Anna Maria Rentals
From $384 per night (USD)VRBO
September Golf Cart Special
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Sea grape trees, hibiscus bushes and palm trees surround this pretty white-roofed daffodil-colored cottage that is just ...
From $384 per night (USD)VRBO
From $1846 per night (USD)Expedia
No Tan Lines by Beach Boutique Rentals
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
The ultimate in beach front Florida island living awaits you at No Tan Lines. *Features include* * Ultimate luxury BE ...
From $1846 per night (USD)Expedia
From $497 per night (USD)VRBO
September Golf Cart Special
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Sea Jay is a newly refreshed, canal front pool home located in the heart of Anna Maria! Enter the home through the kitch ...
From $497 per night (USD)VRBO
From $624 per night (USD)Expedia
September Golf Cart Special
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Blue Palm, your next vibrant home-away-from-home here in Anna Maria. Constructed in 2016 by luxury builders M ...
From $624 per night (USD)Expedia
From $360 per night (USD)VRBO
Coquina Cottage B by Duncan Real Estate
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Coquina Cottage B! Coquina Cottage B is exceptionally located at the northern end of Anna Maria Island, just ...
From $360 per night (USD)VRBO
From $1230 per night (USD)Expedia
4 Bed / 4 Bath with Stunning Views of Bimini Bay !
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
You will love Bimini Bay Vue, its breathtaking, unobstructed 180-degree angle views of Bimini Bay are stunning. Complete ...
From $1230 per night (USD)Expedia
From $1194 per night (USD)VRBO
Luxury home with Pool and Spa, Rooftop deck, Water views, Golf cart, and Bikes!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Sweet Caroline by AMI Locals Home in Anna Maria, FL 34216 VR23-000009 Highlights • Private Pool and In-ground Spa • 2-m ...
From $1194 per night (USD)VRBO
From $936 per night (USD)Expedia
Pier to Pier Paradise by Beach Boutique Rentals
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
This stunning 4-bedroom home, aptly named Pier to Pier Paradise, offers breathtaking views of the Bay, luxury amenities, ...
From $936 per night (USD)Expedia
From $740 per night (USD)VRBO
Deja Blu:1 Block to Beach! Tropical Oasis, Poolside Lounge, Pool & Spa by Anna Maria Life
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Deja Blu by Anna Maria Life Vacation Rentals 208 Palm Ave, Anna Maria, FL 34217 What You'll Love About This Home: Locat ...
From $740 per night (USD)VRBO
From $745 per night (USD)Expedia
Meant to Be:1 Block to Beach! North End! Pool & Spa,Loaded Game Room by Anna Maria Life
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Meant to Be by Anna Maria Life Vacation Rentals 804 Jacaranda Rd, Anna Maria, FL 34216 What You'll Love About This Home ...
From $745 per night (USD)Expedia
From $542 per night (USD)VRBO
Mon Ami: Pine Ave Location! Pool! 3 Blocks to Gulf or Bay by Anna Maria Life Vacation Rentals
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
311 Pine Ave, Anna Maria, FL 34216 What You'll Love About This Home: Location! On Pine Ave! 2 Blocks to Beach! 3 Blocks ...
From $542 per night (USD)VRBO
From $819 per night (USD)Expedia
Sea Creatures Cottage: Steps to beach! Putting Green, Rooftop Deck, Pool by Anna Maria Life
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Sea Creatures Cottage by Anna Maria Life Vacation Rentals 112 Mangrove Ave, Anna Maria, FL 34216 What You'll Love About ...
From $819 per night (USD)Expedia
From $1277 per night (USD)VRBO
Coastal home near the shopping district and Gulf beaches
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 8
Cloud Nine on Pine 303 Pine Ave. Anna Maria FL 34216 Welcome to Cloud Nine on Pine, an incredible newly constructed coa ...
From $1277 per night (USD)VRBO
From $392 per night (USD)Expedia
Bay 2 Bay: Bay Across Street! Amazing Views of Bay & Canal, Pool & Lounge by Anna Maria Life
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Bay 2 Bay by Anna Maria Life Vacation Rentals 803 S. Bay Drive, Anna Maria, FL 34216 What You'll Love About This home: ...
