Key West Rentals
From $466 per night (USD)VRBO
The Barbados | Private Balcony, Pool View!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Barbados | Key West Condo with Pool, Hot Tub & Private Balcony Welcome to The Barbados, a welcoming 2-bedroom condo ...
From $466 per night (USD)VRBO
From $338 per night (USD)Expedia
SALTWATER SOUL - 2 Bedroom / 2.5 Bathroom Waterfront Townhome W/ Shared Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Rare Waterfront Corner Townhouse on the Gulf Side of Key West! Experience the best of island living in this exceptional ...
From $338 per night (USD)Expedia
From $624 per night (USD)VRBO
The Mermaids Retreat nestled near Mary Star of the Sea, walk everywhere!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Location Location, lovely location near Key West’s finest restaurants and bars. Walk everywhere from this lovely spa tow ...
From $624 per night (USD)VRBO
From $466 per night (USD)Expedia
The Grand Turk | Spectacular Sunset View, Private
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Grand Turk | Key West Condo with Pool, Hot Tub & Private Balcony Welcome to The Grand Turk, a spacious and inviting ...
From $466 per night (USD)Expedia
From $251 per night (USD)VRBO
Hidden Key West Cottage - Walk to Duval !!!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to Cozy Key West Cottage !!! A REAL ISLAND GATAWAY IN KEY WEST!!! Stay just around the corner from Duval Street ...
From $251 per night (USD)VRBO
From $1167 per night (USD)Expedia
3-bedroom townhome in beautiful Key West with AC and charm
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Located in the heart of Old Town Key West, just steps from restaurants, shops, and local attractions, this well-appointe ...
From $1167 per night (USD)Expedia
From $200 per night (USD)VRBO
Reynolds Paradise | Walk to Higgs Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Welcome to Reynolds Paradise, a beautifully renovated island retreat designed for relaxation, comfort, and unforgettable ...
From $200 per night (USD)VRBO
From $744 per night (USD)Expedia
**VOGUE VILLA @ OLD TOWN** Home & Pool + Last Key White Glove Service...
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Step into VOG ...
From $744 per night (USD)Expedia
From $165 per night (USD)VRBO
Welcome to Shipyard Unit 155, a charming 2-bedroom, 1-bath ground-level condo located in the desirable Truman Annex community, just two blocks from Duval Street. This convenient Key West is within easy walking distance of the Truman Waterfront.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Shipyard Unit 155, a charming 2-bedroom, 1-bath ground-level condo located in the desirable Truman Annex comm ...
From $165 per night (USD)VRBO
From $1702 per night (USD)Expedia
2-bedroom beachfront condo in beautiful Key West sleeps 6
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Experience the ultimate beachfront escape in this beautifully appointed two-bedroom luxury condominium, where sophistica ...
From $1702 per night (USD)Expedia
From $648 per night (USD)VRBO
**CASA DEL MONO @ MIDTOWN** Home & Pool + Last Key White Glove Service...
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Welcome to CA ...
From $648 per night (USD)VRBO
From $652 per night (USD)Expedia
Key West Front St Studiio
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Your cozy getaway awaits in Key West at this beautiful studio. Nov 8th through checkout on Nov 15 th 2026. The space fe ...
From $652 per night (USD)Expedia
From $88 per night (USD)VRBO
Tranquil condo / AC, WIFI, Outdoor Pool, Full kitchen, Livingroom in Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Unwind in Key West at this fabulous condo. First floor easy in and out access. The space features one bathroom with a re ...
From $88 per night (USD)VRBO
From $163 per night (USD)Expedia
Walkable Home w/ Deck, Office & More in Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Gated Community | Pet Friendly w/ Fee | < 1 Mi to Beaches Pack your flip-flops and escape to a charming oasis built for ...
From $163 per night (USD)Expedia
From $609 per night (USD)VRBO
Pet Friendly Stay | Near Key West International Airport | Pool & Parking Access
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Duval Street, Smathers Beach, & Old Town charm await—Key West escape begins here This listing is for a room within a ho ...
From $609 per night (USD)VRBO
From $682 per night (USD)VRBO
Group Friendly Stay | Outdoor Pool Access | Pets Welcome | Near Jackson Square
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Duval Street, Smathers Beach, & Old Town charm await—Key West escape begins here This listing is for a room within a ho ...
From $682 per night (USD)VRBO
From $549 per night (USD)VRBO
Chic Key West Retreat | Outdoor Pool| Pet Friendly | Near Key West Aquarium
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Duval Street, Smathers Beach, & Old Town charm await—Key West escape begins here This listing is for a room within a ho ...
