Anna Maria Rentals
From $708 per night (USD)VRBO
Seabatical | Beachy Chic Canalfront Home with Large Pool, Hot Tub & Dock!
- Bedrooms:
- 2
- Bathrooms:
- 3
- 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 $708 per night (USD)VRBO
From $532 per night (USD)Expedia
Sea 'Esta in Anna Maria, FL
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Sea'Esta on gorgeous Anna Maria Island! Sea'Esta is a ground level Home that offers all the luxuries and comf ...
From $532 per night (USD)Expedia
From $1916 per night (USD)VRBO
Ground Floor Lakefront Resort, Private Dock, Heated Pool & Spa 🏖️🏖️🏖️🏖️🏖️
- Bedrooms:
- 8
- 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 $1916 per night (USD)VRBO
From $491 per night (USD)Expedia
Resort-Style Ground Floor Suite Heated Pool\/Spa 🐢
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 2
Resort-Style Ground Floor Suite, Prime Location, Lakefront, Heated Pool & Spa 🐢 In our lakefront luxury resort (12,500 ...
From $491 per night (USD)Expedia
From $726 per night (USD)VRBO
Lakefront Groundfloor Suite Heated Pool\/Spa 🦭🦭🦭
- Bedrooms:
- 3
- Bathrooms:
- 4
- 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 $726 per night (USD)VRBO
From $658 per night (USD)Expedia
Resort-Style Ground Floor Suite On Vista Lake, Heated Pool & Spa 🦤🦤🦤
- Bedrooms:
- 3
- Bathrooms:
- 4
- 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 $658 per night (USD)Expedia
From $398 per night (USD)VRBO
AMI North End Private Heated Pool. Great location to beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
You'll fall in love with Diamond Surf's “Old Florida” charm and feel. Our private ground level home means no stairs t ...
From $398 per night (USD)VRBO
From $853 per night (USD)Expedia
Beautiful Beach House, Pool, Spa, Water Views! Great Location! - AMI I Dreaming
- Bedrooms:
- 4
- Bathrooms:
- 4
- 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 $853 per night (USD)Expedia
From $664 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 $664 per night (USD)VRBO
From $728 per night (USD)Expedia
Mermaid House Rooftop deck, Gulf views, beautiful home, steps to the sand!
- Bedrooms:
- 3
- 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 a ...
From $728 per night (USD)Expedia
From $291 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 $291 per night (USD)VRBO
From $1014 per night (USD)Expedia
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 $1014 per night (USD)Expedia
From $570 per night (USD)VRBO
Anna Maria island 3 bedroom, private pool and pet friendly!
- Bedrooms:
- 4
- 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 $570 per night (USD)VRBO
From $1084 per night (USD)Expedia
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 Welcome to Blue Crush, a fantastic vacat ...
From $1084 per night (USD)Expedia
From $420 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
Angel Fish Cottage is on the north, quiet end of Anna Maria Island, removed from condos, hotels, crowds. A short block ...
From $420 per night (USD)VRBO
From $1625 per night (USD)Expedia
Canal-front luxury home! Private pool and spa!
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 13
Serenity Beach by Anna Maria Island Locals Home in Anna Maria, FL Features: • Canal front property with Dock • located ...
From $1625 per night (USD)Expedia
From $1132 per night (USD)VRBO
Brand New Putting Green! Close to beach!
- Bedrooms:
- 5
- Bathrooms:
- 6
- 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 $1132 per night (USD)VRBO
From $883 per night (USD)Expedia
Anna Maria Home with Saltwater Pool Near Beaches & Shopping - Sunrise Shore
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 11
Sunrise Shore by Anna Maria Island Locals Duplex in Anna Maria, FL Welcome to Sunrise Shore, your dream Anna Maria Isl ...
From $883 per night (USD)Expedia
From $787 per night (USD)VRBO
Seaswept Mermaid - Recovery in Progress: Home Currently Unavailable in 2024
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Seaswept Mermaid! On Anna Maria Island (Anna Maria, FL) 2512 sq. ft. Need more room? Reserve the sister 4 b ...
From $787 per night (USD)VRBO
From $374 per night (USD)Expedia
Beachy Boathouse Cottage, 2 BR,1BA, Private Pool, Steps to Beach and Bay
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Boathouse Cottage is on the west side of the duplex on the quiet street of Gladiolus on north end of Anna Maria. Removed ...
From $374 per night (USD)Expedia
From $595 per night (USD)VRBO
Canalfront Anna Maria Cottage w\/ Pool & Hot Tub!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to the sandy shores of Anna Maria Island at ‘Easy Breezy’, a recently renovated canalfront vacation rental cottag ...