From $392 per night (USD)Expedia
From $379 per night (USD)VRBO
Anna Maria Island Direct Beachfront Condo- Awesome View and Amazing Sunsets
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
View dolphins, terns, gulls, sandpipers, and other shorebirds from your 22 foot wide screened lanai. Walk directly out ...
From $379 per night (USD)VRBO
From $925 per night (USD)Expedia
Bean Point Beachfront- Beachfront 4 bedroom private home with pool/spa
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
At A Glance Gulf-Front, Beach side Home Spacious Backyard Deck with Covered Dining Area, TV & Gas BBQ Grill NEW Private ...
From $925 per night (USD)Expedia
From $1196 per night (USD)VRBO
Beautiful Bean Point Home w/ Gulf Views!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
NEW LISTING! Underwent complete INTERIOR REMODEL in Jan 2023!!! This Bean Point beauty is perfect for the family or grou ...
From $1196 per night (USD)VRBO
From $1010 per night (USD)Expedia
The TipSea Turtle managed by Beach Retreats FL Anna Maria Island
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Bay Views! Contactless entry Private heated pool & spa 3 hole mini-putt Parking for 4 Electric vehichle charger Fully Eq ...
From $1010 per night (USD)Expedia
From $877 per night (USD)VRBO
Nirvana:Pool & Hot Tub, Dock, On Canal with Gorgeous Water Views by Anna Maria Life Vacation Rentals
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
235 Oak Ave, Anna Maria, FL 34216 What You'll Love About This Home: Location! On a Canal! 2 Blocks to the Beach! 4 Bedr ...
From $877 per night (USD)VRBO
From $588 per night (USD)Expedia
Soulshine: Dog Friendly! Pool, On a Canal with Dock by Anna Maria Life Vacation Rentals
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Soulshine by Anna Maria Life Vacation Rentals 322 Tarpon Ave, Anna Maria FL, 34216 What You'll Love About This Home: Lo ...
From $588 per night (USD)Expedia
From $371 per night (USD)VRBO
September Golf Cart Special
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Photos Updated March 2025! Welcome to Sandy Cheeks, a luxurious vacation rental house located on the beautiful Anna Mar ...
From $371 per night (USD)VRBO
From $783 per night (USD)Expedia
Anna Belle by Beach Boutique Rentals
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Slip into "island time" immediately and surround yourself with elegance and style in this amazing one-level beauty. The ...
From $783 per night (USD)Expedia
From $1250 per night (USD)VRBO
Summer Strand Resort like pool, close to beach, kayak w/ manatees, Rooftop Deck
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Summer Strand on Anna Maria Island. This new luxury vacation home is perfectly situated a short 5 minute walk ...
From $1250 per night (USD)VRBO
From $1031 per night (USD)Expedia
Playing Hooky: On Canal, Dock, Pool & Spa, Game Room by Anna Maria Life Vacation Rentals
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 14
Playing Hooky by Anna Maria Life Vacation Rentals 513 Loquat Drive, Anna Maria, FL 34216 What You'll Love About This Ho ...
From $1031 per night (USD)Expedia
From $559 per night (USD)VRBO
Villa Maria: 1 Block to Pine! 3 Blocks to Beach! Pool, Ping Pong by Anna Maria Life
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
307 Spring Ave, Anna Maria, FL 34216 What You'll Love About This Home: Location! 3 Blocks to the Beach! 2 Blocks to Bay ...
From $559 per night (USD)VRBO
From $696 per night (USD)Expedia
Once Upon A Tide managed by Beach Retreats FL Anna Maria Island
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Once Upon a Tide! Once Upon A Tide is a fabulous custom design home located on the prestigious North end of ...
From $696 per night (USD)Expedia
From $952 per night (USD)VRBO
Beach a la Mode | Luxury Canal Front Home on AMI w/ Private Pool & Spa
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
Welcome to your dream vacation home on Anna Maria Island - a luxurious 5-bedroom, 4.5-bathroom canal front retreat that ...
From $952 per night (USD)VRBO
From $1094 per night (USD)Expedia
150 Feet to the Beach! Large Beach Home with Heated Pool! - Sunset Paradise
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Sunset Paradise by Anna Maria Vacations 109 Pine Avenue Anna Maria, FL 34216 Get ready to live your dream beach vacatio ...