From $549 per night (USD)VRBO
From $555 per night (USD)VRBO
Elegant Villa Getaway | Pool & Beach Access | Pets Welcome | Near Mallory Square
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Duval Street, Smathers Beach, & Old Town charm await—Key West escape begins here This listing is for a room within a ho ...
From $555 per night (USD)VRBO
From $534 per night (USD)VRBO
Peaceful Family Retreat | Outdoor Pool | Parking | Pets are Welcome
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Duval Street, Smathers Beach, & Old Town charm await—Key West escape begins here This listing is for a room within a ho ...
From $534 per night (USD)VRBO
From $1077 per night (USD)VRBO
2 Stylish Units | Near Key West International Airport- 1.1 mi | Outdoor Pool
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 16
Duval Street, Smathers Beach, & Old Town charm await—Key West escape begins here This listing is for 2 separate rooms w ...
From $1077 per night (USD)VRBO
From $534 per night (USD)VRBO
Group Friendly Stay | Pets Welcome | Near Key West International Airport
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Duval Street, Smathers Beach, & Old Town charm await—Key West escape begins here This listing is for a room within a ho ...
From $534 per night (USD)VRBO
From $265 per night (USD)Expedia
Turtle Nest Condo + Pool / 2nd Floor
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to our charming Key West retreat in the heart of The Meadows! Built in 1932, this unique island home blends his ...
From $265 per night (USD)Expedia
From $562 per night (USD)VRBO
\"CRAWL\" off DUVAL Cottage—only 50 short Steps to the FUN!!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Discover the charm and elegance of this Key West Classic, a newly constructed 2-bedroom, 2.5-bathroom home with pool tha ...
From $562 per night (USD)VRBO
From $892 per night (USD)Expedia
Valhalla - Southernmost Oasis
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Valhalla – Private Pool Cottage in the Heart of Old Town Key West Originally built in the early 1900s, Valhalla is a be ...
From $892 per night (USD)Expedia
From $315 per night (USD)VRBO
A & E's Tranquil Tides at the Truman Annex in Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Charming first floor 2-Bedroom, 1-Bathroom Shipyard Condo in Historic Truman Annex - Key West Escape to the heart of Ke ...
From $315 per night (USD)VRBO
From $1342 per night (USD)Expedia
~HELLO GORGEOUS~ Soak up the sun, swim in the pool, or relax in the jacuzzi!
- 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 $1342 per night (USD)Expedia
From $378 per night (USD)VRBO
**WINDWARD WAVES @ OLD TOWN** Cottage by Duval + Last Key White Glove Service...
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! WINDWARD WAVE ...
From $378 per night (USD)VRBO
From $379 per night (USD)Expedia
Luxury Truman Annex Condo I 3BDR I Pool & Parking I Walk to Duval & Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to Above The Horizon, a stunning 3-bedroom retreat in the exclusive gated Truman Annex — just one block from the ...
From $379 per night (USD)Expedia
From $452 per night (USD)VRBO
SEASIDE ESCAPE- 2 Bed/2 Bath Condo With Shared Pool & Parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Your Peaceful Key West Escape Awaits! Welcome to this comfortably appointed 2-bedroom, 2-bath condo located in the de ...
From $452 per night (USD)VRBO
From $629 per night (USD)Expedia
**LA BELLA CAPRI @ CASA MARINA** Estate & Pool + Last Key White Glove Service...
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Imagine this ...
From $629 per night (USD)Expedia
From $534 per night (USD)VRBO
Family-Friendly Unit in Key West | Onsite Parking | Pool Access | Pets Allowed
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Step into a world of white sands and glimmering pools, where boat drinks and watersports are just steps from your front ...
From $534 per night (USD)VRBO
From $1067 per night (USD)VRBO
2 Stylish Key West Units | Onsite Outdoor Pool | Pet Friendly | Parking
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 16
Step into a world of white sands and glimmering pools, where boat drinks and watersports are just steps from your front ...
From $1067 per night (USD)VRBO
From $609 per night (USD)VRBO
Pet Friendly Stay | Pool & Beach Access| Parking | Near Southernmost Point- 2 mi
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
This listing is for a room within a hotel. ✦ Your room is 1525 sq. ft, equipped with complimentary toiletries, TV. ✦ C ...
