Anna Maria Rentals
From $282 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 $282 per night (USD)VRBO
From $326 per night (USD)Expedia
Beachside Retreat with Pool, Patio and Walk to Pine Ave
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Sand and Sea 111 B by Anna Maria Island Accommodations 111 Magnolia Ave, Unit B, Anna Maria, FL 34216 VR16-000423 We ...
From $326 per night (USD)Expedia
From $496 per night (USD)VRBO
Private Home with Heated Pool and Screened Lanai, 2 Houses to Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- 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 $496 per night (USD)VRBO
From $537 per night (USD)Expedia
Luxury home near the beach and shopping! Private backyard and pool!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Highlights • 2-minute walk from the beach • Private Pool • Near free Anna Maria Island Trolley stop • Outdoor living spa ...
From $537 per night (USD)Expedia
From $1043 per night (USD)VRBO
Sea La Vie Beach House - Luxurious 4BR Home W/ Pool, Spa, Dock, & Canal Access on Anna Maria Island
- Bedrooms:
- 4
- 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 $1043 per night (USD)VRBO
From $454 per night (USD)Expedia
Anna Maria Island, NORTH END 3 bedroom, pet friendly, private pool home!
- Bedrooms:
- 2
- Bathrooms:
- 3
- 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 $454 per night (USD)Expedia
From $625 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 $625 per night (USD)VRBO
From $578 per night (USD)Expedia
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 $578 per night (USD)Expedia
From $805 per night (USD)VRBO
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 $805 per night (USD)VRBO
From $336 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 $336 per night (USD)Expedia
From $490 per night (USD)VRBO
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 $490 per night (USD)VRBO
From $818 per night (USD)Expedia
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 $818 per night (USD)Expedia
From $263 per night (USD)VRBO
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 $263 per night (USD)VRBO
From $860 per night (USD)Expedia
September Golf Cart Special
- 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 $860 per night (USD)Expedia
From $561 per night (USD)VRBO
September Golf Cart Special
- 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 $561 per night (USD)VRBO
From $440 per night (USD)Expedia
September Golf Cart Special
- 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 $440 per night (USD)Expedia
From $420 per night (USD)VRBO
September Golf Cart Special
- 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 $420 per night (USD)VRBO
From $663 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 $663 per night (USD)Expedia
From $718 per night (USD)VRBO
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 $718 per night (USD)VRBO
From $357 per night (USD)Expedia
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 Bradenton Beach Bayside Retreat with Pool VR18-000088 Welcome to Bays ...
From $357 per night (USD)Expedia
From $758 per night (USD)VRBO
Condo Close to Shops, Beach, Restaurants! - Blissful Bay at Bayside Bungalow
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Blissful Bay at Bayside Bungalow by AMI Locals Bradenton Beach Vacation Condo 201 S Bay Blvd, Unit #4, Bradenton Beach ...
From $758 per night (USD)VRBO
From $373 per night (USD)Expedia
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 Anna Maria Island Bayside Condo with Pool VR18-000088 Welcome t ...
From $373 per night (USD)Expedia
From $816 per night (USD)VRBO
Charming North-End Retreat with Pool, Spa and Private Suite
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Blue Pearl by AMI Locals Charming North-End Retreat with Pool, Spa and Private Suite 411 Spring Ave Anna Maria, Florid ...
From $816 per night (USD)VRBO
From $634 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 $634 per night (USD)Expedia
From $403 per night (USD)VRBO
Remodeled Coastal Retreat in Anna Maria, FL – Steps from the Beach!
- 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 $403 per night (USD)VRBO
From $830 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 $830 per night (USD)Expedia
From $895 per night (USD)VRBO
180-degree water views! Shared pool and laundry - Bay Vista at Bayside Bungalow
- Bedrooms:
- 2
- Bathrooms:
- 3
- 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 $895 per night (USD)VRBO
From $625 per night (USD)Expedia
Beautiful Bungalow! Enjoy Resort-Style Pool Steps from the Bay and Pine Ave!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Bay Breezes at Bayside Bungalow by AMI Locals Bradenton Beach Bayside Retreat with Pool VR18-000088 Welcome to Bay Br ...
