Anna Maria Rentals
- From $636 per night (USD)
VRBO
La Casa Costiera - Beachfront Condo w\/Gulf View - Pool - Jacuzzi - BBQ Area
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
La Casa Costiera is a luxuirous condo in the heart of Holmes Beach where the Mediterranean and the Gulf of Mexico meet. ...
From $636 per night (USD)VRBO
- From $1150 per night (USD)
Expedia
Luxury home close to beach! Private pool, spa, and putting green!
- Bedrooms:
- 7
- Bathrooms:
- 5
- Sleeps:
- 8
Anna Maria Beach House by AMI Locals Home in Anna Maria, Florida VR19-000061 Welcome to Anna Maria Beach House, a brea ...
From $1150 per night (USD)Expedia
- From $265 per night (USD)
VRBO
Poolside Cottage at Beachfront Coconuts Resort!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to Coconuts Poolside! This amazing condo is located within the iconic Coconuts Beach Resort located directly on ...
From $265 per night (USD)VRBO
- From $300 per night (USD)
VRBO
Adorable Vintage Anna Maria Cottage. Heated Pool! North End! 2 Blocks to Beach!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
BEFORE YOU BOOK: We only rent through VRBO. No other party is authorized to rent this property. We rent Saturday to S ...
From $300 per night (USD)VRBO
- From $1172 per night (USD)
VRBO
Golf Cart included, private home and only steps to the beach.
- Bedrooms:
- 7
- Bathrooms:
- 4
- Sleeps:
- 8
6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS WITH A CHECK-IN DATE AFTER SEPTEMBER 5, 2023! All Drivers must be ov ...
From $1172 per night (USD)VRBO
- From $883 per night (USD)
Expedia
Brand New Home w\/private Pool and Spa, awesome tropical backyard! Walk to Beach
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Feelin’ Beachy by AMI Locals Home in Holmes Beach, Florida VRC20-000140 Let the good times roll at Feelin' Beachy, a st ...
From $883 per night (USD)Expedia
- From $245 per night (USD)
VRBO
Pets Stay Free! Heated Pool 1.5 Blocks from Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Lower Duplex Home located steps from the Gulf of Mexico, this Beach Bungalow is perfect for couples and families alike.. ...
From $245 per night (USD)VRBO
- From $1150 per night (USD)
VRBO
Beach block\/Pvt Heated Pool\/Spa\/Cabana\/SUP\/Kayaks\/Bicycles\/4 bed\/4.5 bath
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
CabAnna Maria is a completely renovated 4 bedroom, 4.5 bathroom beach block vacation property that sleeps 8 comfortably. ...
From $1150 per night (USD)VRBO
- From $900 per night (USD)
VRBO
Sirenia Beach House - Waterfront\/HotTub\/ Pool\/Dock\/PuttGreen\/Beach
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Recently Renovated! - putting green - master bathroom upstairs - master balcony enlarged and with seating - metal roof ...
From $900 per night (USD)VRBO
- From $608 per night (USD)
VRBO
Custom Home Walking Distance from the Gulf ! NOT LISTED ON FACEBOOK <br>
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This large home was constructed in 2009. It is a decorator furnished, pool home and considered top of the line in vacat ...
From $608 per night (USD)VRBO
- From $200 per night (USD)
VRBO
Note: 30 day minimum rental for January, February, and March, 2025
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
The Ballyhoo is a ground floor cottage located on Bean Point at the very tip of Anna Maria Island. Around the corner, (2 ...
From $200 per night (USD)VRBO
- From $626 per night (USD)
Expedia
Ocean Pearl: *Bay front *Ground-level *Gorgeous views
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Beautiful waterfront home located on the north end of Anna Maria Island. Located on North Shore Drive, approx 9 houses e ...
From $626 per night (USD)Expedia
- From $525 per night (USD)
VRBO
Bean Point Cottage: North End Pool Home, Close to Beach & Bay by Anna Maria Life Vacation Rentals
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
709 North Bay Blvd., Anna Maria, FL 34216 What You'll Love About This Home: Location! North End of AMI and 500 Steps T ...
