Key West, Florida

Vacation Rentals in Key West, Florida

Discover 1,835 vacation rental properties in Key West. From 1 to 13 bedrooms. Average $560/night. 100% have pools.

1,835 verified listings Book securely on VRBO Prices updated March 2026

1,835 properties available

KATE'S KRAWL OFF DUVAL ~ 1 BR, 1 Ba Home w/ Outdoor Area Steps to Duval!

KATE'S KRAWL OFF DUVAL ~ 1 BR, 1 Ba Home w/ Outdoor Area Steps to Duval!

1 bed 1 bath
PoolA/CWiFiBalcony
$337/night
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The Caroline #2 | 2 Bed, 1 Bath

The Caroline #2 | 2 Bed, 1 Bath

2 beds 1 bath
PoolA/CWiFiBalcony
$217/night
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JUST OFF DUVAL~ 2nd Floor Condo in Center of Duval St. with Parking Space!

JUST OFF DUVAL~ 2nd Floor Condo in Center of Duval St. with Parking Space!

2 beds 1 bath
PoolA/CWiFiBalcony
$367/night
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Latitude Adjustment @ Truman Annex Shipyard

Latitude Adjustment @ Truman Annex Shipyard

2 beds 1 bath
PoolA/CWiFiBalcony
$321/night
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Spacious, waterfront condo w/ a full kitchen, shared pool, & furnished balcony

Spacious, waterfront condo w/ a full kitchen, shared pool, & furnished balcony

2 beds 2 baths
PoolA/CWiFiBalcony
$538/night
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Updated Studio with Heated Pool | Carey's Corner

Updated Studio with Heated Pool | Carey's Corner

1 bath
PoolA/CWiFiBalcony
$199/night
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Unique Home with loft @ Truman Annex

Unique Home with loft @ Truman Annex

1 bed 1 bath
PoolA/CWiFiBalcony
$217/night
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Little Casita: Key West Monthly rental Close to Duval - RealKeyWest

Little Casita: Key West Monthly rental Close to Duval - RealKeyWest

1 bed 1 bath
PoolA/CWiFiBalcony
$91/night
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Steps from Duval, Pool & Bikes $129-$299 Night!

Steps from Duval, Pool & Bikes $129-$299 Night!

1 bath
PoolA/CWiFiBalcony
$220/night
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Charming, updated home near Duval St. with enclosed patio & walkable location

Charming, updated home near Duval St. with enclosed patio & walkable location

1 bed 1 bath
PoolA/CWiFiBalcony
$217/night
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Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym

Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym

1 bed 1 bath
PoolA/CWiFiBalcony
$352/night
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~ SOLARIS COTTAGE ~ Live like a local in this bright and cozy retreat.

~ SOLARIS COTTAGE ~ Live like a local in this bright and cozy retreat.

1 bed 1 bath
PoolA/CWiFiBalcony
$189/night
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Direct Ocean View from Your Condo-No Contact Check-In

Direct Ocean View from Your Condo-No Contact Check-In

2 beds 2 baths
PoolA/CWiFiBalcony
$221/night
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Ultimate Beach Adventure! Pool, Restaurant, Bar, Bike Rental, Gym,

Ultimate Beach Adventure! Pool, Restaurant, Bar, Bike Rental, Gym,

1 bed 1 bath
PoolA/CWiFiBalcony
$159/night
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CONCH COTTAGE: Old Town - Hot Tub - 1 Block from Duval - 1BD/1BA RealKeyWest

CONCH COTTAGE: Old Town - Hot Tub - 1 Block from Duval - 1BD/1BA RealKeyWest

1 bed 1 bath
PoolA/CWiFiBalcony
$300/night
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THE SWEET LIFE ~ Charming 2 BR/1 Ba Condo w/ Community Pool!

THE SWEET LIFE ~ Charming 2 BR/1 Ba Condo w/ Community Pool!

