Fleming Key Rentals
From $383 per night (USD)VRBO
**HAVANA HOUSE @ OLD TOWN** Elegant Cottage Near Duval + LAST KEY SERVICES...
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Located on So ...
From $383 per night (USD)VRBO
From $2769 per night (USD)Expedia
**AMERICANA TROPICALE @ OLD TOWN** Home & Pool by Duval + LAST KEY SERVICES...
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! For the ultim ...
From $2769 per night (USD)Expedia
From $4141 per night (USD)VRBO
**THE IBIS & THE CRANE @ OLD TOWN** Compound Near Duval + LAST KEY SERVICES...
- Bedrooms:
- 8
- Bathrooms:
- 6
- Sleeps:
- 16
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Dreaming of a ...
From $4141 per night (USD)VRBO
From $1112 per night (USD)Expedia
Find Sanity in the Heart of Key West
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Experience the charm of this fantastic Old Town location surrounded by local businesses and restaurants, allowing you to ...
From $1112 per night (USD)Expedia
From $1626 per night (USD)VRBO
**PUERTA CORALINA @ OLD TOWN** Cottage Near Duval + LAST KEY SERVICE...
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! This precious ...
From $1626 per night (USD)VRBO
From $4168 per night (USD)Expedia
**CASA VICTORIA @ OLD TOWN** Historic 5BR Home & Pool + LAST KEY SERVICES...
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 12
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! CASA VICTORIA ...
From $4168 per night (USD)Expedia
From $567 per night (USD)VRBO
**THE ARTISTS' MUSE @ LOVE LANE** Immaculate Home & Pool + LAST KEY SERVICES...
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! For many, the ...
From $567 per night (USD)VRBO
From $2206 per night (USD)Expedia
**THE SMILING IBIS @ OLD TOWN** Home & Pool Near Duval + LAST KEY SERVICES...
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Traveling to ...
From $2206 per night (USD)Expedia
From $1064 per night (USD)VRBO
ROOFTOP PENTHOUSE- | 2 Bed, 1.5 Bath
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The high-end sophisticated Rooftop Penthouse is located directly above the famous Wyland Gallery on Duval Street. Enjoy ...
From $1064 per night (USD)VRBO
From $696 per night (USD)VRBO
Poolside Suite with 1 Bedroom, 1 Bath with Kitchen and Pullout Sofa
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
A beautifully renovated suite featuring a living room with a queen sofa bed, a modern kitchenette and a spacious master ...
From $696 per night (USD)VRBO
From $541 per night (USD)VRBO
Bright Condo with Homey Feel, Entertainment & Private Parking - Beach Nearby
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Jasmine Suite Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $541 per night (USD)VRBO
From $1337 per night (USD)Expedia
Three-Condo Getaway in Old Town with WiFi, Shared Pool, and Hot Tub
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Palm Gardens Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $1337 per night (USD)Expedia
From $198 per night (USD)VRBO
Breezy Florida Home with Shared Pool, Dog & Snowbird-Friendly - Walk to Beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The Headquarters Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $198 per night (USD)VRBO
From $536 per night (USD)Expedia
Sunny condo with pool, lovely deck, central AC & washer\/dryer - central location
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Oceana Suite Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $536 per night (USD)Expedia
From $562 per night (USD)VRBO
The Galleon Resort Best Resort Location in KW
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This October condo is a 2BR, 2BA sunset/pool view sleeps 6. Condo has a full modern kitchen with granite/stainless, di ...
From $562 per night (USD)VRBO
From $779 per night (USD)VRBO
Bermuda Retreat-waterfront 2BR 2BA condo w\/ pool & boat slip
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
AGE REQUIREMENT: Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their ...
From $779 per night (USD)VRBO
From $253 per night (USD)VRBO
Banyan Court downtown condo- 2 bedroom, 2 bath, walkable, parking, pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
AGE REQUIREMENT: Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their ...
From $253 per night (USD)VRBO
From $824 per night (USD)Expedia
Centrally located home with private pool & furnished patio - dog-friendly
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Passover Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $824 per night (USD)Expedia
From $337 per night (USD)VRBO
Dog-friendly home w\/ large private pool only a short walk to Historic Seaport
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Seaport Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $337 per night (USD)VRBO
From $610 per night (USD)VRBO
Dominica Retreat-waterfront 2BR 2BA condo w\/ pool & boat slip
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
AGE REQUIREMENT: Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their ...