From $1094 per night (USD)Expedia
From $525 per night (USD)VRBO
Pet Friendly Private Home with Heated Pool, Close to Shopping
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Cabana Breeze by Anna Maria Vacations Home in Anna Maria, Fl 34217 VR16-000457 Dream vacations come true at Cabana Bre ...
From $525 per night (USD)VRBO
From $460 per night (USD)Expedia
Private Home with Pool, Outdoor Dining Area with BBQ! Close to Beach and Pine Av
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Whispering Whale Retreat by Anna Maria Vacations Anna Maria Island Family Retreat with Pool & Beach Access VR16-000195 ...
From $460 per night (USD)Expedia
From $1063 per night (USD)VRBO
Charming Duplex Getaway with Pool, Steps from the Beach
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 8
Sugar Plum Beach by Anna Maria Vacations Charming Duplex Getaway with Pool, Steps from the Beach 114 Mangrove Ave, An ...
From $1063 per night (USD)VRBO
From $605 per night (USD)Expedia
Private Home on North End AMI. Private Heated Pool
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Casa Muratti by Anna Maria Vacations Home in Anna Maria, FL Highlights: -1 King bed, 2 Queens, and 1 Full -Private sal ...
From $605 per night (USD)Expedia
From $865 per night (USD)VRBO
Private Pool, Spa, and Game Room! Short walk to Beach - Absolute Paradise
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 14
Absolute Paradise by Anna Maria Vacations Home in Anna Maria, FL 34216 VR16-000465 Welcome to Absolute Paradise, a beau ...
From $865 per night (USD)VRBO
From $771 per night (USD)Expedia
North End of Anna Maria Island! Private pool, great location.
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Beach Paradise by Anna Maria Island Accommodations Home in Anna Maria, FL Just 3 houses from the Gulf of Mexico beaches ...
From $771 per night (USD)Expedia
From $862 per night (USD)VRBO
Private Home with Private Pool, Outdoor Spa, Game Room, Private Grill, and More!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Antigua Bay by Anna Maria Vacations Home in Anna Maria, FL 34216 VR16-000450 Antigua Bay is a beautiful dog-friendly ho ...
From $862 per night (USD)VRBO
From $573 per night (USD)Expedia
Family-Friendly Canal-Front Home with Pool, Dock, and Games! Close to Beach! - W
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
White Shell by Anna Maria Vacations Anna Maria Island Canal-Front Home with Pool & Dock VRC16-000161 Welcome to White ...
From $573 per night (USD)Expedia
From $423 per night (USD)VRBO
Canalfront Retreat with Saltwater Pool and Private Dock
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Palm Trees and Manatees by Anna Maria Vacations Canalfront Retreat with Saltwater Pool and Private Dock VR16-000462 ...
From $423 per night (USD)VRBO
From $261 per night (USD)Expedia
Short stays available! 5-7 Minute Walk to the Gulf Beaches!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Southern Breeze #1 by Anna Maria Vacations Duplex in Anna Maria, FL 34216 VR16-000199 Welcome to Southern Breeze #1, a ...
From $261 per night (USD)Expedia
From $497 per night (USD)VRBO
Private Pool, Dog Friendly, Cornhole! Short Walk to the Beach - Angelfish
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Angelfish by Anna Maria Vacations VRC16-000003 Welcome to Angelfish, your three-bedroom, two-bathroom ground-level sanc ...
From $497 per night (USD)VRBO
From $730 per night (USD)Expedia
Northend Anna Maria Island. Private Heated Pool
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Lighthouse Lagoon by Anna Maria Vacations Home in Anna Maria, Fl. 34216 VR16-000453 Welcome to Lighthouse Lagoon, a fan ...
From $730 per night (USD)Expedia
From $441 per night (USD)VRBO
Canal Front Home with Dock, Saltwater Pool, Ping Pong - Ama Maria
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Ama Maria by Anna Maria Vacations Home in Anna Maria, FL VR16-000113 Welcome to Ama Maria! This three-bedroom and two ...
From $441 per night (USD)VRBO
From $855 per night (USD)Expedia
Bayfront home with amazing water views! Private pool!! Close to Rod & Reel Pier!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Breakaway by Anna Maria Vacations Home in Anna Maria, FL Highlights: -1 King bed, 1 Queen, 2 Twins, and Twin/Twin Bunk ...
