Holmes Beach, Florida

Vacation Rentals in Holmes Beach, Florida

Discover 770 vacation rental properties in Holmes Beach. From 1 to 10 bedrooms. Average $295/night. 100% have pools.

770 verified listings Book securely on VRBO Prices updated March 2026

770 properties available

Convenient cottage with pool - easy access to trolley stops & the beach

Convenient cottage with pool - easy access to trolley stops & the beach

2 beds 2 baths
PoolA/CWiFiBalcony
$320/night
View Details → Book on VRBO
🌴”Calypso” - Awesome for Couples! Private Pool + Walk to the Beach! 🌞

🌴”Calypso” - Awesome for Couples! Private Pool + Walk to the Beach! 🌞

2 beds 2 baths
PoolA/CWiFiBalcony
$418/night
View Details → Book on VRBO
Home with Private Backyard and Heated Pool - Gulf Breeze Villa B

Home with Private Backyard and Heated Pool - Gulf Breeze Villa B

1 bed 1 bath
PoolA/CWiFiBalcony
$180/night
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Beachfront condo with WiFi, two decks, Gulf views & pool - walk to the trolley

Beachfront condo with WiFi, two decks, Gulf views & pool - walk to the trolley

2 beds 2 baths
PoolA/CWiFiBalcony
$347/night
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Updated House 1 Minute Walk to the Beach

Updated House 1 Minute Walk to the Beach

3 beds 2 baths
PoolA/CWiFiBalcony
$276/night
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Private Pool! Ping-Pong, Pool Table, Putt-Putt!

Private Pool! Ping-Pong, Pool Table, Putt-Putt!

2 beds 2 baths
PoolA/CWiFiBalcony
$281/night
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Anna Maria Island Sunshine Kiss Villa

Anna Maria Island Sunshine Kiss Villa

2 beds 1 bath
PoolA/CWiFiBalcony
$130/night
View Details → Book on VRBO
Inviting Condo with Shared Pool, High-Speed WiFi, and Central AC

Inviting Condo with Shared Pool, High-Speed WiFi, and Central AC

2 beds 2 baths
PoolA/CWiFiBalcony
$122/night
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Heated Pool! 200 Steps to Gulf Beach!

Heated Pool! 200 Steps to Gulf Beach!

1 bed 1 bath
PoolA/CWiFiBalcony
$180/night
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Private Beach Home with Heated Pool!

Private Beach Home with Heated Pool!

3 beds 2 baths
PoolA/CWiFiBalcony
$184/night
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Salt Air East managed by Beach Retreats

Salt Air East managed by Beach Retreats

2 beds 2 baths
PoolA/CWiFiBalcony
$204/night
View Details → Book on VRBO
Quaint & Cozy Beachside Apartment - 75 Steps to Beach - Bamboo Apts. #A4

Quaint & Cozy Beachside Apartment - 75 Steps to Beach - Bamboo Apts. #A4

1 bed 1 bath
PoolA/CWiFiBalcony
$272/night
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Across the street from the Beach, restaurants, free wifi, beach gear provided!

Across the street from the Beach, restaurants, free wifi, beach gear provided!

2 beds 2 baths
PoolA/CWiFiBalcony
$192/night
View Details → Book on VRBO
Bayfront & dog-friendly home with heated private boat dock, pool & spa

Bayfront & dog-friendly home with heated private boat dock, pool & spa

3 beds 3 baths
PoolA/CWiFiBalcony
$226/night
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Resting Beach Place managed by Beach Retreats

Resting Beach Place managed by Beach Retreats

2 beds 2 baths
PoolA/CWiFiBalcony
$301/night
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Perfect view of Beach from deck, Walk to all , free WIFI, beach gear provided!

Perfect view of Beach from deck, Walk to all , free WIFI, beach gear provided!

