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

Holmes Beach Rentals

From $353 per night (USD)
VRBO
Island Time: Gulf front condo 20 ft to the beach with shared pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Island Time 104 at Seaside Beach House is a condominium that has long been a favorite to visitors of Holmes Beach and An ...
From $353 per night (USD)
VRBO
From $437 per night (USD)
Expedia
WONDERFUL BEACH VIEWS AND LARGE POOL!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
4200 Gulf Drive, Holmes Beach, Anna Maria Island Gulf Sands # 203 ... Beautiful views of the gulf from this updated 2 b ...
From $437 per night (USD)
Expedia
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VRBO
Resort Sixty-Six, Holmes Beach, Florida, 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 ...
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VRBO
Click For Pricing
Expedia
Amazing Resort Sixty-Six, 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 $322 per night (USD)
VRBO
Lovely 2 bedroom duplex on Anna Maria Island, great location, pet friendly!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Isle Haven B will let you make beautiful memories - it's the perfect beach getaway to relax and enjoy the classic Florid ...
From $322 per night (USD)
VRBO
From $429 per night (USD)
Expedia
Egret at Blue Lagoon on Anna Maria Island - By Island Real Estate Vacations
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Just perfect! From the tasteful beachy decor to the fully appointed kitchen you won’t find more welcoming accommodations ...
From $429 per night (USD)
Expedia
From $375 per night (USD)
VRBO
Private 3BR Heated Pool Villa - Sea Glass on Anna Maria - By Island Real Estate
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
When you arrive at “SeaGlass” you are greeted with pleasant landscaping, a gorgeous brick driveway, and an adorable home ...
From $375 per night (USD)
VRBO
From $796 per night (USD)
Expedia
Perfect 1-bedroom Beachfront Getaway!! See the sunsets and feel the breeze!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Highlights: -large bay of windows perfectly frame the beach from the kitchen, living, and dining areas -Screened porch - ...
From $796 per night (USD)
Expedia
From $383 per night (USD)
VRBO
Summer Wind- An island getaway in the perfect location.
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Experience all the best elements of the perfect Island vacation in this well-appointed rental home. It is located just a ...
From $383 per night (USD)
VRBO
From $611 per night (USD)
Expedia
One block to beach! 3 bedroom home with pool and backyard oasis.
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Walking on Sunshine by AMI Locals Home in Holmes Beach, Florida VRC19-000232 Your dream vacation awaits at Walking on S ...
From $611 per night (USD)
Expedia
From $280 per night (USD)
VRBO
Island Hideaway East: 5 Minute Walk to Beach, Private Pool by Anna Maria Life Vacation Rentals
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Island Hideaway East by Anna Maria Life Vacation Rentals 308B 67th St., Holmes Beach, FL 34217 What you'll love about t ...
From $280 per night (USD)
VRBO
$Cute 3\/2 Cottage close to Beach and centrally located.$
From $303 per night (USD)
Expedia
Cute 3\/2 Cottage close to Beach and centrally located.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
VRC21-000048 Swizzle On The Sound is just a short stroll to the beautiful beaches of Anna Maria Island from your own pi ...
From $303 per night (USD)
Expedia
From $719 per night (USD)
VRBO
Book Swell Life: 4-Bedroom Paradise Steps from the Beach with Pool
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Swell Life by AMI Locals Home in Holmes Beach, Florida VRC21-000150 Experience a slice of paradise at Swell Life, a ...
From $719 per night (USD)
VRBO
From $222 per night (USD)
Expedia
LOCATION!! Cabana just steps from the beach!
Bedrooms:
1
Bathrooms:
2
Sleeps:
2
Welcome to Anna Maria Island the # 1 spot for a perfect getaway. Bask in the tropical paradise of AMI with white sugar ...
From $222 per night (USD)
Expedia
From $476 per night (USD)
VRBO
Dream luxury home on Anna Maria Island, heated private pool - pet friendly!
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
This lovely new island 2 bedrooms, 2.5 baths luxury home with private heated pool is a dream. Fishful Thinking is positi ...