From $855 per night (USD)Expedia
From $1122 per night (USD)VRBO
Direct Beachfront Home, Steps to the Sand! Private Pool, Amenities for All!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
The Big Yellow House on Pine by Anna Maria Vacations Home in Anna Maria, FL 34216 A perfect beach getaway awaits at T ...
From $1122 per night (USD)VRBO
From $686 per night (USD)Expedia
Island Escape with Pool, EV Charger and Steps to Pine Avenue
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Las Palmas by Anna Maria Vacations Island Escape with Pool, EV Charger and Steps to Pine Avenue 212 Palm Avenue, Anna ...
From $686 per night (USD)Expedia
From $608 per night (USD)VRBO
Private Canal Front Home! Heated Pool and 24 ft Boat Dock! - Tarpon Pointe
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Tarpon Pointe by Anna Maria Vacations Home in Anna Maria, FL 34216 VR16-000430 Your dream vacation starts at Tarp ...
From $608 per night (USD)VRBO
From $559 per night (USD)Expedia
Close to the Beach with Pool n Ping Pong Table! Pelican Villa
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Pelican Villa by Anna Maria Vacations Home in Anna Maria, FL 34216 VR16-000467 Welcome to Pelican Villa, an elevated th ...
From $559 per night (USD)Expedia
From $702 per night (USD)VRBO
Single Level Beach Home, 5 Minutes to the Sand! Private Heated Pool
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Sunshine Reef by Anna Maria Vacations Home in Anna Maria, Fl 34216 VR16-000425 Experience the perfect family getaway at ...
From $702 per night (USD)VRBO
From $811 per night (USD)Expedia
Bayfront Home with Beach Access and Pool! - Beach House 404
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Beach House 404 by Anna Maria Vacations Bayfront Anna Maria Island Home with Pool VR16-000192 Welcome to Beach House ...
From $811 per night (USD)Expedia
From $266 per night (USD)VRBO
Heated Pool. Short stays available!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Southern Breeze #5 by Anna Maria Vacations Duplex in Anna Maria, FL 34216 VR16-000199 Welcome to Southern Breeze #5, a ...
From $266 per night (USD)VRBO
From $710 per night (USD)Expedia
Coastal Retreat with Beach Views, Pool and Serene Outdoor
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
Ocean Sunset by Anna Maria Vacations Coastal Retreat with Beach Views, Pool and Serene Outdoor Living 109 Oak Avenue, ...
From $710 per night (USD)Expedia
From $484 per night (USD)VRBO
Charming cottage located close to beach - private heated pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Tree Top Bungalow by Anna Maria Vacations Home in Anna Maria, Fl. 34216 VR16-000079 Tree Top Bungalow combines the best ...
From $484 per night (USD)VRBO
From $268 per night (USD)Expedia
Near Bean Point!! Short stays available! Heated Pool
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Southern Breeze #3 by Anna Maria Vacations Duplex in Anna Maria, FL 34216 VR16-000199 Welcome to Southern Breeze #3, a ...
From $268 per night (USD)Expedia
From $986 per night (USD)VRBO
Large Private Beach Home. Private Pool and Spa, Outdoor Lighting
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Southern Exposure by Anna Maria Vacations Home in Anna Maria, FL VRC16-000065 Highlights • Less than a 10-minute walk ...
From $986 per night (USD)VRBO
From $243 per night (USD)Expedia
Short stays available! Located on North End of Island.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Southern Breeze #4 by Anna Maria Vacations Duplex in Anna Maria, FL 34216 VR16-000199 Welcome to Southern Breeze #4, a ...
From $243 per night (USD)Expedia
From $443 per night (USD)VRBO
Canal Front Home with Private Dock, Saltwater Pool, Kayaks - Magnolia Breeze
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Magnolia Breeze by Anna Maria Vacations Home in Anna Maria, FL 34216 VR16-000454 Escape to the serenity of Magnolia ...
From $443 per night (USD)VRBO
From $263 per night (USD)Expedia
Bungalow with Community Pool, Laundry, and BBQ - Southern Breeze #2
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Southern Breeze #2 by Anna Maria Vacations Duplex in Anna Maria, FL 34216 VR16-000199 Welcome to Southern Breeze #2, a ...