From $525 per night (USD)VRBO
- From $326 per night (USD)
VRBO
Water Front Sea Waves Cottage With Private Dock, Access To Bimini Bay
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Sea Waves, our newly renovated home with 3 bedrooms / 2 bathrooms, a private dock, and an unobstructed, natur ...
From $326 per night (USD)VRBO
- From $138 per night (USD)
VRBO
Great Beach Retreat w\/Full Kitchen, Free WiFi, Shared Pool, Washer\/Dryer, & More
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Sunrise Garden #9 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $138 per night (USD)VRBO
- From $173 per night (USD)
Expedia
Well-Located & Equipped Beach Condo w\/Shared Pool, Washer\/Dryer, Free WiFi
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Sunrise Garden # 17 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $173 per night (USD)Expedia
- From $299 per night (USD)
VRBO
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Sea Breeze, our newly renovated home with 2 bedrooms / 2 bathrooms, a private dock, and an unobstructed, natu ...
From $299 per night (USD)VRBO
- From $138 per night (USD)
Expedia
Well-appointed beach condo with pool access, washer\/dryer, WiFi & great location
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Sunrise Garden #15 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $138 per night (USD)Expedia
- From $138 per night (USD)
VRBO
Dreamy Beach Condo w\/Incredible Location, Shared Pool, Washer\/Dryer, Free WiFi
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Sunrise Garden #12 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $138 per night (USD)VRBO
- From $138 per night (USD)
Expedia
Incredible Beach Condo w\/Free WiFi, TV, Shared Pool and Washer\/Dryer
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Sunrise Garden #7 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $138 per night (USD)Expedia
- From $138 per night (USD)
VRBO
Friendly Condo w\/ Shared Pool in Great Location w\/ Washer\/Dryer, & Free WiFi
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Sunrise Garden #11 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $138 per night (USD)VRBO
- From $138 per night (USD)
Expedia
Convenient & Well-Located Condo w\/Shared Washer\/Dryer, Pool, and Free WiFi
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Sunrise Garden #2 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $138 per night (USD)Expedia
- From $138 per night (USD)
VRBO
Beach Escapade w\/near the Beach, Shared Pool, Washer\/Dryer, Free WiFi, & More
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Sunrise Garden #16 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $138 per night (USD)VRBO
- From $144 per night (USD)
Expedia
Beach Walk: North Beach Village, Pool, Quick Walk to Beach by Anna Maria Life Vacation Rentals
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
6250 Holmes Blvd. #31, Holmes Beach, FL 34217 What You'll Love About This Home: Location! 2.5 Blocks to the Beach! 2 B ...
From $144 per night (USD)Expedia
- From $375 per night (USD)
VRBO
COZY ISLAND ROOMS at Bali Hai Beach Resort
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
These BRAND NEW Island Rooms have been impeccably furnished to provide the very latest in both style and ambiance. Lavis ...
From $375 per night (USD)VRBO
- From $138 per night (USD)
Expedia
Well-Furnished Beach Condo w\/Shared Swimming Pool, Washer\/Dryer, Free WiFi
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Sunrise Garden #6 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $138 per night (USD)Expedia
- From $138 per night (USD)
VRBO
Budget-Friendly Studio w\/Shared Pool, Washer\/Dryer, Free WiFi, & Private Patio
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Sunrise Garden #3 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $138 per night (USD)VRBO
- From $871 per night (USD)
Expedia
Breathtaking Views and Lasting Memories - Beachfront Fun & Relaxation
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
We welcome you to stay in our family beach house located on beautiful "Bean Point"; the most beautiful spot on Anna Mari ...
From $871 per night (USD)Expedia
- From $201 per night (USD)
VRBO
Convenient Condo Near the Beach w\/Shared Pool, Washer\/Dryer, Free WiFi, & More
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Sunrise Garden #8 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $201 per night (USD)VRBO
- From $330 per night (USD)
VRBO
Spacious beach house with a beautiful view of the gulf
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
The fully air-conditioned house is in a quiet, exclusive residential area at the tip of the island. Miles of white sandy ...
