Fleming Key Rentals
From $598 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 $598 per night (USD)VRBO
From $228 per night (USD)Expedia
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 $228 per night (USD)Expedia
From $153 per night (USD)VRBO
Old Town Getaway
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Newly redecorated by a one of Key West top interior designers!! Elegant and adorable cottage on one of the nicest lanes ...
From $153 per night (USD)VRBO
From $576 per night (USD)VRBO
Perfect Location to Key West Action! Garden View, Pool, 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 $576 per night (USD)VRBO
From $618 per night (USD)VRBO
Wonderful Stay, Amazing Location! 3 Pools, Bar, Pets Allowed!
- 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 $618 per night (USD)VRBO
From $1319 per night (USD)VRBO
Fantastic Stay, Best Location! Pool, Bar, Bike Rental, Pets Allowed
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $1319 per night (USD)VRBO
From $1319 per night (USD)VRBO
Tropical Getaway! Pool, Bar, Pet-friendly!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $1319 per night (USD)VRBO
From $674 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 $674 per night (USD)VRBO
From $733 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 $733 per night (USD)VRBO
From $200 per night (USD)Expedia
Cozy studio cottage in Old Town Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Cute Studio cottage with additional sleeping loft. Nicely landscaped shared pool and outside area. Walking distance to ...
From $200 per night (USD)Expedia
From $655 per night (USD)VRBO
Heart of Key West - 2BR Waterfront at the Galleon Resort
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to the heart of Old Town Key West. This resort overlooks the Gulf of Mexico with a private marina, private beach ...
From $655 per night (USD)VRBO
From $157 per night (USD)Expedia
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 ...
From $157 per night (USD)Expedia
From $710 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 $710 per night (USD)VRBO
From $778 per night (USD)VRBO
Dream Vacation! 3 Pools, Bar, Variety of Water Activities Nearby!
- 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 $778 per night (USD)VRBO
From $810 per night (USD)VRBO
Superb Location! Onsite Dining, 2 Blocks Away from Famous Duval Street!
- 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 $810 per night (USD)VRBO
From $628 per night (USD)VRBO
Tropical Getaway! 3 Pools, Bike Rental, Pets Allowed!
- 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 $628 per night (USD)VRBO
From $555 per night (USD)VRBO
Wonderful Beach Vacation! 3 Pools, Tiki Bar, Bike Rentals, Pets Allowed, Dining!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $555 per night (USD)VRBO
From $1138 per night (USD)VRBO
Superb Location! 3 Pools, Tiki Bar, Pet-friendly!
- 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 $1138 per night (USD)VRBO
From $5712 per night (USD)VRBO
Amazing Vacation! 4 Spacious Units! 3 Pools, Tiki Bar, Bike Rental!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $5712 per night (USD)VRBO
From $1133 per night (USD)VRBO
Luxurious Vacation! 3 Pools, Bar, Pet-friendly, 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 $1133 per night (USD)VRBO
From $665 per night (USD)VRBO
Family and Friends Vacation! Pet-friendly!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $665 per night (USD)VRBO
From $276 per night (USD)Expedia
TROPICAL PROPERTIES VACATION RENTAL - KEY WEST
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
****This property requires a minimum stay of 28 nights in the same calendar month**** ***Brand New Pool with waterfall, ...
From $276 per night (USD)Expedia
From $357 per night (USD)VRBO
Tropical Jewel: Historic Seaport Oldtown - 2BR/2BA - Pool - RealKeyWest
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
WELCOME TO TROPICAL JEWEL! Imagine yourself staying in this immaculate restored home just two blocks away from the H ...
From $357 per night (USD)VRBO
From $900 per night (USD)Expedia
The Palm Villa, Island Oasis blocks from Duval
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
BEWARE! I have been told that someone is scamming individuals by posing as me. Communicate ONLY through VRBO and make ...
From $900 per night (USD)Expedia
From $275 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 $275 per night (USD)VRBO
From $562 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 $562 per night (USD)Expedia
From $400 per night (USD)VRBO
Runaway Bills- 2 BDR house with Cottage and pool in the Key West downtown.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This stylish Conch Home is tucked away on a quiet lane in Old Town Key West. Surrounded by distinctive neighborhoods thi ...
From $400 per night (USD)VRBO
From $403 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 $403 per night (USD)Expedia
From $203 per night (USD)VRBO
★Artist Designed Old Town Getaway★
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Unwind at the comfortable 2BR 2BA condo nestled in the very heart of Old Town. Its prime location allows you to easily e ...
