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Fleming Key Rentals

$Charming 2 room guest house, access to Pool, A\/C, & WiFi, Key West, near Duval$
From $1179 per night (USD)
VRBO
Charming 2 room guest house, access to Pool, A\/C, & WiFi, Key West, near Duval
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Key West is waiting for you at this clean & spacious 2-bedroom guest house. Good for up to 6 people. This cozy retreat o ...
From $1179 per night (USD)
VRBO
From $2443 per night (USD)
VRBO
Spacious 5-bdrm 5 bathroom house in charming Key West with AC, WiFi, Plunge Pool
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Short walk to Duval Street. Central location. Restaurants nearby. Surrounded by charm of Key West. Explore the city the ...
From $2443 per night (USD)
VRBO
$Hyatt resort 2-bdr 2 bath Duvale St in Key West with kitchen washer\/dryer pool$
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VRBO
Hyatt resort 2-bdr 2 bath Duvale St in Key West with kitchen washer\/dryer pool
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Discover the beauty of Key West from this 2-bedroom 2 bath resort. The spacious bedrooms feature a king and queen bed, p ...
Click For Pricing
VRBO
From $153 per night (USD)
Expedia
Contemporary Hideaway in the Heart of Old Town Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Galveston Porches Stylish one bedroom apartment in the heart of Old Town. Totally renovated and beautifully decorated. E ...
From $153 per night (USD)
Expedia
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 $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 $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 $1839 per night (USD)
VRBO
Galleon | Marina | Lux Resort | Pool | Hot Tub
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
The Galleon Resort is a premier destination in Key West, Florida, offering an unbeatable combination of luxury, comfort, ...
From $1839 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 $1145 per night (USD)
VRBO
Charming Bungalow Perfect for Families and Couples': Escape in Old Town
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $1145 per night (USD)
VRBO
From $407 per night (USD)
Expedia
Discover this cozy retreat in the charm of Old Town Key West at Poorhouse Lane!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
This 3-bedroom house is perfect for your escape to Key West. This cozy retreat offers prime location near all the action ...
From $407 per night (USD)
Expedia
From $203 per night (USD)
VRBO
Charming 1-bedroom apartment with WiFi, AC in delightful Key West Old Town
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Your Key West adventure begins at this fabulous 1-bedroom apartment. The cozy bedroom features a queen bed, perfect for ...
From $203 per night (USD)
VRBO
From $462 per night (USD)
Expedia
**SOUTHERN STAR @ THE MEADOWS** Private Home & Pool + LAST KEY SERVICES...
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! SOUTHERN STAR ...
From $462 per night (USD)
Expedia
From $125 per night (USD)
VRBO
Serene Key West Studio with Poolside Peace
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Studio Apartment for Rent in Key West This cozy studio apartment is located in a quiet, gated community on Grinnell Str ...
From $125 per night (USD)
VRBO
From $513 per night (USD)
VRBO
4-bedroom New Construction house with private pool in Key West
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
Experience Island Living In The Treetops… Welcome to your luxurious oasis in Key West, where modern comfort meets tropic ...
From $513 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 $728 per night (USD)
Expedia
Coco's Poolside Retreat
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Coco's Poolside Retreat is a 3-story Key West vacation rental townhouse situated in a one-of-a-kind private tropical poo ...
From $728 per night (USD)
Expedia
From $1558 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 $1558 per night (USD)
VRBO
From $1506 per night (USD)
VRBO
2 Hyatt Sunset Harbor Resort, In Town, Marina
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This stylish place is close to must-see destinations. Discover this relaxing oasis in the heart of Key West's famed Old ...
From $1506 per night (USD)
VRBO
From $628 per night (USD)
VRBO
Cozy home with private pool, BBQ, central AC, enclosed yard
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Key to Paradise Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $628 per night (USD)
VRBO
$Conch Cove - 3br\/3ba with private heated pool and private parking$
From $1622 per night (USD)
Expedia
Conch Cove - 3br\/3ba with private heated pool and private parking
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Conch Cove | Heated Pool & Prime Location! Conch Cove is your private oasis in Old Town Key West! This 3-bedroom, 3-bat ...
