Fleming Key Rentals
From $978 per night (USD)VRBO
**OLD TOWN OASIS @ THE ANNEX** Oceanside 2BR\/2BA Condo & Pool + LAST KEY SERVICE
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! OLD TOWN OASI ...
From $978 per night (USD)VRBO
From $231 per night (USD)Expedia
Cozy studio cottage in Old Town Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Cute Studio cottage with additional sleeping loft. Nicely landscaped shared pool and outside area. Walking distance to ...
From $231 per night (USD)Expedia
From $1018 per night (USD)VRBO
Heart of Key West - 2BR Waterfront at the Galleon Resort
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Minimum Age: 25 years old Pet Policy: No Pets An ID and credit card for a refundable security deposit will be required. ...
From $1018 per night (USD)VRBO
Click For PricingExpedia
Little Casita: Key West Monthly rental Close to Duval - RealKeyWest
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
WELCOME TO LITTLE CASITA! If looking for the perfect couple’s retreat, look no further! This one bedroom, one bath hi ...
Click For PricingExpedia
From $369 per night (USD)VRBO
Welcome to the Shady Palms - Private Pool - RealKeyWest
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Step into this beautifully restored and redecorated 1933 Key West home. This first-floor home has Bahama shutters throug ...
From $369 per night (USD)VRBO
From $901 per night (USD)VRBO
Amazing Stay, Great Location! Bike Rental, Pools, Onsite Bar
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $901 per night (USD)VRBO
From $459 per night (USD)VRBO
Luxurious Vacation! Pools, Tiki Bar, Bike Rental
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $459 per night (USD)VRBO
From $585 per night (USD)Expedia
TROPICAL PROPERTIES VACATION RENTAL - KEY WEST
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
****This property requires a minimum stay of 28 nights in the same calendar month**** ***Brand New Pool with waterfall, ...
From $585 per night (USD)Expedia
From $286 per night (USD)VRBO
Tropical Jewel: Historic Seaport Oldtown - 2BR\/2BA - Pool - RealKeyWest
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
WELCOME TO TROPICAL JEWEL! Near all the action of the historic seaport and Duval Street, you can get out into the cit ...
From $286 per night (USD)VRBO
From $783 per night (USD)VRBO
Getaway in Key West: Tranquil Room w\/ Balcony | Resort w\/ Pool Access
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $783 per night (USD)VRBO
From $851 per night (USD)VRBO
Old Town Key West Family Retreat | Spacious Room w\/ Balcony | Parking Onsite
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $851 per night (USD)VRBO
From $401 per night (USD)Expedia
Casa Verde - Perfection in a monthly rental - private pool - RealKeyWest
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
The moment you walk thru the door you are greeted by soothing tropical colors and high vaulted ceilings. The large mast ...
From $401 per night (USD)Expedia
From $521 per night (USD)VRBO
**SEAPORT SENSATION @ OLD TOWN VILLAS** Condo & 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! It is not so ...
From $521 per night (USD)VRBO
From $577 per night (USD)Expedia
**COASTAL LOVING @ OLD TOWN** Chic 4BR Home & Pool + LAST KEY SERVICES...
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! If you’re loo ...
From $577 per night (USD)Expedia
From $404 per night (USD)VRBO
Runaway Bills | 3 Bed, 1 Bath
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 6
This stylish Conch Home is tucked away on a quiet lane in Old Town Key West. Surrounded by distinctive neighborhoods thi ...
From $404 per night (USD)VRBO
From $561 per night (USD)Expedia
Sunset South: First Floor 2 Bedroom 1 Bath Condo at Bayfront Suites & Marina
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $561 per night (USD)Expedia
Click For PricingVRBO
Sunset views at the Galleon
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
You will be back year after year! Unit features full kitchen with Master King, Guest Twin Beds, and Pull out Sleeper Sof ...
