria Rentals
From $1382 per night (USD)VRBO
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 $1382 per night (USD)VRBO
From $590 per night (USD)Expedia
Sunsets on Carissa - Coastal Retreat w/ Heated Pool, Game Room & Steps from Gulf
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Sunsets on Carissa! On Anna Maria Island (Holmes Beach, FL) Experience Sunsets On Carissa – A Modern Coastal ...
From $590 per night (USD)Expedia
From $492 per night (USD)VRBO
Fins Up – AMI Cozy Island Retreat w/ Private Pool & 4-Min Walk To Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Fins Up! On Anna Maria Island (Holmes Beach, FL) Discover Fins Up, An AMI Island Getaway Where A Private Poo ...
From $492 per night (USD)VRBO
From $892 per night (USD)Expedia
Upscale waterfront home, private pool, beautiful views!
- Bedrooms:
- 3
- 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 $892 per night (USD)Expedia
From $464 per night (USD)VRBO
Anna Maria Island!1 Block to the Beach. Private Home with Heated Pool.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Experience the ultimate luxury of this beautiful private home just minutes from the white private sandy beaches of Anna ...
From $464 per night (USD)VRBO
From $320 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 $320 per night (USD)Expedia
From $344 per night (USD)VRBO
Perfect Vacation Home with Private Pool! Close to the Beach! - Gulf Breeze
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Gulf Breeze by AMI Locals 306 65th St, Unit A, Holmes Beach, FL 34217 VRC21-000001 Welcome to Gulf Breeze, a charming ...
From $344 per night (USD)VRBO
From $349 per night (USD)Expedia
Charming Island Pool Home! Walk to Holmes Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Sea Breeze by AMI Locals 306 65th St, Unit B | Holmes Beach, Florida VRC21-000002 Welcome to Sea Breeze, a peaceful ...
From $349 per night (USD)Expedia
From $328 per night (USD)VRBO
Cozy Home with Private Pool, Close to the Beach! Don't Miss Out!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Island Escape by AMI Locals 6506 Holmes Blvd, Holmes Beach, FL 34217 VRC21-000012 Welcome to Island Escape, a charmin ...
From $328 per night (USD)VRBO
From $419 per night (USD)Expedia
Desirable North-End Gem on Canal with Dock, Heated Pool. Clean and Spacious.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Welcome to paradise! Pelican Perch is a spacious, three-bedroom, two-bath house, located on a canal and a quiet cul-de- ...
From $419 per night (USD)Expedia
From $235 per night (USD)VRBO
Newly renovated Cozy Beach Cottage B 1/2 of a duplex, 3min walk to beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to our newly remodeled 2beds/1bath 1/2 of the duplex, just short walk (3-5min)to the white sandy beaches of Anna ...
From $235 per night (USD)VRBO
From $266 per night (USD)Expedia
Newly renovated Cozy Beach Cottage A1/2 of a duplex, 3min walk to beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to our newly remodeled 2beds/1bath 1/2 of the duplex, UNIT A - just short walk (3-5min)to the white sandy beach ...
From $266 per night (USD)Expedia
From $756 per night (USD)VRBO
White Pearl-Premier AMI 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 $756 per night (USD)VRBO
From $321 per night (USD)Expedia
Dog friendly cottage - One block to the Bay!
- Bedrooms:
- 1
- Bathrooms:
- 2
- 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 $321 per night (USD)Expedia
From $551 per night (USD)VRBO
Golf Cart, Island Haven by SeaBreeze Vacation
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
6 PERSON GOLF CART INCLUDED ON ALL RESERVATIONS STAYING DURING 2025! All Drivers must be over the age of 21. Drivers mus ...
From $551 per night (USD)VRBO
From $790 per night (USD)Expedia
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 $790 per night (USD)Expedia
From $855 per night (USD)VRBO
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 $855 per night (USD)VRBO
From $651 per night (USD)Expedia
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 $651 per night (USD)Expedia
From $485 per night (USD)VRBO
Island Oasis: Ground level canal front pool home
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
***Photos Updated July 2025*** Looking to escape to a beautiful tropical oasis? This is the place for you! Refreshed wit ...
From $485 per night (USD)VRBO
From $490 per night (USD)Expedia
Sharks Eye- Original island cottage on historic Pine Ave.
