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From $195 per night (USD)
VRBO
Vacation Day Is Always A Great Idea! Kitchenette, Clubhouse with BBQ Grill Area
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
This spacious 1250sf apartment located in a private, gated community in a close vicinity from the beautiful white sand b ...
From $195 per night (USD)
VRBO
From $587 per night (USD)
VRBO
Vacation Day Is Always A Great Idea! 3 Convenient Units, Outdoor Pool, Clubhouse
Bedrooms:
6
Bathrooms:
9
Sleeps:
12
This accommodation consists of THREE Spacious 1250sf apartments located in a private, gated community in a close vicinit ...
From $587 per night (USD)
VRBO
From $392 per night (USD)
VRBO
Your Home Away From Home! 2 Convenient Units, Kitchenette, Free Parking, Pool
Bedrooms:
4
Bathrooms:
6
Sleeps:
8
This accommodation consists of TWO Spacious 1250sf apartments located in a private, gated community in a close vicinity ...
From $392 per night (USD)
VRBO
From $587 per night (USD)
VRBO
Vacation is Calling! 3 Family-friendly Units, Children's Playground, Pool
Bedrooms:
6
Bathrooms:
9
Sleeps:
12
This accommodation consists of THREE Spacious 1250sf apartments located in a private, gated community in a close vicinit ...
From $587 per night (USD)
VRBO
From $195 per night (USD)
VRBO
Your Relaxing Getaway Awaits! Kitchenette, Outdoor Pool, Children's Playground
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
This spacious 1250sf apartment located in a private, gated community in a close vicinity from the beautiful white sand b ...
From $195 per night (USD)
VRBO
From $392 per night (USD)
VRBO
Dive Into Your Dream Vacation! 2 Great Units, Kitchenette, Onsite Outdoor Pool
Bedrooms:
4
Bathrooms:
6
Sleeps:
8
This accommodation consists of TWO Spacious 1250sf apartments located in a private, gated community in a close vicinity ...
From $392 per night (USD)
VRBO
From $954 per night (USD)
VRBO
Gorgeous direct bay front home! Steps to beach! Amazing sunrises and pool!!!
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Welcome to Our Charming Bayfront Retreat in Anna Maria! Discover the ultimate coastal retreat at our inviting home, nes ...
From $954 per night (USD)
VRBO
$Bring Your Own Boat! Waterfront Home w\/ Private Heated Pool, 5 Min to AMI$
From $411 per night (USD)
Expedia
Bring Your Own Boat! Waterfront Home w\/ Private Heated Pool, 5 Min to AMI
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to our beautiful Blue Opal vacation home. This 3 bedroom and 2 bathroom waterfront and private pool home is idea ...
From $411 per night (USD)
Expedia
From $454 per night (USD)
VRBO
Bungalow 101: The Superior Coquina Gulf View
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
If stepping outside into the warm Anna Maria Island sand is what you in mind, the Coquina bungalow may just be for you. ...
From $454 per night (USD)
VRBO
From $309 per night (USD)
Expedia
Bungalow 106: The studio in front of Dollar Bay
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Spacious studio style bungalow with a full kitchen, king size bed, pull out sleeper sofa and a single shower bathroom. N ...
From $309 per night (USD)
Expedia
From $469 per night (USD)
VRBO
Bungalow 104: King Studio with Gulf of Hibiscus View
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Directly on the beach with a breathtaking view of the Gulf of Mexico. White sands and the sea green gulf await you just ...
From $469 per night (USD)
VRBO
From $376 per night (USD)
Expedia
Bungalow 105: The Seagull Gulf Front Studio
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Spectacular gulf front views from nearly anywhere in the “Seagull” make this comfortable bungalow your personal tropical ...
From $376 per night (USD)
Expedia
From $362 per night (USD)
VRBO
Cozy couples hideaway! 5-min walk to beautiful white sand beach at Bean Point.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Flexible Check-in and checkout days —with some exceptions for holidays and certain times of the year—and never on Sunday ...
From $362 per night (USD)
VRBO
From $388 per night (USD)
Expedia
Cute & cozy getaway at north end of Anna Maria Island. 5-min walk to the beach!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Located at the quiet North end of Anna Maria Island, this charming 2-bedroom, 1-bath villa is a short walk to beautiful ...