Click For PricingVRBO
From $1108 per night (USD)Expedia
Upper Bayview North: Waterfront 4 Bedroom Condo at Bayfront Suites & Marina
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $1108 per night (USD)Expedia
From $941 per night (USD)VRBO
ISLAND TIME - 5 Bed\/3 Bath OldTown Complex - MONTHLY - Private pool
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
WELCOME TO ISLAND TIME! Key West Island Time is a rare find in old town Key West. It is a total of 5 bedrooms and three ...
From $941 per night (USD)VRBO
From $1038 per night (USD)Expedia
Upper Bayview South: Waterfront 4 Bedroom Condo at Bayfront Suites & Marina
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $1038 per night (USD)Expedia
From $934 per night (USD)VRBO
Middle Sunset: 3 Bedroom 3 Bath Luxury Condo at Bayfront Suites & Marina
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $934 per night (USD)VRBO
From $1026 per night (USD)Expedia
Bayview North One: Waterfront 4 Bedroom 4 Bath Condo at Bayfront Suites
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $1026 per night (USD)Expedia
From $1054 per night (USD)VRBO
Sunset North: Luxury 4 Bedroom 4.5 Bath Condo at Bayfront Suites & Marina
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $1054 per night (USD)VRBO
From $982 per night (USD)Expedia
Upper Sunset South: Luxury 3 Bedroom Condo at Bayfront Suites & Marina
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $982 per night (USD)Expedia
From $1077 per night (USD)VRBO
Bayview South: 4 Bedroom 3 Bath Waterfront Condo at Bayfront Suites & Marina
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $1077 per night (USD)VRBO
From $985 per night (USD)Expedia
Upper Sunset North: Luxury 4 Bedroom Condo at Bayfront Suites & Marina
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $985 per night (USD)Expedia
From $1108 per night (USD)VRBO
Bayview Middle: Waterfront 3 Bedroom Condo at Bayfront Suites & Marina
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $1108 per night (USD)VRBO
From $159 per night (USD)Expedia
coral stone
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Our apartment offers all the comforts of home, 120 paces to Duval Street - shopping, restaurants and nightlife. Near Hem ...
From $159 per night (USD)Expedia
From $387 per night (USD)VRBO
Seaport Walkabout- the best location in town
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Open to annual rental at lower rate Two hundred yards from Schooner Wharf and the seaport and steps from Pepe’s in the ...
From $387 per night (USD)VRBO
From $823 per night (USD)Expedia
~HORSE CONCH~ Amazing location with shared pool and covered balcony!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
THE PROPERTY: Enjoy your stay in the tropics at Horse Conch, part of the highly touted "Queen Conch" complex, which incl ...
From $823 per night (USD)Expedia
From $240 per night (USD)VRBO
Lush Gardens-Pool-Jacuzzi-No Contact Check-In
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
This 3 bedroom home is located one block from where Tennessee Williams home was located. The home has a true historic fl ...
From $240 per night (USD)VRBO
From $306 per night (USD)Expedia
Petite Pearl! Spacious 1 Bedroom, 1 Bath Pool Condo- RealKeyWest
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to Petite Pearl, your hidden gem nestled in the heart of the coveted Meadows district in Key West. A stone's thr ...
From $306 per night (USD)Expedia
From $655 per night (USD)VRBO
~POINCIANA GARDEN~ Casual 1st 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 first-floor duplex home comes with Key West ...
From $655 per night (USD)VRBO
From $266 per night (USD)Expedia
Old Town! Spacious Condo in Historic Home w\/Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- 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 $266 per night (USD)Expedia
From $456 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 $456 per night (USD)VRBO
From $589 per night (USD)Expedia
**VILLA OLIVIETTA @ SOLARES HILL** Upscale 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! This ultimate ...
From $589 per night (USD)Expedia
From $1856 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 $1856 per night (USD)VRBO
From $3278 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 $3278 per night (USD)Expedia
From $735 per night (USD)VRBO
**CASA OLIVIANA @ SOLARES HILL** Grand Home & Pool + LAST KEY SERVICES...
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Finally, a la ...