From $1622 per night (USD)
Expedia
$Charming 1-bedroom\/1-bath apartment in historical home with pool in Key West, FL$
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VRBO
Charming 1-bedroom\/1-bath apartment in historical home with pool in Key West, FL
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Your cozy getaway awaits in Key West at this amazing apartment. Nestled in a beautiful private historical home in the he ...
Click For Pricing
VRBO
From $288 per night (USD)
Expedia
~SUNNY DAZE COTTAGE~ A private, newly constructed home in best location.
Bedrooms:
2
Bathrooms:
2
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 $288 per night (USD)
Expedia
From $363 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 $363 per night (USD)
VRBO
From $195 per night (USD)
Expedia
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 $195 per night (USD)
Expedia
From $2319 per night (USD)
VRBO
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 $2319 per night (USD)
VRBO
$ISLAND DREAMIN' ~ Exceptional 4 BR\/3.5 Ba Home w\/ Pool!$
From $551 per night (USD)
Expedia
ISLAND DREAMIN' ~ Exceptional 4 BR\/3.5 Ba Home w\/ Pool!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
MODERN MEETS CLASSIC KEY WEST STYLE... Located on the perfect corner of White and Petronia Streets, this understated bea ...
From $551 per night (USD)
Expedia
From $352 per night (USD)
VRBO
African Queen | Perfect Suite Near Historic Seaport, Shared Pool!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to African Queen Cottage, a charming retreat within the serene Harbor Walk Hideaways complex in Key West's Histo ...
From $352 per night (USD)
VRBO
From $509 per night (USD)
Expedia
Atocha Cottage at Harbor Walk Hideaways | 2 Blocks From Duval! Shared Pool
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Atocha Cottage at Harbor Walk Hideaways Welcome to Atocha Cottage, a serene getaway nestled within the charming Harbor ...
From $509 per night (USD)
Expedia
$Pilar Cottage | Spectacular Studio w\/ Shared Pool$
From $354 per night (USD)
VRBO
Pilar Cottage | Spectacular Studio w\/ Shared Pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to Pilar Cottage, a charming studio located within the peaceful Harbor Walk Hideaways complex in Key West's Hist ...
From $354 per night (USD)
VRBO
From $1276 per night (USD)
Expedia
Harbor Walk Hideaways | Group Compound In Old Town!
Bedrooms:
3
Bathrooms:
7
Sleeps:
14
Welcome to Harborwalk Hideaways! Overview: Discover Harbor Walk Hideaways, a beautifully renovated vacation rental comp ...
From $1276 per night (USD)
Expedia
$Villa La Isla- Luxury Vacation Rental 1\/2 block from Duval$
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VRBO
Villa La Isla- Luxury Vacation Rental 1\/2 block from Duval
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Villa la Isla is a brand new, professionally designed luxury residence located in the heart of Old Town Key West. Walkin ...
Click For Pricing
VRBO
From $358 per night (USD)
Expedia
Shared Pool & Parking - The Cottage at James House
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
Summary: Escape to this cozy 1-bedroom, 1-bathroom cottage nestled at the historic Curry Mansion Inn, right in the heart ...
From $358 per night (USD)
Expedia
$THE HEMINGWAY SUITE @ the Inn on Fleming ~ 2nd Floor King w\/ Shared Pool!$
From $372 per night (USD)
VRBO
THE HEMINGWAY SUITE @ the Inn on Fleming ~ 2nd Floor King w\/ Shared Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
CAPTIVATING CLASSIC REVIVAL CHARM... Built in 1894, the delightful Inn on Fleming was once the residence of Board of Edu ...
