Fleming Key Rentals
- From $275 per night (USD)
VRBO
~ POINCIANA TREETOP ~ Casual second floor duplex 2 blocks from Duval Street!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
THE PROPERTY: Located on a teeny tiny quiet lane, this comfortably furnished second-floor duplex home comes with Key Wes ...
From $275 per night (USD)VRBO
- From $1280 per night (USD)
VRBO
Very Rare-The Galleon 3 King Bd, 3 Bath w\/ 4th king bd in loft + sleeper sofa
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
The Galleon Resort in Key West is a Perfect Resort for you, your Guests and your Family. The unit is spacious and very b ...
From $1280 per night (USD)VRBO
- From $200 per night (USD)
VRBO
Old Town! Spacious Condo in Historic Home w\/Pool!
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Tony's Conch Retreat is a spacious updated condo is located in a historic home on William Street that was converted into ...
From $200 per night (USD)VRBO
- From $1136 per night (USD)
VRBO
Havana Lane: An updated classic conch cottage with still a rustic edge!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Enter the private courtyard of the home, to a lush tropical oasis. The large, free form pool with coral stone patio mak ...
From $1136 per night (USD)VRBO
- From $238 per night (USD)
VRBO
**MAISON TROPICALE @ OLD TOWN** Historic Home + LAST KEY SERVICES...
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Imagine a tra ...
From $238 per night (USD)VRBO
- From $271 per night (USD)
Expedia
**VILLA OLIVIETTA @ SOLARES HILL** Upscale Home & Pool + LAST KEY SERVICES...
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! This ultimate ...
From $271 per night (USD)Expedia
- From $859 per night (USD)
VRBO
**THE CONTENTED CRANE @ 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 $859 per night (USD)VRBO
- From $1250 per night (USD)
Expedia
**STAR OF THE SEAPORT @ OLD TOWN** Huge Home & Pool + LAST KEY SERVICES...
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! For a truly o ...
From $1250 per night (USD)Expedia
- From $332 per night (USD)
VRBO
**CASA OLIVIANA @ SOLARES HILL** Grand Home & Pool + LAST KEY SERVICES...
- Bedrooms:
- 7
- Bathrooms:
- 6
- Sleeps:
- 12
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Finally, a la ...
From $332 per night (USD)VRBO
- From $360 per night (USD)
VRBO
COLONY CALYPSO - A quaint 1 Bedroom Cottage just two blocks to Duval
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Part of a small collection of cottages known as The Colony, this quaint cottage sits to the back of the property and is ...
From $360 per night (USD)VRBO
- From $278 per night (USD)
VRBO
Quaint, Quiet & Convenient - CasaBianca is The Perfect Old Town Sanctuary
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to CasaBianca! Here you'll find the character & charm of Old Town blended perfectly with all the modern amenitie ...
From $278 per night (USD)VRBO
- From $213 per night (USD)
Expedia
**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 $213 per night (USD)Expedia
- From $995 per night (USD)
VRBO
**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 $995 per night (USD)VRBO
- From $1694 per night (USD)
Expedia
**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 $1694 per night (USD)Expedia
- From $741 per night (USD)
VRBO
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 $741 per night (USD)VRBO
- From $717 per night (USD)
Expedia
**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 $717 per night (USD)Expedia
- From $1393 per night (USD)
VRBO
**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 $1393 per night (USD)VRBO
- From $420 per night (USD)
Expedia
**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 $420 per night (USD)Expedia
- From $780 per night (USD)
VRBO
**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 $780 per night (USD)VRBO
- From $483 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 $483 per night (USD)VRBO
- From $144 per night (USD)
VRBO
Bright Condo with Homey Feel, Entertainment & Private Parking - Beach Nearby
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Jasmine Suite Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $144 per night (USD)VRBO
- From $326 per night (USD)
Expedia
Studio Condo w\/ Entertainment, Full Kitchen & Private Parking - Central Location
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 2
Hibiscus Hideaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $326 per night (USD)Expedia
- From $263 per night (USD)
VRBO
Tropical Escape with Central Locale, Private Hot Tub, WiFi, and Shared Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Flamingo Hideaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $263 per night (USD)VRBO
- From $1075 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 $1075 per night (USD)Expedia
- From $171 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 $171 per night (USD)VRBO
- From $344 per night (USD)
VRBO
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 $344 per night (USD)VRBO
- From $500 per night (USD)
VRBO
The Galleon Resort Best Resort Location in KW
- Bedrooms:
- 2
- Bathrooms:
- 2
- 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 $500 per night (USD)VRBO
- From $399 per night (USD)
VRBO
Pelican Landing Bermuda-2bedroom waterfront condo w\/boat slip, parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their parents and prim ...
