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From $1529 per night (USD)
VRBO
The Flower Power House - Boho Beautiful
Bedrooms:
4
Bathrooms:
6
Sleeps:
13
Boho beautiful, the free-spirited presence of the Key West Flower Power House vacation rental, has much more in common w ...
From $1529 per night (USD)
VRBO
$VIRGINIA VISTA - Steps from Duval, 2B\/R, 2 Bath Retreat with Pool & Large Porch$
From $282 per night (USD)
Expedia
VIRGINIA VISTA - Steps from Duval, 2B\/R, 2 Bath Retreat with Pool & Large Porch
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Just a few houses off Duval on Virginia Street, VIRGINIA VISTA occupies the upper level of an almost 100-year-old home i ...
From $282 per night (USD)
Expedia
$VIRGINIA VERANDA, Stylish Old Town 2 B\/R, 2Bath, with Pool, Steps from Duval$
From $286 per night (USD)
VRBO
VIRGINIA VERANDA, Stylish Old Town 2 B\/R, 2Bath, with Pool, Steps from Duval
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Just a few houses off Duval, this wonderful 2 Bedroom, 2 Bath retreat occupies the ground level of an almost 100-year-ol ...
From $286 per night (USD)
VRBO
From $366 per night (USD)
Expedia
**A BEACHY VIEW @ THE TRUMAN ANNEX IN KEY WEST**
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Come and relax in this 2-bedroom 1 bath, first floor with 3 flat screen TV's, custom kitchen, backyard tropical paradise ...
From $366 per night (USD)
Expedia
From $333 per night (USD)
VRBO
Palm Isle: Tropical 2nd-Floor Unit, Shared Heated Pool, Near Duval St, Historic Seaport & Beaches
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to Palm Isle! A tropical 2nd-floor condo in the charming Meadows area of Key West. Relax on your private front ...
From $333 per night (USD)
VRBO
From $278 per night (USD)
Expedia
Garden of Roses | Private Hot Tub, Prime Key West Location! - Monthly Rental
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Garden of Roses | Private Hot Tub, Prime Key West Location! Experience the essence of Key West living at Garden of Rose ...
From $278 per night (USD)
Expedia
From $198 per night (USD)
VRBO
Cabana at the Golf Club-Monthly Rental Charming 2-Bedroom Golf Course Retreat
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Charming 2-Bedroom Retreat with Golf Course Views | Key West Golf Club Community Nestled in the picturesque Key West Go ...
From $198 per night (USD)
VRBO
From $263 per night (USD)
Expedia
Key West vibes, 2-bedroom townhome with AC, WiFi in marvelous Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Nestled in Key West, this delightful townhome boasts 2 bedrooms with a king bed and a full bed, perfect for a small grou ...
From $263 per night (USD)
Expedia
From $242 per night (USD)
VRBO
Gypsyginny's Hideaway in downtown Key West
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Set in the heart of Key West's vibrant Meadows district, this delightful 3-bedroom vacation rental on iconic White Stree ...
From $242 per night (USD)
VRBO
$Duval Hideaway | Dog-Friendly Home w\/ Shared Hot Tub, Patio & Prime Location$
From $536 per night (USD)
Expedia
Duval Hideaway | Dog-Friendly Home w\/ Shared Hot Tub, Patio & Prime Location
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Duval Hideaway | Dog-Friendly Home with Shared Hot Tub, Patio & Prime Location Duval Hideaway is the perfect home base ...
From $536 per night (USD)
Expedia
$Duval Street Retreat | Dog-Friendly Home w\/ Hot Tub, Patio, & Parking$
From $536 per night (USD)
VRBO
Duval Street Retreat | Dog-Friendly Home w\/ Hot Tub, Patio, & Parking
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Duval Street Retreat | Dog-Friendly Home with Hot Tub, WiFi, & Private Parking Duval Street Retreat is your ideal Key W ...
From $536 per night (USD)
VRBO
From $2322 per night (USD)
Expedia
Meadows Manor | Elegant Oasis with Private Pool & Parking! Weekly Rental
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Meadows Manor | Elegant Oasis with Private Pool & Parking Discover the perfect blend of luxury and tranquility at the M ...
