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 $418 per night (USD)
VRBO
Make Memories at Coveside Cottage: Your Family-Friendly Pool Home Near the Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Coveside Cottage by AMI Locals Home in Holmes Beach, Florida Welcome to Coveside Cottage, a serene coastal retreat feat ...
From $418 per night (USD)
VRBO
$Cute 3\/2 Cottage close to Beach and centrally located.$
From $309 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 $309 per night (USD)
Expedia
From $814 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 $814 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 $478 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 $478 per night (USD)
VRBO
From $2090 per night (USD)
Expedia
AMI’s Largest Rental, 4 kitchens, Spa, Heated Pool, Rooftop Deck.
Bedrooms:
9
Bathrooms:
10
Sleeps:
28
Large family or group rental. This unique property with 4 suites is great for families or groups. Each suite has its own ...
From $2090 per night (USD)
Expedia
From $360 per night (USD)
VRBO
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)
VRBO
From $771 per night (USD)
Expedia
Large Beach Home 5 houses to beach, Heated Pool, Game Room, Sun deck, Tiki bar
Bedrooms:
4
Bathrooms:
5
Sleeps:
8
This spacious property has a Tiki Bar by the heated pool, large kitchen with 4 bedrooms and 4 bathrooms, a large second ...
From $771 per night (USD)
Expedia
From $229 per night (USD)
VRBO
Enjoy the Island Life on Anna Maria Island!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
The location is very quiet and private. It's a short walk to Holmes Beach, Duffy s Tavern, Hurricane Hanks, The Feast, ...
From $229 per night (USD)
VRBO
From $434 per night (USD)
Expedia
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 $434 per night (USD)
Expedia
From $1108 per night (USD)
VRBO
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 $1108 per night (USD)
VRBO
From $332 per night (USD)
Expedia
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)
Expedia
$Beachfront Condo w\/ Large Balcony & Beautiful Views of Gulf of Mexico$
Click For Pricing
VRBO
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 ...
Click For Pricing
VRBO
From $193 per night (USD)
Expedia
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 $193 per night (USD)
Expedia
From $651 per night (USD)
VRBO
Starfish Isle managed by Beach Retreats FL Anna Maria Island
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
VRC 21-000046 5803 Holmes Blvd Holmes Beach, FL 34217 At 4 bedrooms and 3 full bathrooms, this is a great option for one ...
From $651 per night (USD)
VRBO
From $763 per night (USD)
Expedia
Conch Out Beach House managed by Beach Retreats FL Anna Maria Island
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
303 68th St, Holmes Beach 34217 VRC - 19-000273 You may cancel your reservation up to 60 days before check-in for a ful ...
From $763 per night (USD)
Expedia
From $532 per night (USD)
VRBO
Starfish Cove managed by Beach Retreats FL Anna Maria Island
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
302 60th Street Holmes Beach, FL 34217 VRC19-000274 At 3 bedrooms and 2 full bathrooms, this is a beautiful choice for y ...
From $532 per night (USD)
VRBO
From $442 per night (USD)
Expedia
Sun Plaza West Unit 201, gulf front complex on AMI
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Come experience Unit 201 at Sun Plaza West on beautiful Anna Maria Island. This 2 bedroom 2 bathroom Condo is located in ...
From $442 per night (USD)
Expedia
From $288 per night (USD)
VRBO
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 $288 per night (USD)
VRBO
From $277 per night (USD)
Expedia
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 $277 per night (USD)
Expedia
From $265 per night (USD)
VRBO
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 $265 per night (USD)
VRBO
$Driftwood Beach Escape-4 bedrooms with private pool\/spa- 2 blocks from the beach$
From $814 per night (USD)
Expedia
Driftwood Beach Escape-4 bedrooms with private pool\/spa- 2 blocks from the beach
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
At A Glance Only 2 Blocks from the Beach! Private Pool and Outdoor Space (Heated Seasonally) Private Gas Grill Outdoor S ...
From $814 per night (USD)
Expedia
From $387 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 $387 per night (USD)
VRBO
From $167 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 $167 per night (USD)
Expedia
$Beautiful lakeside home w\/ upscale amenities, heated private pool & fishing dock$
From $462 per night (USD)
VRBO
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 $462 per night (USD)
VRBO
From $451 per night (USD)
Expedia
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 $451 per night (USD)
Expedia
$Dog-friendly cottage w\/ island views, shared pool & private patio - beach nearby$
From $464 per night (USD)
VRBO
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)
VRBO
From $1498 per night (USD)
Expedia
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 $1498 per night (USD)
Expedia
From $635 per night (USD)
VRBO
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 $635 per night (USD)
VRBO
From $801 per night (USD)
Expedia
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 $801 per night (USD)
Expedia
From $307 per night (USD)
VRBO
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 $307 per night (USD)