3 beds 2 baths
PoolA/CWiFiBalcony
$245/night
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Sunbow Bay 213 - gorgeous 2 bed/2 bath condo in excellent location

Sunbow Bay 213 - gorgeous 2 bed/2 bath condo in excellent location

2 beds 2 baths
PoolA/CWiFiBalcony
$152/night
View Details → Book on VRBO
Hidden Cove Unit 2 by SeaBreeze Vacation

Hidden Cove Unit 2 by SeaBreeze Vacation

2 beds 2 baths
PoolA/CWiFiBalcony
$339/night
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Charming condo with heated pool - near beach, wetlands, & trolley stop

Charming condo with heated pool - near beach, wetlands, & trolley stop

2 beds 2 baths
PoolA/CWiFiBalcony
$192/night
View Details → Book on VRBO
Beautiful Cottage with Private Pool, Great Location!

Beautiful Cottage with Private Pool, Great Location!

3 beds 2 baths
PoolA/CWiFiBalcony
$161/night
View Details → Book on VRBO
Cute ground-level Villa, Pet Friendly and so close to the beach!

Cute ground-level Villa, Pet Friendly and so close to the beach!

2 beds 2 baths
PoolA/CWiFiBalcony
$130/night
View Details → Book on VRBO
Beach Front condo on Anna Maria Island with pool!

Beach Front condo on Anna Maria Island with pool!

2 beds 2 baths
PoolA/CWiFiBalcony
$254/night
View Details → Book on VRBO
Charming, Family Friendly Newly Renovated Duplex on Holmes Beach

Charming, Family Friendly Newly Renovated Duplex on Holmes Beach

2 beds 2 baths
PoolA/CWiFiBalcony
$175/night
View Details → Book on VRBO
Ground-floor home with fast WiFi, shared pool, & central AC - close to beach

Ground-floor home with fast WiFi, shared pool, & central AC - close to beach

1 bed 1 bath
PoolA/CWiFiBalcony
$180/night
View Details → Book on VRBO
Home with Private Pool, Two Blocks from the Beach! - Queen Palms

Home with Private Pool, Two Blocks from the Beach! - Queen Palms

2 beds 1 bath
PoolA/CWiFiBalcony
$128/night
View Details → Book on VRBO
New Retro Style Home with Large Pool Close to Downtown Holmes Beach and Walk to Beach!

New Retro Style Home with Large Pool Close to Downtown Holmes Beach and Walk to Beach!

2 beds 2 baths
PoolA/CWiFiBalcony
$314/night
View Details → Book on VRBO
BEACHFRONT HOUSE DIRECTLY ON SOFT SUGAR WHITE SANDS

BEACHFRONT HOUSE DIRECTLY ON SOFT SUGAR WHITE SANDS

3 beds 2 baths
PoolA/CWiFiBalcony
$641/night
View Details → Book on VRBO
Coconuts Resort Direct Beachfront Bungalow!

Coconuts Resort Direct Beachfront Bungalow!

1 bed 1 bath
PoolA/CWiFiBalcony
$277/night
View Details → Book on VRBO
Luxury home with Pool, Spa, and Dock -Bayshores

Luxury home with Pool, Spa, and Dock -Bayshores

3 beds 3 baths
PoolA/CWiFiBalcony
$349/night
View Details → Book on VRBO
Contemporary dog-friendly home with shared pool - two blocks from the beach

Contemporary dog-friendly home with shared pool - two blocks from the beach

2 beds 2 baths
PoolA/CWiFiBalcony
$224/night
View Details → Book on VRBO
Liddie's Place: Gulf Front Sun Plaza West Condo, Pool, Tennis by Anna Maria Life Vacation Rentals

Liddie's Place: Gulf Front Sun Plaza West Condo, Pool, Tennis by Anna Maria Life Vacation Rentals

2 beds 2 baths
PoolA/CWiFiBalcony
$156/night
View Details → Book on VRBO
Dragonfly Breeze - Private Home w/ Heated Pool, Fee Wifi, Steps to Beach

Dragonfly Breeze - Private Home w/ Heated Pool, Fee Wifi, Steps to Beach

3 beds 2 baths
PoolA/CWiFiBalcony
$251/night
View Details → Book on VRBO
Oceanfront Waterfront Property Sleeps 6! Golf Cart Option Included!