From $625 per night (USD)Expedia
From $583 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 $583 per night (USD)VRBO
From $626 per night (USD)Expedia
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 $626 per night (USD)Expedia
From $321 per night (USD)VRBO
Heated Pool, FREE WiFi, Close to Beach, Dock your Boat, Dog Friendly See Note!
- 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 $321 per night (USD)VRBO
From $454 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 $454 per night (USD)Expedia
From $884 per night (USD)VRBO
1 block from the Beach w/Pool, Spa, & Game Room -Castaway Cove
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Castaway Cove by AMI Locals Home in Anna Maria, Florida VR16-000471 Welcome to Castaway Cove, a canal-front home with ...
From $884 per night (USD)VRBO
From $469 per night (USD)Expedia
September Golf Cart Special
- 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 $469 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 $509 per night (USD)Expedia
September Golf Cart Special
- 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 $509 per night (USD)Expedia
From $345 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 $345 per night (USD)VRBO
From $363 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 $363 per night (USD)Expedia
From $827 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 12 people with the add-on of the sleeper sofas. Blue Lagoon ...
From $827 per night (USD)VRBO
From $704 per night (USD)Expedia
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 $704 per night (USD)Expedia
From $1031 per night (USD)VRBO
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 $1031 per night (USD)VRBO
From $687 per night (USD)Expedia
September Golf Cart Special
- 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 $687 per night (USD)Expedia
From $1345 per night (USD)VRBO
Luxury island home with a private pool and spa - close to beach!
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 14
A Wave from it All by AMI Accommodations Home in Anna Maria, FL Highlights: • 5-minute walk from the Beach • Private Po ...
From $1345 per night (USD)VRBO
From $284 per night (USD)Expedia
Waterfront Bay Home with Dock Near Pier and Pine Ave
- 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)Expedia
From $473 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 $473 per night (USD)VRBO
From $667 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 $667 per night (USD)Expedia
From $495 per night (USD)VRBO
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 $495 per night (USD)VRBO
From $711 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 $711 per night (USD)Expedia
From $721 per night (USD)VRBO
September Golf Cart Special
- 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 $721 per night (USD)VRBO
From $491 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 $491 per night (USD)Expedia
From $2084 per night (USD)VRBO
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 $2084 per night (USD)VRBO
From $538 per night (USD)Expedia
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 $538 per night (USD)Expedia
From $490 per night (USD)VRBO
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 $490 per night (USD)VRBO
From $752 per night (USD)Expedia
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 $752 per night (USD)Expedia
From $397 per night (USD)VRBO
AMI North End Private Heated Pool. 1.2 blocks to beach!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
What You’ll Love About This House: Location! 1.2 blocks to the Beach and steps away from the Free Trolley. Clean No Stai ...
From $397 per night (USD)VRBO
From $752 per night (USD)Expedia
Beautiful Beach House, Pool, Spa, Water Views! Great Location! - AMI I Dreaming
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
AM I Dreaming by AMI Locals Home in Anna Maria VR19-000055 Welcome to AM I Dreaming, a luxurious three bedrooms and ...
From $752 per night (USD)Expedia
From $405 per night (USD)VRBO
Amazing dog-friendly duplex near beach with private lanai, W/D, patio & WiFi
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
21 Palms on Anna Maria Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $405 per night (USD)VRBO
From $518 per night (USD)Expedia
Mermaid House Rooftop deck, Gulf views, beautiful home, steps to the sand!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
If you love this rental but are not getting a quote with the dates you've selected contact us so we can check the avail ...
From $518 per night (USD)Expedia
From $209 per night (USD)VRBO
Dog-friendly family home with WiFi, central AC, private W/D - close to beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
21 Palms Unit A Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $209 per night (USD)VRBO
From $909 per night (USD)Expedia
Our Great Escape by Duncan Real Estate
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
This beautiful luxury pool home is one of a kind in a secluded prestigious North end location directly on the canal with ...
From $909 per night (USD)Expedia
From $721 per night (USD)VRBO
Unique Island Home on the beach block! Private pool!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Blue Crush by Anna Maria Island Accommodations Home in Anna Maria, Florida VR21-000015 Welcome to Blue Crush, a fan ...
From $721 per night (USD)VRBO
From $530 per night (USD)Expedia
Anna Maria island 3 bedroom, private pool and pet friendly!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Coconut Bayou is a 3 bedroom, 3.5 bath Key West style beauty with all the comforts you may think of. Just a few minutes ...