From $609 per night (USD)VRBO
From $682 per night (USD)VRBO
Spacious Villa Escape | Pool | Pets Allowed | Near Key West Aquarium- 2.2 miles
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
This listing is for a room within a hotel. ✦ Your room is 1525 sq. ft, equipped with complimentary toiletries, TV. ✦ C ...
From $682 per night (USD)VRBO
From $467 per night (USD)VRBO
Modern Villa Stay | Outdoor Pool | Pet Friendly | Near Jackson Square- 2.1 miles
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This listing is for a room within a hotel. ✦ Your room is 925 sq. ft, equipped with complimentary toiletries, TV. ✦ Cl ...
From $467 per night (USD)VRBO
From $458 per night (USD)VRBO
Tropical Retreat | Outdoor Pool | Pets Allowed | Near Mallory Square - 2.2 miles
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Duval Street, Smathers Beach, & Old Town charm await—Key West escape begins here This listing is for a room within a ho ...
From $458 per night (USD)VRBO
From $539 per night (USD)VRBO
Stylish Key West Retreat | Outdoor Pool | Parking | Pets Allowed | Shuttle
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Duval Street, Smathers Beach, & Old Town charm await—Key West escape begins here This listing is for a room within a ho ...
From $539 per night (USD)VRBO
From $322 per night (USD)Expedia
Key West Luxury Home with pool, 28 day minimum
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to the heart of Key West in this charming luxury island retreat located on Petronia Street in the historic Meadow ...
From $322 per night (USD)Expedia
From $469 per night (USD)VRBO
The Tahiti Suite | Updated Key West Condo w/ Pool, Hot Tub, & Balcony!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Tahiti Suite | Updated Key West Condo w/ Pool, Hot Tub, & Balcony! Welcome to The Tahiti Suite, a stylish 2-bedroom ...
From $469 per night (USD)VRBO
From $217 per night (USD)Expedia
Beach Therapy Your Historic Florida Cottage Escape in Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Escape to the charm of Key West in this beautifully styled downstairs cottage located in the heart of the vibrant White ...
From $217 per night (USD)Expedia
From $532 per night (USD)VRBO
Coconut Beach Resort - 1 BR Studio
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Set on the Atlantic Ocean in Key West, this condo-style stay keeps things simple with no on-site restaurants. Plan easy ...
From $532 per night (USD)VRBO
From $343 per night (USD)Expedia
Monthly rental-Old town one level home w/ shared, heated pool, parking, a/c,heat
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
*Key West only allows us to rent the home for 28 nights minimum, so I won't be able to respond to inquiries for rentals ...
From $343 per night (USD)Expedia
From $300 per night (USD)VRBO
Beautiful 2-bedroom centrally located Salt Pond Condo in sunny Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Escape to Key West and settle into this inviting 2-bedroom, 2-bathroom condo—perfect for an extended island getaway. Ple ...
From $300 per night (USD)VRBO
From $615 per night (USD)VRBO
Family Friendly Stay | Free Shuttle | Outdoor Pools | Parking Available
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Duval Street, Smathers Beach, & Old Town charm await—Key West escape begins here This listing is for a room within a ho ...
From $615 per night (USD)VRBO
From $387 per night (USD)VRBO
Romantic Beach Getawat | Onsite Parking | Outdoor Pool Access | Pet Friendly
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Duval Street, Smathers Beach, & Old Town charm await—Key West escape begins here This listing is for a room within a ho ...
From $387 per night (USD)VRBO
From $743 per night (USD)Expedia
Atlantic Parrot | Oceanfront Condo w/ Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This vibrant beachfront condo is the perfect home base for soaking up the sun and sea breezes of Key West. Located direc ...
From $743 per night (USD)Expedia
From $444 per night (USD)VRBO
STAINED GLASS SANCTUARY ~ Newly Renovated 3Br/1.5Ba Private Pool!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
QUINTESSENTIAL HISTORIC CONCH HOME… Exhale the cares of the world as you approach this classic and charming Key West gem ...
From $444 per night (USD)VRBO
From $615 per night (USD)VRBO
Key West Stay | Outdoor Pool Access | Near Roosevelt Blvd & Beaches | Parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Duval Street, Smathers Beach, & Old Town charm await—Key West escape begins here This listing is for a room within a ho ...
From $615 per night (USD)VRBO
From $612 per night (USD)VRBO
Casa Havana | Old Town Condo w/ Pool & Balcony
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Discover the laid-back magic of historic Key West with a stay at Casa Havana, a bright and inviting condo tucked inside ...