From $610 per night (USD)VRBO
From $598 per night (USD)VRBO
Flamingo Retreat-waterfront 2BR 2BA condo w\/ pool & boat slip
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
AGE REQUIREMENT: Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their ...
From $598 per night (USD)VRBO
From $349 per night (USD)VRBO
The Palms -3 bedroom 2 bath home in The Meadows w\/ pool oasis & guest cottage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
AGE REQUIREMENT: Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their ...
From $349 per night (USD)VRBO
From $587 per night (USD)VRBO
Little Paradise, Historic Harbor Old Town Key West 2\/2
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Come enjoy Island Living at it’s finest, Your own “Little Paradise”. This Two Bedroom One and a half bath home is nestl ...
From $587 per night (USD)VRBO
From $1016 per night (USD)VRBO
The Galleon Resort, Waterfront Location, Well-equipped Two Bedroom Villa!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Please choose a Saturday check-in, all rentals will be in seven night increments. Thank you for your interest in bookin ...
From $1016 per night (USD)VRBO
From $267 per night (USD)VRBO
Oasis in Old Town - private heated pool
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 6
Our sweet ‘conch’ cottage in old town Key West has been completely redesigned and custom crafted by 2 architects as our ...
From $267 per night (USD)VRBO
Click For PricingExpedia
7 Nights - Hyatt Sunset Harbor 2 bed\/2bath\/Kitchen\/Sleeps 6. Fantastic Location
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Fantastic location!!! Sunday to Sunday 7 night rental at HYATT SUNSET HARBOR 2 bedrooms 2 bath full kitchen and common a ...
Click For PricingExpedia
From $463 per night (USD)VRBO
Sunny Condo w\/ Entertainment, Balcony, & Great Location Near Beach - Dogs OK
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The Frontier Flat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $463 per night (USD)VRBO
From $539 per night (USD)Expedia
Poolside Studio Villa Steps from Duval!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The Poolside Studio Villa is a stand-alone Key West vacation rental that features full kitchen appliances and a sitting ...
From $539 per night (USD)Expedia
From $853 per night (USD)VRBO
Charming Condo w\/ Entertainment & Private Parking - Great In-Town Location
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Gardenia Getaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $853 per night (USD)VRBO
From $367 per night (USD)Expedia
Contemporary Seaside Cottage with a Private Hot Tub & Shared, Heated Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Heron Hideaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $367 per night (USD)Expedia
From $397 per night (USD)VRBO
Elegant Condo with Entertainment & Private Parking - Great Central Location
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Orchid Suite Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $397 per night (USD)VRBO
From $222 per night (USD)Expedia
Welcoming & Conveniently Located Dog-Friendly Home - Walk to Everything
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Olivia Street Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $222 per night (USD)Expedia
From $500 per night (USD)VRBO
Dog-friendly condo in prime location - walk to dining & sights, near the beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The Frontier Suite Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $500 per night (USD)VRBO
Click For PricingExpedia
Dante's Marina Townhouse 2 bed 1.5 bath unit with a 5 minute walk to Duval!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
A short walk, just blocks away from all the sought-after action on Duval Street and near the infamous Dante's Pool at th ...
Click For PricingExpedia
From $194 per night (USD)VRBO
Modern 2BR Condo Old Town\/Balcony & Pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
*28 day min stay* Come enjoy this fully updated 2/BR condo in the heart of Old Town. The perfect balance of being close ...
From $194 per night (USD)VRBO
From $382 per night (USD)VRBO
Heart of Downtown Key West Cottage With Off-Street Parking
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
A Historic Cigar-Makers Conch Home, privately owned by a native hospitable family in the heart of Downtown, a few minut ...
From $382 per night (USD)VRBO
From $689 per night (USD)VRBO
Duval Dream Loft | Right on Duval!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Located right in the heart of the World Famous Duval Street, enjoy a true downtown Key West experience! This un ...
