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From $963 per night (USD)
VRBO
Anapauo Beachhouse: Million dollar views of Tampa Bay!
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Welcome to Anapauo Beachhouse! Pronounced ahn-ap-ow’-o, it is a Greek word meaning to give rest, refresh, recover and co ...
From $963 per night (USD)
VRBO
From $447 per night (USD)
Expedia
Coquina Beach Club 202 - Anna Maria Island- Condo 2 Bedroom/ 2 Bath ocean...
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Coquina Beach Club 202 - Anna Maria Island - 2 Bedroom/ 2 Bath, maximum occupancy of 6 people. Gulf View Condo - C ...
From $447 per night (USD)
Expedia
From $684 per night (USD)
VRBO
Bay Beauty: Private Intra-Coastal front home with sprawling views
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Welcome to Bay Beauty. This Intracoastal front property has sprawling views from Cortez Bridge all the way to the Sunshi ...
From $684 per night (USD)
VRBO
From $415 per night (USD)
Expedia
Bradenton Beach Club 230 - Anna Maria Island - Condo 2 Bedroom/ 2 Bath,...
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
ELEVATOR WILL BE UNOPERABLE INDEFINITELY Bradenton Beach Club, Unit 230 - Anna Maria Island - 2 Bedroom/ 2 Bath, maximum ...
From $415 per night (USD)
Expedia
From $469 per night (USD)
VRBO
A Time Out: *Quaint Cottage *Heated Pool *Across the street from the Bay!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Welcome to "A Time Out" - your perfect retreat in paradise! This charming 4-bedroom, 2-bathroom home invites you to expe ...
From $469 per night (USD)
VRBO
From $310 per night (USD)
Expedia
Pelican Cove 9 - Anna Maria Island - Condo 2 Bedroom /2 Bath bay side,...
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Pelican Cove 9 - Anna Maria Island - Condo 2 Bedroom /2 Bath maximum occupancy of 5 people. Bay View. ...
From $310 per night (USD)
Expedia
From $538 per night (USD)
VRBO
Bradenton Beach Club 247 - Anna Maria Island - Condo 3 Bedroom/ 2 Bath,...
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Bradenton Beach Club, Unit 247 - Anna Maria Island - 3 Bedroom/ 2 1/2 Bath, maximum occupancy of 6 people. Distanc ...
From $538 per night (USD)
VRBO
From $360 per night (USD)
Expedia
Bradenton Beach Club 228 - Anna Maria Island - Condo 2 Bedroom/ 2 Bath,...
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Bradenton Beach Club, Unit 228 - Anna Maria Island - 2 Bedroom/ 2 Bath, maximum occupancy of 6 people. ELEV ...
From $360 per night (USD)
Expedia
From $299 per night (USD)
VRBO
Gulf Watch 210 - Anna Maria Island - Condo 2 Bedro
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Gulf Watch 210 - Anna Maria Island - 2 Bedroom / 2 Bath, maximum occupancy of 4 people. Distance to the Beach: acr ...
From $299 per night (USD)
VRBO
From $365 per night (USD)
Expedia
Anna Maria Island Club 38, Condo 2 Bedroom/ 2 Bath ocean view, maximum...
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Anna Maria Island Club 38 - Anna Maria Island - Condo - 2 Bedroom/ 2 Bath, maximum occupancy of 4 people. W ...
From $365 per night (USD)
Expedia
From $499 per night (USD)
VRBO
Lovin' the Sannd: North-end cottage, luxury amenities
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
If you're looking to escape the hustle and bustle of everyday life, look no further than "Lovin' the SANND". This three ...
From $499 per night (USD)
VRBO
From $494 per night (USD)
Expedia
707 N Bay The Shell House - Anna Maria Island - Private home 3 Bedroom/ 2 1/2...
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
707 North Bay Boulevard - The Shell House- 3 Bedroom/ 2 1/2 Bath, maximum occupancy of 6 people. Private Pool - Di ...
From $494 per night (USD)
Expedia
From $468 per night (USD)
VRBO
Sunset Terrace 203 - Anna Maria Island - Beach front condo 2 Bedroom/ 2 Bath...
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Sunset Terrace 203 - Anna Maria Island - 2 Bedroom/ 2 Bath, maximum occupancy of 4 people. Gulf Front - Community ...
From $468 per night (USD)
VRBO
From $320 per night (USD)
Expedia
Pelican Cove 10 - Anna Maria Island - Condo 2 Bedroom /2 Bath bay view, ...
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Pelican Cove 10 - Anna Maria Island - Condo 2 Bedroom /2 Bath, maximum occupancy of 5 people. Bay View ...
From $320 per night (USD)
Expedia
From $328 per night (USD)
VRBO
Anna Maria Island Club 26, Condo 2 Bedroom/ 2 Bath ocean view, maximum...
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Anna Maria Island Club 26 - Anna Maria Island - Condo - 2 Bedroom/ 2 Bath, maximum occupancy of 4 people. Gulf Fro ...