2 beds 1 bath
PoolA/CWiFiBalcony
$245/night
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Superb Location, Affordably Priced

Superb Location, Affordably Priced

1 bed 1 bath
PoolA/CWiFiBalcony
$221/night
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Simonton Studio, an Old Town get-away for 2

Simonton Studio, an Old Town get-away for 2

1 bath
PoolA/CWiFiBalcony
$220/night
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J Ferrara #9: Charming Studio Oasis, Steps from Duval Street, Southernmost Point & Shared Pool!

J Ferrara #9: Charming Studio Oasis, Steps from Duval Street, Southernmost Point & Shared Pool!

1 bath
PoolA/CWiFiBalcony
$169/night
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ELIZABETH'S SECRET: 3/2 In Old Town Key West, with a Private pool and Parking

ELIZABETH'S SECRET: 3/2 In Old Town Key West, with a Private pool and Parking

3 beds 2 baths
PoolA/CWiFiBalcony
$585/night
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Pilar's Cottage by Brightwild | Studio w/Pool!

Pilar's Cottage by Brightwild | Studio w/Pool!

1 bed 1 bath
PoolA/CWiFiBalcony
$372/night
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Steps To The Beach And The Sunrise-No Contact Check-In

Steps To The Beach And The Sunrise-No Contact Check-In

2 beds 2 baths
PoolA/CWiFiBalcony
$251/night
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SMOOTH SAILING ~ 2 Bedroom, 1 Bath Renovated Condo w/ Community Pool!

SMOOTH SAILING ~ 2 Bedroom, 1 Bath Renovated Condo w/ Community Pool!

2 beds 1 bath
PoolA/CWiFiBalcony
$292/night
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COCONUT PALM SUITE ~ Adult Only, 1 BR, 1 Ba w/ Kitchen & Shared Pool!

COCONUT PALM SUITE ~ Adult Only, 1 BR, 1 Ba w/ Kitchen & Shared Pool!

1 bed 1 bath
PoolA/CWiFiBalcony
$286/night
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THE HIDDEN GEM ~ Charming Renovated Studio with Large Community Pool!

THE HIDDEN GEM ~ Charming Renovated Studio with Large Community Pool!

1 bath
PoolA/CWiFiBalcony
$110/night
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ShangriLa Suite / Queen Studio / Sleeps 2

ShangriLa Suite / Queen Studio / Sleeps 2

1 bed 1 bath
PoolA/CWiFiBalcony
$189/night
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Sugar Pie Suite by Brightwild | Pool & Grill

Sugar Pie Suite by Brightwild | Pool & Grill

1 bed 1 bath
PoolA/CWiFiBalcony
$271/night
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COHIBA ~ Adults Only, Poolview 1 Bedroom Suite in Historic Azul Mansion!

COHIBA ~ Adults Only, Poolview 1 Bedroom Suite in Historic Azul Mansion!

1 bed 1 bath
PoolA/CWiFiBalcony
$210/night
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Beautiful and Spacious, 4 Bed, 3 Bath home with pool.

Beautiful and Spacious, 4 Bed, 3 Bath home with pool.

4 beds 3 baths
PoolA/CWiFiBalcony
$761/night
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Sky Loft by Brightwild | Penthouse in Prime Spot!

Sky Loft by Brightwild | Penthouse in Prime Spot!

