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From $314 per night (USD)
VRBO
Ideal family retreat with a private pool, outdoor TV, surround sound, & WiFi
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Almost There Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $314 per night (USD)
VRBO
From $883 per night (USD)
Expedia
2nd floor Condo with Beach and Pool Access - Coconuts Gulf View #118
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Coconuts Gulf Views #118 by AMI Locals Condo in Holmes Beach, Florida VRC21-000172 Let the good times roll at Coconu ...
From $883 per night (USD)
Expedia
$Beachfront Condo-Amazing Views of the Sunset from Every Room! 2 King\/4 twins$
From $610 per night (USD)
VRBO
Beachfront Condo-Amazing Views of the Sunset from Every Room! 2 King\/4 twins
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
GULF FRONT CONDO - Exquisite, newly constructed 3 bedroom 2 bath direct gulf front condo. Corner, end unit on top floor. ...
From $610 per night (USD)
VRBO
From $311 per night (USD)
Expedia
Lakeside Beach House 3/2 Pool Home Outdoor Kitchen Close to Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
VRC16-000807 The Lakeside Beach House is a wonderful newly renovated three bedroom, two bath home with a private heated ...
From $311 per night (USD)
Expedia
From $273 per night (USD)
VRBO
Longboat Key Resort Escape - Walk to the Beach!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Prepare yourself for a Gulf Coast getaway at this welcoming 1-bed, 1-bath vacation rental nestled in the tropical Beach ...
From $273 per night (USD)
VRBO
From $1292 per night (USD)
Expedia
Stunning new luxury home, pool + spa, walk to the beach! Summer awaits!
Bedrooms:
6
Bathrooms:
6
Sleeps:
8
Oar House by AMI Locals Home in Anna Maria, FL Located in the most desired North End of Anna Maria Highlights: - Ne ...
From $1292 per night (USD)
Expedia
From $490 per night (USD)
VRBO
Private Pool Home 4 bd 3 ba with 2 King Master Suites Sleep 10 near AMI and IMG
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Private Pool home near Anna Maria Island & Sarasota. About 5 miles to Anna Maria Island and 23 miles to Siesta Key Beach ...
From $490 per night (USD)
VRBO
From $307 per night (USD)
Expedia
Beach, Boat & Paws–Pet-Friendly Pool Home Blue Heron in Longboat Key by RVA
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Blue Heron House by RVA. This three-bedroom plus office, two-bathroom house is located on the Northern end of ...
From $307 per night (USD)
Expedia
From $405 per night (USD)
VRBO
Stunning 3Bed/3 Bath, Heated Pool, FREE WiFi, Close to Beach, On Canal to...
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
**ASK ABOUT LAST MINUTE DEALS! Welcome to paradise at Pelican Point! This stunning 3 bedroom/3 bath home h ...
From $405 per night (USD)
VRBO
From $492 per night (USD)
Expedia
Relaxing Home with Private Pool, High-Speed WiFi, Central AC, & Washer/Dryer
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Southern Magnolia Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $492 per night (USD)
Expedia
From $235 per night (USD)
VRBO
Discounted rates for June! Direct bayfront views!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Enjoy all Longboat Key has to offer from Harbor Villa Club! Beautifully updated 2/2 directly on the bay! Gorgeous views ...
From $235 per night (USD)
VRBO
From $217 per night (USD)
Expedia
LONGBOAT KEY BEAUTY! This 2/2 unit offers stunning views of the bay! Call today to book your fall vacation!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
• Carefree check-in, go straight to your unit no office visit required. • Fully Equipped Kitchen including microwave, st ...
From $217 per night (USD)
Expedia
From $133 per night (USD)
VRBO
Floating Home
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
This beautiful, custom built floating home is located at Bahia Mar West Marina in Bradenton, Fl. She is just a 7 min. c ...
From $133 per night (USD)
VRBO
From $396 per night (USD)
Expedia
Vibrant retreat with pool, beach access, tennis, balcony, & stunning ocean views
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Gulf Place 19 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $396 per night (USD)
Expedia
From $412 per night (USD)
VRBO
Dix-Sea-land Delight: Close to beach, private pool, quiet street
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
This 3 bed 3.5 bath Bradenton Beach Oasis will send you straight to relaxation town with its modern and well-appointed s ...