From $388 per night (USD)
Expedia
From $931 per night (USD)
VRBO
Golf Cart, Salty Shamrock by SeaBreeze Vacation
Bedrooms:
3
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 $931 per night (USD)
VRBO
From $531 per night (USD)
Expedia
4BR Oasis w Pond View! Private Heated Pool & Games
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
If travel is on the horizon, set your sails to luxury and tranquility at this newly updated 4BR/3BA getaway. The sunset ...
From $531 per night (USD)
Expedia
Click For Pricing
VRBO
Two Bedroom Condo, Gulf Front, Bradenton Beach (2106005)
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Via Roma Beach Resort club resort 2408 Gulf Drive North Bradenton Beach, FL 34217 With its white stucco buildings, Io ...
Click For Pricing
VRBO
$WBC 212 Spacious 2\/2 Pool Tennis Condo Close To White Sand Beach Shopping$
From $229 per night (USD)
Expedia
WBC 212 Spacious 2\/2 Pool Tennis Condo Close To White Sand Beach Shopping
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
VRC20-000174 Westbay Cove 212 located at 600 Manatee Ave West in Holmes Beach is a picturesque and luxurious two bedroo ...
From $229 per night (USD)
Expedia
$Beautiful Dog-Friendly Home w\/ Fast WiFi, Central AC, & W\/D - Snowbirds Welcome$
From $308 per night (USD)
VRBO
Beautiful Dog-Friendly Home w\/ Fast WiFi, Central AC, & W\/D - Snowbirds Welcome
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Warner's Bayou Too! Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $308 per night (USD)
VRBO
$Lakeside Retreat! Lakefront Living in Northwest Bradenton w\/ Saltwater Pool$
From $371 per night (USD)
Expedia
Lakeside Retreat! Lakefront Living in Northwest Bradenton w\/ Saltwater Pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Lakeside Retreat truly is a treat! This home is brand new to the rental market with so many extras to make your vacation ...
From $371 per night (USD)
Expedia
From $516 per night (USD)
VRBO
FANTASTIC, RENOVATED 2 BEDROOM HOME STEPS TO BEACH!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
3706 Gulf Drive, Holmes Beach, FL Anna Maria Island Fantastic, recently renovated home located just steps to the beach. ...
From $516 per night (USD)
VRBO
From $347 per night (USD)
Expedia
Stunning & Serene, Minutes to Anna Maria Island, IMG & More
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
When you stay here you'll enjoy these serene and pastoralpark-like grounds with non-stop views of catch and release fish ...
From $347 per night (USD)
Expedia
From $440 per night (USD)
VRBO
Sun Plaza West 105 - Two Bedroom condo, Sleeps 6- on the beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
AT A GLANCE Recently remodeled gulf front condo 2 Bedrooms and 2 Bathrooms with two balconies Complex equipped with a l ...
From $440 per night (USD)
VRBO
$Elegant Beachfront Condo w\/pool! Walking distance to many restaurants and shops$
From $545 per night (USD)
VRBO
Elegant Beachfront Condo w\/pool! Walking distance to many restaurants and shops
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Elegant, Beachfront Top Floor Condo - walk directly onto the Beautiful beaches of Anna Maria Island. Honey maple kitchen ...
From $545 per night (USD)
VRBO
$217 84th - Anna Maria Island- Private home 3 Bedroom\/ 2 Bath with private...$
From $320 per night (USD)
VRBO
217 84th - Anna Maria Island- Private home 3 Bedroom\/ 2 Bath with private...
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
217 84th Street - Anna Maria Island - 3 Bedroom/ 2 Bath, maximum occupancy of 6 people. VRC#20-000113 Private Poo ...
From $320 per night (USD)
VRBO
$Island Beach Club 22 - Anna Maria Island - Condo 2 Bedroom \/ 1 Bath gulf...$
From $347 per night (USD)
Expedia
Island Beach Club 22 - Anna Maria Island - Condo 2 Bedroom \/ 1 Bath gulf...
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Island Beach Club 22 - Anna Maria Island - Condo 2 Bedroom / 1 Bath, maximum occupancy of 4 people. VRC20-000254 ...