From $2322 per night (USD)
Expedia
From $187 per night (USD)
VRBO
Salt Pond Hideaway | Comfortable Condo with Pool, Hot Tub, Close to Beach!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Salt Pond Hideaway | Comfortable Condo with Pool, Hot Tub, and Close to Beach! Salt Pond Hideaway is your ideal retreat ...
From $187 per night (USD)
VRBO
From $1062 per night (USD)
Expedia
Southernmost Retreat | On Duval! With Hot Tub, Patio, & Private Parking
Bedrooms:
2
Bathrooms:
6
Sleeps:
12
Southernmost Retreat | Two Dog-Friendly Homes with Hot Tubs, WiFi, & Private Parking Southernmost Retreat is the perfec ...
From $1062 per night (USD)
Expedia
From $318 per night (USD)
VRBO
Kingfish Keep | Lively Escape on Duval! Balcony!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Kingfish Keep | Lively Escape on Duval! Balcony! Kingfish Keep is the perfect escape in the heart of the historic distr ...
From $318 per night (USD)
VRBO
From $325 per night (USD)
Expedia
Yellowfin Ledge | Inviting Getaway On Duval! Balcony!
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
Yellowfin Ledge | Inviting Getaway On Duval! Balcony! Yellowfin Ledge is the ideal choice for your Key West adventure! ...
From $325 per night (USD)
Expedia
From $325 per night (USD)
VRBO
Wahoo Way | Charming Hideaway On Duval Street!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Wahoo Way | Charming Hideaway On Duval Street! Escape to Wahoo Way for an unforgettable couple’s retreat in Key West! T ...
From $325 per night (USD)
VRBO
From $937 per night (USD)
Expedia
Pescado Penthouse | Vibrant Retreat Overlooking Duval Street!
Bedrooms:
3
Bathrooms:
5
Sleeps:
9
Pescado Penthouse | Vibrant Retreat Overlooking Duval Street! Pescado Penthouse is the ultimate getaway for families or ...
From $937 per night (USD)
Expedia
From $250 per night (USD)
VRBO
Key West Retreat! 3-bedroom house in fabulous Key West with AC, WiFi.
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Located in Key West, this gorgeous house boasts 3 bedrooms - one with a king bed, one with a queen bed, and one with a t ...
From $250 per night (USD)
VRBO
From $423 per night (USD)
Expedia
Poolside Hide-Away @ Palm Gardens offered by Rent Key West Vacations
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Poolside Hide-Away is a first floor one bedroom, one bath historic condo, that can accommodate up to 4 people, with wrap ...
From $423 per night (USD)
Expedia
$WASTIN' A WAYLAND ~ Renovated 2 BR\/2 Ba Home in Old Town!$
From $251 per night (USD)
VRBO
WASTIN' A WAYLAND ~ Renovated 2 BR\/2 Ba Home in Old Town!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
OLD TOWN GEM... This 2 bedroom, 2 bathroom cutie resides down a charming lane surrounded by historic residences and is a ...
From $251 per night (USD)
VRBO
From $1246 per night (USD)
Expedia
**HOUSE OF THE ROYAL PALMS @ OLD TOWN** Estate & Pool Near Duval + LAST KEY SERV
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Key West is k ...
From $1246 per night (USD)
Expedia
From $1337 per night (USD)
VRBO
**The Three Mermaids @ Solaris Hill** New Construction Compound + Last Key Servi
Bedrooms:
5
Bathrooms:
5
Sleeps:
12
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Finding a com ...
From $1337 per night (USD)
VRBO
$INTO THE BLUE ~ Pristine 4 BR\/3.5 Bath Home w\/ Private Pool!$
From $448 per night (USD)
Expedia
INTO THE BLUE ~ Pristine 4 BR\/3.5 Bath Home w\/ Private Pool!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
TOP NOTCH LIVING… Nestled in the exclusive Casa Marina district, this newly constructed sanctuary sits only a few blocks ...
From $448 per night (USD)
Expedia
From $269 per night (USD)
VRBO
Cozy on Caroline - Key West Seaport
Bedrooms:
2
Bathrooms:
1
Sleeps:
4
Experience the quintessential Key West lifestyle in this charming one-bedroom, two-bathroom apartment that perfectly bal ...