- Bedrooms:
- 1
- Bathrooms:
- 2
- 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 $490 per night (USD)Expedia
From $268 per night (USD)VRBO
Freshly Remodeled Island Suite w/ Pool & Pet Friendly
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Sunrise Garden #1 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $268 per night (USD)VRBO
From $219 per night (USD)Expedia
Perfect Family Vacation home just off the beach! Private Pool!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Island Hideaway by AMI Locals Home in Holmes Beach, FL Features: • Private heated pool • Ground-level home, very access ...
From $219 per night (USD)Expedia
From $732 per night (USD)VRBO
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 $732 per night (USD)VRBO
From $770 per night (USD)Expedia
Discounted April 26th thru May 17th stays w/ Private Pool & Dock!
- Bedrooms:
- 2
- Bathrooms:
- 3
- 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 $770 per night (USD)Expedia
From $409 per night (USD)VRBO
Anna Maria Island Bungalow with Pool! Across the street from Beach, near Pine Av
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Bayside Cutie at Bayside Bungalow by AMI Locals 201 S Bay Blvd, Unit #2, Anna Maria, Fl VR18-000088 Welcome to Baysid ...
From $409 per night (USD)VRBO
From $707 per night (USD)Expedia
Bayside Retreat with Pool and Bay Views! Near Beaches, Shops, and Dining
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Blissful Bay at Bayside Bungalow by AMI Locals 201 S Bay Blvd, Unit #4, Anna Maria, FL 34216 VR18-000088 Welcome to Bli ...
From $707 per night (USD)Expedia
From $521 per night (USD)VRBO
Beautiful Bungalow with Pool and Bay Views! - Barefoot by the Bay at Bayside Bun
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 6
Barefoot by the Bay at Bayside Bungalow by AMI Locals 201 S Bay Blvd, Unit #3, Anna Maria, FL VR18-000088 Welcome to ...
From $521 per night (USD)VRBO
From $696 per night (USD)Expedia
Charming North-End Retreat with Pool, Spa and Private Suite
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Blue Pearl by AMI Locals 411 Spring Ave, Anna Maria, Florida VR19-000007 Welcome to Blue Pearl, a luxurious four ...
From $696 per night (USD)Expedia
From $492 per night (USD)VRBO
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 $492 per night (USD)VRBO
From $467 per night (USD)Expedia
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 $467 per night (USD)Expedia
From $904 per night (USD)VRBO
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 $904 per night (USD)VRBO
From $924 per night (USD)Expedia
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 $924 per night (USD)Expedia
From $998 per night (USD)VRBO
Luxury Beach Home! Pool, Spa & Gourmet Kitchen!
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 8
Fortunate Sol by AMI Locals Anna Maria Luxury Beach Home with Pool, Spa, and Steps to the Gulf VR22-000005 Welcome ...
From $998 per night (USD)VRBO
From $813 per night (USD)Expedia
Bayfront Bliss! Pool, BBQ and Dolphin Views!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Bay Vista at Bayside Bungalow by AMI Locals 201 S Bay Blvd, Unit #5, Anna Maria, FL 34216 VR18-000088 Welcome to Ba ...
From $813 per night (USD)Expedia
From $579 per night (USD)VRBO
Resort-Style Pool Steps from the Bay and Pine Ave!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Bay Breezes at Bayside Bungalow by AMI Locals 201 S Bay Blvd, Unit #1, Anna Maria, FL VR18-000088 Welcome to Bay Bree ...
From $579 per night (USD)VRBO
From $596 per night (USD)Expedia
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 $596 per night (USD)Expedia
From $298 per night (USD)VRBO
Pet-Friendly - Rum Dog by SeaBreeze Vacation
- Bedrooms:
- 2
- Bathrooms:
- 2
- 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 $298 per night (USD)VRBO
From $562 per night (USD)Expedia
Willow Cottage: Steps to the beach, heated pool, perfect location!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
***Photos Updated April 2025*** Welcome to Willow Cottage, a charming sunny cottage just steps to the white sandy beache ...
From $562 per night (USD)Expedia
From $441 per night (USD)VRBO
Great Villa! Just updated, private pool and 1 block to the beach!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
AMI Sunrise by AMI Locals Home in Holmes Beach VRC20-000165 Welcome to AMI Sunrise! This fantastic ground-level home i ...