From $412 per night (USD)
VRBO
Click For Pricing
Expedia
Little Gull Resort - Longboat Key, Florida
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Large 4 bedroom Suite on beautiful Sarasota Bay. 2 bathroom Pull-out sofa bed sleeps 2. Large verandah with a great vie ...
Click For Pricing
Expedia
From $435 per night (USD)
VRBO
BEACH FRONT, 2 Bd/2 Bath, FREE WiFi & Trolley, Heated Pool and Awesome Sunsets
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
**ASK ABOUT LAST MINUTE DEALS! Enjoy a fabulous stay at the beach in this beautifully remodeled two bedroom ...
From $435 per night (USD)
VRBO
From $322 per night (USD)
Expedia
Right on the beach.Renovated ground Floor unit 63.
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Completely renovated. Everything is new. Amazing location. Charming studio right on the beach. Condo management will he ...
From $322 per night (USD)
Expedia
From $235 per night (USD)
VRBO
Water-view condo near the beach with pools, dock, pickleball - dog-friendly
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Sunrise Bay Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $235 per night (USD)
VRBO
From $1254 per night (USD)
Expedia
Sea La Vie AM: Bay front, pool, hot tub, rooftop deck, and water sports gear!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
HGTV Beach Hunters Renovated Beach Front Home with a heated pool and 3 bedrooms. 1 Paddle boards & 2 kayak included. ...
From $1254 per night (USD)
Expedia
From $537 per night (USD)
VRBO
A pool home with a dock directly on the Manatee River. Breath taking sunsets!
Bedrooms:
3
Bathrooms:
5
Sleeps:
13
Centrally located on the West Coast of Florida, convenient to many Florida attractions, River Hideaway on the Manatee s ...
From $537 per night (USD)
VRBO
From $671 per night (USD)
Expedia
Beachfront - Sandy Turtle by SeaBreeze Vacation
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Located on the tranquil beaches of Anna Maria Island, Sandy Turtle is mere steps away from the beach and offers pictures ...
From $671 per night (USD)
Expedia
From $403 per night (USD)
VRBO
Upscale 2/2 condo with pool 6 mins from IMG
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: This home is located in a small boutique condominium complex located Bradenton. A quick 15+ minute drive will t ...
From $403 per night (USD)
VRBO
From $164 per night (USD)
Expedia
251 Gorgeous lake view pool house with a golf membership
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Gulf Coast Florida Properties would like to introduce the latest addition to our portfolio of vacation homes. 251 RIVER ...
From $164 per night (USD)
Expedia
From $616 per night (USD)
VRBO
Beach Bay Serenity: Pine Ave canal front pool home
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Welcome to Beach Bay Serenity! This gorgeous 4 bedroom 3.5 bath waterfront home located on Pine Avenue is the perfect p ...
From $616 per night (USD)
VRBO
From $266 per night (USD)
VRBO
Beach Waves-Private Beach Access-Heated Pool-Two Balconies-Free Wi-Fi
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
We understand that plans can change, and we want you to book your stay with peace of mind. That’s why we offer the most ...
From $266 per night (USD)
VRBO
From $821 per night (USD)
VRBO
Sweet Retreat Cottage: Ground level cottage across the street from the beach
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
This Anna Maria Island rental was given the name Sweet Retreat Cottage for a reason. Offering a private heated pool, vie ...
From $821 per night (USD)
VRBO
From $803 per night (USD)
Expedia
Zen Beach Cottage: Beautiful ground level home steps to beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Skilled craftsmanship, a tranquil atmosphere, and an unbeatable location come together at the Zen Beach Cottage, a three ...
From $803 per night (USD)
Expedia
From $203 per night (USD)
VRBO
Bayview Inn #101 | Updated & Steps to Bridge St
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Bayview Inn #101 | Newly Remodeled & Steps from Bridge Street Welcome to Bayview Inn #101, a newly remodeled 1-bedroom, ...