From $269 per night (USD)
VRBO
From $659 per night (USD)
Expedia
~Hibiscus Cottage~ Adults Only cottage near Duval with shared pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
THE PROPERTY: Welcome to your private rocking chair front porch and tropical, Adult Only setting! As you enter your quai ...
From $659 per night (USD)
Expedia
From $353 per night (USD)
VRBO
On the Bright Side of the Key West Golf Club
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Welcome to your serene retreat at The Key West Golf Club! This meticulously cared-for 3-bedroom, 3-bathroom townhome rad ...
From $353 per night (USD)
VRBO
From $530 per night (USD)
Expedia
Royal Palm of Casa Marina
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
EXQUISIT NEW CONSTRUCTION HOME!!!! Discover the epitome of modern luxury and comfort at this brand-new exquisite 4-bedr ...
From $530 per night (USD)
Expedia
From $404 per night (USD)
VRBO
Southern Skies, Stylish Home in Old Town Key West
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Experience the paradise of Southern Skies, an elegant 3 bedroom and 2.5 bath home nestled in the heart of Key West's His ...
From $404 per night (USD)
VRBO
From $282 per night (USD)
Expedia
Seaport Serenity Cottage - Quiet and Quaint
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This charming 2BR/2BA rental is located in the Historic Seaport District offering off-street parking and a prime locatio ...
From $282 per night (USD)
Expedia
From $406 per night (USD)
VRBO
Rooster Doodle Do - Midtown Family Retreat
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Your perfect tropical getaway! This stunning 3-bedroom, 3-bathroom home with an additional guest cottage is designed for ...
From $406 per night (USD)
VRBO
From $256 per night (USD)
Expedia
Charming 1923 2 Bedroom, 1 Bath home with bonus loft.
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
Welcome to The Emma House! A delightful 1923 Key West retreat located in the heart of historic and vibrant Bahama Villa ...
From $256 per night (USD)
Expedia
From $193 per night (USD)
VRBO
Beachfront Condo in heart of Key West, minutes to downtown 1BR-1BA 2 lg pools 🚲
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Key West-Resort style living! Spacious 1 bed/ 1 bath, large living space full-kitchen condo in gated community. Beachf ...
From $193 per night (USD)
VRBO
From $499 per night (USD)
Expedia
Zen Villa - A Luxurious 3-bedroom Sanctuary with WiFi & a Pool in Old Key West
Bedrooms:
4
Bathrooms:
3
Sleeps:
7
Zen Villa - A Luxe Retreat in the Heart of Old Key West! Tucked away on a quiet lane just steps from the vibrant heartbe ...
From $499 per night (USD)
Expedia
From $324 per night (USD)
VRBO
Jerry's Escape - Truman @ Duval | Cozy Studio Perfect for Couples
Bedrooms:
1
Bathrooms:
2
Sleeps:
2
Truman @ Duval - Unit C | Cozy Studio Perfect for Couples Experience your perfect romantic retreat, offering a charming ...
From $324 per night (USD)
VRBO
From $418 per night (USD)
Expedia
Holly's Hideaway - Truman @ Duval | Two-Bedroom Prime Location!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Truman @ Duval - Unit D | Two-Bedroom with Full Kitchen & Prime Location Welcome to your perfect family getaway in the ...
From $418 per night (USD)
Expedia
From $276 per night (USD)
VRBO
Slice of Paradise | 3 bedroom, 2 bathroom pool home in Key West
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Discover your island oasis in this beautifully updated one-story home, where tropical breezes meet modern comfort. Nestl ...
From $276 per night (USD)
VRBO
From $450 per night (USD)
Expedia
Key West 2 BR Villa with full kitchen, ocean view with Infinity pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Located in Key West just minutes from beautiful sunsets at Mallory Square or renowned dining and nightlife of Duval Stre ...
From $450 per night (USD)
Expedia
From $415 per night (USD)
VRBO
Tropical Island Retreat Near Florida Beaches with Pool & Views
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Stylish, pet-friendly, and amazing decor is what awaits you. This boutique hotel offers you a great stay in the heart of ...
From $415 per night (USD)
VRBO
From $404 per night (USD)
Expedia
Tropical Island Retreat Near Florida Beaches with Pool & Views
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Discover Old Town charm, plunge into vibrant Duval Street life, and dive deep into Key West's treasures. We're footsteps ...