From $595 per night (USD)VRBO
From $1650 per night (USD)Expedia
Three Little Birds - Ready for Guests, November 2024!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Three Little Birds! On Anna Maria Island (Anna Maria, FL) BRAND NEW TO THE RENTAL MARKET. Three Little Bird ...
From $1650 per night (USD)Expedia
From $422 per night (USD)VRBO
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 condo that is set up like a single family home. It features wood floors, a king size bed in ...
From $422 per night (USD)VRBO
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A Change in Latitude - 3bed and 3bath By Island Real Estate Vacations
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
<p>Close to ice skating, sailing, and more, this family-friendly vacation home brings it all within reach. There's conve ...
Click For PricingExpedia
From $2921 per night (USD)VRBO
Beachfront Home | Pool + Spa | Games | Ocean Views
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to the exclusive Beachfront Bliss - a custom-built luxury vacation home nestled directly on a sandy beach. This ...
From $2921 per night (USD)VRBO
From $1073 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 $1073 per night (USD)Expedia
From $1322 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 $1322 per night (USD)VRBO
From $395 per night (USD)Expedia
Hidden Oasis - DIRECT BEACHFRONT DUPLEX - 1BR\/1BA Anna Maria - By Island Real Es
- Bedrooms:
- 1
- Bathrooms:
- 2
- 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 $395 per night (USD)Expedia
From $475 per night (USD)VRBO
The Salty Beach Cottage: Canal-front pool home with local personality!
- 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 $475 per night (USD)VRBO
From $835 per night (USD)Expedia
Briney Breezes - Old Florida living with modern comforts
- Bedrooms:
- 3
- Bathrooms:
- 4
- 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 $835 per night (USD)Expedia
From $685 per night (USD)VRBO
Perfect Family-Friendly Home with Putting Green, Pool, and Games
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
The 19th Hole by Anna Maria Island Accommodations 238 Gladiolus St, Anna Maria, Florida VR21-000087 Welcome to The 19 ...
From $685 per night (USD)VRBO
From $305 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 $305 per night (USD)Expedia
From $686 per night (USD)VRBO
Anna Maria Beach Cottage 110 Traditional beach cottage, moments from the sand!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Please note there may be repair work being done onsite during the months of November and December on units that were aff ...
From $686 per night (USD)VRBO
From $393 per night (USD)Expedia
Anna Maria Beach Cottage 109G Old-Florida beach cottage,moments from the sand!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This rental is part of the Anna Maria Beach Cottages. More information on this charming property below! Cottage 109G is ...
From $393 per night (USD)Expedia
From $745 per night (USD)VRBO
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! Cottage 109 is ...
From $745 per night (USD)VRBO
From $497 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 there may be repair work being done onsite during the months of November and December on units that were aff ...
From $497 per night (USD)Expedia
From $655 per night (USD)VRBO
Sassy Seagull -Classic beach cottage, moments from the sand, beautiful pool!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This rental is part of the Anna Maria Beach Cottages. More information on this charming property below! Sassy Seagull C ...
From $655 per night (USD)VRBO
From $535 per night (USD)Expedia
Anna Maria Beach Cottage 107A Pool, bikes, beach gear, moments from the sand!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Please note there may be repair work being done onsite during the months of November and December on units that were aff ...
From $535 per night (USD)Expedia
From $532 per night (USD)VRBO
Anna Maria Beach Cottage 109A -Old-Florida beach cottage, steps to the beach!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Please note there may be repair work being done onsite during the months of November and December on units that were aff ...
From $532 per night (USD)VRBO
From $423 per night (USD)Expedia
Anna Maria Updated Studio moments from the sand w\/ Pool, Beach Gear & Bikes
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This rental is part of the Anna Maria Beach Cottages. More information on this charming property below! Cottage 107G is ...
From $423 per night (USD)Expedia
From $601 per night (USD)VRBO
Charming Cottage with modern amenities close to beach w\/ pool, beach gear, bikes
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Please note there may be repair work being done onsite during the months of November and December on units that were aff ...
From $601 per night (USD)VRBO
From $767 per night (USD)Expedia
Flirty Flamingo Cottage Updated beach cottage, moments from the sand, w\/pool!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Please note there may be repair work being done onsite during the months of November and December on units that were aff ...
