Anna Maria, Florida Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Anna Maria, Florida on RentalSaver.com!

Anna Maria Rentals

From $627 per night (USD)
VRBO
Updated Pool Unit 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 $627 per night (USD)
VRBO
From $727 per night (USD)
Expedia
EV Charger, Portside Paradise by SeaBreeze Vacation
Bedrooms:
6
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 $727 per night (USD)
Expedia
From $1370 per night (USD)
VRBO
Luxury Home with Pool and Spa! 4 Minutes to the Beach! - Feelin' Beachy
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Feelin' Beachy by AMI Locals Holmes Beach Luxury Beach Retreat with Pool VRC20-000140 Prepare for endless enjoyment a ...
From $1370 per night (USD)
VRBO
From $913 per night (USD)
VRBO
CabAnna Maria Beach Block 4 Bedroom 4.5 Bath
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
CabAnna Maria is a newly renovated 4 bedroom, 4.5 bath house, that sleeps 8 (max) comfortably, a quick 450 ft to the pri ...
From $913 per night (USD)
VRBO
From $489 per night (USD)
VRBO
OCT DEALS - Waterfront/HotTub/ Pool/Boat Dock/Putting Green/Beach
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Last Minute Deals! - Oct 18 to 25, 2025 now $1,999/wk* plus fees & taxes - Oct 25 - Nov 1, 2025 now $1,999/wk* plus fees ...
From $489 per night (USD)
VRBO
From $778 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 $778 per night (USD)
VRBO
From $282 per night (USD)
VRBO
The Ballyhoo on Bean Point, 200 feet to a beautiful bayside beach and views!
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 $282 per night (USD)
VRBO
From $386 per night (USD)
Expedia
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 $386 per night (USD)
Expedia
From $247 per night (USD)
VRBO
Freshly Remodeled Island Suite w/ Pool & Pet Friendly
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 $247 per night (USD)
VRBO
From $275 per night (USD)
Expedia
Freshly Remodeled Island Suite w/ Pool & Pet Friendly
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 $275 per night (USD)
Expedia
From $381 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 $381 per night (USD)
VRBO
From $232 per night (USD)
Expedia
Freshly Remodeled Island Suite w/ Pool & Pet Friendly
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 $232 per night (USD)
Expedia
From $234 per night (USD)
VRBO
Freshly Remodeled Island Suite w/ Pool & Pet Friendly
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 $234 per night (USD)
VRBO
From $413 per night (USD)
Expedia
Freshly Remodeled Island Suite w/ Pool & Pet Friendly
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 $413 per night (USD)
Expedia
From $249 per night (USD)
VRBO
Freshly Remodeled Island Suite w/ Pool & Pet Friendly
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Sunrise Garden #11 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $249 per night (USD)
VRBO
From $362 per night (USD)
Expedia
Freshly Remodeled Island Suite w/ Pool & Pet Friendly
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 $362 per night (USD)
Expedia
From $250 per night (USD)
VRBO
Freshly Remodeled Island Suite w/ Pool & Pet Friendly
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 $250 per night (USD)
VRBO
From $289 per night (USD)
Expedia
Beach Walk: North Beach Village, Pool, Quick Walk to Beach by Anna Maria Life Vacation Rentals
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Beach Walk by Anna Maria Life Vacation Rentals 6250 Holmes Blvd, #31, Holmes Beach, FL 34217 What You'll Love About Thi ...
From $289 per night (USD)
Expedia
From $245 per night (USD)
VRBO
Freshly Remodeled Island Suite w/ Pool & Pet Friendly
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 $245 per night (USD)
VRBO
From $238 per night (USD)
Expedia
Freshly Remodeled Island Suite w/ Pool & Pet Friendly
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 $238 per night (USD)
Expedia
From $268 per night (USD)
VRBO
Freshly Remodeled Island Suite w/ Pool & Pet Friendly
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 $268 per night (USD)
VRBO
From $443 per night (USD)
Expedia
Spacious beach house with a beautiful view of the gulf
Bedrooms:
2
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 $443 per night (USD)
Expedia
From $702 per night (USD)
VRBO
Crescent Palms north end AMI, 2 King suites,walk to bay beach stunning pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Create unforgettable memories at Crescent Palms. This *perfect island house* has been fully renovated in 2025. Crescent ...