From $404 per night (USD)
Expedia
From $513 per night (USD)
VRBO
Charming Hideaway with Pool – Walk to Duval St & Local Attractions
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Enjoy vibrant Key West: steps to Duval Street's nightlife, historic sites, and serene beaches. Perfect for culture and s ...
From $513 per night (USD)
VRBO
From $464 per night (USD)
Expedia
Sunny Florida Escape with Pool, Beach Access & Stunning Views
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Explore, dine, and relax in downtown Key West! We're steps from the Hemingway Home, Duval Street nightlife, and Southern ...
From $464 per night (USD)
Expedia
From $392 per night (USD)
VRBO
Cozy Key West Escape – Near Shops, Bars & Famous Duval Street
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $392 per night (USD)
VRBO
$CASA DEL SUR ~ Renovated 2 BR\/2Ba Home with Dip Pool & Outdoor Spa!$
From $608 per night (USD)
Expedia
CASA DEL SUR ~ Renovated 2 BR\/2Ba Home with Dip Pool & Outdoor Spa!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
QUAINT AND PRIVATE HIDEAWAY... This Key West classic checks all the boxes for your blissful getaway to our tiny island p ...
From $608 per night (USD)
Expedia
From $318 per night (USD)
VRBO
Ricky's Retreat - Truman @ Duval | Perfect for a Getaway in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Truman @ Duval Unit A | Perfect for a Getaway in Key West Escape to this cozy, vibrant cottage in the heart of downtown ...
From $318 per night (USD)
VRBO
From $325 per night (USD)
Expedia
Scott's Cottage - Truman @ Duval | Perfect Location! Ideal for Solos &Couples
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Scott's Cottage - Truman @ Duval F | Perfect Location! Ideal for Solos & Couples Looking for a relaxing retreat in the ...
From $325 per night (USD)
Expedia
From $318 per night (USD)
VRBO
Abbey's Attic - Truman @ Duval | Cozy Getaway in the Heart of Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Truman @ Duval - Unit E | Cozy Getaway in the Heart of Key West Duval Studio is your perfect launchpad for an unforgett ...
From $318 per night (USD)
VRBO
From $646 per night (USD)
Expedia
Amazing Key West location 3 bed 3 bath home, with HEATED PRIVATE POOL, WIFI
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local ...
From $646 per night (USD)
Expedia
From $193 per night (USD)
VRBO
Cozy & modern guest house in Key West with AC, WiFi
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Your cozy getaway awaits in Key West at this marvelous apartment. With a bedroom, washing & drying machine, AC, and WiFi ...
From $193 per night (USD)
VRBO
From $935 per night (USD)
VRBO
Ocean Front Balcony King at Southernmost Beach Resort!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Experience the best of Key West, where modern design meets a romantic, tropical setting. Nestled just steps away from le ...
From $935 per night (USD)
VRBO
From $435 per night (USD)
VRBO
Key West Comfort | Bungalow with Patio, 3 Pools & Steps to Duval Street
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $435 per night (USD)
VRBO
From $644 per night (USD)
Expedia
Central Key West Stay | 3 Pools, Free Daily Breakfast, Pet-Friendly
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $644 per night (USD)
Expedia
From $436 per night (USD)
VRBO
Tropical Bungalow, 3 Pools, Breakfast Included, Pets Allowed, Near Shops & Bars
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $436 per night (USD)
VRBO
From $413 per night (USD)
Expedia
Pet-Friendly & Cozy Bungalow, Daily Breakfast & Poolside Lounging!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $413 per night (USD)
Expedia
From $436 per night (USD)
VRBO
Bungalow in Heart of Key West | 3 Pool, Free Breakfast, Shops & Bars Nearby
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $436 per night (USD)
VRBO
From $413 per night (USD)
Expedia
Key West Charm | 3 Pools, Complimentary Breakfast, Near Duval Street!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $413 per night (USD)
Expedia
From $586 per night (USD)
VRBO
Key West Getaway | Romantic Bungalow, Pools, Breakfast & Pets Allowed
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $586 per night (USD)
VRBO
From $603 per night (USD)
Expedia
Cozy Home in Paradise
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to your home away from home in beautiful Key West! This cozy and comfortable 3-bedroom retreat is nestled on a d ...