From $767 per night (USD)Expedia
From $402 per night (USD)VRBO
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 $402 per night (USD)VRBO
From $909 per night (USD)Expedia
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 $909 per night (USD)Expedia
From $1332 per night (USD)VRBO
Funky Beach Farmhouse: Beautiful Bay views, heated pool, hot tub, lounge area
- Bedrooms:
- 5
- 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 $1332 per night (USD)VRBO
From $606 per night (USD)Expedia
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 $606 per night (USD)Expedia
From $305 per night (USD)VRBO
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 $305 per night (USD)VRBO
From $752 per night (USD)Expedia
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 $752 per night (USD)Expedia
From $737 per night (USD)VRBO
Charming cottage with heated pool, tropical landscaping in prime location.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The Starfish Cottage has been recently renovated while maintaining all the charm of an old Florida Key West style bungal ...
From $737 per night (USD)VRBO
From $221 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 $221 per night (USD)Expedia
From $580 per night (USD)VRBO
Dog friendly oasis with heated private pool and very close to the beach
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
A Cozy Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $580 per night (USD)VRBO
From $1497 per night (USD)Expedia
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 $1497 per night (USD)Expedia
From $739 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 $739 per night (USD)VRBO
From $1693 per night (USD)Expedia
Tern Key - Ready for Guests, November 2024!
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Tern Key! On Anna Maria Island (Anna Maria, FL) Pristine Newly Built Spacious Luxury Canal Front Home with P ...
From $1693 per night (USD)Expedia
From $1479 per night (USD)VRBO
Pink Palm: Dog-friendly, 6-bedroom, 3-min walk to beach!
- Bedrooms:
- 5
- 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 $1479 per night (USD)VRBO
From $1227 per night (USD)Expedia
Thanksgiving dinner included: 15lb Turkey\/Sweet Potato Mash\/Pumpkin Pie
- Bedrooms:
- 6
- 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 $1227 per night (USD)Expedia
From $864 per night (USD)VRBO
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 $864 per night (USD)VRBO
From $911 per night (USD)Expedia
Quiet Canal Home, Walking Distance to Bay Beach, Heated Pool!
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Our Tern by Anna Maria Island Accommodations Home in Anna Maria, FL 34216 VR22-000023 Welcome to Our Tern, a stunnin ...
From $911 per night (USD)Expedia
From $1369 per night (USD)VRBO
DISCOUNT OFFER! Rum Cove-Magical Tropical Oasis: Pool\/Hot Tub, Golf Cart, Kayak
- Bedrooms:
- 7
- Bathrooms:
- 7
- Sleeps:
- 14
Welcome to the Rum Cove Experience! Rum Cove DISCOUNT OFFER and Construction Disclaimer: Thank you for checking out R ...
From $1369 per night (USD)VRBO
From $895 per night (USD)Expedia
Over the Moon - By Island Real Estate Vacations
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
“Over the Moon” located on the North end of Anna Maria is an adorable 3 bedroom, 2 bathroom cottage that spaciously acco ...
From $895 per night (USD)Expedia
From $540 per night (USD)VRBO
Lovely island home w\/ heated private pool - 1 block to Pine Street, 2 dogs OK
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Spring Oasis Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $540 per night (USD)VRBO
From $718 per night (USD)Expedia
North End Escape: Luxury Custom Built Home on North End - Steps to Beach - Outdoor Kitchen
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Discover the perfect beach getaway at North End Escape! This luxurious custom-built vacation rental offers the ultimate ...
From $718 per night (USD)Expedia
From $1345 per night (USD)VRBO
Banyan Beach: No Storm Damage! Pool Open! by Anna Maria Life Vacation Rentals
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 8
Banyan Beach by Anna Maria Life Vacation Rentals 104 Beach Ave, Anna Maria, FL 34216 What You'll Love About This Home: ...
From $1345 per night (USD)VRBO
From $1534 per night (USD)Expedia
Snook Lookout: No Storm Damage! Pool Open! by Anna Maria Life Vacation Rentals
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 8
Snook Lookout is ready for your vacation! We had to take a brief pause to regroup but…Snook Lookout is ready for you! ...
From $1534 per night (USD)Expedia
From $1210 per night (USD)VRBO
Just steps to the beach, private pool, spa, and balconies!
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
Under the Sea by Anna Maria Island Locals Home in Anna Maria, FL Features: • Private Pool and Spa • On the beach block, ...
From $1210 per night (USD)VRBO
From $1270 per night (USD)Expedia
Stunning 5 bedroom Luxury home, Pool and Spa, beach VIEWS!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Coastal Queen by Anna Maria Island Locals Home in Anna Maria, FL Located just one street from the sugary white sands of ...