From $702 per night (USD)
VRBO
From $719 per night (USD)
Expedia
Pineapple Cottage, walk to the beach &Pine Ave, tropical oasis pool and spa.
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Welcome to Pineapple Cottage a beautifully updated ground-level beach cottage located in the heart of Anna Maria City a ...
From $719 per night (USD)
Expedia
From $629 per night (USD)
VRBO
Island in the Sun, luxury beach house with private pool, walk to Pine Ave
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
WELCOME to Island in the Sun this newly renovated home on AMI offers charm, comfort, and luxury. No damage from hurrica ...
From $629 per night (USD)
VRBO
From $1609 per night (USD)
Expedia
Luxury home with private Pool, Rooftop Putting green, Golf cart, and Bikes!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Palmetto Paradise by AMI Locals Home in Anna Maria, Florida Highlights • 1-minute walk to the beach • Dog friendly wit ...
From $1609 per night (USD)
Expedia
From $375 per night (USD)
VRBO
Beautiful, decorated and furnished, spacious Great Room family & kid friendly,
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Beautifully decorated and furnished home located an easy walk from Gulf beaches and Tampa bay. Includes a master suite ...
From $375 per night (USD)
VRBO
From $373 per night (USD)
Expedia
Freshly Remodeled Island Suite w/ Pool & Pet Friendly
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 $373 per night (USD)
Expedia
From $557 per night (USD)
VRBO
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 $557 per night (USD)
VRBO
From $240 per night (USD)
Expedia
Freshly Remodeled Island Suite w/ Pool & Pet Friendly
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 $240 per night (USD)
Expedia
From $554 per night (USD)
VRBO
Coconut Lagoon – AMI Pet Friendly Home w/ Heated Pool, Screened Porch & Cabana TV
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Coconut Lagoon! On Anna Maria Island (Anna Maria, FL) Discover Coconut Lagoon, Where Pet Friendly Comfort Me ...
From $554 per night (USD)
VRBO
From $280 per night (USD)
Expedia
Freshly Remodeled Island Suite w/ Pool & Pet Friendly
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 $280 per night (USD)
Expedia
From $287 per night (USD)
VRBO
Shell Cottage - sleeps 2
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Shell Cottage is situated towards the top end of Anna Maria Island. It is one of a cluster of the 3 cottages sharing th ...
From $287 per night (USD)
VRBO
From $295 per night (USD)
VRBO
Bungalow On The Bayou (Best Location on the Island)
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Located on the "best" street on Anna Maria Island, this two-bedroom, one-bath second floor vacation rental with a specta ...
From $295 per night (USD)
VRBO
$Hear The Surf/Feel The Breeze... skip to beach!\nLocated on Anna Maria Island$
From $822 per night (USD)
VRBO
Hear The Surf/Feel The Breeze... skip to beach!\nLocated on Anna Maria Island
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Just 5 houses from the white sandy beach of the Gulf. Located in the city of Anna Maria sits this spacious home with ...
From $822 per night (USD)
VRBO
From $1035 per night (USD)
Expedia
On the BEACH block! Luxury home, Pool and Spa, stay and relax with your friends!
Bedrooms:
4
Bathrooms:
6
Sleeps:
12
Villa La Concha by Anna Maria Island Accommodations 113 Maple Ave, Anna Maria, FL, 34216 VR16-000446 Welcome to Vi ...