From $441 per night (USD)VRBO
From $462 per night (USD)Expedia
Lovely 3 bd island cottage with a private pool + close to the beach!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
AMI Sunset by Anna Maria Island Locals Home in Holmes Beach, FL Only 75 yards to the beach! Highlights: • Private back ...
From $462 per night (USD)Expedia
From $634 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 $634 per night (USD)VRBO
From $374 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 $374 per night (USD)Expedia
From $547 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 $547 per night (USD)VRBO
From $401 per night (USD)Expedia
Beautiful AMI Beach House with Pool and Fenced Backyard, Dog Friendly!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Sol y Mar by AMI Locals 221 84th Street, Holmes Beach, FL 34217 VRC21-000118 Welcome to Sol y Mar, a bright and newly ...
From $401 per night (USD)Expedia
From $395 per night (USD)VRBO
Pelican Bay in Anna Maria
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
**ASK ABOUT LAST MINUTE DEALS! A contemporary aesthetic combined with a top-notch location is sure to make Pelican Bay ...
From $395 per night (USD)VRBO
From $405 per night (USD)Expedia
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 $405 per night (USD)Expedia
From $1019 per night (USD)VRBO
Canal front Home with Private Dock, Pool, Games, and Water Adventures
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Castaway Cove by AMI Locals 211 Willow Avenue, Anna Maria, Florida VR16-000471 Experience the ultimate island escape a ...
From $1019 per night (USD)VRBO
From $369 per night (USD)Expedia
One Bedroom Condo at Beachfront Resort!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to Coconuts Courtyard! This amazing condo is located within the iconic Coconuts Beach Resort located directly on ...
From $369 per night (USD)Expedia
From $588 per night (USD)VRBO
Lake La Vista Beach House: Canal front beauty in quiet neighborhood, pool
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Spacious Island Home w/Pool, Steps to Beach Perfect for families and groups, this coastal retreat offers a private pool ...
From $588 per night (USD)VRBO
From $525 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 $525 per night (USD)Expedia
From $764 per night (USD)VRBO
Pet Friendly Bay-Canal Waterfront! Tiki Bar 5BR, 5BA Huge Pool, 2 Kayaks/Bikes
- 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 $764 per night (USD)VRBO
From $404 per night (USD)Expedia
Gulf Place Unit 22 in Holmes Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
**ASK ABOUT LAST MINUTE DEALS! Enjoy a fabulous stay at the beach in this beautifully remodeled two bedroom, two bath u ...
From $404 per night (USD)Expedia
From $532 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 $532 per night (USD)VRBO
From $787 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 $787 per night (USD)Expedia
From $274 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 $274 per night (USD)VRBO
From $1103 per night (USD)Expedia
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 $1103 per night (USD)Expedia
From $666 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 $666 per night (USD)VRBO
From $343 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 $343 per night (USD)Expedia
From $340 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 $340 per night (USD)VRBO
From $744 per night (USD)Expedia
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 12 people with the add-on of the sleeper sofas. Blue Lagoon ...
From $744 per night (USD)Expedia
From $681 per night (USD)VRBO
Pool/Spa - Anchor Splash by SeaBreeze Vacation
- Bedrooms:
- 3
- Bathrooms:
- 4
- 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 $681 per night (USD)VRBO
From $1421 per night (USD)Expedia
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 $1421 per night (USD)Expedia
From $416 per night (USD)VRBO
Blue Palm Paradise: Dog friendly, Pool, 3 Minute Walk to Beach by Anna Maria Life Vacation Rentals
- Bedrooms:
- 3
- 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 $416 per night (USD)VRBO
From $526 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 $526 per night (USD)Expedia
From $492 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 $492 per night (USD)VRBO
From $623 per night (USD)Expedia
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 the Bay beaches, and fa ...
From $623 per night (USD)Expedia
Click For PricingVRBO
Blue Haven Beach House - 3BR Coastal Retreat w/ Heated Pool, Gulf Views & Steps to the Beach
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Blue Haven Beach House! On Anna Maria Island (Holmes Beach, FL) Discover island charm and modern comforts at ...