From $689 per night (USD)VRBO
From $763 per night (USD)Expedia
The Collins on Duval
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 10
Summary: Located right in the heart of the World Famous Duval Street, enjoy a true downtown Key West experience! The Col ...
From $763 per night (USD)Expedia
From $146 per night (USD)VRBO
Ocean-breeze Key West Cottage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
This property recently fully renovated. Original house was built in 1892. 1 bedroom 1 bathroom apartment with hardwood f ...
From $146 per night (USD)VRBO
From $1043 per night (USD)VRBO
Southard Love - 2.5 Blocks to Downtown, Walk to Beach. 4 Bedrooms, 3 Baths
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 7
'SOUTHARD LOVE' is located on Southard Street on the corner of LOVE Lane This home is a perfect example of WHY people c ...
From $1043 per night (USD)VRBO
From $188 per night (USD)VRBO
Cottage in Paradise, Old Town. Walk to Duval & beaches. Hot tub, Pet Friendly.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Our home is in Old Town Key West, within walking distance of Duval Street, White Street art galleries, restaurants, bars ...
From $188 per night (USD)VRBO
From $308 per night (USD)VRBO
ShangriLa Suite \/ Queen Studio \/ Sleeps 2
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Mingle with other guests around the tropical gardens surrounding the heated pool and sundeck creating the perfect settin ...
From $308 per night (USD)VRBO
From $349 per night (USD)VRBO
LA PUERTA ROSA~Charming 3 bed\/2 bath Conch Home in Old Town Key West!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
**Please note that this rental only allows for payment by check/E-check. Credit card payment will be subject to additio ...
From $349 per night (USD)VRBO
From $174 per night (USD)VRBO
Peaceful One Bedroom Retreat Located Blocks From Duval Street And The Harbor.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This one bedroom loft apartment with full kitchen and laundry has everything you need for an extended stay! Located on o ...
From $174 per night (USD)VRBO
From $1455 per night (USD)VRBO
Duval's Duet on Duval
- Bedrooms:
- 2
- Bathrooms:
- 6
- Sleeps:
- 18
Summary: Located right in the heart of the World Famous Duval Street, enjoy a true downtown Key West experience! Duval's ...
From $1455 per night (USD)VRBO
From $301 per night (USD)Expedia
Old Town home a short walk to Duval\/Couples Oasis
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Add this listing to your wishlist by clicking the ♥ in the upper right hand corner. This 1 bedroom/1.5 bathroom ...
From $301 per night (USD)Expedia
From $341 per night (USD)VRBO
Relaxing island home\/Great location\/Stylish
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Only 4 short blocks to Duval, this 1 bedroom/1.5 bathroom home is walking distance to your favorite Key West sp ...
From $341 per night (USD)VRBO
From $361 per night (USD)Expedia
NEW! Completely Renovated \/ Close to Everything
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Located in the Heart of Historic Old Town Monthly Rental Pet Friendly.Up to 2 dogs, 40 lbs. max each. La Cala is a Newl ...
From $361 per night (USD)Expedia
From $671 per night (USD)VRBO
Historic, Cozy, prime location with amazing pool and garden in Historic Seaport
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Looking for a little piece of Key West Paradise? Well, this is it! This stunning cottage is only steps away from the His ...
From $671 per night (USD)VRBO
From $394 per night (USD)Expedia
The Emelina, Key West Monthly Rental
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The Emelina is located in a beautiful historic home. This unit is luxuriously appointed with elegant materials and impe ...
From $394 per night (USD)Expedia
From $180 per night (USD)VRBO
NEW MONTHLY RENTAL, Old Town, Duplex, private backyard, pets welcome
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Sea Monkey and The Mermaid. Our home is a duplex located in Old Town and full of Key West charm. Walk to a ...
From $180 per night (USD)VRBO
From $151 per night (USD)Expedia
Conch Cottage, Near Downtown! | Quiet w\/ Shared Pool
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Escape to this cozy Key West Cottage and enjoy all the island has to offer! Whether you plan to stay in or go o ...
From $151 per night (USD)Expedia
From $692 per night (USD)VRBO
Enjoy Old Town Key West in this Beautifully furnished house
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
We recently bought this house because we LOVE Key West! It is a 2 story Key West style house. The bedrooms are upstair ...