From $399 per night (USD)VRBO
- From $536 per night (USD)
VRBO
2 bdrm Condo w\/ boat slip Pelican Landing Bonaire
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Our beautiful waterfront condos have a range of room types to suite your every need. Whether you want a suite for two or ...
From $536 per night (USD)VRBO
- From $199 per night (USD)
VRBO
Banyan Court downtown condo- 2 bedroom, 2 bath, walkable, parking, pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their parents and prim ...
From $199 per night (USD)VRBO
- From $510 per night (USD)
VRBO
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 $510 per night (USD)VRBO
- From $256 per night (USD)
Expedia
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 $256 per night (USD)Expedia
- From $435 per night (USD)
VRBO
Pelican Landing Dominica-2bedroom waterfront condo w\/boat slip, parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their parents and prim ...
From $435 per night (USD)VRBO
- From $486 per night (USD)
VRBO
Pelican Landing Falmingo-2bedroom waterfront condo w\/boat slip, parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their parents and prim ...
From $486 per night (USD)VRBO
- From $250 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
Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their parents and prim ...
From $250 per night (USD)VRBO
- From $315 per night (USD)
Expedia
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 $315 per night (USD)Expedia
- Click For Pricing
Expedia
Fleming-O 2 bedrooms | 1 bath | sleeps up to 6
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Fleming-O (pronounced “Flamingo”) is located on one-way Fleming Street in the middle of historic Old Town Key West and o ...
Click For PricingExpedia
- From $686 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 $686 per night (USD)VRBO
- From $240 per night (USD)
VRBO
Oasis in Old Town - private heated pool
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
Our sweet ‘conch’ cottage in old town Key West has been completely redesigned and custom crafted by 2 architects as our ...
From $240 per night (USD)VRBO
- Click For Pricing
Expedia
7 Nights - Hyatt Sunset Harbor 2 bed\/2bath\/Kitchen\/Sleeps 6. Fantastic Location
- Bedrooms:
- 2
- Bathrooms:
- 2
- 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 $70 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 $70 per night (USD)VRBO
- From $349 per night (USD)
Expedia
Poolside Studio Villa Steps from Duval!
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 2
The Poolside Studio Villa is a stand-alone Key West vacation rental that features full kitchen appliances and a sitting ...
From $349 per night (USD)Expedia
- From $59 per night (USD)
VRBO
Charming Condo w\/ Entertainment & Private Parking - Great In-Town Location
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Gardenia Getaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $59 per night (USD)VRBO
- From $138 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 $138 per night (USD)Expedia
- From $270 per night (USD)
VRBO
Elegant Condo with Entertainment & Private Parking - Great Central Location
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Orchid Suite Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $270 per night (USD)VRBO
- From $208 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 $208 per night (USD)Expedia
- From $191 per night (USD)
VRBO
Dog-friendly condo in prime location - walk to dining & sights, near the beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Frontier Suite Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $191 per night (USD)VRBO
- Click For Pricing
Expedia
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 $185 per night (USD)
VRBO
Modern 2BR Condo Old Town\/Balcony & Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Come enjoy this fully updated 2/BR condo in the heart of Old Town. The perfect balance of being close to all the action ...