From $203 per night (USD)
VRBO
From $560 per night (USD)
Expedia
Gulf Front 1 Bedroom Condo - Amazing Views
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Coconuts Beachfront #112 Condo in Holmes Beach, Florida VRC21-000175 Your dream beach vacation awaits at Coconuts Beach ...
From $560 per night (USD)
Expedia
Click For Pricing
VRBO
Cozy & Bright... 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 ...
Click For Pricing
VRBO
From $613 per night (USD)
VRBO
Relax and Unwind! 3 Convenient Units, Outdoor Pool, Tennis Courts, Free Parking
Bedrooms:
6
Bathrooms:
6
Sleeps:
12
This accommodation consists of THREE Spacious 1250sf apartments located in a private, gated community in a close vicinit ...
From $613 per night (USD)
VRBO
From $613 per night (USD)
VRBO
Making The Best Memories Along The Way! 3 Great Units, Basketball Court, Pool
Bedrooms:
6
Bathrooms:
6
Sleeps:
12
This accommodation consists of THREE Spacious 1250sf apartments located in a private, gated community in a close vicinit ...
From $613 per night (USD)
VRBO
From $204 per night (USD)
VRBO
Dream Bradenton Getaway! Free Parking, Pool, Basketball Court, 2 Tennis Courts
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This spacious 1250sf apartment located in a private, gated community in a close vicinity from the beautiful white sand b ...
From $204 per night (USD)
VRBO
From $190 per night (USD)
VRBO
Look No Further, Bradenton Getaway! Free Parking, Kitchenette, Outdoor Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This spacious 1250sf apartment located in a private, gated community in a close vicinity from the beautiful white sand b ...
From $190 per night (USD)
VRBO
From $409 per night (USD)
VRBO
Better Choice for your Vacation! 2 Comfortable Units, 2 Lighted Tennis Courts
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
This accommodation consists of TWO Spacious 1250sf apartments located in a private, gated community in a close vicinity ...
From $409 per night (USD)
VRBO
From $204 per night (USD)
VRBO
Comfort and Convenience! Free Parking, 2 Pools, Short Drive to IMG Academy
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This spacious 1250sf apartment located in a private, gated community in a close vicinity from the beautiful white sand b ...
From $204 per night (USD)
VRBO
From $204 per night (USD)
VRBO
Your Home Away From Home! Kitchenette, 2 Outdoor Pool and Hot Tub, Free Parking
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This spacious 1250sf apartment located in a private, gated community in a close vicinity from the beautiful white sand b ...
From $204 per night (USD)
VRBO
From $409 per night (USD)
VRBO
Vacation is Calling! 2 Family-friendly Units, Free Parking, Kitchenette, Pool
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
This accommodation consists of TWO Spacious 1250sf apartments located in a private, gated community in a close vicinity ...
From $409 per night (USD)
VRBO
From $204 per night (USD)
VRBO
Vacation Day Is Always A Great Idea! Kitchenette, Clubhouse with BBQ Grill Area
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This spacious 1250sf apartment located in a private, gated community in a close vicinity from the beautiful white sand b ...
From $204 per night (USD)
VRBO
From $569 per night (USD)
VRBO
Vacation Day Is Always A Great Idea! 3 Convenient Units, Outdoor Pool, Clubhouse
Bedrooms:
6
Bathrooms:
6
Sleeps:
12
This accommodation consists of THREE Spacious 1250sf apartments located in a private, gated community in a close vicinit ...
From $569 per night (USD)
VRBO
From $409 per night (USD)
VRBO
Your Home Away From Home! 2 Convenient Units, Kitchenette, Free Parking, Pool
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
This accommodation consists of TWO Spacious 1250sf apartments located in a private, gated community in a close vicinity ...
From $409 per night (USD)
VRBO
From $613 per night (USD)
VRBO
Vacation is Calling! 3 Family-friendly Units, Children's Playground, Pool
Bedrooms:
6
Bathrooms:
6
Sleeps:
12
This accommodation consists of THREE Spacious 1250sf apartments located in a private, gated community in a close vicinit ...