From $476 per night (USD)
VRBO
From $360 per night (USD)
Expedia
Salty Harbor AMI pool retreat near the Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Stunning Fall 2024 renovation completed! Charming Salty Harbor boasts a private heated pool and sits on a quaint corner ...
From $360 per night (USD)
Expedia
From $429 per night (USD)
VRBO
3 bedroom, on AMI, heated private pool, PET FRIENDLY!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
The family friendly Florida vacation you need is waiting at Mykonos! This Anna Maria Island beach rental has it all. Fro ...
From $429 per night (USD)
VRBO
From $1089 per night (USD)
Expedia
Conch House - 7 Homes to the Beach - Amazing Pool Area with TV
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
Welcome to the Conch House, a Charleston inspired beach house unlike any other home and without compromise in craftsmans ...
From $1089 per night (USD)
Expedia
From $332 per night (USD)
VRBO
Cozy Retro Cottage located less then 2 blocks from the Gulf Beach - Heated Pool in Private Oasis!
Bedrooms:
2
Bathrooms:
1
Sleeps:
2
Welcome to Flip Cottage located just 1 block from the Gulf beaches of Anna Maria Island. Flip is a ground level half dup ...
From $332 per night (USD)
VRBO
$Beachfront Condo w\/ Large Balcony & Beautiful Views of Gulf of Mexico$
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Expedia
Beachfront Condo w\/ Large Balcony & Beautiful Views of Gulf of Mexico
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
NOTE: the elevator at this property are currently not available. Imagine waking up every morning to a million dollar v ...
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Expedia
From $185 per night (USD)
VRBO
Crow's Nest Spinnakers Cottages: 250 Steps to Beach! Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Crow's Nest Spinnakers Cottages by Anna Maria Life Vacation Rentals 202 56th St. #2, Holmes Beach, FL 34217 What You'll ...
From $185 per night (USD)
VRBO
From $250 per night (USD)
Expedia
AMI Sand Dollar: Dog Friendly, Private Pool, 2 Blocks to Beach by Anna Maria Life Vacation Rentals
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
AMI Sand Dollar by Anna Maria Life Vacation Rentals 6403 B Holmes Blvd, Holmes Beach, FL 34217 What You'll Love About T ...
From $250 per night (USD)
Expedia
From $272 per night (USD)
VRBO
Sunset Beach 102: Gulf Front, Stunning Views, On the Beach, Pool by Anna Maria Life Vacation Rentals
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
2716 Gulf Dr., #102, Holmes Beach, FL 34217 What You'll Love About This Homes: Location! Beach Front with Gulf Views! ...
From $272 per night (USD)
VRBO
From $272 per night (USD)
Expedia
AMI Starfish: Private Pool, Dog Friendly, 2 Blocks to Beach by Anna Maria Life Vacation Rentals
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
AMI Starfish by Anna Maria Life Vacation Rentals 6403 A Holmes Blvd., Holmes Beach, FL 34217 What You'll Love About Thi ...
From $272 per night (USD)
Expedia
From $353 per night (USD)
VRBO
Island villa with heated private pool, tranquil courtyard, easy beach access
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Blue Wave Villa West Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $353 per night (USD)
VRBO
From $148 per night (USD)
Expedia
Peaceful condo with pool, tennis, fishing dock, & tennis - serenity awaits
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
West Bay Point 12 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $148 per night (USD)
Expedia
From $391 per night (USD)
VRBO
Dog-friendly seaside home - heated private pool & spa, great location near beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Tropical Oasis Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $391 per night (USD)
VRBO
$Dog-friendly cottage w\/ island views, shared pool & private patio - beach nearby$
From $464 per night (USD)
Expedia
Dog-friendly cottage w\/ island views, shared pool & private patio - beach nearby
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Starfish Beach Cottage #3 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ent ...