From $347 per night (USD)
Expedia
Click For Pricing
VRBO
LIME IN DE COCONUT- DOWNSTAIRS
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
LIME IN DE COCONUT- DOWNSTAIRS..... Adorable, ground level two bedroom, two bath in a 2 unit cottage. Cheery beach de ...
Click For Pricing
VRBO
$Sand Of Times-Beautiful 6 bedrooms with private pool\/spa with a water slide$
From $773 per night (USD)
Expedia
Sand Of Times-Beautiful 6 bedrooms with private pool\/spa with a water slide
Bedrooms:
5
Bathrooms:
6
Sleeps:
12
Sands of Time 6908 Holmes Blvd Holmes Beach, FL 34217 Sands of Time is a newly built 6 bedroom, 4.5 bathroom vacation ...
From $773 per night (USD)
Expedia
$Island Beach Club 21 - Anna Maria Island - Condo 2 Bedroom \/ 2 Bath gulf...$
From $386 per night (USD)
VRBO
Island Beach Club 21 - Anna Maria Island - Condo 2 Bedroom \/ 2 Bath gulf...
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Island Beach Club 21 - Anna Maria Island - Condo 2 Bedroom / 2 Bath, maximum occupancy of 4 people. Gulf/Beach Fr ...
From $386 per night (USD)
VRBO
$Island Beach Club 24 - Anna Maria Island - Condo 2 Bedroom \/ 1 Bath gulf...$
From $329 per night (USD)
Expedia
Island Beach Club 24 - Anna Maria Island - Condo 2 Bedroom \/ 1 Bath gulf...
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Island Beach Club 24 - Condo 2 Bedroom / 1 Bath gulf front , maximum occupancy of 4 people. VRC16-000069 Max 1 veh ...
From $329 per night (USD)
Expedia
From $319 per night (USD)
VRBO
2nd House from the Beach with No Roads to Cross
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
The Seaside Sanctuary is the upper level unit of a beachfront duplex. It is the 2nd house from the beach with no roads ...
From $319 per night (USD)
VRBO
$Island Beach Club 1- Anna Maria Island-Condo 2 Bedroom\/2 Bath gulf front,...$
From $381 per night (USD)
Expedia
Island Beach Club 1- Anna Maria Island-Condo 2 Bedroom\/2 Bath gulf front,...
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Island Beach Club 1 - Condo 2 Bedroom / 2 Bath, maximum occupancy of 4 people. VRC16-000745 Beach/Gulf Front - Com ...
From $381 per night (USD)
Expedia
From $402 per night (USD)
VRBO
BAY PALMS - SPACIOUS POOL HOME WITH WONDERFUL AMENITIES. WALK TO A GREAT BEACH! A MUST SEE!
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Bay Palms..... Exceptional, newer 3 bedroom, 2.5 bath villa located just a short walk to the beach. This wonderful renta ...
From $402 per night (USD)
VRBO
From $502 per night (USD)
Expedia
AM I Dreaming: Heated Pool, Family Friendly Home, 3-min walk to beach!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
The vacation you have imagined finally becomes a reality. AM I dreaming is a bright and charming 3 bedroom, 2 bathroom c ...
From $502 per night (USD)
Expedia
From $358 per night (USD)
VRBO
Restored 1920's Anna Maria Island Cottage . 1 block to the beach with no roads to cross! Quaint, ch
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
110 31st St., Holmes Beach, FL 34217 "Almost to the Beach" ... Charming, updated 1920's cottage with 2 bedrooms and 1 b ...
From $358 per night (USD)
VRBO
From $429 per night (USD)
Expedia
Bay Breeze Cottages #3
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Summary: Bay Breeze Cottages is an Old Florida Charm Boutique Resort located on historic Anna Maria Island. Bask in the ...
From $429 per night (USD)
Expedia
From $170 per night (USD)
VRBO
White Palm-2 bedroom monthly condo getaway awaits you with beautiful bay views
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
At a Glance Newly redecorated condo located on the northeastern Bayfront of Anna Maria Island 2 bedrooms and 2 bathro ...
From $170 per night (USD)
VRBO
$Anna Maria Island Club 31, Condo 2 Bedroom\/ 2 Bath ocean view, maximum...$
From $989 per night (USD)
Expedia
Anna Maria Island Club 31, Condo 2 Bedroom\/ 2 Bath ocean view, maximum...