From $613 per night (USD)
VRBO
From $204 per night (USD)
VRBO
Your Relaxing Getaway Awaits! Kitchenette, Outdoor Pool, Children's Playground
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This spacious 1250sf apartment located in a private, gated community in a close vicinity from the beautiful white sand b ...
From $204 per night (USD)
VRBO
From $379 per night (USD)
VRBO
Dive Into Your Dream Vacation! 2 Great Units, Kitchenette, Onsite Outdoor Pool
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
This accommodation consists of TWO Spacious 1250sf apartments located in a private, gated community in a close vicinity ...
From $379 per night (USD)
VRBO
Click For Pricing
Expedia
Longboat Key Cottage: Extended Stays Welcome!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Head to Florida for a much-needed, month-long getaway when you book and stay at this amenity-packed 2-bedroom, 2-bathroo ...
Click For Pricing
Expedia
From $511 per night (USD)
VRBO
The Cottage on Pine - Charming Pine Ave Cottage w/ Heated Pool in the Heart of Anna Maria Island
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to The Cottage on Pine! On Anna Maria Island (Anna Maria, FL) After sustaining hurricane damage, this charming ...
From $511 per night (USD)
VRBO
From $576 per night (USD)
Expedia
Mango Bay – Luxury 4BR w/ Heated Pool, Spa & Game Room
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Welcome to Mango Bay! On Anna Maria Island (Holmes Beach, FL) 3,000 sqft of a Beautifully Restored Island Home with Poo ...
From $576 per night (USD)
Expedia
From $728 per night (USD)
VRBO
Gorgeous direct bay front home! Steps to beach! Amazing sunrises and pool!!!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Our Charming Bayfront Retreat in Anna Maria! Discover the ultimate coastal retreat at our inviting home, nes ...
From $728 per night (USD)
VRBO
From $367 per night (USD)
Expedia
Waterfront Home w/ Private Heated Pool, 5 Min to AMI
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
*** PLEASE NOTE: THE BOAT DOCK IS CURRENTLY NOT USABLE DUE TO STORM DAMAGES TO IT *** Welcome to our beautiful Blue Opa ...
From $367 per night (USD)
Expedia
From $285 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 $285 per night (USD)
VRBO
From $293 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 $293 per night (USD)
Expedia
From $703 per night (USD)
VRBO
Golf Cart, Salty Shamrock by SeaBreeze Vacation
Bedrooms:
2
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 $703 per night (USD)
VRBO
From $337 per night (USD)
Expedia
Pickleball Escape! Pond! Private Pool! Foosball
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Welcome to Once Upon A Pond, by Stayawhilewithus! If travel is on the horizon, set your sails to luxury and tranquility ...
From $337 per night (USD)
Expedia
Click For Pricing
VRBO
Two Bedroom Condo, Gulf Front, Bradenton Beach (2106005)
Bedrooms:
1
Bathrooms:
2
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 $188 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 $188 per night (USD)
Expedia
Click For Pricing
VRBO
Beautiful Dog-Friendly Home w/ Fast WiFi, Central AC, & W/D - Snowbirds Welcome
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Warners Bayou Too Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
Click For Pricing
VRBO
From $275 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 $275 per night (USD)
Expedia
From $433 per night (USD)
VRBO
FANTASTIC, RENOVATED 2 BEDROOM HOME STEPS TO BEACH!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
3706 Gulf Drive, Holmes Beach, FL Anna Maria Island Fantastic, recently renovated home located just steps to the beach. ...
From $433 per night (USD)
VRBO
Click For Pricing
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 ...
Click For Pricing
Expedia
From $363 per night (USD)
VRBO
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 $363 per night (USD)
VRBO
From $323 per night (USD)
Expedia
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 $323 per night (USD)
Expedia
From $411 per night (USD)
VRBO
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 $411 per night (USD)
VRBO
From $333 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 $333 per night (USD)
Expedia
From $419 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 $419 per night (USD)
VRBO
From $480 per night (USD)
Expedia
Elegant Beachfront Condo w/pool! Walking distance to many restaurants and shops
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Elegant, Beachfront Top Floor Condo - walk directly onto the Beautiful beaches of Anna Maria Island. Honey maple kitchen ...