VRBO
From $415 per night (USD)
Expedia
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 $415 per night (USD)
Expedia
$Darling beachside villa w\/ space & privacy - a cozy coastal florida experience$
From $848 per night (USD)
VRBO
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 $848 per night (USD)
VRBO
From $470 per night (USD)
Expedia
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 $470 per night (USD)
Expedia
From $230 per night (USD)
VRBO
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 $230 per night (USD)
VRBO
From $260 per night (USD)
Expedia
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)
Expedia
Click For Pricing
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 $448 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 $448 per night (USD)
Expedia
From $710 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 $710 per night (USD)
VRBO
From $378 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 $378 per night (USD)
Expedia
From $289 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 $289 per night (USD)
VRBO
From $479 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 $479 per night (USD)
Expedia
From $534 per night (USD)
VRBO
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 $534 per night (USD)
VRBO
From $577 per night (USD)
Expedia
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 $577 per night (USD)
Expedia
$Large Single Level-1 Minute Walk To The Beach-5 minute walk to Restaurant\/Shops$
From $1100 per night (USD)
VRBO
Large Single Level-1 Minute Walk To The Beach-5 minute walk to Restaurant\/Shops
Bedrooms:
4
Bathrooms:
6
Sleeps:
12
Recently renovated with all new kitchens and more! Welcome to our Blue Grotto on the beautiful Anna Maria Island. We h ...
From $1100 per night (USD)
VRBO
From $511 per night (USD)
Expedia
Private Pool - Summer Breeze by SeaBreeze Vacation
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Summer Breeze is a custom home nestled in the quiet residential area in the heart of Holmes Beach. Offering 4 bedrooms/3 ...
From $511 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 $1233 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 $1233 per night (USD)
Expedia
From $334 per night (USD)
VRBO
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)
VRBO
$Inviting Coastal Getaway w\/ Easy Beach Access, Full Kitchen$
From $325 per night (USD)
Expedia
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 $325 per night (USD)
Expedia
$Ground Floor Luxury Villa in Prime Location, Steps to Beach, Heated Pool\/Spa$
From $852 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 $852 per night (USD)
VRBO
From $180 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 $180 per night (USD)
Expedia
From $1140 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 $1140 per night (USD)
VRBO
From $1166 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 $1166 per night (USD)
Expedia
From $563 per night (USD)
VRBO
Northshore Villa - 3 Bedroom, 2 Bathroom Vacation Rental Across from the Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Come for the SUN, stay for the FUN!!! Find everything that makes a fun beach getaway on Anna Maria Island memorable whe ...
From $563 per night (USD)
VRBO
From $405 per night (USD)
Expedia
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 $405 per night (USD)
Expedia
From $437 per night (USD)
VRBO
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 $437 per night (USD)
VRBO
From $537 per night (USD)
Expedia
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 $537 per night (USD)
Expedia
From $280 per night (USD)
VRBO
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 $280 per night (USD)
VRBO
From $250 per night (USD)
Expedia
Contemporary dog-friendly home with shared pool - two blocks from the beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Fountain Head 5 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $250 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 $622 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 $622 per night (USD)
Expedia
From $363 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 $363 per night (USD)
VRBO
From $337 per night (USD)
Expedia
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 $337 per night (USD)
Expedia
From $1785 per night (USD)
VRBO
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 $1785 per night (USD)
VRBO
From $326 per night (USD)
Expedia
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 $326 per night (USD)
Expedia
From $1082 per night (USD)
VRBO
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)
VRBO
From $549 per night (USD)
Expedia
Caribbean Surf managed by Beach Retreats FL Anna Maria Island
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
306 67th Street Unit B Holmes Beach, FL 34217 VRC 19-000277 You may cancel your reservation up to 60 days before check-i ...
From $549 per night (USD)
Expedia
From $1020 per night (USD)
VRBO
307 65th Street managed by Beach Retreats FL Anna Maria Island
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
VRC 18-000047 Luxury Vacation Rental on Anna Maria Island – Steps from the Beach! Welcome to your dream getaway on Anna ...
From $1020 per night (USD)
VRBO
Click For Pricing
Expedia
Friendly home with private pool & spa, WiFi, central AC, and Ping-Pong table
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Hidden Treasure Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