From $692 per night (USD)VRBO
From $175 per night (USD)VRBO
Old Town. Spacious 1 bedroom, private heated pool, yard, deck, covered porch.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Old Town. Spacious 1 bedroom on 1st floor. Only 2 other condos in compound. On desirable Frances Street, just 3 blocks ...
From $175 per night (USD)VRBO
From $360 per night (USD)VRBO
Yellow Room at Grand Maloney by Brightwild
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: The Grand Maloney Hotel is a new boutique hotel located in the heart of downtown Key West. Our signature red br ...
From $360 per night (USD)VRBO
From $359 per night (USD)Expedia
Blue Room at the Grand Maloney by Brightwild
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: The Grand Maloney Hotel is a new boutique hotel located in the heart of downtown Key West. Our signature red br ...
From $359 per night (USD)Expedia
From $391 per night (USD)VRBO
Green Room at the Grand Maloney by Brightwild
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: The Grand Maloney Hotel is a new boutique hotel located in the heart of downtown Key West. Our signature red br ...
From $391 per night (USD)VRBO
From $468 per night (USD)Expedia
Poolside King Room Steps from Duval!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The Poolside King Room is a hotel-style room adjacent to the pool. It can sleep up to four persons, two in the king-size ...
From $468 per night (USD)Expedia
From $506 per night (USD)VRBO
Loft Villa Steps from Duval!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Looking for where to stay in Key West, Florida? Look no further! Our One Bedroom Loft Villa features a queen bed downsta ...
From $506 per night (USD)VRBO
From $417 per night (USD)Expedia
Poolside Queen Room Steps from Duval!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The Poolside Queen Room is a hotel-style bedroom and bath unit that offers the amenities of our Key West villas for thos ...
From $417 per night (USD)Expedia
From $542 per night (USD)VRBO
One Bedroom Deck Villa Steps from Duval!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Enjoy a wonderful Key West accommodation. Our One Bedroom Deck Villa features a living room, a separate bedroom with ki ...
From $542 per night (USD)VRBO
From $181 per night (USD)Expedia
MONTHLY RENTAL, Old Town, Duplex, private yard, 2 BR\/2 BA
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Sea Monkey and The Mermaid! Our home is a duplex located in Old Town and full of Key West charm. Both unit ...
From $181 per night (USD)Expedia
From $243 per night (USD)VRBO
WINDSONG DELIGHT - Cute house on Windsor Ln
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
This two story townhome has both location and amenities for a wonderful month long visit to Key West. Secluded at the r ...
From $243 per night (USD)VRBO
Click For PricingExpedia
Penthouse Suite @ KW, Galleon Resort, Not Available in 2024-2025
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
The Galleon Resort is the best location - Old Town Key West, walking location to all the bars, many high quality restaur ...
Click For PricingExpedia
From $647 per night (USD)VRBO
Galleon Resort beach hotel luxury in Old Town Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
This is a large (1245 SF) 1BR/1BA condo on the 6th floor of the Galleon Resort & Marina.....and is a one of a kind. It ...
From $647 per night (USD)VRBO
From $1992 per night (USD)Expedia
**THE ZESTY LIME @ OLD TOWN** Beautifully Restored Home + LAST KEY SERVICES…
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Key West is k ...
From $1992 per night (USD)Expedia
From $843 per night (USD)VRBO
Poolside Cottage 2 Bedroom, 2 Bath with Full Kitchen and Pullout Sofa
- Bedrooms:
- 0
- Bathrooms:
- 0
- Sleeps:
- 6
This comfortable two story, two bedroom standalone cottage’s first floor features a private bedroom (with queen bed and ...
From $843 per night (USD)VRBO
From $651 per night (USD)VRBO
Tropical Suite sleeps 4
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This newly renovated 2nd story unit features a living room with soaring lofted ceilings, a modern kitchenette and a top ...
From $651 per night (USD)VRBO
From $412 per night (USD)VRBO
Paradise on Pine in Key West
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Paradise on Pine, is a picture perfect home that sits high above this lovely one way street with an inviting front porc ...