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Anna Maria Island Club 31 - Anna Maria Island - Condo - 2 Bedroom/ 2 Bath, maximum occupancy of 4 people. Gulf Vie ...
From $989 per night (USD)
Expedia
$Thanksgiving dinner included: 15lb Turkey\/Sweet Potato Mash\/Pumpkin Pie$
From $940 per night (USD)
VRBO
Thanksgiving dinner included: 15lb Turkey\/Sweet Potato Mash\/Pumpkin Pie
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
If you are looking to enjoy Anna Maria Island in a beautiful home, look no further than "Sunny Side of the Beach" on 66t ...
From $940 per night (USD)
VRBO
$Bradenton Beach Club A - Anna Maria Island- Condo 3 Bedroom\/ 2 Bath ocean...$
From $977 per night (USD)
Expedia
Bradenton Beach Club A - Anna Maria Island- Condo 3 Bedroom\/ 2 Bath ocean...
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Bradenton Beach Club, Unit A - Anna Maria Island - 3 Bedroom/ 2 Bath, maximum occupancy of 6 people. Gulf Front ...
From $977 per night (USD)
Expedia
$Sandy Point 111 - Anna Maria Island - Condo 2 Bedroom\/ 2 Bath, maximum...$
From $408 per night (USD)
VRBO
Sandy Point 111 - Anna Maria Island - Condo 2 Bedroom\/ 2 Bath, maximum...
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Sandy Point 111 - Anna Maria Island - 2 Bedroom/ 2 Bath, maximum occupancy of 4 people. VRC16-000289 Distan ...
From $408 per night (USD)
VRBO
Click For Pricing
Expedia
Lime In De Coconut - Upstairs 1 bedroom, 1 bath shared pool. Walk to beaches!
Bedrooms:
1
Bathrooms:
2
Sleeps:
2
LIME IN DE COCONUT- UPSTAIRS..... Adorable, one bedroom, one bath in a 2 unit cottage. Cheery beach decor and a shared ...
Click For Pricing
Expedia
$Sandy Point Cove 112 - Anna Maria Island -Condo 2 Bedroom\/ 2 Bath, maximum...$
From $418 per night (USD)
VRBO
Sandy Point Cove 112 - Anna Maria Island -Condo 2 Bedroom\/ 2 Bath, maximum...
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Sandy Point Cove 112 - Anna Maria Island - 2 Bedroom/ 2 Bath, maximum occupancy of 6 people. VRC19-000138 Distance ...
From $418 per night (USD)
VRBO
From $515 per night (USD)
Expedia
Cuddlefish Cove: Heated Pool, rooftop deck, gorgeous views!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Cuddlefish Cove Your flip flops have found a new retreat by the beach! Stay for a week or a month at this dazzling Key W ...
From $515 per night (USD)
Expedia
Click For Pricing
VRBO
Two Bedroom Condo, Gulf Front, Bradenton Beach (2105996)
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Via Roma Beach Resort club resort 2408 Gulf Drive North Bradenton Beach, FL 34217 With its white stucco buildings, Io ...
Click For Pricing
VRBO
From $494 per night (USD)
Expedia
Luxury Sarasota HEATED Pool Oasis Close to Beaches!!
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
Completely updated 3 bedroom 3 bathroom home that has been beautifully renovated and furnished in a modern coastal desig ...
From $494 per night (USD)
Expedia
$Island Walk 313 - Anna Maria Island - Townhouse 3 Bedroom\/ 2 .5 Bath with...$
From $349 per night (USD)
VRBO
Island Walk 313 - Anna Maria Island - Townhouse 3 Bedroom\/ 2 .5 Bath with...
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Island Walk 313 - Anna Maria Island - Townhouse - 3 Bedroom/ 2 .5 Bath, maximum occupancy of 6 people. VRC16-000052 ...
From $349 per night (USD)
VRBO
From $462 per night (USD)
Expedia
South Beach Village 111-By Island Real Estate Vacations
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Enjoy a home-away-from-home vacation here. This 3 bedroom town home is very spacious with an open floor plan. Open the s ...