Click For PricingVRBO
From $353 per night (USD)Expedia
Chic Island Escape with Pool, Spa and Short Walk to the Beach
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Island Princess by AMI Locals 213 84th St, Holmes Beach, FL, 34217 VCR19-000296 Welcome to Island Princess, a beaut ...
From $353 per night (USD)Expedia
From $1302 per night (USD)VRBO
A Wave From It All! 5BR Luxury Home with Pool, Spa, Game Room and Walk to Beach
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 14
A Wave From It All by Anna Maria Island Accommodations 404 Spring Ave, Anna Maria, FL, 34216 VR19-000058 / DWE5105449 ...
From $1302 per night (USD)VRBO
From $475 per night (USD)VRBO
Putting Green - Flip Flops Forever by SeaBreeze Vacation
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Recently renovated! Flip Flops Forever is a traditional Florida home just steps from the beach nestled in the quiet resi ...
From $475 per night (USD)VRBO
From $284 per night (USD)VRBO
Waterfront Charm! Walk to Bayfront Park!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
*As of May 2025, the dock is temporarily unavailable* Bay Haven by AMI Locals 510 South Drive Unit A, Anna Maria, FL ...
From $284 per night (USD)VRBO
From $1844 per night (USD)Expedia
Luxury home just steps away from the beach with pool, spa & rooftop!
- Bedrooms:
- 6
- Bathrooms:
- 7
- Sleeps:
- 14
The Ritz by Anna Maria Island Locals Home in Holmes Beach, FL Highlights: • Rooftop deck • Heated pool and spa • Coffee ...
From $1844 per night (USD)Expedia
From $554 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
This is a beautiful newly remodeled 3-bedroom, 2-bathroom private home situated right on the canal in the quiet, private ...
From $554 per night (USD)VRBO
From $288 per night (USD)Expedia
2 bedroom unit, West of Gulf Drive. Only steps to the beach!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome! This quaint 2-bedroom, 1-bathroom single level home is nestled on Anna Maria Island. The master suite has a ...
From $288 per night (USD)Expedia
From $705 per night (USD)VRBO
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 $705 per night (USD)VRBO
From $527 per night (USD)Expedia
Luxury 4 bedroom, 3 bath private home with a heated pool in the heart of Anna Maria.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This luxury Key West style home has 4-bedrooms and 3-bathrooms and is situated in Anna Maria. The kitchen has lovely gr ...
From $527 per night (USD)Expedia
From $572 per night (USD)VRBO
Naut 2 Shabby Cottage Next-Level Pool Area, Darling FL Cottage - Best of Both!
- 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 $572 per night (USD)VRBO
From $627 per night (USD)Expedia
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 and spa on private drive. Two bedrooms have king sized ...
From $627 per night (USD)Expedia
From $425 per night (USD)VRBO
Sapphire Beach House by Duncan Real Estate
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome back to Sapphire Beach House! Casual yet luxurious, this three-bedroom duplex with a private, heated pool and cl ...
From $425 per night (USD)VRBO
From $444 per night (USD)Expedia
Seabatical -Beachy Chic Canalfront Home with Large Pool, Hot Tub & 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 $444 per night (USD)Expedia
From $496 per night (USD)VRBO
Ideal Family Getaway: Private Pool 2 Mins from the Beach - Lay'By, Too
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Lay'By, Too by AMI Locals Home in Holmes Beach, Florida VRC16-000175 Welcome to Lay'By, Too! This vibrant ground-level ...
From $496 per night (USD)VRBO
From $774 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 $774 per night (USD)Expedia
From $771 per night (USD)VRBO
Yellowfin Inn: Luxury canal-front, pool home on Anna Maria Island
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to The Yellowfin Inn. Our new home away from home. This new construction offers an open floor plan and an awesom ...
From $771 per night (USD)VRBO
From $448 per night (USD)Expedia
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 $448 per night (USD)Expedia
From $315 per night (USD)VRBO
While Away A: Beach Bliss Reimagined
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
VRC16-000510 Modern Charm Meets Island Ease Step into While Away A, where laid-back Florida vibes meet modern elegance ...