From $464 per night (USD)
Expedia
From $1261 per night (USD)
VRBO
Luxury beachside home with heated private pool - tranquil & close to everything
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
Wine Down Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $1261 per night (USD)
VRBO
From $535 per night (USD)
Expedia
Historic beach cottage with private pool - walk 1 block to beach & free trolley
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Sea Palm Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $535 per night (USD)
Expedia
From $742 per night (USD)
VRBO
Oceanview getaway with pool & private patio - steps from the beach
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Palm Gables 106 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $742 per night (USD)
VRBO
From $292 per night (USD)
Expedia
Waterfront condo with pool and easy access to sugar sand beach
Bedrooms:
2
Bathrooms:
1
Sleeps:
4
A Gulf Front Getaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $292 per night (USD)
Expedia
From $347 per night (USD)
VRBO
Waterfront condo with furnished balcony overlooking the pristine beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Gulf Shores 205 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $347 per night (USD)
VRBO
$Darling beachside villa w\/ space & privacy - a cozy coastal florida experience$
From $841 per night (USD)
Expedia
Darling beachside villa w\/ space & privacy - a cozy coastal florida experience
Bedrooms:
2
Bathrooms:
5
Sleeps:
8
Playa Casanas Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $841 per night (USD)
Expedia
From $432 per night (USD)
VRBO
Modern home near Gulf beaches with private heated pool & WiFi
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Neolinda 305 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $432 per night (USD)
VRBO
From $211 per night (USD)
Expedia
Charming condo with heated pool - near beach, wetlands, & trolley stop
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Sandy Pointe Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $211 per night (USD)
Expedia
From $260 per night (USD)
VRBO
Ocean-front condo with WiFi, pool & Gulf views - steps to the beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Martinique 401S Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $260 per night (USD)
VRBO
$Beautiful lakeside home w\/ upscale amenities, heated private pool & fishing dock$
From $406 per night (USD)
Expedia
Beautiful lakeside home w\/ upscale amenities, heated private pool & fishing dock
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Spectacular Saltwater Seas Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply en ...
From $406 per night (USD)
Expedia
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VRBO
Delightful condo with pool, two lanais - walk to beach, dining, shopping
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Beach View 5 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
Click For Pricing
VRBO
$Tropical-themed getaway w\/ heated private pool - walk to free trolley, shopping$
From $400 per night (USD)
Expedia
Tropical-themed getaway w\/ heated private pool - walk to free trolley, shopping
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Island Time Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $400 per night (USD)
Expedia
From $565 per night (USD)
VRBO
Beachfront condo with WiFi, two decks, Gulf views & pool - walk to the trolley
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
Hidden Cove Unit 6 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $565 per night (USD)
VRBO
From $328 per night (USD)
Expedia
Comfortable island villa with private heated pool, courtyard & easy beach access
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Blue Wave Villa East Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $328 per night (USD)
Expedia
From $184 per night (USD)
VRBO
Seaside family-friendly condo with WiFi, pool & prime location
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Serenity Now Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $184 per night (USD)
VRBO
From $448 per night (USD)
Expedia
Island-style townhome with WiFi & pool - minutes from the beach
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
North Beach Village 27 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $448 per night (USD)
Expedia
From $486 per night (USD)
VRBO
Home near the Beach. SUP Paddleboards, Large Private Pool - Pure Beach
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
Pure Beach by Anna Maria Island Locals Home in Holmes Beach, FL VRC21-000101 Welcome to Pure Beach, a luxurious three- ...
From $486 per night (USD)
VRBO
From $334 per night (USD)
Expedia
Holmes Beach Family Home: Private Pool & 3 Decks!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Explore Florida’s beautiful Anna Maria Island from ‘Salty Dogs Beach House,’ a 3-bedroom, 2.5-bathroom, single family Ho ...
From $334 per night (USD)
Expedia
$Inviting Coastal Getaway w\/ Easy Beach Access, Full Kitchen$
From $296 per night (USD)
VRBO
Inviting Coastal Getaway w\/ Easy Beach Access, Full Kitchen
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Cozy Crab Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $296 per night (USD)
VRBO
From $487 per night (USD)
Expedia
Waterfront home with heated pool + spa, patio, grill, & free WiFi - dog-friendly
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
3 Oars Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $487 per night (USD)
Expedia
$Ground Floor Luxury Villa in Prime Location, Steps to Beach, Heated Pool\/Spa$
From $883 per night (USD)
VRBO
Ground Floor Luxury Villa in Prime Location, Steps to Beach, Heated Pool\/Spa
Bedrooms:
7
Bathrooms:
7
Sleeps:
12
Prime Location! VERY CLOSE TO BEACH!!! Luxurious ground level home located at 124 50th Street, Holmes Beach, in the „Gol ...