From $462 per night (USD)
Expedia
From $732 per night (USD)
VRBO
Casa Morado-Pet Friendly Pool Home West of Gulf Dr-By Island Real Estate Vacatio
Bedrooms:
4
Bathrooms:
5
Sleeps:
8
Just a few short blocks with no busy roads to cross to get to the beach. The home is very spacious with 4 bedrooms. Th ...
From $732 per night (USD)
VRBO
$2 Bd\/2 Bath Condo on Sarasota Bay Across from Gulf of Mexico 3-6 month rental$
From $175 per night (USD)
Expedia
2 Bd\/2 Bath Condo on Sarasota Bay Across from Gulf of Mexico 3-6 month rental
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Available from June 1st - December 15, 2023. Long-term renter desired. Beautiful corner unit condo with an abundance of ...
From $175 per night (USD)
Expedia
Click For Pricing
VRBO
Beautiful Longboat Key, Florida - Little Gull Resort
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Large 2 bedroom, 2 bathroom suite (plus pull-out sofa bed) Fully equipped kitchen with dishwasher 3 TVs and WIFI Firepla ...
Click For Pricing
VRBO
From $423 per night (USD)
Expedia
Viva La Flamingo! Newly Furnished Home, 10 Min to Anna Maria, Heated Pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Important: This home can sleep a maximum of 6 adults. Welcome to our beautiful Viva La Flamingo home. Newly decorated i ...
From $423 per night (USD)
Expedia
$Family (and snowbird) friendly home w\/ ocean view, central AC, & private hot tub$
From $444 per night (USD)
VRBO
Family (and snowbird) friendly home w\/ ocean view, central AC, & private hot tub
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Sunset Oasis Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $444 per night (USD)
VRBO
From $223 per night (USD)
VRBO
Anna Maria Island Sunshine Kiss Villa
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
The Sunshine Kissed Villa has everything you need for a complete holiday! Our villa has all you need for staying in, an ...
From $223 per night (USD)
VRBO
From $178 per night (USD)
VRBO
GORGEOUS BAY VIEWS! Quiet Escape! Any day check-ins now until November, Call for Fall rates!!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The alluring island of Anna Maria invites you to this refreshing, colorfully decorated, 2 bedroom/ 2 bathroom condo. Loc ...
From $178 per night (USD)
VRBO
$1\/1 Bungalow NW Bradenton$
Click For Pricing
Expedia
1\/1 Bungalow NW Bradenton
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Intimate and tranquil serene cottage with parking for boat trailer, and public ramp just a few blocks away. Minutes awa ...
Click For Pricing
Expedia
From $361 per night (USD)
VRBO
DIRECT BEACHFRONT! PANARAMIC SUNSET VIEWS!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Marbella Villa 10 is a beautiful beach front Condo that gives you that home away from home type of feeling. Bask in the ...
From $361 per night (USD)
VRBO
Click For Pricing
Expedia
Come aboard our nautical adventure
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
2 bedroom 1 bath live aboard yacht. Enjoy the Florida sunshine and Fabulous sunsets! Escape the hustle and bustle of dow ...
Click For Pricing
Expedia
Click For Pricing
VRBO
Relaxing Via Roma Beach Resort, 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 Pricing
VRBO
From $309 per night (USD)
Expedia
Bungalow 108: Dolphin Courtyard-Bungalow
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
A charming 1 bedroom bungalow complete with a full kitchen, queen size bed, queen sleeper sofa, and jacuzzi jet bathtub ...
From $309 per night (USD)
Expedia
$Anna Maria Island \Star Fish\Condo & Boat Slip-2BR-2BA-Sleeps4$
From $256 per night (USD)
VRBO
Anna Maria Island \"Star Fish\"Condo & Boat Slip-2BR-2BA-Sleeps4
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Starfish Condo on Anna Maria Island -2 BR 2 BA With a 25' Boat Slip Wonderful quiet residential area overlooks pool; bey ...
From $256 per night (USD)
VRBO
$2\/2 blocks from the water, bike ride to the beach THE FLORIDIAN$
From $206 per night (USD)
Expedia
2\/2 blocks from the water, bike ride to the beach THE FLORIDIAN
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
Beautiful beach getaway all to yourself in a very quiet neighborhood with 2 bed 2 bath newly remodeled home that can sle ...