From $372 per night (USD)
VRBO
$THE CORNISH SUITE @ Inn on Fleming ~ 3rd Floor 2 Bedroom w\/Shared Pool!$
From $428 per night (USD)
Expedia
THE CORNISH SUITE @ Inn on Fleming ~ 3rd Floor 2 Bedroom w\/Shared Pool!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
CAPTIVATING CLASSIC REVIVAL CHARM... Built in 1894, the delightful Inn on Fleming was once the residence of Board of Edu ...
From $428 per night (USD)
Expedia
$THE SIMONTON ROOM @ The Inn on Fleming ~ 1st Floor King Room w\/ Shared Pool!$
From $323 per night (USD)
VRBO
THE SIMONTON ROOM @ The Inn on Fleming ~ 1st Floor King Room w\/ Shared Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
CAPTIVATING CLASSIC REVIVAL CHARM... Built in 1894, the delightful Inn on Fleming was once the residence of Board of Edu ...
From $323 per night (USD)
VRBO
$THE GATO ROOM @ The Inn on Fleming ~ 2nd Floor Queen Room w\/ Shared Pool!$
From $317 per night (USD)
Expedia
THE GATO ROOM @ The Inn on Fleming ~ 2nd Floor Queen Room w\/ Shared Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
CAPTIVATING CLASSIC REVIVAL CHARM... Built in 1894, the delightful Inn on Fleming was once the residence of Board of Edu ...
From $317 per night (USD)
Expedia
$THE FLAGLER ROOM @ The Inn on Fleming ~ 1st Floor King Room w\/ Shared Pool!$
From $323 per night (USD)
VRBO
THE FLAGLER ROOM @ The Inn on Fleming ~ 1st Floor King Room w\/ Shared Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
CAPTIVATING CLASSIC REVIVAL CHARM... Built in 1894, the delightful Inn on Fleming was once the residence of Board of Edu ...
From $323 per night (USD)
VRBO
$THE WHITEHEAD ROOM @ The Inn on Fleming ~ 2nd Floor Queen w\/ Shared Pool!$
From $317 per night (USD)
Expedia
THE WHITEHEAD ROOM @ The Inn on Fleming ~ 2nd Floor Queen w\/ Shared Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
CAPTIVATING CLASSIC REVIVAL CHARM... Built in 1894, the delightful Inn on Fleming was once the residence of Board of Edu ...
From $317 per night (USD)
Expedia
Click For Pricing
Expedia
Waterfront Resort, Songwriter’s Fest, Old Town, Sleeps 6, Swimming Pool, Hot Tub
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Have I mentioned that this listing is for the Songwriter’s Festival in sunny Key West, FL? You will be staying at the Hy ...
Click For Pricing
Expedia
$THE MALLORY SUITE @ the Inn on Fleming ~ 1st Floor King Suite w\/ Shared Pool!$
From $342 per night (USD)
Expedia
THE MALLORY SUITE @ the Inn on Fleming ~ 1st Floor King Suite w\/ Shared Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
CAPTIVATING CLASSIC REVIVAL CHARM... Built in 1894, the delightful Inn on Fleming was once the residence of Board of Edu ...
From $342 per night (USD)
Expedia
Click For Pricing
VRBO
Waterfront Resort, Songwriter’s Fest, Old Town, Sleeps 4, Swimming Pool, Hot Tub
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Have I mentioned that this listing is for the Songwriter’s Festival in sunny Key West, FL? You will be staying at the Hy ...
Click For Pricing
VRBO
$THE GEIGER ROOM @ the Inn on Fleming ~ 3rd Floor 2 Bed Suite w\/ Shared Pool!$
From $386 per night (USD)
Expedia
THE GEIGER ROOM @ the Inn on Fleming ~ 3rd Floor 2 Bed Suite w\/ Shared Pool!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
CAPTIVATING CLASSIC REVIVAL CHARM... Built in 1894, the delightful Inn on Fleming was once the residence of Board of Edu ...