From $530 per night (USD)Expedia
From $509 per night (USD)VRBO
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 $509 per night (USD)VRBO
From $699 per night (USD)Expedia
Anna Maria Home with Saltwater Pool Near Beaches & Shopping - Sunrise Shore
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 11
Sunrise Shore by Anna Maria Island Locals Duplex in Anna Maria, FL Welcome to Sunrise Shore, your dream Anna Maria Isl ...
From $699 per night (USD)Expedia
From $1075 per night (USD)VRBO
Large Canal Front Family Rental on Anna Maria with Pool, Dock & Mini Golf!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 13
Serenity Beach by AMI Locals Home in Anna Maria, Florida VR16-000464 Welcome to Serenity Beach! This stunning canal-f ...
From $1075 per night (USD)VRBO
From $869 per night (USD)Expedia
Brand New Putting Green! Close to beach!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Blue Marlin by AMI Locals Home in Anna Maria, FL Highlights • 10-minute walk from the Beach • Private Pool and Hot Tub ...
From $869 per night (USD)Expedia
From $334 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 $334 per night (USD)VRBO
From $570 per night (USD)Expedia
Canal-front Gem w/ Pool & Hot Tub in Anna Maria
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Escape to the sandy shores of Anna Maria Island at ‘Easy Breezy’, a recently renovated canalfront vacation rental cottag ...
From $570 per night (USD)Expedia
From $1130 per night (USD)VRBO
Three Little Birds - Luxury Gulf Views, Heated Pool, Steps to Bean Point on Anna Maria Island
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Three Little Birds! On Anna Maria Island (Anna Maria, FL) Luxury Waterfront Living with Gulf Views, Heated P ...
From $1130 per night (USD)VRBO
From $448 per night (USD)Expedia
3 bedroom on Pine in Anna Maria Island, private pool and PET friendly!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Seashell is 3 bedroom 2 bath second story condo that is set up like a single family home. It features wood floors, a kin ...
From $448 per night (USD)Expedia
From $2330 per night (USD)VRBO
Beachfront Home | Pool + Spa | Games | Ocean Views
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to the exclusive Beachfront Bliss - a custom-built luxury vacation home nestled directly on a sandy beach. This ...
From $2330 per night (USD)VRBO
From $892 per night (USD)Expedia
Visit AMI in Luxury! Pool, Spa, and AMAZING Rooftop Deck Views!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Beach Escape by AMI Locals Home in Anna Maria, FL Highlights • 5-minute walk from the Beach • Private Pool and Hot Tub ...
From $892 per night (USD)Expedia
From $651 per night (USD)VRBO
1 block to the beach! Adorable bungalow with Pool and Spa, great for families!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Highlights • 3-minute walk from the Beach • 2-minute walk from Pine Ave • Private Pool and Hot Tub • Dog friendly w ...
From $651 per night (USD)VRBO
From $303 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 $303 per night (USD)Expedia
From $362 per night (USD)VRBO
September Golf Cart Special
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
308 TARPON ST. BRINEY BREEZES This three bedroom, three bath dream home is the perfect way to experience all that Anna M ...
From $362 per night (USD)VRBO
From $418 per night (USD)Expedia
Updated bayside condo with heated pool - across the street from the beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
South Bay Inn 1 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $418 per night (USD)Expedia
From $614 per night (USD)VRBO
September Golf Cart Special
- 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 $614 per night (USD)VRBO
From $755 per night (USD)Expedia
September Golf Cart Special
- 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 $755 per night (USD)Expedia
From $604 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 $604 per night (USD)VRBO
From $282 per night (USD)Expedia
Stylish bayside condo with WiFi & pool - close to the beach & restaurants
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
South Bay Inn 3 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $282 per night (USD)Expedia
From $579 per night (USD)VRBO
Beach House w/ pool on the north end of AMI
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Charming 3 bedroom elevated home with a private pool at 123 Hammock Road in Anna Maria which is only 2 short blocks to t ...
From $579 per night (USD)VRBO
From $551 per night (USD)Expedia
Anna Maria Beach Cottage 110 Traditional beach cottage, moments from the sand!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
This rental is part of the Anna Maria Beach Cottages. More information on this charming property below! Cottage 110 is ...