From $612 per night (USD)VRBO
From $499 per night (USD)Expedia
Duval Street Retreat | Dog-Friendly w/ Shared Hot Tub
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Duval Street Retreat | Dog-Friendly Home with Hot Tub, WiFi, & Private Parking Duval Street Retreat is your ideal Key W ...
From $499 per night (USD)Expedia
From $365 per night (USD)VRBO
Boat Slip - Waterfront Condo - Key West Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Summary: Be among the first to experience this spacious waterfront Key West getaway, newly available as a vacation rent ...
From $365 per night (USD)VRBO
From $463 per night (USD)VRBO
Ocean Getaway | Outdoor Pool | Shuttle Service | Parking | Pet Friendly
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Duval Street, Smathers Beach, & Old Town charm await—Key West escape begins here This listing is for a room within a ho ...
From $463 per night (USD)VRBO
From $370 per night (USD)VRBO
Elegant Beach Stay | Minutes to Southernmost Point - 2 miles | Onsite Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Duval Street, Smathers Beach, & Old Town charm await—Key West escape begins here This listing is for a room within a ho ...
From $370 per night (USD)VRBO
From $325 per night (USD)VRBO
Key West Beach Retreat | Pool Access | Near Key West Aquarium- 2.2 miles
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This listing is for a room within a hotel. ✦ Your room is 375 sq. ft, equipped with complimentary toiletries, TV. ✦ Cl ...
From $325 per night (USD)VRBO
From $517 per night (USD)VRBO
Romance on William Street- 3BR Old Town Retreat w/ Private Pool & Spa
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Discover the perfect blend of classic Key West charm and modern elegance at `Romance on William.` This stunning 3 to 3.5 ...
From $517 per night (USD)VRBO
From $293 per night (USD)VRBO
The Tipsy Parrot Walkable Old Town Key West Retreat
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
More than just a rental, this thoughtfully designed island home invites you to settle into the relaxed rhythm of Key Wes ...
From $293 per night (USD)VRBO
From $442 per night (USD)VRBO
Hidden Beach #1, Sea Breeze Escape
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
Experience the very best of Key West from this exceptional beachfront one bedroom, 1 bath apartment in the heart of hist ...
From $442 per night (USD)VRBO
From $330 per night (USD)VRBO
The Lightkeeper | 3BR Old Town Key West Home w/ Parking, Widow`s Walk, & Pool
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
<b>A Nautical Home on United Street</b> <b>Where Every Direction Points to the Water</b> Set behind a gate on United St ...
From $330 per night (USD)VRBO
From $179 per night (USD)VRBO
Bella Noni Golf Key West -Only adult
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Make this condo your home away from home while exploring Key West! This charming two-story home, with a maximum capacity ...
From $179 per night (USD)VRBO
From $1952 per night (USD)VRBO
2BDR Sunset Harbor Resort Key West Florida
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Discover this relaxing oasis in the heart of Key West's famed Old Town. Lush, verdant foliage surrounds the grounds and ...
From $1952 per night (USD)VRBO
From $1952 per night (USD)VRBO
2 Sunset Harbor Resort Key West, Hot Tub, Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Discover this relaxing oasis in the heart of Key West's famed Old Town. Lush, verdant foliage surrounds the grounds and ...
From $1952 per night (USD)VRBO
From $883 per night (USD)VRBO
Dona Calabash, Key West Elegance and Serenity Just 90 Steps from Duval
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Dona Calabash! 90 Miles to Cuba, 90 steps to Duval! Named for the prized and rare 100 year old Calabash tree ...
From $883 per night (USD)VRBO
From $275 per night (USD)VRBO
Spectacular Waterfront Pool Dock Min 28 days
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Experience Key West like a local in this 3-bedroom waterfront unobstructed open water view home with heated and chilled ...
From $275 per night (USD)VRBO
From $1588 per night (USD)VRBO
1/1 Galleon Resort, Hot Tub, Pool, Marina, Gym
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Overlooking the shimmering span of Gulf of Mexico in historic Old Town, The Galleon Resort puts you in an ideal spot to ...
From $1588 per night (USD)VRBO
From $1008 per night (USD)VRBO
Galleon Resort - Waterfront Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
The Galleon is on the Marina Walk in Old Town, close to dozens of the waterfront restaurants and a few blocks walk to Du ...
From $1008 per night (USD)VRBO
From $365 per night (USD)VRBO
Renovated Old Town 2 Bedroom with Private Backyard
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Newly Renovated Townhome in Prime Old Town Key West located just 3 blocks from the beach! Experience the best of island ...