From $883 per night (USD)
VRBO
From $175 per night (USD)
Expedia
Cabin 2 Spinnakers Cottages: Dog Friendly - 250 Steps to Beach Home
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Cabin 2 Spinnakers Cottages by Anna Maria Life Vacation Rentals 204 56th St. #2, Holmes Beach, FL 34217 What You'll Lov ...
From $175 per night (USD)
Expedia
From $1133 per night (USD)
VRBO
BUENA VISTA LUXURY BEACHFRONT 4BR - Anna Maria Island - By Island Real Estate Va
Bedrooms:
4
Bathrooms:
5
Sleeps:
8
Top 10 Gulfview on Anna Maria Island!!! You can see for miles in both direction down the beach. Luxury condominium “Buen ...
From $1133 per night (USD)
VRBO
From $1125 per night (USD)
Expedia
DIRECT BEACH FRONT - Luxury 4BR Condo - Anna Maria Island- By Island Real Estate
Bedrooms:
4
Bathrooms:
5
Sleeps:
8
DIRECT BEACH FRONT - Luxury 4BR Condo - Buena Vista #3 - 101 67th Street - 4 Bedrooms and 3 and a 1/2 Baths - Bed/s: 3 ...
From $1125 per night (USD)
Expedia
From $317 per night (USD)
VRBO
One Bedroom Island Luxury Cottage located less than 2 blocks from the beach.
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Welcome to Flop Cottage located 1 block from the Gulf beaches of Anna Maria Island. Flop Cottage is a ground level half ...
From $317 per night (USD)
VRBO
From $1372 per night (USD)
Expedia
Beach Front Home on Anna Maria Island - Great Views! Pool! Sleeps 10!
Bedrooms:
6
Bathrooms:
5
Sleeps:
10
Experience Anna Maria Island at its best! This luxury beach-front home located in Holmes Beach is in the monthly rental ...
From $1372 per night (USD)
Expedia
From $391 per night (USD)
VRBO
Casual beachside getaway with pool, and easy beach access
Bedrooms:
2
Bathrooms:
2
Sleeps:
2
Water's Edge 105 South Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $391 per night (USD)
VRBO
From $400 per night (USD)
Expedia
Welcoming condo close to the beach with private heated pool & WiFi
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
LaMadeira 305 Unit A Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $400 per night (USD)
Expedia
From $469 per night (USD)
VRBO
Upscale condo with large deck & shared pool - just steps from the beach
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
La Casa Karen Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $469 per night (USD)
VRBO
From $272 per night (USD)
Expedia
Quaint beachfront duplex in ideal location with screened lanai & free trolley
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Playa Casanas North Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $272 per night (USD)
Expedia
From $240 per night (USD)
VRBO
Adorable beachfront rental in a great location with Gulf access right outside
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Playa Casanas South Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $240 per night (USD)
VRBO
From $595 per night (USD)
Expedia
Aquarius-Pool Home West of Gulf Dr-By Island Real Estate Vacations
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Spend your Anna Maria Island vacation in five star luxury when you visit “Aquarius”. This fully renovated Holmes Beach v ...
From $595 per night (USD)
Expedia
From $360 per night (USD)
VRBO
Breezy Harbor AMI pool retreat near the Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Stunning Fall 2024 renovation completed! Charming Breeze Harbor boasts a private heated pool and sits on a quaint corne ...
From $360 per night (USD)
VRBO
From $1666 per night (USD)
Expedia
Buena Vista #2: Luxury Beach Front Condo, Amazing Views, Pool by Anna Maria Life Vacation Rentals
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Buena Vista #2 by Anna Maria Life Vacation Rentals 101 67th St #2, Holmes Beach, FL 34217 What You'll Love About This H ...