From $206 per night (USD)
Expedia
$Sandy Point 114 - Anna Maria Island -Townhouse 3 Bedroom\/ 3 Bath, maximum...$
From $389 per night (USD)
VRBO
Sandy Point 114 - Anna Maria Island -Townhouse 3 Bedroom\/ 3 Bath, maximum...
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Sandy Pointe 114 - Anna Maria Island - Townhouse 3 Bedroom/ 3 Bath, maximum occupancy of 6 people. VRC16-000070 Di ...
From $389 per night (USD)
VRBO
$Villa Treasure Island - Beautifully Renovated Private Pool Home w\/ Hottub$
From $461 per night (USD)
Expedia
Villa Treasure Island - Beautifully Renovated Private Pool Home w\/ Hottub
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
LOCATED IN A QUIET NEIGHBORHOOD, our elegant Villa Treasure Island is exactly what you've been looking for. Imagine spe ...
From $461 per night (USD)
Expedia
$Thanksgiving dinner included: 15lb Turkey\/Sweet Potato Mash\/Pumpkin Pie$
From $842 per night (USD)
VRBO
Thanksgiving dinner included: 15lb Turkey\/Sweet Potato Mash\/Pumpkin Pie
Bedrooms:
4
Bathrooms:
6
Sleeps:
10
The minute you walk in the front door at Silver Surf you'll be convinced that you're about to experience the very best o ...
From $842 per night (USD)
VRBO
From $892 per night (USD)
Expedia
For Shore: Steps to beach, partial Gulf views, heated pool!
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
If you are hoping to stay on the perfect Old Florida island in the perfect beach home, you have found your destination a ...
From $892 per night (USD)
Expedia
From $619 per night (USD)
VRBO
GORGEOUS 3 BEDROOM POOL HOME JUST STEPS TO BEACH
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Two For Sea ... Light and bright, beautifully decorated 3 bedroom, 3 bath newer home located in the city of Holmes Beac ...
From $619 per night (USD)
VRBO
From $1061 per night (USD)
Expedia
Sea Grape Inn#8- Beach Front Condo
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
BEACH FRONT Condo- 2nd Floor of Beach Front Property, 3 Bdrms/2.5 Baths or UPGRADE to 4 Bdrms/ 3.5 Baths Condo! 3 BDRMS ...
From $1061 per night (USD)
Expedia
From $381 per night (USD)
VRBO
Waterslide & Pool ** Wimpy’s Whereabouts!**
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This cute cozy 2 bedroom and 2 full bathroom duplex is completely remodeled. The bedrooms both have king size beds. The ...
From $381 per night (USD)
VRBO
From $522 per night (USD)
Expedia
WATER SLIDE & POOL ** Sugarcane Hideaway**
Bedrooms:
2
Bathrooms:
3
Sleeps:
16
This unit has 3 bedroom 2 full baths. The master has a king size bed and on-suite full bathroom. The 2nd bedroom has a q ...
From $522 per night (USD)
Expedia
From $484 per night (USD)
VRBO
WATER SLIDE & POOL ** SUGAR SHACK**
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
It’s welcoming and a completely remodeled cottage. It has everything you need for a relaxing vacation. There are three b ...
From $484 per night (USD)
VRBO
$Sandy Point 205 - Anna Maria Island - Condo 2 Bedroom\/ 2 Bath, maximum...$
From $342 per night (USD)
Expedia
Sandy Point 205 - Anna Maria Island - Condo 2 Bedroom\/ 2 Bath, maximum...
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Sandy Point 205 - Anna Maria Island - 2 Bedroom/ 2 Bath, maximum occupancy of 4 people. VRC16-000291 Distan ...
From $342 per night (USD)
Expedia
$510 Bayview - Anna Maria Island - Private home 5 Bedroom \/ 5 Bath with...$
From $1047 per night (USD)
VRBO
510 Bayview - Anna Maria Island - Private home 5 Bedroom \/ 5 Bath with...
Bedrooms:
5
Bathrooms:
5
Sleeps:
6
510 Bayview - Anna Maria Island - 5 Bedroom / 5 Bath, maximum occupancy of 6 people. Canal Home - Private Pool - ...
From $1047 per night (USD)
VRBO
$LaPlayita 5 - Anna Maria Island - Condo 2 Bedroom \/ 2 Bath , maximum...$
From $545 per night (USD)
Expedia
LaPlayita 5 - Anna Maria Island - Condo 2 Bedroom \/ 2 Bath , maximum...