From $386 per night (USD)
Expedia
$THE TRUMAN ROOM @ The Inn on Fleming ~ 2nd Floor Queen Room w\/ Shared Pool!$
From $369 per night (USD)
VRBO
THE TRUMAN ROOM @ The Inn on Fleming ~ 2nd Floor Queen Room w\/ Shared Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
CAPTIVATING CLASSIC REVIVAL CHARM... Built in 1894, the delightful Inn on Fleming was once the residence of Board of Edu ...
From $369 per night (USD)
VRBO
$Southern Escape at Truman Annex - 2 Bed \/ 2.5 Bath with Parking & Shared Pool$
From $599 per night (USD)
Expedia
Southern Escape at Truman Annex - 2 Bed \/ 2.5 Bath with Parking & Shared Pool
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
WELCOME to Southern Escape! Located in the Truman Annex Foundry building. This newly remodeled 2-bedroom, 2.5-bathroo ...
From $599 per night (USD)
Expedia
From $1040 per night (USD)
VRBO
Pool, Laundry, and grilling area
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
Upscale historic cigar barons mansion in walking distance to everything you desire in Key West. 3 spacious 1Br’s with o ...
From $1040 per night (USD)
VRBO
From $474 per night (USD)
Expedia
New Listing! Truman Show - Private, heated pool and chef's kitchen
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Truman Show combines a rich history, a modern renovation and a desirable Old Town location. This beautiful home is con ...
From $474 per night (USD)
Expedia
From $808 per night (USD)
VRBO
Sailfish Suite on Duval
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to the Sailfish Suite, your tropical retreat located in the heart of Key West! Situated on lively Duval Street, ...
From $808 per night (USD)
VRBO
From $776 per night (USD)
Expedia
Charming 4-bedroom house with pool - 10 MIN. WALK TO DUVAL STREET
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
Welcome to 1015 Eaton Street, nestled in the heart of the Historic Seaport neighborhood. Renovated in 2024, this 4-bedro ...
From $776 per night (USD)
Expedia
From $155 per night (USD)
VRBO
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)
VRBO
From $228 per night (USD)
Expedia
Abuela's at Casa Antigua | Historic Monthly Rental in the Heart of Old Town!
Bedrooms:
2
Bathrooms:
1
Sleeps:
2
Abuela's @ Casa Antigua | Historic Monthly Rental in the Heart of Old Town! Step back in time and experience the charm ...
From $228 per night (USD)
Expedia
From $506 per night (USD)
VRBO
Sunshine State at Custom House Inn | Bright Studio on Duval Street!
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
Sunshine State at Custom House Inn | Bright Studio on Duval Street! Welcome to Sunshine State, your vibrant Key West es ...
From $506 per night (USD)
VRBO
From $893 per night (USD)
Expedia
Two Vibrant Suites on Duval - Custom House Inn
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Feather Queen at Custom House Inn: A Key West Gem on Duval Street Located in the vibrant heart of Duval Street, Feather ...
From $893 per night (USD)
Expedia
From $2473 per night (USD)
VRBO
Custom House Inn | Colorful Suites & Rooftop Vibes on Duval Street!
Bedrooms:
5
Bathrooms:
5
Sleeps:
20
Custom House Inn | Colorful Suites & Rooftop Vibes on Duval Street! Experience the ultimate group getaway at Custom Hou ...
From $2473 per night (USD)
VRBO
From $894 per night (USD)
Expedia
Two Modern Suites on Duval - Custom House Inn
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Chicken Water Cabana at Custom House Inn Located in the heart of vibrant Duval Street, Chicken Water Cabana at Custom H ...
From $894 per night (USD)
Expedia
From $470 per night (USD)
VRBO
Underwater Cabana at Custom House Inn | Right In The Heart, On Duval!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Underwater Cabana at Custom House Inn | Stay on Duval Street! Experience the heart of Key West with a stay at the Under ...