From $603 per night (USD)
Expedia
From $1263 per night (USD)
VRBO
The Penthouse at Custom House Inn | New! Coastal Escape on Duval Street!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
The Penthouse at Custom House Inn | Serene Coastal Escape on Duval Street! Immerse yourself in the calm and comfort of ...
From $1263 per night (USD)
VRBO
From $636 per night (USD)
Expedia
Most Beautiful View on Key West?
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Make yourself at home in this 2-bedroom Key West retreat. This cool condo features a beautiful view from every room. Spa ...
From $636 per night (USD)
Expedia
From $1492 per night (USD)
VRBO
Charmayne’s Cottages | Your Private Group Oasis in the Heart of Key West
Bedrooms:
6
Bathrooms:
7
Sleeps:
14
Charmayne’s Cottages | Your Private Group Oasis in the Heart of Key West Experience the ultimate Key West getaway at Ch ...
From $1492 per night (USD)
VRBO
From $153 per night (USD)
Expedia
Charming island retreat with balcony, king bed, desk space & dog-friendly vibe
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Periwinkle Place Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $153 per night (USD)
Expedia
From $231 per night (USD)
VRBO
Quiet 2-bedroom plus office townhome on the Key West golf course!
Bedrooms:
3
Bathrooms:
2
Sleeps:
5
Just a short walk from the Resort style pool and fitness center, our townhome, situated on the 1st fairway of the Key We ...
From $231 per night (USD)
VRBO
From $657 per night (USD)
Expedia
Upscale 2-bedroom villa in the heart of Old Town. Minutes to Duval & Mallory Sq
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to this upscale condo in Key West. This terrific property features 2 bedrooms with 1 king bed and 1 queen bed, a ...
From $657 per night (USD)
Expedia
From $171 per night (USD)
VRBO
Charming island cottage with sunny patio, modern kitchen, AC & dog friendly yard
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Casa Sirena Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $171 per night (USD)
VRBO
$Serenity by the Sea, 2BR\/2BA Condo w\/Pool at La Brisa across from Smathers Beach$
From $509 per night (USD)
Expedia
Serenity by the Sea, 2BR\/2BA Condo w\/Pool at La Brisa across from Smathers Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Serenity by the Sea | 2BR/2BA Key West Condo at La Brisa Welcome to your tropical retreat in paradise! This beautifully ...
From $509 per night (USD)
Expedia
From $169 per night (USD)
VRBO
Charming Cottage in Old Town
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Your Key West adventure begins at this charming 1-bedroom cottage. The lovely bedroom features a comfortable queen bed, ...
From $169 per night (USD)
VRBO
From $155 per night (USD)
Expedia
Charming 1-bedroom apartment in Key West with AC, WiFi. Enjoy
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Your cozy getaway awaits in Key West at this brilliant apartment. This marvelous space features 1 bedroom with a queen b ...
From $155 per night (USD)
Expedia
From $1826 per night (USD)
VRBO
Coconut Beach | Hot Tub | Lux Resort | Pool | Concierge
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Coconut Beach Resort transports you to your very own private oasis, where the charm of old island architecture meets lus ...
From $1826 per night (USD)
VRBO
From $1824 per night (USD)
VRBO
3| Galleon | Marina | Spa | Hot Tub | Pool
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
The Galleon Resort is a premier destination in Key West, Florida, offering an unbeatable combination of luxury, comfort, ...
From $1824 per night (USD)
VRBO
From $183 per night (USD)
VRBO
Island Oasis-2 Bedroom Townhouse in the Gated Community of the Key West Golf Club
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Step into our Island Oasis! A very spacious 2-bedroom, 1 1/2 -bathroom home, perfect for your island getaway, in the cov ...
From $183 per night (USD)
VRBO
From $253 per night (USD)
Expedia
2 Bedroom Townhome in the Key West Golf Club
Bedrooms:
3
Bathrooms:
2
Sleeps:
5
**Beautiful 2-Bedroom Townhome in Key West Golf Club** Welcome to this charming 2-bedroom, 2.5-bathroom townhome locate ...