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
LaPlayita 5 - Anna Maria Island - Condo 2 Bedroom / 2 Bath, maximum occupancy of 4 people. VRC19-000138 Community ...
From $545 per night (USD)
Expedia
From $470 per night (USD)
VRBO
Chillifish: Peaceful Floridian pool home in great location
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
You can’t imagine anyone not falling in love with the exquisite "Chillifish" - a peaceful gem, decorated with the utmost ...
From $470 per night (USD)
VRBO
From $1252 per night (USD)
Expedia
Hogfish: Stunning Southern-style large family home, minutes from Tampa Bay
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Location, location, location! Hogfish is a spacious 4 bedroom, 3 ½ bath home within walking distance to Pine Avenue, Ci ...
From $1252 per night (USD)
Expedia
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VRBO
Beach Bay Serenity: Pine Ave canal front pool home
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
If you enjoy salt air and sea breezes, morning coffee on your patio, walking miles and miles of white sandy beach and sw ...
Click For Pricing
VRBO
From $386 per night (USD)
Expedia
Bay Breeze Cottages #2
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Bay Breeze Cottages is an Old Florida Charm Boutique Resort located on historic Anna Maria Island. Bask in the ...
From $386 per night (USD)
Expedia
$BEAUTIFUL Remodeled 2 Bedroom 2.5 Bath Right on the Water w\/Solar Heated...$
From $265 per night (USD)
VRBO
BEAUTIFUL Remodeled 2 Bedroom 2.5 Bath Right on the Water w\/Solar Heated...
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
**ASK ABOUT LAST MINUTE DEALS! Set sail from this completely remodeled two-bedroom, two-and-a-half-bath tow ...
From $265 per night (USD)
VRBO
From $762 per night (USD)
Expedia
AMI Peppertree Paradise - Restored and Ready for Guests for November 2024!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to AMI Peppertree Paradise! On Anna Maria Island (Anna Maria, FL) 1970 sq. ft HIGHLIGHTS: - Kitchen, Dining Ar ...
From $762 per night (USD)
Expedia
From $797 per night (USD)
VRBO
Endless Summer: Gulf Front, On the Beach, Panoramic Views, Pool by Anna Maria Life Vacation Rentals
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Endless Summer AMIC 23 by Anna Maria Life Vacation Rentals 2600 Gulf Drive, #23, Bradenton Beach, FL 34217 What You'll ...
From $797 per night (USD)
VRBO
From $210 per night (USD)
Expedia
Longbeach Lucky #13 Condo by RVA
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
No luck needed here to know you've stumbled upon one of the best spots Longboat Key has to offer. Longbeach Lucky 13 by ...
From $210 per night (USD)
Expedia
From $207 per night (USD)
VRBO
POOL HOME OPEN FOR THE SUMMER! BRING YOUR BOAT! MONTH MINIMUM - GREAT PRICE AND A GREAT LOCATION!
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
239 85th Street, Holmes Beach, Anna Maria Island Bailey's Home ... Lovely and spacious 3 bedroom, 2 bath home. Recently ...
From $207 per night (USD)
VRBO
From $199 per night (USD)
Expedia
6715-204 Beautiful Veranda with golf next to the pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Gulf Coast Florida Properties would like to introduce the latest addition to our portfolio of vacation homes. 6715 GRAND ...
From $199 per night (USD)
Expedia
Click For Pricing
VRBO
Secluded, Two-Story Home with a Lanai, Bar, & Private Pool - Steps from the Bay
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Palma Sola Paradise Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
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VRBO
From $695 per night (USD)
Expedia
Sea La Vie: 1.5 Blocks to Beach, Pool, Tropical Backyard & Pool by Anna Maria Life Vacation Rentals
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Sea La Vie by Anna Maria Life Vacation Rentals 205 55th St, Holmes Beach, FL 34217 What You'll Love About This Home: Lo ...