From $263 per night (USD)Expedia
From $406 per night (USD)VRBO
North End Home w/backyard close to the beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Sea Esta by Anna Maria Vacations Home in Anna Maria, FL 34216 VR22-000085 Welcome to Sea Esta, a refreshed beach getawa ...
From $406 per night (USD)VRBO
From $749 per night (USD)Expedia
Dog friendly and located in the heart of Anna Maria! Near the Beach and Pine Ave
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The Hideaway by AMI Locals Anna Maria Island Classic Beach Cottage with Pool & Water Activities VR16-000481 Welcome t ...
From $749 per night (USD)Expedia
From $519 per night (USD)VRBO
Private Duplex, 1 Minute from the Beach! Heated Pool, Beautiful Updates
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Sugar Plum Beach East by Anna Maria Vacations Duplex in Anna Maria, 34216 VRC18-000058 Relaxation and memorable beach d ...
From $519 per night (USD)VRBO
From $528 per night (USD)Expedia
Heated Pool, Gas Grill, 1 Minute Walk to Beach! Updated Throughout
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Sugar Plum Beach West by Anna Maria Vacations Home in Anna Maria, FL 34216 VRC18-000058 Welcome to Sugar Plum Beach Wes ...
From $528 per night (USD)Expedia
From $257 per night (USD)VRBO
Beach Cottage Close to Beach with Community Pool and Grill - Southern Breeze #6
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Southern Breeze 6 by Anna Maria Vacations Duplex in Anna Maria, FL 34216 VR16-000199 Escape to Southern Breeze #6, you ...
From $257 per night (USD)VRBO
From $580 per night (USD)Expedia
Anna Margaritas by Beach Boutique Rentals
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to your new favorite Anna Maria Island escape. With its prime location and incredible amenities, Anna Margaritas ...
From $580 per night (USD)Expedia
From $556 per night (USD)VRBO
Idyll Tides by Beach Boutique Rentals
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Discover the ultimate island retreat you've been dreaming of ~ Idyll Tides ~ a stunning vacation home nestled on the nor ...
From $556 per night (USD)VRBO
From $598 per night (USD)Expedia
Canal-Front Oasis with Private Dock, Pool, Near Beach & Shops - Aqua Cove
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Aqua Cove by Anna Maria Vacations Home in Anna Maria, FL 34216 VR16-000429 Welcome to Aqua Cove, a dream retreat for fa ...
From $598 per night (USD)Expedia
From $508 per night (USD)VRBO
Beach Front Home with Beautiful Sunset Views
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Shells and Sunshine by Anna Maria Vacations Private Home in Anna Maria, FL Highlights: -On our Professional Linen Servi ...
From $508 per night (USD)VRBO
From $500 per night (USD)Expedia
Golf Cart, Simpatico by SeaBreeze Vacation
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS! All drivers must be over the age of 21. Drivers must provide valid ...
From $500 per night (USD)Expedia
From $1537 per night (USD)VRBO
Salty Sister: Stunning Beachfront Vacation Home with Heated Pool, Steps from Anna Maria Island Beach
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Salty Sister, the pinnacle of coastal luxury on Anna Maria Island, where the crystal-clear waters of the Gulf ...
From $1537 per night (USD)VRBO
From $711 per night (USD)Expedia
AMI Lucky: North End! Pool! by Anna Maria Life Vacation Rentals
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
AMI Lucky by Anna Maria Life Vacation Rentals 524 South Drive, Anna Maria, FL 34216 What You'll Love About This House: ...
From $711 per night (USD)Expedia
From $1113 per night (USD)VRBO
An \"Old Florida\" home, with private, sandy beach and sparkling green/blue water.
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
ENJOY PARADISE AT THIS UNIQUE, "OLD FLORIDA" HOME, NEWLY REMODELED, TO SHOW OFF ITS FLORIDA CHARM, LOCATED DIRECTLY ON ...
From $1113 per night (USD)VRBO
From $241 per night (USD)Expedia
Adorable home near the beach! - Bo's Beach Bungalow
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Bo's Beach Bungalow by Anna Maria Island Accommodations Home in Anna Maria, FL 34216 Welcome to Bo's Beach Bungalow, a ...