From $330 per night (USD)VRBO
- From $532 per night (USD)
VRBO
Crescent Palms in Anna Maria
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Treat yourself to “Crescent Palms” on the north end of Anna Maria Island. This ground level, newly renovated and profess ...
From $532 per night (USD)VRBO
- From $784 per night (USD)
Expedia
Pineapple Cottage in Anna Maria
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to “Pineapple Cottage” – a beautifully updated ground level beach cottage located in the heart of Anna Maria Cit ...
From $784 per night (USD)Expedia
- From $588 per night (USD)
VRBO
Zen Gardens in Anna Maria
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
*3 Night Minimum stays are allowed during low season, please refer to the rate table for the specific date ranges* ...
From $588 per night (USD)VRBO
- From $535 per night (USD)
Expedia
Island in the Sun in Anna Maria
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
WELCOME to “Island in the Sun” ... this newly renovated home on AMI offers charm, comfort, and luxury. Island in the Sun ...
From $535 per night (USD)Expedia
- From $390 per night (USD)
VRBO
Unique beach house near Bean Point, heated pool and just 2 min to beach.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Beautiful elevated Beach House with a private heated pool situated in the sought after residential north end of Anna Mar ...
From $390 per night (USD)VRBO
- From $320 per night (USD)
Expedia
Coconuts Resort Direct Beachfront Bungalow!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to Coconuts Beachside! This amazing condo is located within the iconic Coconuts Beach Resort located directly on ...
From $320 per night (USD)Expedia
- From $184 per night (USD)
VRBO
ONE HOUSE TO THE BEACH - 2BR\/2BA House - Anna Maria Island - By Island Real Esta
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
DISCLOSURE!!: There is currently an ongoing disagreement regarding the beach access path on 78th Street. In the meantime ...
From $184 per night (USD)VRBO
- From $1920 per night (USD)
Expedia
Luxury Home with Rooftop Putting Green and More!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Palmetto Paradise by AMI Locals Home in Anna Maria, Florida Welcome to Palmetto Paradise, a new vacation home just two ...
From $1920 per night (USD)Expedia
- From $425 per night (USD)
VRBO
Gorgeous house with a private pool\/spa! Bonus loft for kids!
- Bedrooms:
- 8
- Bathrooms:
- 4
- Sleeps:
- 8
Surfer’s Dream by AMI Locals Home in Holmes Beach, Florida VRC19-000029 Welcome to Surfer's Dream, a four-bedroom and s ...
From $425 per night (USD)VRBO
- From $700 per night (USD)
VRBO
Beautiful, decorated and furnished, spacious Great Room family & kid friendly,
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Beautifully decorated and furnished home located an easy walk from Gulf beaches and Tampa bay. Includes a master suite ...
From $700 per night (USD)VRBO
- From $142 per night (USD)
VRBO
Convenient & Well-Equipped Condo w\/Shared Pool, Washer\/Dryer, Free WiFi
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Sunrise Garden #4 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $142 per night (USD)VRBO
- From $638 per night (USD)
Expedia
Experience Island Life! Great private Pool and Spa
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Island Life by AMI Locals Home in Holmes Beach VRC#18-000083 Welcome to Island Life, a fully renovated and updated vac ...
From $638 per night (USD)Expedia
- From $142 per night (USD)
VRBO
Beach Condo Near the Beach, Shared Pool, and High-Speed WiFi
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Sunrise Garden #5 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $142 per night (USD)VRBO
- From $542 per night (USD)
Expedia
Coconut Lagoon - Lovely Historic Renovated Cottage w\/Huge Heated Pool & Backyard Oasis\/Cabana\/Bar
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Coconut Lagoon! On Anna Maria Island (Anna Maria, FL) Ground Level Completely Updated Luxury Historic Home ...
From $542 per night (USD)Expedia
- From $138 per night (USD)
VRBO
Budget-friendly beach condo with pool access, washer\/dryer, WiFi & full kitchen
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Sunrise Garden #14 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $138 per night (USD)VRBO
- From $243 per night (USD)
Expedia
Shell Cottage is a cosy 1 bed cottage sharing a free form pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Idyllic Holiday Properties is a small friendly holiday company offering an honest and efficient service for our privatel ...