From $695 per night (USD)
Expedia
From $648 per night (USD)
VRBO
Manatee Lookout by SeaBreeze Vacation
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Manatee Lookout is a charming 3 bedroom/3 bath home with a private heated pool located on the sought after north end of ...
From $648 per night (USD)
VRBO
From $588 per night (USD)
Expedia
Seaside Beach House 203 Gulf Front Condo Pool Unforgettable Sunset Views
Bedrooms:
2
Bathrooms:
2
Sleeps:
3
VRC20-000296 This property is thoroughly cleaned and sanitized prior to your arrival. We pay special attention to high ...
From $588 per night (USD)
Expedia
$191 Pineneedle Drive- Bradenton- Ground level Condo-2 Bedroom \/ 2 Bath,...$
From $180 per night (USD)
VRBO
191 Pineneedle Drive- Bradenton- Ground level Condo-2 Bedroom \/ 2 Bath,...
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
191 Pineneedle Drive - Bradenton - Ground level - 2 Bedroom / 2 Bath, maximum occupancy of 4 people. Community Poo ...
From $180 per night (USD)
VRBO
From $510 per night (USD)
Expedia
Florida Breeze: Pool home in perfect central location!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Florida Breeze is the perfect vacation rental for your next trip to Anna Maria Island! The location with the short walk ...
From $510 per night (USD)
Expedia
From $354 per night (USD)
VRBO
Lazy Days at Runaway Bay 162 by SeaBreeze Vacation
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Lazy Days at Runaway Bay is the perfect place to take time out and relax at your home away from home. This ground floor ...
From $354 per night (USD)
VRBO
From $245 per night (USD)
Expedia
Unlimited Golf with membership transfer- Lakewood National
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Premium furnishings penthouse (top floor) condo within highly sought after Lakewood National. Lakewood National is a ful ...
From $245 per night (USD)
Expedia
From $370 per night (USD)
VRBO
Sea Spray 3: *Steps to the beach *Close to shops, restaurants *Quiet street
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
The Sea Spray Cottages are an adorable group of 4 Units located in the North End of Anna Maria, West of Gulf Drive and o ...
From $370 per night (USD)
VRBO
From $549 per night (USD)
Expedia
Sea Spray 4: *Heated Pool *Pet-Friendly *Steps to beach *Shops, dining close
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
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 $549 per night (USD)
Expedia
From $171 per night (USD)
VRBO
Near to the Beach, UTC mall, SCF, IMG, Airport, Ringling Museum and much more
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Private entrance, Keurig coffee maker, mini fridge, microwave, internet access, roku TV, Netflix, hair dryer, desk, outs ...
From $171 per night (USD)
VRBO
$Waterfront Duplex with WiFi, AC, Washer\/Dryer, Water Views - Dogs - Snowbirds OK$
Click For Pricing
Expedia
Waterfront Duplex with WiFi, AC, Washer\/Dryer, Water Views - Dogs - Snowbirds OK
Bedrooms:
5
Bathrooms:
6
Sleeps:
14
Bayshore Panorama Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
Click For Pricing
Expedia
From $622 per night (USD)
VRBO
Bayfront getaway with gorgeous view, private dock, AC & kayaks - dog-friendly
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Bayshore Panorama Two Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $622 per night (USD)
VRBO
$Waterfront Retreat - WiFi, AC, Washer\/Dryer, Water Views - Dogs OK, Snowbirds OK$
Click For Pricing
Expedia
Waterfront Retreat - WiFi, AC, Washer\/Dryer, Water Views - Dogs OK, Snowbirds OK
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Bayshore Panorama One Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
Click For Pricing
Expedia
From $353 per night (USD)
VRBO
(2) Bedroom (2) Bath with Private 10' x 30' Sun Deck
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Anna Maria Island's "Castnetter 5" is a delightful Island local located directly across the street from the seven acre " ...
From $353 per night (USD)
VRBO
From $1124 per night (USD)
Expedia
ISLAND LIFE VILLA is Luxury at it's Finest! Incredible Water Views!
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
*During high season, we currently rent Saturday – Saturday. Please adjust your date range or contact our reservations of ...
From $1124 per night (USD)
Expedia

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