From $1270 per night (USD)Expedia
From $2213 per night (USD)VRBO
Thanksgiving dinner included: 15lb Turkey\/Sweet Potato Mash\/Pumpkin Pie
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 8
Welcome to Gulfview Estate, your exquisite beachfront retreat where luxury meets tranquility. This stunning 5-bedroom, 4 ...
From $2213 per night (USD)VRBO
From $936 per night (USD)Expedia
4 Beds 4.5 Bath with Pool 3 Blocks to Beach
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
You won't be disappointed with this home! This 4 bedroom, 4.5 bathroom home is located in the heart on ANNA MARIA ISLAND ...
From $936 per night (USD)Expedia
From $896 per night (USD)VRBO
4 Bed 4.5 Bath Family Friendly, 3 Blocks to Gulf
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
You won't be disappointed with this brand home! This home has 4 bedrooms each with an en-suite washroom, home is located ...
From $896 per night (USD)VRBO
From $450 per night (USD)Expedia
Beach N Bay 206 by Duncan Real Estate
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Beach N Bay 206! Pool COOLING for hot summer days! A honeymooners delight or a couple’s retreat! ...
From $450 per night (USD)Expedia
From $1082 per night (USD)VRBO
Canal-front luxury home, with private pool + spa and boat dock!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
Hammock Daze by AMI Locals Home in Anna Maria, Florida VR20-000017 This stunning 4 Bedroom/ 3.5 Bath luxury canal home ...
From $1082 per night (USD)VRBO
From $675 per night (USD)Expedia
Sea Song - DIRECT GULFRONT HOUSE - By Island Real Estate Vacations
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
“Sea Song” is an adorable Anna Maria Island vacation rental cottage nestled in the flour soft sand of Bean Point to allo ...
From $675 per night (USD)Expedia
From $1066 per night (USD)VRBO
Sand Dollar Dream - Remodeled Canal Private Pool Home - By Island Real Estate Va
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
The perfect spot for your next island getaway, “Sand Dollar Dream” is a gorgeous canal front private pool home with ever ...
From $1066 per night (USD)VRBO
From $615 per night (USD)Expedia
Beautiful Villa, Perfect Small Getaway. Close to beach, beach gear provided!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Cute Villa in the heart of Anna Maria! Palm Court Villas are located in the heart of Anna Maria Village with a short st ...
From $615 per night (USD)Expedia
From $728 per night (USD)VRBO
Dog friendly home with heated pool and balconies! Great location!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Spring Haven by Anna Maria Island Locals Home in Anna Maria, FL Highlights: - Heated pool surrounded by loungers and lu ...
From $728 per night (USD)VRBO
From $738 per night (USD)Expedia
AMI Bay Breeze: Heated pool, outdoor bar, beautifully updated.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to AMI Bay Breeze! This newly renovated, 3 bedroom 2 bathroom home is the perfect escape for your next vacation ...
From $738 per night (USD)Expedia
From $1182 per night (USD)VRBO
Gorgeous island luxury home just one block to the Beach! Come stay with us!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Tahiti Bay by AMI Locals Home in Anna Maria, FL VR16-000466 Welcome to Tahiti Bay, a stunning vacation rental wi ...
From $1182 per night (USD)VRBO
From $361 per night (USD)Expedia
Bay-facing condo with amazing views and heated pool - beach across the street
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
South Bay Inn 2 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $361 per night (USD)Expedia
From $850 per night (USD)VRBO
Bayside Bliss by Duncan Real Estate
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to the serene luxury of Bayside Bliss which is a fully remodeled three-bedroom/three-bathroom, ground level cott ...
From $850 per night (USD)VRBO
From $506 per night (USD)Expedia
Sea Spray 5: *Heated Pool *Steps to beach *Close to shops and dining
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
The Sea Spray Cottages are an adorable group of Units located in the North End of Anna Maria, West of Gulf Drive and onl ...
From $506 per night (USD)Expedia
From $973 per night (USD)VRBO
Golf Cart, Bimini Cove by SeaBreeze Vacation
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 12
A 6-person electric golf cart is included with any new reservation for this property! You must be 21 years old and show ...
From $973 per night (USD)VRBO
From $836 per night (USD)Expedia
Salty C Cottage Spectacular canal front home with pool and hot tub!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
Gorgeous and recently remodeled 4 bedroom, 3 1/2 bath ground level home with amazing designer touches and finishes throu ...