From $1035 per night (USD)
Expedia
From $2186 per night (USD)
VRBO
Island Retreat! Pool, Spa, Rooftop Views and Covered Outdoor Dining
Bedrooms:
7
Bathrooms:
7
Sleeps:
16
Bay View Beauty by AMI Locals 881 N Shore Dr, Anna Maria, Florida VR18-000097 Welcome to Bay View Beauty, a luxury ...
From $2186 per night (USD)
VRBO
From $599 per night (USD)
Expedia
Palm Beach House: Pet friendly pool home, close to the beach!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Photo Updated March 2025! Treat yourself to the beachside vacation you’ve been dreaming of with this relaxing and dog-f ...
From $599 per night (USD)
Expedia
From $532 per night (USD)
VRBO
OCT DEALS - Waterfront Canal /Hot Tub/Htd Pool/ Boat Dock/ AMIHomeRental
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Last Minute Deals! - Oct 4 - 11, 2025 now $1,799/wk* plus fees & taxes - Oct 18 - 25, 2025 now $1,799/wk* plus fees & ta ...
From $532 per night (USD)
VRBO
From $321 per night (USD)
Expedia
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 $321 per night (USD)
Expedia
From $412 per night (USD)
VRBO
Island Serenity: North Beach Village, Dog Friendly, Short Walk to Beach by Anna Maria Life
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Island Serenity by Anna Maria Life Vacation Rentals 6250 Holmes Blvd. #54, Holmes Beach, FL 34217 What You'll Love Abou ...
From $412 per night (USD)
VRBO
$Perfect Anna Maria-20% off Aug/Sep\n 3 blocks to sugar sand beach. Heated pool.$
From $372 per night (USD)
Expedia
Perfect Anna Maria-20% off Aug/Sep\n 3 blocks to sugar sand beach. Heated pool.
Bedrooms:
2
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 $372 per night (USD)
Expedia
From $316 per night (USD)
VRBO
Blue Heron Cottage - Anna Maria Island
Bedrooms:
1
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 $316 per night (USD)
VRBO
From $575 per night (USD)
Expedia
Sandy Rose: Putting green, heated pool, outdoor living spaces
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
***Photos Updated October 2025*** Situated on the north end of Anna Maria Island, The Sandy Rose is the perfect locatio ...
From $575 per night (USD)
Expedia
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VRBO
Luxury Home Close to Beach! Pool, Putting Green, and Outdoor Games!
Bedrooms:
4
Bathrooms:
7
Sleeps:
16
Seaside Magnolia by Anna Maria Island Accommodations Holmes Beach Luxury Vacation Home Near Beaches VRC18-000096 Step ...
Click For Pricing
VRBO
From $418 per night (USD)
Expedia
Gulf Place Unit 8 in Holmes Beach
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, Gulf Place ...
From $418 per night (USD)
Expedia
From $493 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 $493 per night (USD)
VRBO
From $452 per night (USD)
Expedia
STEPS TO THE BEACH WITH POOL! CAN BE RENTED AS A 4 BEDROOM!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Quiet and quaint is this spectacular 2 Bedroom/1 Bath Duplex with a large HEATED POOL in a lush tropical landscaped sett ...
From $452 per night (USD)
Expedia
From $452 per night (USD)
VRBO
STEPS TO THE BEACH WITH POOL! CAN BE RENTED AS A 4 BEDROOM!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Quiet and quaint is this spectacular 2 Bedroom/1 Bath Duplex with a large HEATED POOL in a lush tropical landscaped sett ...
From $452 per night (USD)
VRBO
From $297 per night (USD)
Expedia
Seahorse Cottage - sleeps 2 guests in 1 bedroom
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
The property is situated towards the top end of Anna Maria Island. It is one of a cluster of 3 cottages which have the ...
From $297 per night (USD)
Expedia
From $1011 per night (USD)
VRBO
Palmetto Pointe! 5BR Luxury Home with Pool, Spa, Rooftop Deck and Walk to Beach
Bedrooms:
5
Bathrooms:
5
Sleeps:
8
Palmetto Pointe by AMI Locals 201 Palmetto Ave, Anna Maria, FL VR19-000033 Welcome to Palmetto Pointe, a luxurious ...