From $185 per night (USD)VRBO
- From $336 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 $336 per night (USD)VRBO
- Click For Pricing
Expedia
Hidden Oasis- 1 bedroom 1 bath in Old Town
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Tucked among a colony of freestanding Conch style cottages, amid lush tropical landscaping, sits the newly renovated Hid ...
Click For PricingExpedia
- From $450 per night (USD)
Expedia
Duval Dream Loft by Brightwild | Right on Duval!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
Summary: Located right in the heart of the World Famous Duval Street, enjoy a true downtown Key West experience! This un ...
From $450 per night (USD)Expedia
- From $436 per night (USD)
VRBO
The Collins on Duval by Brightwild
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 10
Summary: Located right in the heart of the World Famous Duval Street, enjoy a true downtown Key West experience! The Col ...
From $436 per night (USD)VRBO
- From $109 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 $109 per night (USD)VRBO
- From $800 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 $800 per night (USD)VRBO
- From $299 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 $299 per night (USD)VRBO
- From $209 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 $209 per night (USD)VRBO
- From $270 per night (USD)
VRBO
LA PUERTA ROSA~Charming 3 bed\/2 bath Conch Home in Old Town Key West!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
**Please note that this rental only allows for payment by check/E-check. Credit card payment will be subject to additio ...
From $270 per night (USD)VRBO
- Click For Pricing
Expedia
Casa Loca- 3 bedroom | 2.5 bath | sleeps up to 8 with private pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Casa Loca is perfect for guests who want to enjoy the finest Key West has to offer! The perfect location, less than one ...
Click For PricingExpedia
- From $150 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 $150 per night (USD)VRBO
- From $849 per night (USD)
VRBO
Duval's Duet on Duval by Brightwild
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 18
Summary: Located right in the heart of the World Famous Duval Street, enjoy a true downtown Key West experience! Duval's ...
From $849 per night (USD)VRBO
- Click For Pricing
VRBO
Charming House - 3 Bedroom 1 Bath with pool.
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Quaint property on the edge of Old Town. Minutes walk to White street with cool galleries, yoga studios, restaurants and ...
Click For PricingVRBO
- From $260 per night (USD)
VRBO
Old Town home a short walk to Duval\/Couples Oasis
- Bedrooms:
- 2
- Bathrooms:
- 1
- 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 $260 per night (USD)VRBO
- From $230 per night (USD)
Expedia
Relaxing island home\/Great location\/Stylish
- Bedrooms:
- 2
- Bathrooms:
- 1
- 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 $230 per night (USD)Expedia
- From $369 per night (USD)
VRBO
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 ...
From $369 per night (USD)VRBO
- From $350 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 $350 per night (USD)VRBO
- From $134 per night (USD)
VRBO
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 $134 per night (USD)VRBO
- Click For Pricing
Expedia
Osprey- 1 Bed\/1 Bath Nightly Rental
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to Osprey—a beautiful studio in the heart of Old Town Key West! Ideally located at the Colony on Olivia Street. ...
Click For PricingExpedia
- From $151 per night (USD)
VRBO
NEW MONTHLY RENTAL, Old Town, Duplex, private backyard, pets welcome
- Bedrooms:
- 2
- Bathrooms:
- 2
- 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 $151 per night (USD)VRBO
- Click For Pricing
Expedia
Conch Cottage by Brightwild | 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 ...
Click For PricingExpedia
- From $600 per night (USD)
VRBO
Enjoy Old Town Key West in this Beautifully furnished house
- Bedrooms:
- 2
- Bathrooms:
- 2
- 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 $600 per night (USD)VRBO
- From $166 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 $166 per night (USD)VRBO
- From $255 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 $255 per night (USD)VRBO
- From $297 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 $297 per night (USD)Expedia
- From $309 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 $309 per night (USD)VRBO
- From $299 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 $299 per night (USD)Expedia
- From $399 per night (USD)
VRBO
Loft Villa Steps from Duval!