From $470 per night (USD)
VRBO
From $459 per night (USD)
Expedia
Birds of a Feather at Custom House Inn | Perfect Spot On Duval!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Birds of a Feather at Custom House Inn | Vibrant Stay on Duval Street! Discover the heart of Key West at Birds of a Fea ...
From $459 per night (USD)
Expedia
From $468 per night (USD)
VRBO
Chicken Run at Custom House Inn | Unbeatable Location On Duval!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Chicken Run at Custom House Inn | Stay on Duval Street! Welcome to Chicken Run, a vibrant and uniquely themed studio lo ...
From $468 per night (USD)
VRBO
From $470 per night (USD)
Expedia
Citrus Queen at Custom House Inn | Ideal Location On Duval!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Citrus Queen at Custom House Inn | On Duval St! | Bright & Modern Studio Welcome to Citrus Queen, your vibrant, modern ...
From $470 per night (USD)
Expedia
From $515 per night (USD)
VRBO
Penthouse Near Downtown - The Maloney
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Woven throughout this 2,000+ square foot luxury penthouse is a story that can only be revealed by experience. ...
From $515 per night (USD)
VRBO
From $425 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 $425 per night (USD)
Expedia
$PATHWAY TO PARADISE ~ 2 BR\/2.5 Ba Townhome w\/ Shared Pool!$
From $213 per night (USD)
VRBO
PATHWAY TO PARADISE ~ 2 BR\/2.5 Ba Townhome w\/ Shared Pool!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
SHINY NEW ACCOMMODATION… This newly constructed townhome checks all the boxes for must-haves on your picture perfect Key ...
From $213 per night (USD)
VRBO
From $251 per night (USD)
Expedia
**SOUTHARD PEARL @ OLD TOWN** Condo & Community Pool + LAST KEY SERVICES…
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Among the man ...
From $251 per night (USD)
Expedia
$First Mate's Escape | Historic Apartment Near Duval w\/ Pool!$
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VRBO
First Mate's Escape | Historic Apartment Near Duval w\/ Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Step back in time and embrace the enchanting history of Key West with a stay at First Mate's Escape, a stunning loft apa ...
Click For Pricing
VRBO
$Hyatt Sunset Harbor 1-bedroom suite w\/AC, WiFi, Pool, Walk to Duval & Mallory$
From $484 per night (USD)
Expedia
Hyatt Sunset Harbor 1-bedroom suite w\/AC, WiFi, Pool, Walk to Duval & Mallory
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Experience Key West in this enchanting 1-bedroom sleep4 suite with kitchen, living area with a queen sofa bed. Perfect f ...
From $484 per night (USD)
Expedia
From $685 per night (USD)
VRBO
~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 $685 per night (USD)
VRBO
$WASTIN' A WAYLAND ~ Renovated 2 BR\/2 Ba Home in Old Town!$
From $242 per night (USD)
Expedia
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 $242 per night (USD)
Expedia
From $1389 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 $1389 per night (USD)
VRBO
From $265 per night (USD)
Expedia
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 $265 per night (USD)
Expedia
From $287 per night (USD)
VRBO
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 $287 per night (USD)
VRBO
From $417 per night (USD)
Expedia
Welcome Matt's - Truman @ Duval | Ideal One-Bedroom Retreat
Bedrooms:
1
Bathrooms:
2
Sleeps:
2
Truman @ Duval Unit B | Ideal One-Bedroom Retreat for Couples Escape to a charming one-bedroom apartment in the heart o ...
From $417 per night (USD)
Expedia
From $512 per night (USD)
VRBO
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 $512 per night (USD)
VRBO
From $604 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 $604 per night (USD)
VRBO
From $535 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 $535 per night (USD)
VRBO
From $759 per night (USD)
Expedia
**GRENN TURTLE COTTAGE @ THE ANNEX** Stunning Private Home + LAST KEY SERVICES…
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! GREEN TURTLE ...