Click For Pricing
Expedia
From $237 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 $237 per night (USD)
VRBO
$March Dates! Ground Floor Luxury Home, Heated Pool\/Spa 🌴🌴🌴🌴$
From $711 per night (USD)
Expedia
March Dates! Ground Floor Luxury Home, Heated Pool\/Spa 🌴🌴🌴🌴
Bedrooms:
5
Bathrooms:
5
Sleeps:
8
Ground Floor Luxury Home with Heated Pool/Spa, very close to Beach 🌴🌴🌴🌴 Welcome to the AMI Beach Home on beautiful ...
From $711 per night (USD)
Expedia
From $464 per night (USD)
VRBO
Island Getaway: Tropical Oasis Backyard, Pool, Dog Friendly, 1.5 blocks to Beach by Anna Maria Life
Bedrooms:
2
Bathrooms:
3
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 $464 per night (USD)
VRBO
From $442 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 $442 per night (USD)
Expedia
From $335 per night (USD)
VRBO
Beachfront Bliss at Bamboo Apartments #2– A Hidden Gem on Anna Maria Island!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Hello, Guest! Welcome to Bamboo Apartments, Apartment #2, part of our family-owned five-unit beachfront retreat featur ...
From $335 per night (USD)
VRBO
$Minnie Cottage- Beautiful 3 bedroom heated pool\/spa and short walk to the beach$
From $485 per night (USD)
Expedia
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)
Expedia
From $289 per night (USD)
VRBO
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)
VRBO
From $323 per night (USD)
Expedia
View of Beach from the deck, Walk to all , free WIFI.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Immerse yourself in the ultimate Anna Maria Island getaway with this charming vacation rental just minutes away from th ...
From $323 per night (USD)
Expedia
From $682 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 $682 per night (USD)
VRBO
$Sandy Cheeks & Barefeet, Gorgeous Gulf beach Place, Summer\nspecials$
From $400 per night (USD)
Expedia
Sandy Cheeks & Barefeet, Gorgeous Gulf beach Place, Summer\nspecials
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Gulf views from several rooms and lanai! Quick access (only 1 small house between you and sun & sand). 2 Bedroom, 2 Bath ...
From $400 per night (USD)
Expedia
From $254 per night (USD)
VRBO
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)
VRBO
$Sea Pirate 7 2\/1 Condo Pool Just Steps To Beach$
From $268 per night (USD)
Expedia
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 $268 per night (USD)
Expedia
From $545 per night (USD)
VRBO
Kickback Cabana managed by Beach Retreats FL Anna Maria Island
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
411 79th Street Holmes Beach, Fl 34217 VRC19-000189 You may cancel your reservation up to 60 days before check-in for a ...
From $545 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 $437 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 $437 per night (USD)
VRBO
From $435 per night (USD)
Expedia
Relax & Unwind at Bryant’s Beach Bungalow!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to your perfect beach getaway! This spacious three-story home is designed for comfort, convenience, and fun—just ...
From $435 per night (USD)
Expedia
From $271 per night (USD)
VRBO
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 $271 per night (USD)
VRBO
From $264 per night (USD)
Expedia
Hidden Gem 2 BR Condo by A Shore Thing Vacations!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
The search for the perfect Anna Maria Island beach condo is over—you've found your Hidden Gem! 🏡 Property Highlights: ...
From $264 per night (USD)
Expedia
From $243 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 $243 per night (USD)
VRBO
From $290 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 $290 per night (USD)
Expedia
From $894 per night (USD)
VRBO
Beach Dance in Holmes Beach
Bedrooms:
6
Bathrooms:
5
Sleeps:
10
Beach Dance is the perfect family home in a convenient location just steps to the Gulf, Restaurants, Shops and the Free ...
From $894 per night (USD)
VRBO
$BeachView Condo #8 - Anna Maria Island - Condo 2 Bedroom \/ 2 Bath, maximum...$
From $310 per night (USD)
Expedia
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 $310 per night (USD)
Expedia
From $379 per night (USD)
VRBO
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 $379 per night (USD)
VRBO
From $434 per night (USD)
Expedia
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)
Expedia
From $537 per night (USD)
VRBO
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)
VRBO
From $246 per night (USD)
Expedia
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 $246 per night (USD)
Expedia
From $337 per night (USD)
VRBO
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 $337 per night (USD)
VRBO
From $346 per night (USD)
Expedia
★ Spacious Condo ★ Steps to the Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Very private! Spacious 2 bedroom 2 full bath condo is just steps to Holmes Beach beach. Ocean view from your unit with t ...
From $346 per night (USD)
Expedia
From $438 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 $438 per night (USD)
VRBO
$She's Always Right - Luxurious 5-Bed Home w\/ Heated Pool, Spa, Steps to Beach & Central Location$
From $992 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 $992 per night (USD)
Expedia

Search Your Destination Now!

Holmes Beach Rentals

Rental Rates ($USD weekly)

Guests

Check Rates & Availability:

Results: 1,000 Rentals