From $1666 per night (USD)
Expedia
From $344 per night (USD)
VRBO
Luxury Beach House, 1 Block from beach!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This charming Anna Maria Island Vacation Home is located just a few houses from the white sand beaches! Holmes Beach is ...
From $344 per night (USD)
VRBO
From $1082 per night (USD)
Expedia
GLORIOUS DAZE Beach House POOL! SPA! GOLFCART! ELEVATOR! PUTTING GREEN!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Welcome to Glorious Daze! Our four bedroom/four bath private home is located along the sugary white sands of beautiful H ...
From $1082 per night (USD)
Expedia
From $208 per night (USD)
VRBO
Breezy house with great location near beach, shopping & dining
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Guava Getaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $208 per night (USD)
VRBO
$March Dates! Ground Floor Luxury Home, Heated Pool\/Spa 🌴🌴🌴🌴$
From $680 per night (USD)
Expedia
March Dates! Ground Floor Luxury Home, Heated Pool\/Spa 🌴🌴🌴🌴
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
Ground Floor Luxury Home with Heated Pool/Spa, very close to Beach 🌴🌴🌴🌴 Welcome to the AMI Beach Home on beautiful ...
From $680 per night (USD)
Expedia
From $455 per night (USD)
VRBO
Island Getaway: Tropical Oasis Backyard, Pool, Dog Friendly, 1.5 blocks to Beach by Anna Maria Life
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Island Getaway by Anna Maria Life Vacation Rentals 205 56th St., Holmes Beach, FL 34217 What You'll Love About This Hom ...
From $455 per night (USD)
VRBO
From $419 per night (USD)
Expedia
Retro Style Home with Large Pool Close to Downtown Holmes Beach and Walk to Beach!
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
Welcome to Gumbo Cottage located just 7 houses from the Gulf beaches of Anna Maria Island and a street away from downtow ...
From $419 per night (USD)
Expedia
$Minnie Cottage- Beautiful 3 bedroom heated pool\/spa and short walk to the beach$
From $485 per night (USD)
VRBO
Minnie Cottage- Beautiful 3 bedroom heated pool\/spa and short walk to the beach
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
AT A GLANCE Beautiful 3-bedroom 3 bath homes West of Gulf Drive, a short stroll to the beach Gorgeous private heated wit ...
From $485 per night (USD)
VRBO
From $289 per night (USD)
Expedia
EXCELLENT LOCATION IN THE HEART OF HOLMES BEACH ON ANNA MARIA ISLAND!
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Renovated in 2025, bright, sunny, spacious and clean townhouse in a great location on Anna Maria Island, just a few minu ...
From $289 per night (USD)
Expedia
From $642 per night (USD)
VRBO
Pool & Spa! Short Walk to Beach & Restaurants! Rooftop Views!
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Beach View Retreat by AMI Locals Home in Holmes Beach, Florida VRC19-000046 Welcome to Beach View Retreat, a custom-bu ...
From $642 per night (USD)
VRBO
From $254 per night (USD)
Expedia
1 Block To Beach! Convenient, Modern, Comfortable, Clean.
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Comfortable, convenient townhouse one block to beach and close to other attractions. 2BR/2BA with 1 BR and BA with showe ...
From $254 per night (USD)
Expedia
$Sea Pirate 7 2\/1 Condo Pool Just Steps To Beach$
From $267 per night (USD)
VRBO
Sea Pirate 7 2\/1 Condo Pool Just Steps To Beach
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
VRC16-000815 Sea Pirate Condo #7, located at 3301 Gulf Drive in the heart of Holmes Beach is just across the street fro ...
From $267 per night (USD)
VRBO
From $190 per night (USD)
Expedia
Island Retreat by SeaBreeze Vacation
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to Island Retreat where you can enjoy the tranquility of listening to waves, watching dolphins, coastal birds an ...
From $190 per night (USD)
Expedia
From $417 per night (USD)
VRBO
Lovely family condo with a private heated pool & Gulf view, close to the beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Crab Shack Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $417 per night (USD)
VRBO
From $268 per night (USD)
Expedia
Cozy cottage on Anna Maria Island, 2 bedroom - pet friendly!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
The cozy front porch of Gulf Winds B invites you to have your morning coffee or your evening cocktail and in the back ya ...