From $412 per night (USD)VRBO
From $422 per night (USD)Expedia
SECOND WIND ~ Charming 2 Bedroom, 2 Bathroom Home w\/ Pool!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
CATCH YOUR SECOND WIND… Unplug in this newly renovated and elegant refuge, a place of tranquility with an island ambianc ...
From $422 per night (USD)Expedia
From $338 per night (USD)VRBO
Lock-Out Unit at the Galleon Resort - Best Resort Location In KW
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Studio(lock-out) for rent 5th floor. The Galleon Resort has its own marina, fishing charters on-site, tiki bar that serv ...
From $338 per night (USD)VRBO
From $290 per night (USD)Expedia
Historic Charm, Heart of Old Town, Tropical Paradise, Key West Quaint.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
3-Bedroom, 1.5-Bath Historic Conch House in the Heart of Old Town Key West This charming Conch house features a queen b ...
From $290 per night (USD)Expedia
From $722 per night (USD)VRBO
A BANANA REPUBLIC in Old Town Key West
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
A Banana Republic Gem. This Old Town house may be the nicest property in Key West. Totally redone and professionally dec ...
From $722 per night (USD)VRBO
From $4724 per night (USD)Expedia
STARS AND STRIPES ~ Magnificent Home Located In The Heart of Old Town!
- Bedrooms:
- 4
- Bathrooms:
- 9
- Sleeps:
- 20
ABUNDANCE IN OLD TOWN... Majestic home in the Historic Seaport area of Old Town Key West. This is THE house to bring eve ...
From $4724 per night (USD)Expedia
From $322 per night (USD)VRBO
~ MY HAPPY PLACE ~ A charmingly beautiful treasure in a perfect location!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local ...
From $322 per night (USD)VRBO
From $205 per night (USD)VRBO
Dreamworks Conch Cottage
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
PEACEFUL RETREAT... A quintessential Key West cottage in the heart of Old Town and only a few blocks away from Higgs Bea ...
From $205 per night (USD)VRBO
From $571 per night (USD)VRBO
Tropical Seclusion On Old Town Lane With Pool And Detached Bungalow. Sleeps 6
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Hidden at the end of one of the most beautiful lanes in Old Town, Casa Escondida awaits you with its tropical seclusion ...
From $571 per night (USD)VRBO
From $1842 per night (USD)Expedia
**THE TOASTED COCONUT @ OLD TOWN** Fully Restored + Pool + LAST KEY SERVICES…
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Throughout Ke ...
From $1842 per night (USD)Expedia
From $197 per night (USD)VRBO
Secret Casita: Relaxing 2BD\/2BA escape RealKeyWest
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
WELCOME TO SECRET CASITA! This hidden gem is a wonderful way to embrace the Key West laid-back lifestyle. This first-f ...
From $197 per night (USD)VRBO
From $266 per night (USD)VRBO
Studio overlooking historic Key West waterfront.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Overlooking the Historic Key West Bight, this bright and clean studio features a fully equipped kitchen, renovated bathr ...
From $266 per night (USD)VRBO
From $484 per night (USD)VRBO
Key West Cottage Located in Old Town Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Key West Cottage. Located in the Historic Seaport Area of Old Town. 2 BR. 2 BR. Three HD TV's. Streaming on every TV. W ...
From $484 per night (USD)VRBO
From $678 per night (USD)Expedia
Harbor Walk Hideaways - Atocha Cottage | Downtown
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Atocha is part of the quiet complex called "Harbor Walk Hideaways," located in the Historic Seaport district of ...
From $678 per night (USD)Expedia
From $1441 per night (USD)VRBO
NEW LISTING Old Town Private Pool in Garden Of Eden tropical spa-like Oasis
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
( NEW LISTING SEE VRBO LISTING 1223004 for reviews on my other property ) Newly renovated, invitingly spacious, serenely ...
From $1441 per night (USD)VRBO
From $3772 per night (USD)Expedia
Contra House | Luxury Home w\/Pool
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
Summary: This captivating modern home with a striking exterior and vaulted ceilings makes for the perfect vacation home. ...