- Bedrooms:
- 1
- Bathrooms:
- 0
- 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 $399 per night (USD)VRBO
- From $249 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 $249 per night (USD)Expedia
- From $399 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 $399 per night (USD)VRBO
- From $200 per night (USD)
Expedia
MONTHLY RENTAL, Old Town, Duplex, newly renovated, private backyard
- 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 $200 per night (USD)Expedia
- From $337 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 $337 per night (USD)VRBO
- Click For Pricing
Expedia
Price Reduction!!! Penthouse Suite @ KW, Galleon Resort, Avail 6\/29 - 7\/6\/2024
- Bedrooms:
- 2
- Bathrooms:
- 3
- 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 $106 per night (USD)
VRBO
Key Limetini: Your Charming Studio Retreat for Exploring Key West, Near Beaches and Duval Street
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 2
Welcome to Key Limetini - Your Key West Studio Retreat! Key Limetini is perfectly positioned between the vibrant White S ...
From $106 per night (USD)VRBO
- From $395 per night (USD)
Expedia
Galleon Resort beach hotel luxury in Old Town Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- 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 $395 per night (USD)Expedia
- From $835 per night (USD)
VRBO
**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 $835 per night (USD)VRBO
- From $275 per night (USD)
Expedia
Historic Caroline Street Condo!1 Bedroom 2 Bath, Pool, Amazing Old Town Location
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
The gracious building at 616 Caroline Street, exquisitely renovated into 6 condominiums, claims a long and proud history ...
From $275 per night (USD)Expedia
- Click For Pricing
VRBO
Townhouse Suite with 1 Bed, 1 Bath, Kitchen, and Pullout Sofa
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This two story town house features a first floor living room with queen sofa bed, full kitchen and double French doors o ...
Click For PricingVRBO
- From $350 per night (USD)
Expedia
Paradise on Pine in Key West
- Bedrooms:
- 3
- Bathrooms:
- 3
- 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 $350 per night (USD)Expedia
- From $197 per night (USD)
VRBO
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 $197 per night (USD)VRBO
- Click For Pricing
VRBO
Galleon Key West Resort - Waterfront Marina 2-Bedroom Suite + Beach + Amenities
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Best view in Key West! Sitting atop the Galleon Resort in a penthouse room with a clear view of the Galleon Marina and h ...
Click For PricingVRBO
- From $330 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 $330 per night (USD)VRBO
- From $306 per night (USD)
Expedia
Historic Charm, Heart of Old Town, Tropical Paradise, Key West Quaint.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
3 Bedroom 1 & half bath Historic Conch House in the Heart of Old Town Key West Queen in the Master, 1 Queen in 1st guest ...
From $306 per night (USD)Expedia
- From $483 per night (USD)
VRBO
A BANANA REPUBLIC in Old Town Key West
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
A Banana Republic Gem. This Old Town house may be the nicest property in Key West. Totally redone and professionally dec ...
From $483 per night (USD)VRBO
- From $1754 per night (USD)
VRBO
STARS AND STRIPES ~ Magnificent Home Located In The Heart of Old Town!
- Bedrooms:
- 4
- Bathrooms:
- 8
- 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 $1754 per night (USD)VRBO
- From $208 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 $208 per night (USD)VRBO
- From $175 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 $175 per night (USD)VRBO
- Click For Pricing
VRBO
Welcome Aboard! Prime location in Key West on a 46' Luxury Catamaran
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Join us on a 46' luxury sailing catamaran, The Space Between, enjoying all the comforts of home and the added beauty and ...
Click For PricingVRBO
- From $373 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 $373 per night (USD)VRBO
- From $861 per night (USD)
VRBO
**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 $861 per night (USD)VRBO
- From $140 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 $140 per night (USD)VRBO