From $243 per night (USD)Expedia
- From $629 per night (USD)
VRBO
Salty Pirate - Luxury Canal Front Home w\/Water View, Pool\/Spa, Bikes, Kayaks, Toys!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Salty Pirate! On Anna Maria Island (Anna Maria, FL) 2512 sq. ft. Need more room? Reserve the sister 4 bedro ...
From $629 per night (USD)VRBO
- From $172 per night (USD)
VRBO
Bungalow On The Bayou (Best Location on the Island)
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Located on the "best" street on Anna Maria Island, this two-bedroom, one-bath second floor vacation rental with a specta ...
From $172 per night (USD)VRBO
- From $742 per night (USD)
VRBO
Hear The Surf\/Feel The Breeze... Steps To The Gulf Beach From This 4 Bd\/4Ba
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Just 5 houses from the white sandy beach of the Gulf. Near the heart of Anna Maria village sits this spacious home wit ...
From $742 per night (USD)VRBO
- From $515 per night (USD)
Expedia
On the BEACH block! Luxury home, Pool and Spa, stay and relax with your friends!
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
Villa La Concha by Anna Maria Island Accommodations Home in Anna Maria, FL Welcome to Villa La Concha, a marvelous ...
From $515 per night (USD)Expedia
- From $960 per night (USD)
VRBO
One block off the beach! Waterslide and Rooftop deck! - Pineapple Paradise
- Bedrooms:
- 7
- Bathrooms:
- 4
- Sleeps:
- 8
Pineapple Paradise by AMI Locals Home in Holmes Beach, Florida VRC19-000039 Come and visit Pineapple Paradise! This ...
From $960 per night (USD)VRBO
- From $2405 per night (USD)
Expedia
Luxury waterfront home with private pool and putting green!
- Bedrooms:
- 8
- Bathrooms:
- 7
- Sleeps:
- 16
Bay View Beauty by AMI Locals Home in Anna Maria, FL Highlights: • Ocean Front with Private Beach Access • Private Po ...
From $2405 per night (USD)Expedia
- From $530 per night (USD)
VRBO
Palm Beach House: Pet friendly pool home, close to the beach!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Treat yourself to the beachside vacation you’ve been dreaming of with this relaxing and dog-friendly Anna Maria vacation ...
From $530 per night (USD)VRBO
- From $428 per night (USD)
VRBO
Apr 27 - May 4 Deal - Canal \/Hot Tub\/Htd Pool\/ Dock\/Backyard Beach
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
April 27 - May 4, 2024 now $2099/wk plus fees and taxes. Many new items not shown in photos; - New exterior Polywood d ...
From $428 per night (USD)VRBO
- From $270 per night (USD)
VRBO
Beach Haven Ranked #204 for businesses in Holmes Beach FL
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Beach Haven #204 at Seaside Beach House is favorite for guests of Holmes Beach and Anna Maria Island. This 1050 sq ft ...
From $270 per night (USD)VRBO
- From $199 per night (USD)
Expedia
Island Serenity: North Beach Village, Dog Friendly, Short Walk to Beach by Anna Maria Life
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
6250 Holmes Blvd. #54, Holmes Beach, FL 34217 What You'll Love About This Home: Location! 2.5 Blocks to the Beach! 3 Be ...
From $199 per night (USD)Expedia
- From $385 per night (USD)
VRBO
Best of Anna Maria \n 3 blocks to sugar sand beach! Heated pool\/20 ft dock.
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 5
3 short blocks to the sugar sand beaches of the Gulf of Mexico and 5 blocks to Tampa Bay. This traditional Florida home ...
From $385 per night (USD)VRBO
- From $266 per night (USD)
VRBO
Blue Heron Cottage - Anna Maria Island
- Bedrooms:
- 3
- Bathrooms:
- 1
- Sleeps:
- 4
Great 1 bedroom, 1.5 bathroom cottage on the quiet north end of island. The house is conveniently located and within wal ...