From $328 per night (USD)
VRBO
From $305 per night (USD)
Expedia
Gulf Watch 216 - Anna Maria Island - Condo 2 Bedro
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Gulf Watch 216 - Anna Maria Island - 2 Bedroom / 2 Bath, maximum occupancy of 4 people. Direct Bay View - Heated C ...
From $305 per night (USD)
Expedia
From $503 per night (USD)
VRBO
Havana Cay- Adorable cottage- only 4 houses from beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Havana Cay 109 Cedar Ave, Anna Maria, FL 34216 What you will love about this property: • Historic 1924 Latin style home ...
From $503 per night (USD)
VRBO
From $329 per night (USD)
Expedia
Bayview Condo D - Anna Maria Island - Condo 2 Bedroom/ 2 Bath bay view,...
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Bayview Condo, Unit D - Anna Maria Island - 2 Bedroom/ 2 Bath, maximum occupancy of 4 people. Community Pool - Bay ...
From $329 per night (USD)
Expedia
From $452 per night (USD)
VRBO
Cute Condo with Beach front and Pool Access - Coconuts Gulf View #118
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Coconuts Gulf Views #118 by AMI Locals 100 73rd Street, Unit #118, Holmes Beach, FL 34217 VRC21-000172 Welcome to Coco ...
From $452 per night (USD)
VRBO
From $1316 per night (USD)
Expedia
Stunning new luxury home, pool + spa, walk to the beach! Summer awaits!
Bedrooms:
6
Bathrooms:
6
Sleeps:
8
Welcome to Oar House! A spectacular, newly constructed home located in the most desired North End of Anna Maria feature ...
From $1316 per night (USD)
Expedia
From $514 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 $514 per night (USD)
VRBO
From $220 per night (USD)
Expedia
Dog-Friendly Riverfront Condo w/ a Shared Pool, Sports Courts, Gym, & Fast WiFi
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Carlton Arms View B1 # A Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ente ...
From $220 per night (USD)
Expedia
From $362 per night (USD)
VRBO
A Shore Thing - Relaxing Island Living , Large Heated Pool, Boat Lift
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This beach house is "A Shore Thing" for creating fantastic vacation memories. This newly furnished ground level home is ...
From $362 per night (USD)
VRBO
From $1638 per night (USD)
Expedia
Island Escape! Pool, Spa, Ping Pong and Fire Pit for Group Fun
Bedrooms:
6
Bathrooms:
6
Sleeps:
8
Sail Away by AMI Locals 241 Willow Avenue, Anna Maria, Florida 34216 VR19-000048 Welcome to Sail Away, a spectacular si ...
From $1638 per night (USD)
Expedia
From $274 per night (USD)
VRBO
Sunset Condo #156 on Anna Maria Island
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This totally renovated condo offers the Gulf of Mexico across the street (west) and Palma Sola Bay (east) of property wi ...
From $274 per night (USD)
VRBO
From $380 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 $380 per night (USD)
Expedia
From $532 per night (USD)
VRBO
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 $532 per night (USD)
VRBO
From $347 per night (USD)
Expedia
Pelican Point in Anna Maria
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
**ASK ABOUT LAST MINUTE DEALS! Welcome to paradise at Pelican Point! This stunning 3 bedroom/3 bath home has everythin ...
From $347 per night (USD)
Expedia
From $561 per night (USD)
VRBO
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 $561 per night (USD)
VRBO
From $301 per night (USD)
Expedia
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 $301 per night (USD)
Expedia
From $276 per night (USD)
VRBO
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 $276 per night (USD)
VRBO
From $438 per night (USD)
Expedia
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 $438 per night (USD)
Expedia
From $414 per night (USD)
VRBO
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 $414 per night (USD)
VRBO
From $425 per night (USD)
Expedia
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 $425 per night (USD)
Expedia
From $334 per night (USD)
VRBO
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 h ...
From $334 per night (USD)
VRBO
From $1560 per night (USD)
Expedia
Sea La Vie AM: Bay front, pool, hot tub, rooftop deck, and water sports gear!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
***Photos Updated September 2025*** Experience the ultimate waterfront getaway at this stunning bayfront property in Ann ...
From $1560 per night (USD)
Expedia
From $636 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 $636 per night (USD)
VRBO
From $536 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 $536 per night (USD)
Expedia
From $311 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 $311 per night (USD)
VRBO
From $199 per night (USD)
Expedia
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 $199 per night (USD)
Expedia
From $566 per night (USD)
VRBO
Beautiful 1 Bedroom Condo with Beach Facing Balcony and Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Coconuts Beachfront #112 by Anna Maria Vacations 100 73rd Street, Unit #112, Holmes Beach, Florida VRC21-000175 Your d ...
From $566 per night (USD)
VRBO
Click For Pricing
Expedia
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
Expedia
From $557 per night (USD)
VRBO
The Cottage on Pine - Charming Pine Ave Cottage w/ Heated Pool in Heart of AMI
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to The Cottage on Pine! On Anna Maria Island (Anna Maria, FL) Highlights - Living & Dining Area: Open-concept s ...
From $557 per night (USD)
VRBO
From $542 per night (USD)
Expedia
Mango Bay – Luxury Island Home w/ Heated Pool, Spa & Walk To Beach
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Welcome to Mango Bay! On Anna Maria Island (Holmes Beach, FL) Discover Mango Bay, A Stunning Coastal Home Designed For ...