From $268 per night (USD)
Expedia
From $237 per night (USD)
VRBO
Beach Potato: Gulf View Condo, Pool, Steps to the beach by Anna Maria Life Vacation Rentals
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Beach Potato by Anna Maria Life Vacation Rentals 3404 Gulf Drive, #5, Holmes Beach, FL 34217 What You'll Love Ab ...
From $237 per night (USD)
VRBO
From $306 per night (USD)
Expedia
Barefoot Dreams: Dog Friendly, Private Pool,1 Block to Beach by Anna Maria Life Vacation Rentals
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Barefoot Dreams by Anna Maria Life Vacation Rentals 201 76th St. East Unit B, Holmes Beach, FL 34217 What You'll Love A ...
From $306 per night (USD)
Expedia
$BeachView Condo #8 - Anna Maria Island - Condo 2 Bedroom \/ 2 Bath, maximum...$
From $303 per night (USD)
VRBO
BeachView Condo #8 - Anna Maria Island - Condo 2 Bedroom \/ 2 Bath, maximum...
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
Beach View Condominum, #8 - Anna Maria Island - 2 Bedroom / 2 Bath, maximum occupancy of 7 people. VRC22-000101 Co ...
From $303 per night (USD)
VRBO
From $351 per night (USD)
Expedia
2 minute walk to the beach! Off the main road in a quiet and tropical setting
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
What you'll love about this home: - Location! 2 min walk to the beach - 3 Bedrooms / 2 full bathrooms - 1 King, 1 Que ...
From $351 per night (USD)
Expedia
From $434 per night (USD)
VRBO
Weekly Discounts! Exceptional Rating-A Pearl of a Beach Home- private pool & spa
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Tropical rear yard with private luxury heated Saltwater pool and hot tub/spa and spacious paved area plus large ground f ...
From $434 per night (USD)
VRBO
From $537 per night (USD)
Expedia
Easy walk to beach, enjoy private splash pool, super clean!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Custom built this three bedroom, two bath home is beautifully designed for six guests. Come to Island Breeze and relax w ...
From $537 per night (USD)
Expedia
From $243 per night (USD)
VRBO
Sea Pirate Cottage By The Sea on Anna Maria Island, Smart TV in every room.
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Cottage By the Sea is a (no smoking) Unit within the charming Sea Pirate condo complex located on a tranquil and des ...
From $243 per night (USD)
VRBO
From $339 per night (USD)
Expedia
SS Salamander North | Steps to the Beach + Heated Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
VRC16-000499 Your Cozy Island Getaway in Holmes Beach Just one block from the sugar-white sands of the Gulf, SS Salaman ...
From $339 per night (USD)
Expedia
From $405 per night (USD)
VRBO
Your Own Oasis: A Tropical Retreat with Lagoon Style Pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Your Own Oasis - An Island Retreat with Lagoon Style Pool, close to Bay and Beach Escape to "Your Own Oasis" on Anna Ma ...
From $405 per night (USD)
VRBO
$She's Always Right - Luxurious 5-Bed Home w\/ Heated Pool, Spa, Steps to Beach & Central Location$
From $878 per night (USD)
Expedia
She's Always Right - Luxurious 5-Bed Home w\/ Heated Pool, Spa, Steps to Beach & Central Location
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Welcome to She's Always Right! On Anna Maria Island (Holmes Beach, FL) This spacious and luxurious island home is perfe ...
From $878 per night (USD)
Expedia
From $354 per night (USD)
VRBO
Direct Beach Front, FREE WiFi & Trolley, Heated Pool and Awesome Sunsets
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
**ASK ABOUT LAST-MINUTE DEALS! Stay DIRECTLY on the beach in this gorgeous two-bedroom, two-bath condo! Our ...
From $354 per night (USD)
VRBO
$2 Bedroom \/ 2 Bath Ground Level With a Heated Pool$
From $316 per night (USD)
Expedia
2 Bedroom \/ 2 Bath Ground Level With a Heated Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This listing is for a Weekly rental located in the heart of Anna Maria Island at 305 61st St, Unit A, Holmes Beach, FL, ...