From $241 per night (USD)Expedia
From $744 per night (USD)VRBO
A Charming Beach Cottage on Elm - 2 min walk to Gulf Beaches
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
A Charming Beach Cottage on Elm by AMI Locals Home in Anna Maria, FL 34216 Welcome to A Charming Beach on Elm! This coa ...
From $744 per night (USD)VRBO
From $413 per night (USD)Expedia
Thrill of the Chase: Canal, Dock, Pool, Spa
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
325 Hardin Ave, Anna Maria, FL 34216 What You'll Love About This Home: Location! 3 Blocks to the Beach! On a Canal! 3 Be ...
From $413 per night (USD)Expedia
From $702 per night (USD)VRBO
Gulf-View Villa, Swim Spa and Walk to Sandbar
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
Villa Del Sol by Anna Maria Vacations Anna Maria Vacation Home 110 Spring Ave, Anna Maria, FL 34216 Welcome to Villa ...
From $702 per night (USD)VRBO
From $1161 per night (USD)Expedia
Elevated North-End Home Near the Beach!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Sunshine State of Mind by AMI Locals Anna Maria Island Beachfront Home with Gulf Views VR16-000484 Experience panoram ...
From $1161 per night (USD)Expedia
From $716 per night (USD)VRBO
Ocean Minded by Beach Boutique Rentals
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to your dream beach retreat - Ocean Minded - where barefoot luxury meets effortless island living. *Features in ...
From $716 per night (USD)VRBO
From $494 per night (USD)Expedia
Limelight by Beach Boutique Rentals
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Discover Limelight, a stunning 3 bedroom vacation home perfectly situated on the picturesque north end of Anna Maria, ju ...
From $494 per night (USD)Expedia
From $736 per night (USD)VRBO
Bean Point North End Private Home. Large Heated Pool. Steps to beach.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Anna Maria Chateau is a well appointed coastal home located just a quick walk from the beach/Bean Point. Walk to the loc ...
From $736 per night (USD)VRBO
From $533 per night (USD)Expedia
Anna Maria Guest House 401- 3 bedrooms in the middle of everything
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Highlights Less than a 10-minute walk to the beach Private Pool Spacious 2,000 sq. ft. condo on Pine Avenue. Convenient ...
From $533 per night (USD)Expedia
From $580 per night (USD)VRBO
September Golf Cart Special
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Photos Updated March 2025! Escape to the secluded paradise of Coconut Cove on Anna Maria Island, a 3-bedroom, 3-bathroo ...
From $580 per night (USD)VRBO
From $1123 per night (USD)Expedia
Manatee Lookout: Canal Front, Pool, Spa, Dock, Putting Green by Anna Maria Life Vacation Rentals
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Manatee Lookout by Anna Maria Life Vacation Rentals 214 Oak Ave, Anna Maria, FL 34216 What You'll Love About This Home: ...
From $1123 per night (USD)Expedia
From $678 per night (USD)VRBO
Villa Rozafa\n Cozy,spacious,walking distance from downtown white sandy beach.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Villa Rozafa Very comfortable plenty of space walking distance from restaurants bar and also beautiful and gorgeous whit ...
From $678 per night (USD)VRBO
From $1062 per night (USD)Expedia
Coconut Hut: Pool & Spa, Pool Table, Putting Green by Anna Maria Life Vacation Rentals
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Coconut Hut by Anna Maria Life Vacation Rentals 213 Coconut Ave, Anna Maria, FL 34217 What You'll Love About This Home: ...
From $1062 per night (USD)Expedia
From $498 per night (USD)VRBO
Dock Holiday: On Canal, Pool & Spa by Anna Maria Life Vacation Rentals
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Dock Holiday by Anna Maria Life Vacation Rentals 235 Chilson Ave, Anna Maria, FL 34216 What You'll Love About This Home ...
From $498 per night (USD)VRBO
From $809 per night (USD)Expedia
West O' Gulf, amazing location, steps to beach and fun on AMI
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to West O' Gulf. This property suffered minimal damage from hurricanes Helene and Milton and is better than eve ...
From $809 per night (USD)Expedia
From $1333 per night (USD)VRBO
Tropical gem near beach with amazing Gulf view, pool, spa, game room & roof deck
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Tropical Gulf View Estate Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ent ...