From $551 per night (USD)Expedia
From $351 per night (USD)VRBO
Anna Maria Beach Cottage 109G Old-Florida beach cottage,moments from the sand!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This rental is part of the Anna Maria Beach Cottages. More information on this charming property below! Cottage 109G is ...
From $351 per night (USD)VRBO
From $560 per night (USD)Expedia
Adorable Cottage moments to beach w/ pool, beach gear, bikes
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This rental is part of the Anna Maria Beach Cottages. More information on this charming property below! Escape to Cotta ...
From $560 per night (USD)Expedia
From $321 per night (USD)VRBO
Anna Maria Beach Cottage 110B Updated studio beach cottage, steps to the sand!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This rental is part of the Anna Maria Beach Cottages. More information on this charming property below! Cottage 110B is ...
From $321 per night (USD)VRBO
From $507 per night (USD)Expedia
Sassy Seagull -Classic beach cottage, moments from the sand, beautiful pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This rental is part of the Anna Maria Beach Cottages. More information on this charming property below! Sassy Seagull C ...
From $507 per night (USD)Expedia
From $367 per night (USD)VRBO
Anna Maria Beach Cottage 107A Pool, bikes, beach gear, moments from the sand!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This rental is part of the Anna Maria Beach Cottages. More information on this charming property below! Cottage 107A is ...
From $367 per night (USD)VRBO
From $538 per night (USD)Expedia
Anna Maria Beach Cottage 109A -Old-Florida beach cottage, steps to the beach!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This rental is part of the Anna Maria Beach Cottages. More information on this charming property below! Cottage 109A i ...
From $538 per night (USD)Expedia
From $515 per night (USD)VRBO
Anna Maria Updated Studio moments from the sand w/ Pool, Beach Gear & Bikes
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This rental is part of the Anna Maria Beach Cottages. More information on this charming property below! Cottage 107G is ...
From $515 per night (USD)VRBO
From $680 per night (USD)Expedia
Charming Cottage with modern amenities close to beach w/ pool, beach gear, bikes
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This rental is part of the Anna Maria Beach Cottages. More information on this charming property below! Cottage 110A i ...
From $680 per night (USD)Expedia
From $943 per night (USD)VRBO
Flirty Flamingo Cottage Updated beach cottage, moments from the sand, w/pool!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This rental is part of the Anna Maria Beach Cottages. More information on this charming property below! Flirty Flaming ...
From $943 per night (USD)VRBO
From $391 per night (USD)Expedia
Anna Maria Beach Cottage 110G Updated beach cottage, with pool and beach gear!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This rental is part of the Anna Maria Beach Cottages. More information on this charming property below! Cottage 110G is ...
From $391 per night (USD)Expedia
From $628 per night (USD)VRBO
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 $628 per night (USD)VRBO
From $209 per night (USD)Expedia
Ground-floor duplex with fast WiFi, central AC & grill
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
21 Palms Unit B Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $209 per night (USD)Expedia
From $453 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 $453 per night (USD)VRBO
From $1277 per night (USD)Expedia
Tern Key - Luxury Canal-Front Home w/ Heated Pool, Spa, Dock, & Close to Bean Point Beaches
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Tern Key! On Anna Maria Island (Anna Maria, FL) Newly Built Luxury Canal-Front Home with Pool, Spa, and Priv ...
From $1277 per night (USD)Expedia
From $1029 per night (USD)VRBO
Impressive Luxury Home steps to the Beach! Great Pool and Spa! - Grande Haven
- Bedrooms:
- 3
- Bathrooms:
- 7
- Sleeps:
- 16
Grande Haven by AMI Locals Home in Anna Maria, Florida VR18-000049 Welcome to Grande Haven, a sleek vacation home direc ...
From $1029 per night (USD)VRBO
From $830 per night (USD)Expedia
September Golf Cart Special
- 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 $830 per night (USD)Expedia
From $877 per night (USD)VRBO
September Golf Cart Special
- 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 $877 per night (USD)VRBO
From $602 per night (USD)Expedia
Fun in the Sun 😎 | Gulf front, steps to the sand, 4-bed with spectacular views!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Recently Updated Vintage Island Beach Front home has 4 sleeping rooms and 2 bathrooms. Enjoy the charm of yesterday in t ...
From $602 per night (USD)Expedia