From $365 per night (USD)VRBO
From $846 per night (USD)VRBO
Impeccable 3BR/3.5BA Coastal Escape Steps from Casa Marina & Higgs Beach
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Discover Old Town living at its finest. Tucked away on a quiet, tree-lined residential street in the coveted Historic Di ...
From $846 per night (USD)VRBO
From $718 per night (USD)VRBO
Luxurious Mid-Century Modern Oasis with Private Pool & Rooftop Deck in Key West
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to the Von Phister House — a stunningly renovated mid-century modern home perfectly reimagined for sophisticated ...
From $718 per night (USD)VRBO
From $1741 per night (USD)VRBO
2 Galleon Resort, Hot Tub, Pool, Marina, Gym!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Overlooking the shimmering span of Gulf of Mexico in historic Old Town, The Galleon Resort puts you in an ideal spot to ...
From $1741 per night (USD)VRBO
From $217 per night (USD)VRBO
Art-Filled 1,700SF 3BR/2BA Old Town Key West Home with 2 Decks, Pool, Parking,++
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Large art-filled, two story Key West condo boasts 3 inviting bedrooms, including a king bed, queen bed, and an office or ...
From $217 per night (USD)VRBO
From $865 per night (USD)VRBO
Coastal Living Charm with Pool and Backyard Oasis
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to your getaway in The Meadows, one of Key West’s most desirable and peaceful neighborhoods. This newly construc ...
From $865 per night (USD)VRBO
From $1469 per night (USD)VRBO
2-bedroom Villa in peaceful Key West at the beautiful Hyatt Beachouse Resort
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Located in Key West, this adorable villa at Hyatt Beachouse offers a perfect retreat for guests seeking comfort and styl ...
From $1469 per night (USD)VRBO
From $283 per night (USD)VRBO
Sun, Sea, & Citrus - Bright 2-Bedroom Monthly Rental in Old Town Key West with Private Pool. Sleeps 5-6
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Our guests are in for a treat at such a bright and beautiful entire first-floor unit in Key West. This inviting two-bedr ...
From $283 per night (USD)VRBO
From $380 per night (USD)VRBO
Starfish Oasis at Casa Marina, 2BR - Heated Pool - Hot Tub - 2 Parking - Pets OK
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Starfish Oasis at Casa Marina offers 2BR, heated & chilled pool, hot tub, private parking for 2 large vehicles, pet-frie ...
From $380 per night (USD)VRBO
From $252 per night (USD)VRBO
Cool Change
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Tropical 3BDR/3BA Home with Large Pool The Space: Tucked within lush tropical gardens, this stunning two-s ...
From $252 per night (USD)VRBO
From $299 per night (USD)VRBO
The Little Mermaid
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to your charming Key West retreat with private pool and a lush, tropical garden. Designed for comfort this 2 be ...
From $299 per night (USD)VRBO
From $211 per night (USD)VRBO
Simonton Loft-3BR Old Town Retreat Near Duval
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Charming Three-Bedroom Key West Condo Just One Block from Duval Experience Key West from this beautifully refreshed thr ...
From $211 per night (USD)VRBO
From $434 per night (USD)VRBO
Southernmost Charm. Steps to Duval and southern most point.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Experience Island living in this beautiful island home. Steps away from the Southern Most Point and Duval St. Ideally ...
From $434 per night (USD)VRBO
From $311 per night (USD)VRBO
Modern Luxury with Additional Guest Home, Garage and Pool in Key West!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy the best of Key West in modern and spacious comfort. This pet-friendly home is within minutes of restaurants, shop ...
From $311 per night (USD)VRBO
From $508 per night (USD)VRBO
Key West Resort Stay – 2BR Villa Near Beaches & Sunset Views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Hyatt Vacation Club at Beach House is an oceanfront resort located along the Gulf side of Key West. The property feature ...
From $508 per night (USD)VRBO
From $512 per night (USD)VRBO
Key West Resort Stay – 2BR Villa Near Beaches & Sunset Views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Hyatt Vacation Club at Beach House is an oceanfront resort located along the Gulf side of Key West. The property feature ...
From $512 per night (USD)VRBO
From $925 per night (USD)VRBO
5BR/5.5BA + Loft, heated pool, steps to Duval- Your Key West getaway
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 14
Welcome to your dream getaway in the heart of Key West. This spacious 5‑bedroom, 5.5‑bath luxury retreat blends island c ...