From $1333 per night (USD)VRBO
From $453 per night (USD)Expedia
Canal Place: Boat Dock, Pool & Spa, On Canal by Anna Maria Life Vacation Rentals
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
238 Chilson Ave, Anna Maria, FL 34216 What You'll Love About This Home: Location! 2 Blocks to Gulf Beach! On a Canal! 3 ...
From $453 per night (USD)Expedia
From $250 per night (USD)VRBO
Gone Coastal: *3 mins to beach *Pet-Friendly *Budget-friendly
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Gone Coastal, a budget-friendly retreat perfect for your vacation. This affordable, 2-bedroom, 2-bathroom hom ...
From $250 per night (USD)VRBO
From $811 per night (USD)Expedia
Sentimental Sunset: Pool & Spa, Near Bean Point & Pine! by Anna Maria Life Vacation Rentals
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Sentimental Sunset by Anna Maria Life Vacation Rentals 755 Jacaranda Rd, Anna Maria, FL 34216 What You'll Love About Th ...
From $811 per night (USD)Expedia
From $636 per night (USD)VRBO
Golf Cart, Stonehenge by SeaBreeze Vacation
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS! All drivers must be over the age of 21. Drivers must provide valid ...
From $636 per night (USD)VRBO
From $514 per night (USD)Expedia
Coral Cove: Walk to the Beach! Heated pool! Prime North End!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
*Features include* * Prime north end location! Bean Point! * Walk to the beach! * Private, saltwater heated pool * Larg ...
From $514 per night (USD)Expedia
Click For PricingVRBO
North Beach Village 40 - 3BR Townhome - Anna Maria Island - By Island Real Estat
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Experience the magic of Anna Maria Island with our stunning vacation rental, "Sans Souci - North Beach Village 40." This ...
Click For PricingVRBO
Click For PricingExpedia
Periwinkle Getaway: 2 Blocks to the Beach, Private Pool by Anna Maria Life Vacation Rentals
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
207 Periwinkle Plaza, Anna Maria, FL 34216 What You'll Love About This Home: Location! 1.5 Blocks to the Beach! 3 Bedroo ...
Click For PricingExpedia
From $715 per night (USD)VRBO
4/3 Canal front oasis with Private heated pool & dock
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
You won't be disappointed with this newly renovated beach house! This 4-bedroom, 3-bathroom home is located in the hea ...
From $715 per night (USD)VRBO
From $725 per night (USD)VRBO
*NEWLY RENOVATED* Boutique Spanish-Style Villa - perfect for family & friends
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This unique, beautifully appointed Boutique Spanish Style Villa on the North End of Anna Maria Island is a perfect getaw ...
From $725 per night (USD)VRBO
From $395 per night (USD)VRBO
The Wee Cottage | House in Anna Maria
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The Wee Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $395 per night (USD)VRBO
From $456 per night (USD)Expedia
Anna Maria Aloha – Beach Block Cottage, Steps to Gulf, Outdoor Living, Pet OK
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Anna Maria Aloha! On Anna Maria Island (Anna Maria, Florida) Highlights - Prime Location: Beach block, only ...
From $456 per night (USD)Expedia
From $537 per night (USD)VRBO
September Golf Cart Special
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Escape to The Poop Deck, an enchanting 4-bedroom, 3.5-bathroom A-frame haven on Anna Maria Island. Its charming design a ...
From $537 per night (USD)VRBO
From $543 per night (USD)Expedia
Canal front with Dock and Pool -Honeywood House
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Honeywood House by Anna Maria Island Accommodations Home in Anna Maria, Florida Relaxation and adventure await you at ...
From $543 per night (USD)Expedia
From $495 per night (USD)VRBO
Welcome to Gulf Shore Cottage!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Gulf Shore Cottage by Anna Maria Island Accommodations Cottage in Anna Maria, Florida VR16-000101 Your dream beach vac ...
From $495 per night (USD)VRBO
From $890 per night (USD)Expedia
Canal-Front Escape: Pool, Dock and Walk to Beach
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Acquaviva by Anna Maria Island Accommodations 310 Tarpon St, Anna Maria, Florida Welcome to Acquaviva, a stunning ca ...
From $890 per night (USD)Expedia