From $1011 per night (USD)
VRBO
From $356 per night (USD)
Expedia
Beautifully updated home with private pool, close to beach, 2 bedrooms!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Sea Grape Escape by AMI Locals Home in Holmes Beach, FL Features: • Pool • Backyard Patio with TV • Beach chairs for g ...
From $356 per night (USD)
Expedia
From $273 per night (USD)
VRBO
A lovely 2 bed and 2 bath property just moments from the beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Seabreeze Cottage is situated on a quiet road with access to the beach, via a leafy lane, just 200 feet away. The prope ...
From $273 per night (USD)
VRBO
From $202 per night (USD)
Expedia
Adorable Cottage ONLY STEPS to Anna Maria Beach, No Roads to Cross! FREE WiFi...
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
**ASK ABOUT LAST MINUTE DEALS! Enjoy a simple, old fashioned seaside vacation in this adorable duplex west ...
From $202 per night (USD)
Expedia
From $215 per night (USD)
VRBO
FREE WiFi & Trolley ONLY STEPS to Pristine Sandy Beach NO Roads to Cross!
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
**ASK ABOUT LAST MINUTE DEALS! Island fun is easy in this 2 unit charming cottage located two houses from t ...
From $215 per night (USD)
VRBO
From $306 per night (USD)
Expedia
Perfectly Located Near the Beach, Dining, and Shopping!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Saltwater Palms by AMI Locals 6321 Gulf Dr, Holmes Beach, FL 34217 VRC21-000078 Welcome to Saltwater Palms, a stylish ...
From $306 per night (USD)
Expedia
From $649 per night (USD)
VRBO
La Buena Vida – Canal Home w/ Pool, Spa, Dock, Pets OK & Walk To Beach
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Welcome to La Buena Vida! On Anna Maria Island (Anna Maria, FL) Nestled Along The Canal, La Buena Vida Is A Pet-Friendl ...
From $649 per night (USD)
VRBO
From $1242 per night (USD)
Expedia
Luxe Island Escape by Beach Boutique Rentals
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Welcome to Luxe Island Escape! A next-level, brand new construction tropical retreat. *Features include* * Huge heat ...
From $1242 per night (USD)
Expedia
From $799 per night (USD)
VRBO
Charming Beachfront Bungalow with Sunset Views and Coastal Comfort
Bedrooms:
3
Bathrooms:
3
Sleeps:
4
High Tide by AMI Locals 108 Elm Ave, Unit B Anna Maria, Florida VR21-000077 Wake up to the soothing sound of the w ...
From $799 per night (USD)
VRBO
From $258 per night (USD)
Expedia
Freshly Remodeled Island Suite w/ Pool & Pet Friendly
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 $258 per night (USD)
Expedia
From $661 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 $661 per night (USD)
VRBO
From $538 per night (USD)
Expedia
Aqua Marine By The Bay
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Discover an Anna Maria little secret --BAYFRONT HOME WITH A WHITE SANDY BEACH -- offering the best of both worlds. Nes ...
From $538 per night (USD)
Expedia
From $442 per night (USD)
VRBO
Peaceful Poolside Escape Near Holmes Beach!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Blue Oasis East by AMI Locals 401 72nd St A, Holmes Beach, FL 34217 VRC21-000102 Welcome to Blue Oasis East, a beaut ...
From $442 per night (USD)
VRBO
From $447 per night (USD)
Expedia
Blue Oasis West! Family-Friendly Duplex Near Shops and Dining
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Blue Oasis West by AMI Locals 401 72nd St B, Holmes Beach, FL VRC21-000103 Welcome to Blue Oasis West, a newly remod ...