From $253 per night (USD)
Expedia
From $1771 per night (USD)
VRBO
Sleeps 6 | Lux Resort | Hot Tub | Pool | Concierge
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to your private sanctuary at Hyatt Beach House Resort, where the lush landscapes of Key West meet unparalleled l ...
From $1771 per night (USD)
VRBO
From $11524 per night (USD)
VRBO
Galleon | Hot Tub | Marina | Lux Resort | Concierge
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The Galleon Resort is a premier destination in Key West, Florida, offering an unbeatable combination of luxury, comfort, ...
From $11524 per night (USD)
VRBO
From $2236 per night (USD)
VRBO
Sunset Harbor | Hyatt | Hot Tub | Pool | Marina | Lux Resort
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Welcome to your serene oasis in the heart of Key West’s iconic Old Town, where lush greenery and contemporary design cre ...
From $2236 per night (USD)
VRBO
From $1733 per night (USD)
VRBO
Sleeps 6 | Hyatt | Lux Resort | Concierge | Pool | Spa
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Set along the stunning Atlantic Ocean, Hyatt Windward Pointe Resort seamlessly blends Key West’s laid-back vibe with mod ...
From $1733 per night (USD)
VRBO
From $2236 per night (USD)
VRBO
Sunset Harbor | Marina | Hot Tub | Pool | Concierge
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to your serene oasis in the heart of Key West’s iconic Old Town, where lush greenery and contemporary design cre ...
From $2236 per night (USD)
VRBO
From $1759 per night (USD)
VRBO
Parrot Key | Beachfront | Kitchen | Hot Tub | Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Step into a paradise of white sands and glimmering pools, where boat drinks and watersports are just steps away at Parro ...
From $1759 per night (USD)
VRBO
From $1941 per night (USD)
VRBO
The Banyan | Concierge | Beach Access | Pool
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Located in the heart of historic Old Town Key West, The Banyan Resort is a charming escape set on a mid-1800s estate ste ...
From $1941 per night (USD)
VRBO
From $1759 per night (USD)
VRBO
Coconut Beach | Hot Tub | Lux Resort | Pool | Concierge
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Coconut Beach Resort transports you to your very own private oasis, where the charm of old island architecture meets lus ...
From $1759 per night (USD)
VRBO
From $1759 per night (USD)
VRBO
Coconut Beach | Beach | Concierge | Pool | Gym
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Coconut Beach Resort transports you to your very own private oasis, where the charm of old island architecture meets lus ...
From $1759 per night (USD)
VRBO
From $2148 per night (USD)
VRBO
Hyatt Beach | Concierge | Spa | Pool | Hot Tub
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to your private sanctuary at Hyatt Beach House Resort, where the lush landscapes of Key West meet unparalleled l ...
From $2148 per night (USD)
VRBO
From $1839 per night (USD)
VRBO
Galleon | Marina | Concierge | Hot Tub | Spa
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Nestled along the sparkling Gulf of Mexico in historic Old Town, The Galleon Resort places you in the heart of Key West’ ...
From $1839 per night (USD)
VRBO
From $900 per night (USD)
Expedia
𝐅𝐢𝐧𝐝𝐢𝐧𝐠𝐌𝐞𝐢𝐥𝐢 Near Duval Street, Waterfront Sunset Harbor Resort. 2BR
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to 𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢🌴 Experience Paradise at Hyatt Vacation Club at Sunset Harbor! 🌅 Nestled in the he ...
From $900 per night (USD)
Expedia
From $863 per night (USD)
VRBO
𝐅𝐢𝐧𝐝𝐢𝐧𝐠𝐌𝐞𝐢𝐥𝐢 Near Duval Street, Waterfront Sunset Harbor Resort. 2BR
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to 𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢🌴 Experience Paradise at Hyatt Vacation Club at Sunset Harbor! 🌅 Nestled in the he ...
From $863 per night (USD)
VRBO
From $809 per night (USD)
VRBO
𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢 Dream Getaway at the Beach House Resort+Amenities. 2BR
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to 𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢🌴 Experience Key West Paradise at the Beach House Resort Retreat! 🏖️ Additional $ ...