From $266 per night (USD)VRBO
- From $493 per night (USD)
VRBO
Sandy Rose: Putting green, heated pool, outdoor living spaces
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Situated on the north end of Anna Maria Island, The Sandy Rose is the perfect location for your next getaway! This 4 bed ...
From $493 per night (USD)VRBO
- From $1038 per night (USD)
Expedia
Luxury home close to beach! Pool & putting green
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 16
Seaside Magnolia by Anna Maria Island Locals Home in Anna Maria, FL Features: • Private pool and spa • newly installed ...
From $1038 per night (USD)Expedia
- From $442 per night (USD)
VRBO
GULF BEACH Directly in Front w\/ Heated Pool, FREE WiFi & Trolley, Great Sunsets!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
**ASK ABOUT LAST MINUTE DEALS! Perfectly situated on the Gulf of Mexico in the center of Anna Maria Island, ...
From $442 per night (USD)VRBO
- From $405 per night (USD)
VRBO
BEST LOCATION! NORTH END OF ANNA MARIA, FL STEPS TO BEACH & DINING - UPPER UNIT
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Location!!! North end of Anna Maria Island . Steps to the Bean Point Beach and everything you need for your perfect Anna ...
From $405 per night (USD)VRBO
- From $525 per night (USD)
VRBO
STEPS TO THE BEACH WITH POOL! CAN BE RENTED AS A 4 BEDROOM!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Zebra Hut A: Quiet and quaint is this spectacular 2 Bedroom/1 Bath Duplex with a large HEATED POOL in a lush tropical la ...
From $525 per night (USD)VRBO
- Click For Pricing
Expedia
Resort Sixty-Six, Holmes Beach, Florida, 1 Bedroom Suite
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This is a full-service resort. Your check-in procedures will model that of a hotel and your room number will be assigned ...
Click For PricingExpedia
- From $525 per night (USD)
VRBO
STEPS TO THE BEACH WITH POOL! CAN BE RENTED AS A 4 BEDROOM!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Zebra Hut B: Quiet and quaint is this spectacular 2 Bedroom/1 Bath Duplex with a large HEATED POOL in a lush tropical la ...
From $525 per night (USD)VRBO
- From $510 per night (USD)
Expedia
Chillin' on Chilson: 3 BR, 3 BA House in Anna Maria, Sleeps 8
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Come stay at this mid-century, old Florida-style canal home located on the coveted north end of Anna Maria Island. You ...
From $510 per night (USD)Expedia
- From $280 per night (USD)
VRBO
Seahorse Cottage is a spacious 1 bed property sharing a free form pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Idyllic Holiday Properties is a small friendly holiday company offering an honest and efficient service for our privatel ...
From $280 per night (USD)VRBO
- From $764 per night (USD)
Expedia
Stunning luxury home just 1 block to beach! Pool, spa, and elevator!
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 8
Palmetto Pointe by AMI Locals Home in Anna Maria, FL Highlights: - Private wrap around balconies - Rooftop deck - Foos ...
From $764 per night (USD)Expedia
- From $129 per night (USD)
VRBO
Adorable Cottage ONLY STEPS to Anna Maria Beach, No Roads to Cross! FREE WiFi...
- Bedrooms:
- 0
- Bathrooms:
- 0
- Sleeps:
- 0
**ASK ABOUT LAST MINUTE DEALS! Enjoy a simple, old fashioned seaside vacation in this adorable duplex west ...
From $129 per night (USD)VRBO
- From $128 per night (USD)
Expedia
FREE WiFi & Trolley ONLY STEPS to Pristine Sandy Beach NO Roads to Cross!
- Bedrooms:
- 0
- Bathrooms:
- 0
- Sleeps:
- 0
**ASK ABOUT LAST MINUTE DEALS! Island fun is easy in this 2 unit charming cottage located two houses from t ...
From $128 per night (USD)Expedia
- From $330 per night (USD)
VRBO
Perfectly Located Near the Beach and Shopping!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Saltwater Palms by AMI Locals Townhome in Holmes Beach, FL Located just across the street from the Gulf Beaches! Highl ...