From $315 per night (USD)VRBO
From $196 per night (USD)Expedia
WE 106 Lovely Gulf Front 1/1 Pool Condo Relax On Sugar Sand Beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
VRC21-000074 Waters Edge Unit 106S, located at 5806 Gulf Drive in the northern end of Holmes Beach, is a spacious one b ...
From $196 per night (USD)Expedia
From $389 per night (USD)VRBO
Seaside Condo – Pool & Epic Sunset Views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
VRC16-000507 Seaside Beach House #201 located at 102 68th Street in Holmes Beach is a direct Gulf front complex with a ...
From $389 per night (USD)VRBO
From $1273 per night (USD)Expedia
A Shore Thing – AMI Waterfront Home: Pool, Spa, Rooftop, Deck & Dock by Bean Point
- Bedrooms:
- 6
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to A Shore Thing! On Anna Maria Island (Anna Maria, FL) Walk to Pine Ave from this designer 4BR/4.5BA home on A ...
From $1273 per night (USD)Expedia
From $749 per night (USD)VRBO
Sunkissed&Salty: Prime Location!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
No hurricane damage from Helene or Milton! We are welcoming guests for 2025! Dreamy Amenities. Prime Island Location. ...
From $749 per night (USD)VRBO
From $642 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. PLEASE be sensitive to the fact (and ...
From $642 per night (USD)VRBO
From $209 per night (USD)VRBO
Sea Esta 3/2 Duplex Private Pool Close To Tennis Boat Ramp Dining
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
VRC19-000216 Sea-Esta located at 409 63rd St in Holmes Beach is a three bedroom two bathroom, ground level unit, that s ...
From $209 per night (USD)VRBO
From $249 per night (USD)Expedia
WE 102 Beautiful Gulf Front 2/2 Pool Condo Relax On Sugar Sand Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
VRC21-000027 Waters Edge Condo 102N is a newly renovated two bedroom, two bath unit, located at 5808 Gulf Drive in Holm ...
From $249 per night (USD)Expedia
From $830 per night (USD)VRBO
Luxe AMI Stay! Saltwater Pool, Rooftop Views & Walk to Pier
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
AM I Dreaming by AMI Locals 113 N Bay Blvd, Anna Maria, Florida VR19-000055 Welcome to AM I Dreaming, a luxurious ...
From $830 per night (USD)VRBO
From $377 per night (USD)Expedia
The Bungalow on Guava-Pool Home-By Island Real Estate Vacations
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Just a quick flip-flop walk from the beach, you will find this completely updated beach retreat. This private pool bunga ...
From $377 per night (USD)Expedia
From $213 per night (USD)VRBO
Bollinger Duplex A Pet Friendly 2 Bedroom One Block From Beach
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
VRC16-000478 Bollinger Duplex is thoroughly cleaned and sanitized prior to your arrival. We pay special attention to hi ...
From $213 per night (USD)VRBO
From $2004 per night (USD)Expedia
Ground Floor Lakefront Resort, Private Dock, Heated Pool & Spa 🏖️🏖️🏖️🏖️🏖️
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 14
Welcome to AMI Beach Lagoon, your dream vacation on Anna Maria Island! In our lakefront luxury resort (12,500 sqft) we ...
From $2004 per night (USD)Expedia
From $415 per night (USD)VRBO
Resort-Style Ground Floor Suite Heated Pool/Spa 🐢
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Resort-Style Ground Floor Suite, Prime Location, Lakefront, Heated Pool & Spa 🐢 In our lakefront luxury resort (12,500 ...
From $415 per night (USD)VRBO
From $591 per night (USD)Expedia
Lakefront Groundfloor Suite Heated Pool/Spa 🦭🦭🦭
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to the Manatee Suite of AMI Beach Lagoon on Anna Maria Island! In our luxury resort (12,500 sqft) located right ...
From $591 per night (USD)Expedia
From $543 per night (USD)VRBO
Resort-Style Ground Floor Suite On Vista Lake, Heated Pool & Spa 🦤🦤🦤
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to the Pelican Suite of AMI Beach Lagoon on Anna Maria Island! In our lakefront luxury resort (12,500 sqft) we ...
From $543 per night (USD)VRBO
From $409 per night (USD)Expedia
AMI North End Private Heated Pool. 1.2 blocks to 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 $409 per night (USD)Expedia