From $836 per night (USD)Expedia
From $1032 per night (USD)VRBO
Vibrant Island Home w\/ Pool, 1 Block to Beach
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
A tropical paradise awaits when you book this stylish Anna Maria retreat! Ideally situated just 0.1 miles from the gorge ...
From $1032 per night (USD)VRBO
From $1066 per night (USD)Expedia
A Bay From It All: Private backyard oasis, steps to Bay, Bean Point
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Leave the stress of everyday life and get "A Bay From it All"! This amazing 3 bedroom / 3 full bathroom home on the cove ...
From $1066 per night (USD)Expedia
From $351 per night (USD)VRBO
MI Oasis Getaway! Just 200 Steps to the Beach on a very quiet street
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
MI Oasis Getaway is a true oasis on both the outside and inside! When you step into our vacation rental, your eyes are i ...
From $351 per night (USD)VRBO
From $375 per night (USD)Expedia
Ideal Location, Stunning Villa! Close to beach, beach gear provided!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
❗ Flexible check in days for most of the year--with the exception of holidays. Friday arrivals and departures during Pe ...
From $375 per night (USD)Expedia
From $1071 per night (USD)VRBO
Luxury Home with Pool and Dock for Fishing!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Pelican's Nest by AMI Locals Home in Anna Maria, FL Features: • Private Pool • Gorgeous Brand New Construction home • ...
From $1071 per night (USD)VRBO
From $383 per night (USD)Expedia
Charming 2br \/ 1ba Cottage < 2 Min Walk From Beach on Anna Maria Island Florida
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Built in 1924, Sunset Cottages’ beautifully maintained woodwork coupled with updated amenities delivers an authentic Flo ...
From $383 per night (USD)Expedia
From $656 per night (USD)VRBO
Island Time: AMI North End, Pool, Close to City Pier & Pine Ave by Anna Maria Life Vacation Rentals
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
426 Spring Ave., Anna Maria, FL 34216 What You'll Love About This Home Location! In the heart of Anna Maria, and withi ...
From $656 per night (USD)VRBO
From $1017 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 $1017 per night (USD)Expedia
From $805 per night (USD)VRBO
Sunset Point- Beachfront 4 bedroom with private pool with views
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Sunset Point 765 North Shore Drive, Anna Maria What you will love about this property: • Direct Gulf Front • Beach is ...
From $805 per night (USD)VRBO
From $1307 per night (USD)Expedia
Golf Cart, Stonehenge by SeaBreeze Vacation
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS WITH A CHECK-IN DATE BETWEEN 4/26/25 - 12/31/25! All Drivers must be ...
From $1307 per night (USD)Expedia
From $562 per night (USD)VRBO
*NEW LISTING* Boutique Spanish-Style Villa - perfect for family\/couple getaway
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This unique, beautifully appointed Boutique Spanish Style Villa on the North End of Anna Maria Island is a perfect getaw ...
From $562 per night (USD)VRBO
From $213 per night (USD)Expedia
2nd-floor condo across the street from the beach with heated pool, balcony, W\/D
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
South Bay Inn 4 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $213 per night (USD)Expedia
From $1068 per night (USD)VRBO
Island Therapy: Pool, Canal, Dock, Outdoor Fun & Games!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
103 Gull Drive, Anna Maria, FL 34216 What You'll Love About This Home: Location! North End, On Canal! 4 Bedroom / 3 Bath ...
From $1068 per night (USD)VRBO
From $782 per night (USD)Expedia
Tinas Piece of Paradise - 4BR private pool home - Anna Maria Island - By Island
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
When looking to accommodate a large group during you paradise Anna Maria Island vacation look no further than “Tina’s Pi ...
From $782 per night (USD)Expedia
From $666 per night (USD)VRBO
Reel Deal: No Storm Damage! Pool Open! by Anna Maria Life Vacation Rentals
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
Reel Deal is ready for your vacation! We had to take a brief pause to regroup but…Reel Deal is ready for you! We can' ...
From $666 per night (USD)VRBO
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Pirates Lookout by Beach Boutique Rentals
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Pirates Lookout, a slice of island paradise. This eclectic, surfer-chic carriage house is nestled on Anna Mar ...
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Click For PricingVRBO
Pirates Bounty by Beach Boutique Rentals
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
The ultimate 5 bedroom beachfront retreat on the secluded and desirable North end of Anna Maria. Only steps to the Rod a ...
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Pirates Bay by Beach Boutique Rentals
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Beachfront pool home on the secluded and desirable North end of Anna Maria just steps to the Rod and Reel Pier! *Featur ...
Click For PricingExpedia