From $925 per night (USD)VRBO
From $453 per night (USD)VRBO
Key West 2BR Retreat – Ocean Views & Island Adventure
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Hyatt Vacation Club at Windward Pointe sits along the Atlantic side of Key West with beautiful oceanfront views and a re ...
From $453 per night (USD)VRBO
From $766 per night (USD)VRBO
Key West 2BR Retreat – Ocean Views & Island Adventure
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Hyatt Vacation Club at Windward Pointe sits along the Atlantic side of Key West with beautiful oceanfront views and a re ...
From $766 per night (USD)VRBO
From $508 per night (USD)VRBO
Hidden Beach #3, Sea Breeze Escape
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
Experience the very best of Key West from this exceptional beachfront townhouse apartment in the heart of historic Old T ...
From $508 per night (USD)VRBO
From $442 per night (USD)VRBO
Hidden Beach #2, Sea Breeze Escape
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Experience the very best of Key West from this exceptional beachfront one bedroom, 1 bath apartment in the heart of hist ...
From $442 per night (USD)VRBO
From $567 per night (USD)VRBO
1800 ATLANTIC 2-bedroom condo with Particle Ocean view in Key West Florida
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Your Key West adventure begins at this 2-bedroom condo. Inside, guests find two king beds that promise restful nights Th ...
From $567 per night (USD)VRBO
From $335 per night (USD)VRBO
Chic Duval Street Loft | Cozy 1BR + Balcony in Historic Cuban Club
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Immerse yourself in the vibrant heart of Key West at the Cayo Hueso Suite at the Cuban Club, where modern comfort meets ...
From $335 per night (USD)VRBO
From $472 per night (USD)VRBO
Tropical 3BR Casa Marina Retreat w/ Private Pool — Steps to Higgs Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Higgs Beach Hideaway, your stylish island home in the heart of Key West’s desirable Casa Marina neighborhood, ...
From $472 per night (USD)VRBO
From $320 per night (USD)VRBO
Key of Blue: A Monthly Key West Retreat with Boat Parking
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
A Relaxed Monthly Rental in Key West Designed for Comfortable, Everyday Living Set in the easygoing rhythm of New Town, ...
From $320 per night (USD)VRBO
From $271 per night (USD)VRBO
Quaint Conch House Located In Historic Bahama Village.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
One bedroom Conch house with hot tub. Private back yard with barbeque in lush setting. Just two blocks off Duval Street ...
From $271 per night (USD)VRBO
From $960 per night (USD)VRBO
Poolside Paradise, unique 3BR home with Private Heated pool/spa, off-street private parking!
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Beautiful architect designed home from the 1990`s in the process of being lovingly restored and redecorated. This is a ...
From $960 per night (USD)VRBO
From $230 per night (USD)VRBO
Charming 2-bedroom house with AC, WiFi in cool Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Consider this house your home away from home while you visit Key West. This wonderful property features 2 queen bedrooms ...
From $230 per night (USD)VRBO
Click For PricingVRBO
Conchtail Club – Shipyard
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Conchtail Club a Tropical Oasis in the Heart of Old Town – Shipyard Condo in Truman Annex Welcome to your sunny esc ...
Click For PricingVRBO
From $577 per night (USD)VRBO
Serenity by the Sea | La Brisa
- 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 $577 per night (USD)VRBO
From $457 per night (USD)VRBO
Island Links Escape
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Summary: 2 Bedroom 2 1/2 Bathroom Townhouse in Key West Golf Club The Space: **Beautiful 2-Bedroom Townhome in Key ...
From $457 per night (USD)VRBO
From $308 per night (USD)VRBO
Nate's Place in Key West
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Summary: 3 Bedroom 2 Bathroom Near Beaches and Galleries The Space: Spacious 3-Bedroom, 2-Bathroom Retreat in Key W ...
From $308 per night (USD)VRBO
From $404 per night (USD)VRBO
Helluva Happy Place
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Escape to Old Town Key West - 3 Bedroom 2.5 Bathroom Townhome with a Private Pool The Space: Escape to Old ...
From $404 per night (USD)VRBO
From $332 per night (USD)VRBO
Half block to Duval @ Mango Hideaway -studio apt
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The Mango Hideaway is comfortable junior suite, with sofa sitting area with adjoining king bedroom. The suite features ...
From $332 per night (USD)VRBO
From $627 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 $627 per night (USD)VRBO