From $316 per night (USD)
Expedia
From $638 per night (USD)
VRBO
Beautiful home with fenced yard, heated pool, hot tub, and elevator!
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Sand Castle by Anna Maria Island Accommodations Holmes Beach, FL 34217 VRC19-000022 Welcome to Sand Castle! Nestled in ...
From $638 per night (USD)
VRBO
From $347 per night (USD)
Expedia
Beautiful home near the beach with heated pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Highlights • Less than a five-minute walk to the beach • Private pool • Washer and dryer • Less than a 10-minute troll ...
From $347 per night (USD)
Expedia
From $244 per night (USD)
VRBO
Great Condo 3 Mins from the Beach! Community Pool - Seabreeze D
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Seabreeze D by Anna Maria Island Accommodations Condo in Holmes Beach, FL 34217 VRC16-000111 Welcome to Seabreeze D! T ...
From $244 per night (USD)
VRBO
From $544 per night (USD)
Expedia
Family Home with Pool Near Gulf Beaches - Corona Joe's Beach Cottage
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Corona Joe's Beach Cottage by AMI Accommodations Home in Holmes Beach, FL VRC17-000163 Experience the perfect family g ...
From $544 per night (USD)
Expedia
$Beautiful, Ground Level 4 bedroom\/3 bath home, just a short block to the beach$
From $568 per night (USD)
VRBO
Beautiful, Ground Level 4 bedroom\/3 bath home, just a short block to the beach
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Simply Chic 1.5 Blocks to Beach Beautiful, Ground Level 4 bedroom/3 bath home, just a short block to the beach. Beaut ...
From $568 per night (USD)
VRBO
From $263 per night (USD)
Expedia
Home with Private Backyard and Heated Pool - Gulf Breeze Villa B
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Gulf Breeze Villa B by Anna Maria Island Accommodations Home in Holmes Beach, FL 34217 VRC16-000146 Gulf Breeze Vill ...
From $263 per night (USD)
Expedia
From $852 per night (USD)
VRBO
Tropical Pool, Sunset Views, Game Room - It's a Jungle Out There
Bedrooms:
4
Bathrooms:
6
Sleeps:
12
It's a Jungle Out There by Anna Maria Island Accommodations Home in Holmes Beach, FL 34217 VRC19-000173 It’s a Ju ...
From $852 per night (USD)
VRBO
From $438 per night (USD)
Expedia
Private home with Pool, Spa, and Ping Pong! 6 mins to Beach! - Banana Cabana
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Banana Cabana by Anna Maria Island Accommodations 318 64th St Holmes Beach, FL 34217 Relaxation awaits at Banana Caba ...
From $438 per night (USD)
Expedia
From $248 per night (USD)
VRBO
Adorable ground-level condo near the beach. Large heated pool!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Palm Cay 6 by Anna Maria Island Accommodations Condo in Holmes Beach, FL 34217 VRC16-000127 Welcome to Palm Cay 6, a g ...
From $248 per night (USD)
VRBO
From $510 per night (USD)
Expedia
Luxury home with Pool, Spa, and Dock -Bayshores
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Bayshores by Anna Maria Island Accommodations Home in Holmes Beach, FL 34217 VRC18-000040 Welcome to Bayshores, a breat ...
From $510 per night (USD)
Expedia
From $477 per night (USD)
VRBO
Centrally located. 3 blocks to the beach. Private pool and hot tub.
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Sand Dollar by Anna Maria Island Accommodations Home in Holmes Beach, FL 34217 VRC16-000117 Welcome to Sand Dollar, a ...
From $477 per night (USD)
VRBO
From $252 per night (USD)
Expedia
Family-Friendly Condo, just 1 block from the Beach! - Seabreeze A
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Seabreeze A by Anna Maria Island Accommodations Condo in Holmes Beach, FL 34217 VRC16-000112 Welcome to Seabreeze A, y ...
From $252 per night (USD)
Expedia

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