From $480 per night (USD)
Expedia
From $257 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 $257 per night (USD)
VRBO
From $363 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 $363 per night (USD)
Expedia
From $610 per night (USD)
VRBO
Sand Of Times-Beautiful 6 bedrooms with private pool/spa with a water slide
Bedrooms:
4
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 $610 per night (USD)
VRBO
From $385 per night (USD)
Expedia
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 $385 per night (USD)
Expedia
From $424 per night (USD)
VRBO
Bay Breeze Cottages #3
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
Summary: Bay Breeze Cottages is an Old Florida Charm Boutique Resort located on historic Anna Maria Island. Bask in the ...
From $424 per night (USD)
VRBO
From $164 per night (USD)
Expedia
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 $164 per night (USD)
Expedia
From $400 per night (USD)
VRBO
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 $400 per night (USD)
VRBO
From $574 per night (USD)
Expedia
Sunnyside of the Beach: Updated, 5-bedroom home, pool, close to beach!
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 $574 per night (USD)
Expedia
From $564 per night (USD)
VRBO
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 $564 per night (USD)
VRBO
From $223 per night (USD)
Expedia
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 $223 per night (USD)
Expedia
From $234 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 $234 per night (USD)
VRBO
From $428 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 $428 per night (USD)
Expedia
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VRBO
Two Bedroom Condo, Gulf Front, Bradenton Beach (2105996)
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Via Roma Beach Resort club resort 2408 Gulf Drive North Bradenton Beach, FL 34217 With its white stucco buildings, Io ...
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VRBO
From $348 per night (USD)
Expedia
Luxury HEATED Salt-Water Pool Oasis Close to Beaches and Downtown!!
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Completely updated 3 bedroom 3 bathroom home that has been beautifully renovated and furnished in a modern coastal desig ...
From $348 per night (USD)
Expedia
From $345 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 $345 per night (USD)
VRBO
From $426 per night (USD)
Expedia
South Beach Village 111-By Island Real Estate Vacations
Bedrooms:
2
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 $426 per night (USD)
Expedia
From $499 per night (USD)
VRBO
Casa Morado-Pet Friendly Pool Home West of Gulf Dr-By Island Real Estate Vacatio
Bedrooms:
3
Bathrooms:
4
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 $499 per night (USD)
VRBO
From $126 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 $126 per night (USD)
Expedia
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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 $300 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 $300 per night (USD)
Expedia
From $609 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 $609 per night (USD)
VRBO
From $283 per night (USD)
VRBO
Anna Maria Island Sunshine Kiss Villa
Bedrooms:
1
Bathrooms:
2
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 $283 per night (USD)
VRBO
From $337 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 $337 per night (USD)
VRBO
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
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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 ...
Click For Pricing
VRBO
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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 ...
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Expedia
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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 $369 per night (USD)
Expedia
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 $369 per night (USD)
Expedia
From $404 per night (USD)
VRBO
Villa Treasure Island - Beautifully Renovated Private Pool Home w/ Hottub
Bedrooms:
2
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 $404 per night (USD)
VRBO
From $578 per night (USD)
Expedia
Silver Surf- A stunning family home 2 blocks from the beach.
Bedrooms:
4
Bathrooms:
5
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 $578 per night (USD)
Expedia
From $530 per night (USD)
VRBO
For Shore: Sleeps 10, steps to beach, heated pool!
Bedrooms:
4
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 $530 per night (USD)
VRBO
From $621 per night (USD)
Expedia
GORGEOUS 3 BEDROOM POOL HOME JUST STEPS TO BEACH
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Two For Sea ... Light and bright, beautifully decorated 3 bedroom, 3 bath newer home located in the city of Holmes Beac ...
From $621 per night (USD)
Expedia
$Anna Maria Island \Star Fish\Condo & Boat Slip-2BR-2BA-Sleeps4$
From $210 per night (USD)
VRBO
Anna Maria Island \"Star Fish\"Condo & Boat Slip-2BR-2BA-Sleeps4
Bedrooms:
1
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 $210 per night (USD)
VRBO
From $1046 per night (USD)
Expedia
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 $1046 per night (USD)
Expedia

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