From $809 per night (USD)
VRBO
From $5625 per night (USD)
VRBO
Key West Florida Charming 1-bedroom resort with WiFi, AC
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Experience a serene oasis nestled in the heart of Key West’s historic Old Town. Surrounded by lush greenery, this retrea ...
From $5625 per night (USD)
VRBO
From $5625 per night (USD)
Expedia
Key West Studio Charming resort with WiFi, AC, fitness room
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Experience a serene oasis nestled in the heart of Key West’s historic Old Town. Surrounded by lush greenery, this retrea ...
From $5625 per night (USD)
Expedia
From $5625 per night (USD)
VRBO
Hyatt Beach House Resort Key West 2-bedroom with WiFi, AC
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to your private sanctuary in the lush landscape of Key West. Imagine old-fashioned screen-enclosed porches, gard ...
From $5625 per night (USD)
VRBO
From $5625 per night (USD)
Expedia
Key West Hyatt Charming 2-bedroom resort with WiFi, AC
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Experience a serene oasis nestled in the heart of Key West’s historic Old Town. Surrounded by lush greenery, this retrea ...
From $5625 per night (USD)
Expedia
$Helluva Happy Place | Escape to Old Town Key West - 3 bed\/2.5 bath townhome with private pool$
From $305 per night (USD)
VRBO
Helluva Happy Place | Escape to Old Town Key West - 3 bed\/2.5 bath townhome with private pool
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Escape to Old Town Key West and indulge in a monthly retreat at our charming 3-bedroom, 2.5-bathroom townhome. Nestled i ...
From $305 per night (USD)
VRBO
Click For Pricing
Expedia
ROYAL POINCIANA COTTAGE - Quaint Old Town location
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Royal Poinciana is a studio cottage with a queen bed, kitchen ,and private bath. The queen bed sleeps 2 people and the k ...
Click For Pricing
Expedia
From $400 per night (USD)
VRBO
Oceanfront Splendor @ the Key West Beach Club
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
29 NIGHT MINIMUM RENTAL ... This property is not allowed to accept pets. Enjoy endless views of the tranquil waters of ...
From $400 per night (USD)
VRBO
$Life is a Breeze at Windward Breeze by RENT KEY WEST VACATIONS - 2\/2 townhome -$
From $535 per night (USD)
Expedia
Life is a Breeze at Windward Breeze by RENT KEY WEST VACATIONS - 2\/2 townhome -
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Windward Breeze is part of the Windward Park gated community just off Simonton Street, one block from Duval Street. Ther ...
From $535 per night (USD)
Expedia
From $1073 per night (USD)
VRBO
Relax in Style at Windsor Townhomes #4
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Elegance and modern sophistication are apparent as you enter any one of these six conveniently located townhomes in a q ...
From $1073 per night (USD)
VRBO
From $316 per night (USD)
Expedia
Rent at PORCHSIDE PARADISE - Steps to Duval
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Porchside Paradise is located in the front section of the Conch Republic Cottages. This beautiful home-away-from-home fe ...
From $316 per night (USD)
Expedia
From $258 per night (USD)
VRBO
In the heart of Old Town lies the HAVEN HOUSE
Bedrooms:
2
Bathrooms:
1
Sleeps:
2
Haven House provides the perfect home base to be near the center of everything but be able to retreat to home and watch ...
From $258 per night (USD)
VRBO
From $390 per night (USD)
Expedia
Half block to Duval @ Mango Hideaway -studio apt
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
The Mango Hideaway is comfortable junior suite, with sofa sitting area with adjoining king bedroom. The suite features ...
From $390 per night (USD)
Expedia
$ALOHA - Large 1 level 4bd\/4ba Monthly Rental$
From $439 per night (USD)
VRBO
ALOHA - Large 1 level 4bd\/4ba Monthly Rental
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Aloha is a stunning private residence on corner lot in the Casa Marina District. Updated 2 years ago, this beautiful hom ...
From $439 per night (USD)
VRBO
$Eyebrow Suite - 2bd\/1.5ba Suite off Duval$
From $524 per night (USD)
Expedia
Eyebrow Suite - 2bd\/1.5ba Suite off Duval
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Eyebrow Suite is a spacious two-bedroom suite with one of the best locations on the island. Its large front porch and pa ...
From $524 per night (USD)
Expedia

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