Anna Maria Rentals
- From $1218 per night (USD)
VRBO
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 $1218 per night (USD)VRBO
- From $300 per night (USD)
VRBO
Newly Renovated Vintage AMI 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 $1143 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 $1143 per night (USD)VRBO
- From $458 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 $458 per night (USD)VRBO
- From $588 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 $588 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 $582 per night (USD)
VRBO
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 $582 per night (USD)VRBO
- From $491 per night (USD)
Expedia
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 $491 per night (USD)Expedia
- From $305 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 $305 per night (USD)VRBO
- From $177 per night (USD)
Expedia
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 $177 per night (USD)Expedia
- From $173 per night (USD)
VRBO
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)VRBO
- From $295 per night (USD)
Expedia
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 $295 per night (USD)Expedia
- From $173 per night (USD)
VRBO
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 $173 per night (USD)VRBO
- From $188 per night (USD)
Expedia
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 $188 per night (USD)Expedia
- From $191 per night (USD)
VRBO
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 $191 per night (USD)VRBO
- From $173 per night (USD)
Expedia
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 $173 per night (USD)Expedia
- From $177 per night (USD)
VRBO
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 $177 per night (USD)VRBO
- From $173 per night (USD)
Expedia
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 $173 per night (USD)Expedia
- From $201 per night (USD)
VRBO
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 $201 per night (USD)VRBO
- From $173 per night (USD)
Expedia
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 $173 per night (USD)Expedia
- From $900 per night (USD)
VRBO
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 $900 per night (USD)VRBO
- From $192 per night (USD)
Expedia
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 $192 per night (USD)Expedia
- From $299 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 $299 per night (USD)VRBO
- From $441 per night (USD)
Expedia
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 $441 per night (USD)Expedia
- From $532 per night (USD)
VRBO
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 $532 per night (USD)VRBO
- From $562 per night (USD)
Expedia
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 $562 per night (USD)Expedia
- From $414 per night (USD)
VRBO
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 $414 per night (USD)VRBO
- From $375 per night (USD)
Expedia
Unique beach house near Bean Point, heated pool and just 3 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 $375 per night (USD)Expedia
- From $1376 per night (USD)
VRBO
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 $1376 per night (USD)VRBO
- From $648 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 $648 per night (USD)VRBO
- From $173 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 $173 per night (USD)VRBO
- From $199 per night (USD)
Expedia
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 $199 per night (USD)Expedia
- From $554 per night (USD)
VRBO
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 $554 per night (USD)VRBO
- From $176 per night (USD)
Expedia
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 $176 per night (USD)Expedia
- From $244 per night (USD)
VRBO
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 $244 per night (USD)VRBO
- From $488 per night (USD)
Expedia
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 $488 per night (USD)Expedia
- 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 $738 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 $738 per night (USD)VRBO
- From $652 per night (USD)
VRBO
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 $652 per night (USD)VRBO
- From $1816 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 $1816 per night (USD)Expedia
- From $515 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 $515 per night (USD)VRBO
- From $414 per night (USD)
VRBO
Sirenia Cove - Canal \/Hot Tub\/Htd Pool\/ Dock\/Backyard Beach - prime location
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Many new items not shown in photos; - New exterior Polywood dining table - New interior dining table set - New screened ...
From $414 per night (USD)VRBO
- From $385 per night (USD)
VRBO
Desirable north end Anna Maria. \n 3 blocks to sugar sand beach. Heated pool.
- 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 $268 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 $268 per night (USD)VRBO
- From $491 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 $491 per night (USD)VRBO
- From $1160 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 $1160 per night (USD)Expedia
- From $357 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 $357 per night (USD)VRBO
- From $422 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 $422 per night (USD)Expedia
- From $270 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 $270 per night (USD)VRBO
- From $742 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 $742 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 $129 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 $129 per night (USD)Expedia
- From $488 per night (USD)
VRBO
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 $488 per night (USD)VRBO
- 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 $560 per night (USD)
VRBO
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 $560 per night (USD)VRBO
- From $389 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 $389 per night (USD)VRBO
- From $188 per night (USD)
VRBO
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 $188 per night (USD)VRBO
- From $486 per night (USD)
Expedia
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 $486 per night (USD)Expedia
- From $436 per night (USD)
VRBO
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 $436 per night (USD)VRBO
- From $550 per night (USD)
Expedia
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 $550 per night (USD)Expedia
- From $410 per night (USD)
VRBO
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 $410 per night (USD)VRBO
- From $683 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 $683 per night (USD)Expedia
- From $495 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 $495 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 $306 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 $306 per night (USD)VRBO
- From $150 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 $150 per night (USD)Expedia
- From $454 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 $454 per night (USD)VRBO
- From $235 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 $235 per night (USD)Expedia
- From $786 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 $786 per night (USD)VRBO
- From $252 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 $252 per night (USD)Expedia
- From $736 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 $736 per night (USD)VRBO
- From $526 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 $526 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 $329 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 $329 per night (USD)VRBO
- From $369 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 $369 per night (USD)VRBO
- From $3756 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 $3756 per night (USD)Expedia
- From $348 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 $348 per night (USD)VRBO
- From $703 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 $703 per night (USD)Expedia
- From $607 per night (USD)
VRBO
Coconut Breeze Estate by SeaBreeze Vacation
- 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 $607 per night (USD)VRBO
- From $241 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 $241 per night (USD)VRBO
- From $359 per night (USD)
VRBO
A Mermaid's Tale - By Island Real Estate Vacations
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
When you arrive at Anna Maria Island vacation rental home “A Mermaid's Tale” you are greeted with true island style and ...