From $447 per night (USD)
Expedia
From $710 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 $710 per night (USD)
VRBO
From $356 per night (USD)
Expedia
DIRECT GULFRONT CONDO - 2BR/2BA Condo with pool and tennis - By Island Real Esta
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
*Please Note: Exterior painting and roofing projects are scheduled between Sept 22–Dec 31, 2025. Work may cause noise or ...
From $356 per night (USD)
Expedia
From $306 per night (USD)
VRBO
Spacious Condo on the Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Newly remodeled condo with a view of the gulf from your relaxing balcony. Large heated pool and hot tub amid lush landsc ...
From $306 per night (USD)
VRBO
From $1620 per night (USD)
Expedia
Canal Front Home with Dock! Putting Green, Pool with Waterslide
Bedrooms:
3
Bathrooms:
5
Sleeps:
8
Tortuga Bay by Anna Maria Island Locals Home in Anna Maria, FL Welcome to the newly remodeled Tortuga Bay! This five-be ...
From $1620 per night (USD)
Expedia
From $476 per night (USD)
VRBO
Bean Point Bungalow! Pet Friendly Home with Pool and Walk to Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Bean Point Bungalow by AMI Locals 770 N Shore Dr, Anna Maria, FL VR17-000061 Welcome to Bean Point Bungalow, a char ...
From $476 per night (USD)
VRBO
Click For Pricing
Expedia
Resort Sixty-Six - Anna Maria Island Quiet Studio
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
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 Pricing
Expedia
From $846 per night (USD)
VRBO
AMI Stay! Family-Friendly Home with Pool, Soaking Tub and Bay Views
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Bay Happy by AMI Locals 403 N Bay Blvd, Anna Maria, FL VR21-000047 Welcome to Bay Happy, a four bedroom, three bath ...
From $846 per night (USD)
VRBO
Click For Pricing
Expedia
Luxury Home with Private Covered Pool and Putting Green - AMI Oasis
Bedrooms:
4
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 ...
Click For Pricing
Expedia
From $904 per night (USD)
VRBO
Anna Maria Luxury Home with Private Pool, Rooftop Deck & Gulf Views! 1.5 Blocks
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Montego Bay by AMI Locals 211 Magnolia Avenue, Anna Maria, Florida 34216 VPR16-000472 Escape to Montego Bay, a stunnin ...
From $904 per night (USD)
VRBO
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Expedia
Batley's Beach House: Perfect location, ground-level rental
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Photos Updated April 2025 Located in the "heart" of Anna Maria City, sits this ground level, 3 bedroom, 2 bath home jus ...
Click For Pricing
Expedia
From $967 per night (USD)
VRBO
Reef Romance managed by Beach Retreats FL Anna Maria Island
Bedrooms:
4
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 $967 per night (USD)
VRBO
From $600 per night (USD)
Expedia
At Last: Ground-level, pool, hot tub, canalfront, dock
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
***Photos Updated May 2025*** Come slip away to this luxurious island retreat where all of your cares will drift away! T ...
From $600 per night (USD)
Expedia
From $421 per night (USD)
VRBO
Turtle Cottage - Anna Maria Island
Bedrooms:
1
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 $421 per night (USD)
VRBO
From $515 per night (USD)
Expedia
SeaStarVilla by Duncan Real Estate
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Welcome to Sea Star Villa! This well constructed 2-bedroom, 3-bathroom Island home with a bonus room is ready to host gu ...
From $515 per night (USD)
Expedia
From $270 per night (USD)
VRBO
Shell Game: Playa Encantada - Beachfront Community Steps to the Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Shell Game has recently been transformed into a fun and stunning tropical retreat that offers 1,154 sq. ft. of spacious ...
From $270 per night (USD)
VRBO
From $386 per night (USD)
Expedia
Cozy Cabana East – AMI w/ Heated Pool, Pets & Walk To The Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Cozy Cabana East! On Anna Maria Island (Holmes Beach, Florida) Discover Cozy Cabana East, Where Island Comfo ...