From $735 per night (USD)VRBO
From $383 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 $383 per night (USD)Expedia
From $2769 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 $2769 per night (USD)VRBO
From $4141 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 $4141 per night (USD)Expedia
From $1112 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 $1112 per night (USD)VRBO
From $1626 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 $1626 per night (USD)Expedia
From $4168 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 $4168 per night (USD)VRBO
From $567 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 $567 per night (USD)Expedia
From $2206 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 $2206 per night (USD)VRBO
From $1064 per night (USD)Expedia
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)Expedia
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 $198 per night (USD)Expedia
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)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 $853 per night (USD)Expedia
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)Expedia
From $367 per night (USD)VRBO
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)VRBO
From $397 per night (USD)Expedia
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)Expedia
From $222 per night (USD)VRBO
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)VRBO
From $500 per night (USD)Expedia
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)Expedia
Click For PricingVRBO
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 PricingVRBO
From $194 per night (USD)Expedia
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)Expedia
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
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 $689 per night (USD)Expedia
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)Expedia
From $763 per night (USD)VRBO
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)VRBO
From $1455 per night (USD)Expedia
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)Expedia
From $301 per night (USD)VRBO
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)VRBO
From $341 per night (USD)Expedia
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)Expedia
From $361 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 Newl ...
From $361 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 $360 per night (USD)Expedia
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)Expedia
From $359 per night (USD)VRBO
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)VRBO
From $391 per night (USD)Expedia
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)Expedia
From $468 per night (USD)VRBO
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)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 $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 $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 $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 $678 per night (USD)VRBO
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)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 $2754 per night (USD)Expedia
**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)Expedia
From $3049 per night (USD)VRBO
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)VRBO
From $324 per night (USD)Expedia
~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)Expedia
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
Click For PricingVRBO
3 blocks from waterfront and 1 block off Duval in heart of Old Town Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Want to “ Get away from it all” but still be in the heart of Olde Town Key West with everything you need right there? Th ...
Click For PricingVRBO
Click For PricingExpedia
3 blocks from waterfront and 1 block off Duval in Old Town Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Want to “ Get Away from it all” but still in the heart of Old Town Key West with everything you need within walking dist ...
Click For PricingExpedia
From $543 per night (USD)VRBO
Historic House, Gorgeous Porch, Great Location, See 5 Star Reviews
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Treat yourself, your family and friends to a grand Key West home ideal for an extended stay on the island. This wonderfu ...
From $543 per night (USD)VRBO
From $354 per night (USD)Expedia
Conch House in the Historic District
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Discover a piece of paradise with a beautiful conch home located in the historic district of Key West. 4-bedrooms, 2 ba ...
From $354 per night (USD)Expedia
Click For PricingVRBO
Luxury Galleon Resort & Marina 2 Bed\/2 Bath Marina View
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Galleon Resort is located in the heart of Old Town Key West and the Marina is one of the most desired harbors in the ...
Click For PricingVRBO
From $4559 per night (USD)Expedia
**THE LIME & THE COCONUT @ OLD TOWN** 6BR\/6BA Compound + 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! According to ...
From $4559 per night (USD)Expedia
From $209 per night (USD)VRBO
The Marguerite, 603 #3 Elizabeth Street, Old Town Key West monthly Rental
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
One bedroom, One Bathroom apartment in Old Key West. It is located upstairs with an outside entrance and has dormer ceil ...
From $209 per night (USD)VRBO
From $1328 per night (USD)Expedia
Commodore's Cove | Epic Location!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Summary: Commodore's Cove offers the best of Key West: a prime location and all the amenities of home. Up to 12 can stay ...
From $1328 per night (USD)Expedia
From $2738 per night (USD)VRBO
Commodore's Compound| HUGE Home!
- Bedrooms:
- 7
- Bathrooms:
- 10
- Sleeps:
- 24
Summary: Welcome to Commodore's Compound, an incredible 8 bed, 7 bath home in prime location situated just one short blo ...
From $2738 per night (USD)VRBO
From $1458 per night (USD)Expedia
Seaport Suite | 2nd Story Hideaway!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Summary: Situated in the heart of Old Town Key West, Seaport Suite is the perfect vacation spot for large groups of up t ...
From $1458 per night (USD)Expedia