From $330 per night (USD)VRBO
- From $612 per night (USD)
Expedia
La Buena Vida - Bright Beachy & Canal Front! Steps to Beach, Pool\/Spa, Dock, Dogs OK
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to La Buena Vida! On Anna Maria Island (Anna Maria, FL) The waterfront 3-bedroom home has a private heated pool ...
From $612 per night (USD)Expedia
- Click For Pricing
Expedia
Beachfront Home with Amazing Deck Views! Perfect Location!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Low Tide by AMI Locals Home in Anna Maria, FL Highlights: - Beachfront location - Fully equipped kitchen - Open air dec ...
Click For PricingExpedia
- From $757 per night (USD)
Expedia
Beachfront Home with Amazing Deck Views! Near Shops and Restaurants! -High Tide
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 4
High Tide by AMI Locals Home in Anna Maria, Florida VR21-000077 Welcome to High Tide! This stunning three-bedroom a ...
From $757 per night (USD)Expedia
- From $375 per night (USD)
VRBO
Barefoot Gypsy = Steps to beach | Near Bayfront Park | Bean Point | Rod & Reel
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
The Barefoot Gypsy is an enchanted cottage tucked in the north end of Anna Maria Island in the City of Anna Maria, .Flor ...
From $375 per night (USD)VRBO
- From $166 per night (USD)
Expedia
Budget-Friendly Condo in Great Location w\/Shared Pool, Washer\/Dryer, & Free WiFi
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Sunrise Garden #10 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $166 per night (USD)Expedia
- From $513 per night (USD)
VRBO
Bellablu: A Waterfront Haven, The Ideal Retreat for Your Next Getaway!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Escape to waterfront paradise at Bellablu! This newly renovated haven offers the ideal retreat for your next vacation. W ...
From $513 per night (USD)VRBO
- From $530 per night (USD)
Expedia
Aqua Marine By The Bay
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Discover an Anna Maria little secret --BAYFRONT HOMES WITH A WHITE SANDY BEACH -- offering the best of both worlds. Ne ...
From $530 per night (USD)Expedia
- From $650 per night (USD)
VRBO
The Happy Hibiscus Island Oasis With Ocean Views
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to The Happy Hibiscus! We are located in a perfect location where we can catch the sunrise and sunset, less than ...
From $650 per night (USD)VRBO
- From $537 per night (USD)
Expedia
3 BR, 2 BA Home with Private Pool and Spa on the North End of Anna Maria Island
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Adorable beach cottage on the north end of Anna Maria Island! The beach access trail to the famous Bean Point beach is r ...
From $537 per night (USD)Expedia
- From $386 per night (USD)
VRBO
DIRECT GULFRONT CONDO - 2BR\/2BA Condo with pool and tennis - By Island Real Esta
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
“Water’s Edge 204S” is part of the beach side Water’s Edge Condominiums. These condos are perfectly placed, as you’ll se ...
From $386 per night (USD)VRBO
- From $854 per night (USD)
Expedia
Canal front home with a private Pool, Spa and Waterslide! The kids will love it!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
Tortuga Bay by Anna Maria Island Locals Home in Anna Maria, FL Closest canal-front home in relation to the beach on the ...
From $854 per night (USD)Expedia
- From $773 per night (USD)
VRBO
Adorable Beach cottage just steps Bean Point beach!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Bean Point Bungalow by Anna Maria Island Locals Home in Anna Maria, FL Highlights • 5-minute walk from the Beach • Pri ...
From $773 per night (USD)VRBO
- Click For Pricing
Expedia
Beachlovers: Pool home, north end, close to Gulf beaches
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
Excellent home vacation property with all the amenities and more that you would expect from a modern and up to date home ...
Click For PricingExpedia
- From $548 per night (USD)
VRBO
Beautiful Home with Breathtaking Views and Private Pool!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Bay Happy by Anna Maria Island Locals Home in Anna Maria, FL Highlights • 1-minute walk from the Bay beach • Private P ...
From $548 per night (USD)VRBO
- From $250 per night (USD)
Expedia
Dog Friendly Cottage - Near the Beach and Shopping!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
Aquaville A by AMI Locals Duplex in Anna Maria VR18-000018 Welcome to Aquaville A, a two bedroom and one bath beach- ...