1 bed 1 bath
PoolA/CWiFiBalcony
$408/night
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**JASMINE JEWEL @ THE ANNEX** Lush Private Home & Pool + LAST KEY SERVICES…

**JASMINE JEWEL @ THE ANNEX** Lush Private Home & Pool + LAST KEY SERVICES…

2 beds 2 baths
PoolA/CWiFiBalcony
$732/night
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Poolside Retreat by Brightwild | Cottage w/ Pool

Poolside Retreat by Brightwild | Cottage w/ Pool

1 bed 1 bath
PoolA/CWiFiBalcony
$363/night
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Key West Lighthouse Suite | 1 Bed, 1 Bath

Key West Lighthouse Suite | 1 Bed, 1 Bath

1 bed 1 bath
PoolA/CWiFiBalcony
$352/night
View Details → Book on VRBO
Tom's Spectacular OceanFront 3 Bdrm Endless Atlantic view, Key West Amazing

Tom's Spectacular OceanFront 3 Bdrm Endless Atlantic view, Key West Amazing

3 beds 2 baths
PoolA/CWiFiBalcony
$606/night
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Bahama Palms

Bahama Palms

2 beds 1 bath
PoolA/CWiFiBalcony
$201/night
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Heart of Downtown Key West Cottage With Off-Street Parking

Heart of Downtown Key West Cottage With Off-Street Parking

2 beds 1 bath
PoolA/CWiFiBalcony
$325/night
View Details → Book on VRBO
Old Town Oasis - Sleeps 4, Steps to Duval and Beaches.

Old Town Oasis - Sleeps 4, Steps to Duval and Beaches.

1 bed 1 bath
PoolA/CWiFiBalcony
$251/night
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TIDES ON SIMONTON ~ Perfectly located just off Duval and all the fun!

TIDES ON SIMONTON ~ Perfectly located just off Duval and all the fun!

1 bed 1 bath
PoolA/CWiFiBalcony
$243/night
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Beach House with Ocean View-No Contact Check-In

Beach House with Ocean View-No Contact Check-In

1 bed 1 bath
PoolA/CWiFiBalcony
$226/night
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Hemingway Hideaway in the Truman Annex

Hemingway Hideaway in the Truman Annex

2 beds 2 baths
PoolA/CWiFiBalcony
$377/night
View Details → Book on VRBO
Two Bed One Bath Ground Floor End Unit in the Heart of Old Town

Two Bed One Bath Ground Floor End Unit in the Heart of Old Town

2 beds 1 bath
PoolA/CWiFiBalcony
$290/night
View Details → Book on VRBO
Charming home in Old Town, walk to shops & restaurants - dog-friendly

Charming home in Old Town, walk to shops & restaurants - dog-friendly

1 bed 1 bath
PoolA/CWiFiBalcony
$84/night
View Details → Book on VRBO
Spanish Lime Cottage by AvantStay | Old Town Key West Location | Long Stays Only

Spanish Lime Cottage by AvantStay | Old Town Key West Location | Long Stays Only

1 bed 1 bath
PoolA/CWiFiBalcony
$109/night
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Location, Location, Location!!! Downtown Key West - Truman Annex!!!

Location, Location, Location!!! Downtown Key West - Truman Annex!!!

2 beds 1 bath
PoolA/CWiFiBalcony
$301/night
View Details → Book on VRBO
SUGAR PALM STUDIO ~ Adult Only Studio w/Community Pool & Close to Town!

SUGAR PALM STUDIO ~ Adult Only Studio w/Community Pool & Close to Town!

1 bath
PoolA/CWiFiBalcony
$246/night
View Details → Book on VRBO
The Hollinsed House "Victorian Delights" - Large 1 Bedroom

The Hollinsed House "Victorian Delights" - Large 1 Bedroom

1 bed 1 bath
PoolA/CWiFiBalcony
$218/night
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CORONA ~ Adults Only, Historic Azul Mansion Suite with Community Pool!

CORONA ~ Adults Only, Historic Azul Mansion Suite with Community Pool!

1 bed 1 bath
PoolA/CWiFiBalcony
$224/night
View Details → Book on VRBO
COLONY CALYPSO - A quaint 1 Bedroom Cottage just two blocks to Duval

COLONY CALYPSO - A quaint 1 Bedroom Cottage just two blocks to Duval

1 bed 1 bath
PoolA/CWiFiBalcony
$305/night
View Details → Book on VRBO

Showing 48 of 1,835 properties

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