From $359 per night (USD)VRBO
- From $439 per night (USD)
Expedia
Marias Way - 3BR\/2BA Pool Home - Anna Maria City -By Island Real Estate Vacation
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
BRAND NEW POOL! Located on the coveted northern end of Anna Maria Island, “Maria's Way” is a charming beach cottage off ...
From $439 per night (USD)Expedia
- From $500 per night (USD)
VRBO
One block off Pine Ave w\/ Amazing Rooftop Views! - AMI Memories
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
AMI Memories by AMI Locals Home in Anna Maria VR20-000052 Welcome to AMI Memories! This three-level home boasts fiv ...
From $500 per night (USD)VRBO
- From $1055 per night (USD)
VRBO
Stunning new 4 bedroom 4.5 bath home with heated pool\/spa and views of Tampa Bay
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Low season, which is a beautiful time to visit Anna Maria, stay for 7 nights and only pay for 6. The dates that this app ...
From $1055 per night (USD)VRBO
- From $482 per night (USD)
VRBO
Blue Bayou | Family fun pool home with hot tub, canalfront with a dock!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
❗ Check-in and checkout days are typically Monday or Friday—with some exceptions for holidays and certain times of the ...
From $482 per night (USD)VRBO
- From $575 per night (USD)
Expedia
Bean Point Gem awaits your stay!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Castaway Cove, this beautiful residence is a Bean Point gem, a stunning 4 bedroom property and 2.5 bathroom o ...
From $575 per night (USD)Expedia
- From $200 per night (USD)
VRBO
Charming cottage in quiet area, close to beach & bay.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Anna Maria Island ''paradise without an attitude''. Our ground level newly renovated unit is located in t ...
From $200 per night (USD)VRBO
- From $618 per night (USD)
Expedia
Hop, Skip and a Beach - 4Bed Pool Home in Anna Maria City - By Island Real Estat
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Oh so close to the beach all it takes is a Hop, Skip and a Jump to get to the Beach! This newer 4 bedroom private pool h ...
From $618 per night (USD)Expedia
- From $430 per night (USD)
VRBO
Waterfront house with pool - bring boat and rod - close to Gulf and Bay Beaches
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
This beautifully spacious home sits on a very large waterfront lot on the northern tip of AMI. The house is embedded in ...
From $430 per night (USD)VRBO
- From $294 per night (USD)
VRBO
Sand Dollar Cottage - Vintage - updated - flip flop walk to Gulf Beaches
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
We only rent thru VRBO! Your safety is our priority. We are writing here as the owners of this lovely cottage. If you ...
From $294 per night (USD)VRBO
- From $340 per night (USD)
VRBO
Dreamscape: North End Pool Home, 2 Blocks to Beach by Anna Maria Life Vacation Rentals
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
773 Jacaranda Rd., Anna Maria, FL 34216 What You'll Love About This Home: Location! Just two blocks from the North En ...
From $340 per night (USD)VRBO
- From $818 per night (USD)
Expedia
5 O'Clock Somewhere: Dog Friendly Canal Front, Elevator, Pool, Beach 2 Blocks by Anna Maria Life
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
216 Chilson Ave, Anna Maria, FL 34216 What You'll Love About This Home: Location! North End of AMI - 2 Blocks to the B ...
From $818 per night (USD)Expedia
- From $211 per night (USD)
VRBO
Beach N Bay 204 by Duncan Real Estate
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Beach N Bay 204! A honeymooners delight or a couple’s retreat! Enjoy a romantic getaway! Don't miss your ch ...
From $211 per night (USD)VRBO
- From $999 per night (USD)
VRBO
North End of AMI, Heated\/Chilled Pool, Ocean Views, Tropical Oasis with elevator
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
This home is a showcase stunner! Sea Breeze was has been remodeled and professionally decorated. It is located at the q ...
From $999 per night (USD)VRBO
- From $879 per night (USD)
VRBO
Large Home Directly on the Beach - By Island Real Estate Vacations
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 14
Family friendly with fantastic views and directly on the Gulf of Mexico sound like your idea of a perfect vacation renta ...
From $879 per night (USD)VRBO
- From $610 per night (USD)
Expedia
Private Tropical Oasis so close to BEACH with a great Pool and Spa!
- Bedrooms:
- 6
- Bathrooms:
- 8
- Sleeps:
- 16
Tropical Oasis by Anna Maria Island Locals Home in Holmes Beach, FL Highlights: • Private pool with waterfall, hot tub ...
From $610 per night (USD)Expedia
- From $462 per night (USD)
VRBO
Home just steps to BEACH! Private pool and spa - Sign of the Mermaid
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 12
Sign of the Mermaid by AMI Locals Home in Anna Maria, Florida VR17-000054 Welcome to Sign of the Mermaid, a luxurious ...
From $462 per night (USD)VRBO
- From $518 per night (USD)
Expedia
Mainsail Beach Inn 2 Bedroom
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
The stunning interiors in your private Holmes Beach vacation rental are elegant, fresh and bright. The two bedroom, 2.5 ...
From $518 per night (USD)Expedia
- From $676 per night (USD)
VRBO
The Perfect Gulf Front Vacation, Directly on the Beach!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Osprey House, Gulf front vacation rental-located on the North end of Anna Maria Island. Located directly on t ...
From $676 per night (USD)VRBO
- From $572 per night (USD)
Expedia
Jacaranda Gem by Beach Boutique Rentals
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Take a break from the hustle and bustle, and relax in the calm and serene atmosphere of this spotless vacation home. Jac ...
From $572 per night (USD)Expedia