From $250 per night (USD)Expedia
- From $610 per night (USD)
VRBO
Luxury Home with Private Covered Pool and Putting Green - AMI Oasis
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
AMI Oasis by AMI Locals Home in Anna Maria, FL Welcome to AMI Oasis! This luxurious four-bedroom and four-bathroom retr ...
From $610 per night (USD)VRBO
- From $295 per night (USD)
Expedia
Dog Friendly Cottage - Near the Beach and Shopping!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Aquaville B by AMI Locals Home in Anna Maria VR18-000018 Welcome to Aquaville B, a three-bedroom and one bath beach-s ...
From $295 per night (USD)Expedia
- From $690 per night (USD)
VRBO
On the beach block! Beautiful Home with Rooftop Deck, Pool and Spa!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Montego Bay by AMI Locals Home in Anna Maria, Florida VR16-000472 Welcome to Montego Bay, a spectacular home with a pri ...
From $690 per night (USD)VRBO
- From $321 per night (USD)
Expedia
Batley's Beach: 3 BR, 2 BA House in Anna Maria, Sleeps 8
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Located in the "heart" of Anna Maria City, sits this ground level, 3 bedroom, 2 bath home just waiting for you! It has b ...
From $321 per night (USD)Expedia
- From $1386 per night (USD)
VRBO
Reef Romance managed by Beach Retreats
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
It's all about location on vacation, and Reef Romance does not disappoint! Sail away to this beautiful four-bedroom, fou ...
From $1386 per night (USD)VRBO
- From $557 per night (USD)
Expedia
renovated canal front home in Anna Maria City.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Come slip away to this luxurious island retreat where all of your cares will drift away! This beautiful, professionally ...
From $557 per night (USD)Expedia
- Click For Pricing
Expedia
Just steps to the beach! -Sol Searcher
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Sol Searcher by Anna Maria Island Locals Home in Anna Maria, FL Only 5 houses away from the Gulf beaches! Highlights: ...
Click For PricingExpedia
- From $375 per night (USD)
VRBO
Turtle Cottage - Anna Maria Island
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Great 1 bedroom, 1 bathroom cottage on the quiet north end of island. The house is conveniently located and within walki ...
From $375 per night (USD)VRBO
- From $425 per night (USD)
VRBO
Dog friendly home near the Gulf!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Coast is Clear by AMI Locals Home in Anna Maria, Florida VR22-000035 Welcome to Coast is Clear, a refreshing beach home ...
From $425 per night (USD)VRBO
- From $4000 per night (USD)
Expedia
Beachfront -Two Masters with Ocean Views- Walk Everywhere- Best Location in AMI!
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 8
The Diamond Star – ***Brand New 2025 Remodel*** BEACHFRONT / MOST PREMIER LOCATION ON ISLAND/ WHITE SANDY BEACHES / B ...
From $4000 per night (USD)Expedia
- From $229 per night (USD)
VRBO
Dolphin's Delight: Old Florida Home w\/Pool, Steps to the Bay!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Dolphin's Delight located on the North End of Anna Maria Island! This beautiful 2 bedroom 2 bathroom beach co ...
From $229 per night (USD)VRBO
- From $910 per night (USD)
Expedia
Luxury home with AMAZING backyard Pool and Spa! So close to beach and shopping!
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Daiquiri Deck by AMI Locals Home in Anna Maria, Florida VR18-000093 Welcome to Daiquiri Deck, a stunning four-bedroom a ...
From $910 per night (USD)Expedia
- From $700 per night (USD)
VRBO
Huge Outdoor Kitchen,Roof Top Deck w\/ 360 Views and Heated Pool
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Looking for a relaxing retreat just steps to the soft white sand and turquoise waters? Coconut Breeze offers the perfect ...
From $700 per night (USD)VRBO
- From $300 per night (USD)
VRBO
Northshore Beach House near Pine Ave, north end of Anna Maria Island
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Pine Ave and Northshore Drive adorable beach home. Anna Maria Island vacation beach house located at the north end of th ...
From $300 per night (USD)VRBO