From $542 per night (USD)
Expedia
From $594 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 $594 per night (USD)
VRBO
From $594 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 $594 per night (USD)
VRBO
From $198 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 $198 per night (USD)
VRBO
From $198 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 $198 per night (USD)
VRBO
From $396 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 $396 per night (USD)
VRBO
From $198 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 $198 per night (USD)
VRBO
From $198 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 $198 per night (USD)
VRBO
From $396 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 $396 per night (USD)
VRBO
From $198 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 $198 per night (USD)
VRBO
From $594 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 $594 per night (USD)
VRBO
From $396 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 $396 per night (USD)
VRBO
From $594 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 $594 per night (USD)
VRBO
From $198 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 $198 per night (USD)
VRBO
From $396 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 $396 per night (USD)
VRBO
From $758 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 $758 per night (USD)
VRBO
From $389 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 $389 per night (USD)
Expedia
From $199 per night (USD)
VRBO
Family Friendly Home with Pool, 4 mins to Beach! - Starfish Cove, B
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Starfish Cove, B by AMI Locals 7802 Palm Dr, Unit B, Holmes Beach, FL 34217 VRC21-000189 Welcome to Starfish Cove, B, ...
From $199 per night (USD)
VRBO
From $200 per night (USD)
Expedia
Dog-Friendly Home with Pool! 4 mins to the Beach - Starfish Cove, A
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Starfish Cove, A by AMI Locals 7802 Palm Dr, Unit A, Holmes Beach, FL 34217 VRC17-000165 Welcome to Starfish Cove, A, ...
From $200 per night (USD)
Expedia
From $388 per night (USD)
VRBO
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 $388 per night (USD)
VRBO
From $352 per night (USD)
Expedia
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 $352 per night (USD)
Expedia
From $306 per night (USD)
VRBO
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 $306 per night (USD)
VRBO
Click For Pricing
Expedia
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 ...
Click For Pricing
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 $398 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 $398 per night (USD)
Expedia
From $203 per night (USD)
VRBO
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 $203 per night (USD)
VRBO
From $303 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 $303 per night (USD)
Expedia
From $441 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 $441 per night (USD)
VRBO
From $206 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 $206 per night (USD)
Expedia
From $409 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 $409 per night (USD)
VRBO
From $373 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 $373 per night (USD)
Expedia
From $416 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 $416 per night (USD)
VRBO
From $409 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 $409 per night (USD)
Expedia
From $523 per night (USD)
VRBO
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 $523 per night (USD)
VRBO
From $378 per night (USD)
Expedia
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 $378 per night (USD)
Expedia
From $401 per night (USD)
VRBO
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 $401 per night (USD)
VRBO
From $383 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 $383 per night (USD)
Expedia
From $419 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 $419 per night (USD)
VRBO
From $460 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. W ...
From $460 per night (USD)
Expedia
From $617 per night (USD)
VRBO
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 $617 per night (USD)
VRBO
From $667 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 $667 per night (USD)
Expedia
From $234 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 $234 per night (USD)
VRBO
From $471 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 $471 per night (USD)
Expedia
From $339 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 $339 per night (USD)
VRBO
From $179 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 $179 per night (USD)
Expedia
From $436 per night (USD)
VRBO
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 $436 per night (USD)
VRBO
From $495 per night (USD)
Expedia
Casa Morado-Pet Friendly Pool Home West of Gulf Dr-By Island Real Estate Vacatio
Bedrooms:
3
Bathrooms:
3
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 $495 per night (USD)
Expedia
From $360 per night (USD)
VRBO
Viva La Flamingo! 10 Min to Anna Maria, Heated Pool, Pet Friendly
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Important: This home can sleep a maximum of 6 adults. Welcome to our beautiful Viva La Flamingo home. This approximatel ...
From $360 per night (USD)
VRBO
Click For Pricing
Expedia
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
Expedia
From $138 per night (USD)
VRBO
2-Bed/2Bath/1Den First Floor Townhouse in a lovely gated golf course community.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
1st Floor Townhouse overlooking the golf course, in a secure gated community with multiple pools for both adults and chi ...
From $138 per night (USD)
VRBO
$Anna Maria Island \Star Fish\Condo & Boat Slip-2BR-2BA-Sleeps4$
From $277 per night (USD)
Expedia
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 $277 per night (USD)
Expedia
From $369 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 $369 per night (USD)
VRBO
From $432 per night (USD)
Expedia
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 $432 per night (USD)
Expedia
From $691 per night (USD)
VRBO
September Golf Cart Special
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 $691 per night (USD)
VRBO
From $619 per night (USD)
Expedia
For Shore: Sleeps 10, steps to beach, heated pool!
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
***Photos Updated September 2025*** If you are hoping to stay on the perfect Old Florida island in the perfect beach ho ...
From $619 per night (USD)
Expedia
From $657 per night (USD)
VRBO
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 $657 per night (USD)
VRBO
From $1047 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 $1047 per night (USD)
Expedia

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