From $759 per night (USD)
Expedia
$SUNNY OUTLOOK~2 BR\/2Ba 2nd FL, Waterfront views, Pool Access & Dockage!$
From $254 per night (USD)
VRBO
SUNNY OUTLOOK~2 BR\/2Ba 2nd FL, Waterfront views, Pool Access & Dockage!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This home is currently listed for sale and has been priced to offset showings that may be requested during your stay. ...
From $254 per night (USD)
VRBO
From $902 per night (USD)
VRBO
Dos Casas - 2 House Compound in Old Town Key West - A Monthly Rental
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Dos Casas can be the answer to your fabulous Old Town Key West vacation. We've been renting to discerning travelers for ...
From $902 per night (USD)
VRBO
From $373 per night (USD)
VRBO
This cottage is a 1 bedroom(s), 1 bathrooms, located in Key West, FL.
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to 734 Passover Lane, a charming one-bedroom cottage nestled in the heart of Key West’s historic district. This ...
From $373 per night (USD)
VRBO
From $951 per night (USD)
Expedia
COME HIDE AT THE KEY WEST HOTEL. A HIDDEN WORLD RIGHT IN THE HEART OF IT ALL.
Bedrooms:
1
Bathrooms:
1
Sleeps:
50
(PLEASE REACH OUT TO GET ROOM DETAILA AND A SPECIAL DISCOUNT WHEN BOOKING!) Welcome to The Key West Hotel, tucked i ...
From $951 per night (USD)
Expedia
From $402 per night (USD)
VRBO
Charming 2-bedroom cottage 3 blocks from Duval
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Consider this cottage your home away from home while you visit Key West. This adorable property features 2 bedrooms with ...
From $402 per night (USD)
VRBO
Click For Pricing
Expedia
Magnificent views of the Gulf, Sunset Harbor is the ultimate island retreat.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Nestled in Key West, this delightful resort offers 2 bedrooms with a king and queen bed, 2 bathrooms with luxurious amen ...
Click For Pricing
Expedia
$BELLE MAISON ~ 5 BR\/3 Ba Home w\/ Pool\/Spa in The Meadows!$
From $562 per night (USD)
VRBO
BELLE MAISON ~ 5 BR\/3 Ba Home w\/ Pool\/Spa in The Meadows!
Bedrooms:
3
Bathrooms:
6
Sleeps:
14
A LEGACY OF TIMELESS BEAUTY... This exquisite grand dame of quintessential Key West is a world of dreams! Yours is comin ...
From $562 per night (USD)
VRBO
$Pet Friendly \/ Hot Tub \/ Close to Everything$
From $230 per night (USD)
Expedia
Pet Friendly \/ Hot Tub \/ Close to Everything
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Located in Historic Old Town Monthly Rental La Cala is Situated on a Corner Lot within Walking Distance to Everything yo ...
From $230 per night (USD)
Expedia
Click For Pricing
VRBO
Charming condo in awesome Key West - great location!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Your cozy getaway awaits in Key West at this wonderful condo. With amenities like King Size Bed, Private Front Porch, Pr ...
Click For Pricing
VRBO
From $475 per night (USD)
VRBO
Coral Palms Spacious 1BR Condo, King, Queen, Sofa Bed, Pool, Block to Duval
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Escape to this charming 1BR, 2nd-floor condo in the heart of Historic Key West. Sleep soundly in a plush king bed with r ...
From $475 per night (USD)
VRBO
$**BARBUDA SUITE @ SEAPORT INN** Guest Suite w\/ Pool Access + LAST KEY SERVICES..$
From $267 per night (USD)
VRBO
**BARBUDA SUITE @ SEAPORT INN** Guest Suite w\/ Pool Access + LAST KEY SERVICES..
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Looking for a ...