From $386 per night (USD)
Expedia
From $1025 per night (USD)
VRBO
Tropical Backyard Escape with Pool, Hot Tub, and Waterslide
Bedrooms:
4
Bathrooms:
6
Sleeps:
12
Conch House by AMI Locals 307 66th St, Unit B | Holmes Beach, Florida VRC18-000085 Welcome to Conch House, a gorge ...
From $1025 per night (USD)
VRBO
From $1347 per night (USD)
Expedia
Beachfront Bliss! Pool, Spa & Sunsets!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Beachfront Bungalow by AMI Locals Holmes Beach Gulf-Front Cottage with Private Pool and Spa VRC19-000270 Welcome to ...
From $1347 per night (USD)
Expedia
From $811 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 $811 per night (USD)
VRBO
From $430 per night (USD)
Expedia
Beach Condo with Pool Near Holmes Beach
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Coconuts Poolside #104 by AMI Locals 100 73rd St, Unit #104, Holmes Beach, FL 34217 VRC16-000664 Welcome to Coconuts ...
From $430 per night (USD)
Expedia
From $2512 per night (USD)
VRBO
Beachfront - New Listing!
Bedrooms:
5
Bathrooms:
5
Sleeps:
8
The Diamond Star Beach House ***Brand New 2025 Remodel*** Welcome to The Diamond Star! Experience beachfront living ...
From $2512 per night (USD)
VRBO
From $669 per night (USD)
Expedia
Sul Mare at Vista Grande on Anna Maria Island - By Island Real Estate Vacations
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
By far the BEST direct view of the Gulf you will find on Anna Maria Island. Exclusive SUL MARE with floor to ceiling win ...
From $669 per night (USD)
Expedia
From $909 per night (USD)
VRBO
Luxury home with AMAZING backyard Pool and Spa! So close to beach and shopping!
Bedrooms:
4
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 $909 per night (USD)
VRBO
From $379 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. Recently remodeled we are open for guests . Anna Maria Island vacatio ...
From $379 per night (USD)
VRBO
From $397 per night (USD)
VRBO
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 $397 per night (USD)
VRBO
From $1102 per night (USD)
Expedia
One block off Pine Ave w/ Amazing Rooftop Views! - AMI Memories
Bedrooms:
3
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 $1102 per night (USD)
Expedia
From $1151 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
THANK YOU TO ALL OUR PAST, FUTURE AND POTENTIAL GUESTS WHO HAVE REACHED OUT TO US IN THE LAST FEW WEEKS TO INQUIRE ABOUT ...
From $1151 per night (USD)
VRBO
From $215 per night (USD)
Expedia
Lazy Lizard! A Newly Renovated Island Cottage, Close to the Beach!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Photos Updated January 2025! LONG-TERM DISCOUNT: Stays of 4-weeks (28 nights) or more enjoy a 25% discount on the night ...
From $215 per night (USD)
Expedia
From $703 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 $703 per night (USD)
VRBO
From $781 per night (USD)
Expedia
North end AMI, 5* luxury home in one of the prettiest towns on gulf coast!
Bedrooms:
2
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 $781 per night (USD)
Expedia
From $298 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 $298 per night (USD)
VRBO
From $655 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 $655 per night (USD)
Expedia
From $902 per night (USD)
VRBO
4 Bedroom Townhouse - Your private Holmes Beach vacation home
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Welcome to the spacious Unit 12, a four-bedroom, three-bathroom townhouse attractively adorned with white walls, cool pa ...
From $902 per night (USD)
VRBO
From $334 per night (USD)
Expedia
AMI Moana Villa 3-minute walk to the beach plus community heated pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Find everything you need for a fun and memorable beach getaway at this three-bedroom Holmes Beach rental! You'll have a ...
From $334 per night (USD)
Expedia
From $585 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 $585 per night (USD)
VRBO
From $401 per night (USD)
Expedia
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 $401 per night (USD)
Expedia

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