From $3772 per night (USD)Expedia
From $471 per night (USD)VRBO
Island Time Hideaway at Old Town Key West Historic Seaport - 3 Blocks to Duval
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
LOCATION, LOCATION, LOCATION! Located on a picturesque Old Town street, in one of the most desirable areas of the hist ...
From $471 per night (USD)VRBO
From $289 per night (USD)VRBO
OLD TOWN SUMMER’24! Private pool, stunning decor, 5-star reviews. NO PETS
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Sun yourself on the back patio, then cool off in the pool. Rinse off in the outdoor shower with hot/cold running water. ...
From $289 per night (USD)VRBO
From $196 per night (USD)VRBO
GOOD FEELIN ~ Charming 2 BR\/2 Ba Home Conveniently Located w\/ Parking!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
SPOIL YOURSELF… Come unwind in this tropical retreat allowing for your delightful Key West story to unfold. Sounds of sw ...
From $196 per night (USD)VRBO
From $187 per night (USD)Expedia
POSITIVE VIBES ~ Charming 2 BR, 1 Ba Cottage in Peaceful Area w\/ Parking!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
LOST ON ISLAND TIME… Treasure your time together within this charming Key West cottage tucked away on this peaceful and ...
From $187 per night (USD)Expedia
From $336 per night (USD)VRBO
GOOD VIBES ~ 2 Cottages w\/ 4 BR\/3 Ba w\/ Outdoor Oasis and Parking!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
MEMORIES TO LAST A LIFETIME… This unique set of 2 charming, Conch style homes provide the perfect compound setting for y ...
From $336 per night (USD)VRBO
From $302 per night (USD)Expedia
Downtown Conch House-Historic Old Town 3 bedroom, 3 bath home w\/private pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
AGE REQUIREMENT: Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their ...
From $302 per night (USD)Expedia
From $2754 per night (USD)VRBO
**GOOD VIBRATIONS @ OLD TOWN** Unique Villa & Pool + LAST KEY SERVICES…
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Key West has ...
From $2754 per night (USD)VRBO
From $3049 per night (USD)Expedia
Bananas Foster, Downtown | Epic Guesthouse!
- Bedrooms:
- 8
- Bathrooms:
- 9
- Sleeps:
- 19
Summary: Palm trees, sunsets, and the blissful pace of island time will all be yours when you stay at this large histori ...
From $3049 per night (USD)Expedia
From $324 per night (USD)VRBO
~Bahari House, Seaport~Walk to the harbor from this quintessential conch home
- Bedrooms:
- 3
- 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 $324 per night (USD)VRBO
From $736 per night (USD)VRBO
Architect's Personal Residence, Private Pool, 1 Blk. to Duval
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Completed in 1992, this two bedroom two bath home was designed by a local architect for the relaxed Key West tropical li ...
From $736 per night (USD)VRBO
From $390 per night (USD)VRBO
Updated home with private pool, patio, & grill in enclosed tropical backyard
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Margaret Street Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $390 per night (USD)VRBO
From $399 per night (USD)Expedia
Hip Studio in Old Town - Walk to the Beach!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Location, location, location! Situated in the heart of the Cuban district, steps from arguably the best 'con leche' in ...
From $399 per night (USD)Expedia
From $201 per night (USD)VRBO
Conch Republic Studio - Key West Millionaires Row
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
In the center of Key West's prestigious "Millionaires Row," Conch Republic Studio is a tranquil getaway for one or a cou ...
From $201 per night (USD)VRBO
From $394 per night (USD)Expedia
Galleon Resort Efficiency in the old town
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This efficiency is located on the 5th floor of the Galleon Resort. One of only two efficiencies with both a king size b ...
From $394 per night (USD)Expedia
From $362 per night (USD)VRBO
Galleon Resort available Jan 4-18 2025
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
You can book 1 or both weeks. Saturday-Saturday. This unit has a queen size bed. Updated ceramic stand up shower. The un ...
From $362 per night (USD)VRBO
From $928 per night (USD)VRBO
Near Duval - Tiki Bar - Private Beach - 2BR Condo - Old Town Key West - Sleeps 6
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Located in the heart of Old Town Key West. This resort overlooks the Gulf of Mexico with a private marina, private beach ...
From $928 per night (USD)VRBO