From $267 per night (USD)
VRBO
$**MATECUMBE SUITE @ SEAPORT INN** Guest Suite w\/ Pool Access + LAST KEY SERVICES$
From $299 per night (USD)
Expedia
**MATECUMBE SUITE @ SEAPORT INN** Guest Suite w\/ Pool Access + LAST KEY SERVICES
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! If you’d like ...
From $299 per night (USD)
Expedia
$**ANTIGUA SUITE @ SEAPORT INN** Guest Suite w\/ Pool Access + LAST KEY SERVICES..$
From $270 per night (USD)
VRBO
**ANTIGUA SUITE @ SEAPORT INN** Guest Suite w\/ Pool Access + LAST KEY SERVICES..
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! If the allure ...
From $270 per night (USD)
VRBO
From $613 per night (USD)
Expedia
Cozy home with private pool, BBQ, central AC, enclosed yard
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Key to Paradise Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $613 per night (USD)
Expedia
From $1556 per night (USD)
VRBO
SEVENTH HEAVEN~Waterfront 5 BR, 4 Ba Townhome with Pool, Elevator & Dockage!
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
OLD KEY WEST ELEGANCE WITH AN ELEVATOR, PRIVATE POOL AND BOAT DOCKAGE... Indulge in island chic as you approach this lux ...
From $1556 per night (USD)
VRBO
From $366 per night (USD)
Expedia
Large Penthouse suite in the charming Bayan Resort in beautiful Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The Banyan Resort Key West, Florida In the heart of historic Old Town Key West, The Banyan Resort boasts a storied hist ...
From $366 per night (USD)
Expedia
From $359 per night (USD)
VRBO
**KOKOMO SUITE @ SEAPORT INN** Historic Charm & Community Pool + LAST KEY SERVIC
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! You can skip ...
From $359 per night (USD)
VRBO
From $325 per night (USD)
Expedia
ISLAND IN THE SUN ~ Newly Renovated 3 BR Townhome in Old Town with Parking!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
EXCEPTIONAL SANCTUARY IN OLD TOWN... Lose yourself in this light and airy upscale retreat in a prime location, just 1.5 ...
From $325 per night (USD)
Expedia
From $558 per night (USD)
VRBO
Partial Harbor View King Room at Marker Key West Harbor Resort – Pet-friendly
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This listing is for a room within a hotel. ✦ Your room is 400 sq. ft, equipped with complimentary toiletries, high defi ...
From $558 per night (USD)
VRBO
$Harbor View King w\/ Balcony at Marker Harbor Resort – Your Waterfront Oasis$
From $629 per night (USD)
VRBO
Harbor View King w\/ Balcony at Marker Harbor Resort – Your Waterfront Oasis
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This listing is for a room within a hotel. ✦ Your room is 400 sq. ft, equipped with complimentary toiletries, high defi ...
From $629 per night (USD)
VRBO
From $453 per night (USD)
VRBO
Marker Key West Harbor, Classic Queen Room, 3 Swimming Pools & Pet-friendly
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This listing is for a room within a hotel. ✦ Your room is 400 sq. ft, equipped with complimentary toiletries, high defi ...
From $453 per night (USD)
VRBO
From $640 per night (USD)
VRBO
Relax by the Water with Stunning Pools and Access to Watersports Activities
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This listing is for a room within a hotel. ✦ Your room is 400 sq. ft, equipped with complimentary toiletries, high defi ...
From $640 per night (USD)
VRBO
From $385 per night (USD)
VRBO
Waterfront Living with Private Pools, Calm Waters, and Poolside Dining
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This listing is for a room within a hotel. ✦ Your room is 400 sq. ft, equipped with complimentary toiletries, high defi ...
From $385 per night (USD)
VRBO
From $973 per night (USD)
VRBO
Marker Key West Harbor, 2 Classic 2 Queens, 3 Onsite Pools & Pets are Welcome
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
This listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms. ✦ Each room is ...
From $973 per night (USD)
VRBO

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