Oceanfront Waterfront Property Sleeps 6! Golf Cart Option Included!

2 beds 1 bath
PoolA/CWiFiBalcony
$330/night
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Gulf Front 1 Bedroom Condo - Amazing Views

Gulf Front 1 Bedroom Condo - Amazing Views

1 bed 1 bath
PoolA/CWiFiBalcony
$372/night
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Quaint beachfront duplex in ideal location with screened lanai & free trolley

Quaint beachfront duplex in ideal location with screened lanai & free trolley

2 beds 1 bath
PoolA/CWiFiBalcony
$271/night
View Details → Book on VRBO
Coastal home with pool and tropical landscaping!

Coastal home with pool and tropical landscaping!

2 beds 2 baths
PoolA/CWiFiBalcony
$170/night
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Salty Harbor AMI pool retreat near the Beach

Salty Harbor AMI pool retreat near the Beach

2 beds 1 bath
PoolA/CWiFiBalcony
$310/night
View Details → Book on VRBO
Villa near shopping, dining, and the beach! - Butterfly Beach Villas Unit B

Villa near shopping, dining, and the beach! - Butterfly Beach Villas Unit B

2 beds 1 bath
PoolA/CWiFiBalcony
$116/night
View Details → Book on VRBO
Island Walk, Cove 207 Overlooking Natural Preserve With A Pool

Island Walk, Cove 207 Overlooking Natural Preserve With A Pool

2 beds 2 baths
PoolA/CWiFiBalcony
$137/night
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Cool Breeze by Beach Boutique Rentals

Cool Breeze by Beach Boutique Rentals

2 beds 2 baths
PoolA/CWiFiBalcony
$323/night
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Shell Game | 2 Bed, 2 Bath

Shell Game | 2 Bed, 2 Bath

2 beds 2 baths
PoolA/CWiFiBalcony
$231/night
View Details → Book on VRBO
Incredible pool home near the beach - Take Me Away

Incredible pool home near the beach - Take Me Away

4 beds 4 baths
PoolA/CWiFiBalcony
$502/night
View Details → Book on VRBO
TIKI AMAZING BEACH FRONT VIEWS- Just Renovated December 2021

TIKI AMAZING BEACH FRONT VIEWS- Just Renovated December 2021

3 beds 2 baths
PoolA/CWiFiBalcony
$671/night
View Details → Book on VRBO
Villa-style condo with pool and beach access - Condo 8

Villa-style condo with pool and beach access - Condo 8

1 bed 1 bath
PoolA/CWiFiBalcony
$215/night
View Details → Book on VRBO
Martinique 505 South

Martinique 505 South

2 beds 2 baths
PoolA/CWiFiBalcony
$277/night
View Details → Book on VRBO
Perfect 1-bedroom Beachfront Getaway!! See the sunsets and feel the breeze!

Perfect 1-bedroom Beachfront Getaway!! See the sunsets and feel the breeze!

1 bed 1 bath
PoolA/CWiFiBalcony
$411/night
View Details → Book on VRBO
Poolside unit at The Coconuts beachside complex

Poolside unit at The Coconuts beachside complex

1 bed 1 bath
PoolA/CWiFiBalcony
$290/night
View Details → Book on VRBO
Sandy Feet: 1 Block to Beach by Anna Maria Life Vacation Rentals

Sandy Feet: 1 Block to Beach by Anna Maria Life Vacation Rentals

2 beds 1 bath
PoolA/CWiFiBalcony
$144/night
View Details → Book on VRBO

Showing 48 of 770 properties

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