From $203 per night (USD)VRBO
From $499 per night (USD)Expedia
Sunset South: First Floor 2 Bedroom 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 $499 per night (USD)Expedia
From $385 per night (USD)VRBO
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 ...
From $385 per night (USD)VRBO
From $1099 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 $1099 per night (USD)Expedia
From $1116 per night (USD)VRBO
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 $1116 per night (USD)VRBO
From $819 per night (USD)Expedia
Middle Sunset: 3 Bedroom 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 $819 per night (USD)Expedia
From $1163 per night (USD)VRBO
Bayview North One: Waterfront 4 Bedroom 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 $1163 per night (USD)VRBO
From $1069 per night (USD)Expedia
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 $1069 per night (USD)Expedia
From $866 per night (USD)VRBO
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 $866 per night (USD)VRBO
From $1099 per night (USD)Expedia
Bayview South: Luxury 4 Bedroom 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 $1099 per night (USD)Expedia
From $1048 per night (USD)VRBO
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 $1048 per night (USD)VRBO
From $993 per night (USD)Expedia
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 $993 per night (USD)Expedia
From $430 per night (USD)VRBO
Hidden Gem-Key West 3/2 wading pool home with parking -RealKeyWest
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Stroll down Higgs Lane to arrive at your Old Town Key West vacation home. Unpack and unwind at this Gem of a house wh ...
From $430 per night (USD)VRBO
From $798 per night (USD)Expedia
**BEYOND BALI @ THE SEAPORT** Island Home & Pool / Near Duval + LAST KEY SERVICE
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! For a month i ...
From $798 per night (USD)Expedia
From $100 per night (USD)VRBO
coral stone Castle
- 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 $100 per night (USD)VRBO
From $219 per night (USD)VRBO
Seaport Walkabout- the best location in town
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Two hundred yards from Schooner Wharf and the seaport, and steps from Pepe’s, this completely renovated two bedroom conc ...
From $219 per night (USD)VRBO
From $139 per night (USD)VRBO
Lush Gardens-Pool-Jacuzzi-No Contact Check-In
- Bedrooms:
- 2
- Bathrooms:
- 3
- 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 $139 per night (USD)VRBO
From $191 per night (USD)Expedia
Petite Pearl! Spacious 1 Bedroom, 1 Bath Pool Condo- RealKeyWest
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to Petite Pearl, a chic and stylish condo tucked away in the coveted Meadows neighborhood of Key West. This prim ...
From $191 per night (USD)Expedia
From $395 per night (USD)VRBO
~HORSE CONCH~ Adorable Apt in PERFECT Location w/ Breathtaking Pool!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
THE PROPERTY: Horse Conch is a Key West hidden gem in perhaps the best location you could imagine. The one-bedroom vacat ...
From $395 per night (USD)VRBO
From $330 per night (USD)Expedia
Luxury Condominium in Old Town | Monthly Rental at Steamplant Key West
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
5 star luxury condo with 2 bedrooms and 2.5 baths. This spacious 2-story condominium has plenty of room for relaxing ...
From $330 per night (USD)Expedia
From $235 per night (USD)VRBO
*New Listing* 2/2 with a sleeping loft, off street parking and a pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
For 3d tour type into your browser - bit.ly/3uSKrPd The Location Located in Old Town Key West, just a five-minute ri ...
From $235 per night (USD)VRBO
From $328 per night (USD)Expedia
~POINCIANA GARDEN~ Casual 1st floor duplex 2 blocks from Duval Street!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
THE PROPERTY: This comfortably furnished first-floor duplex home comes with Key West charm and contemporary touches. To ...
From $328 per night (USD)Expedia
From $263 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 $263 per night (USD)VRBO
From $505 per night (USD)Expedia
**HEAVENLY ZEN @ THE SEAPORT** Lavish 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! In the Histor ...
From $505 per night (USD)Expedia
From $406 per night (USD)VRBO
**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 $406 per night (USD)VRBO
From $1135 per night (USD)Expedia
**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 $1135 per night (USD)Expedia
From $1940 per night (USD)VRBO
**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 $1940 per night (USD)VRBO
From $512 per night (USD)Expedia
**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 $512 per night (USD)Expedia
From $229 per night (USD)VRBO
**LA CASITA EN CIMA @ OLD TOWN** Quaint Cottage By Duval + 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! This quaint l ...
From $229 per night (USD)VRBO
From $343 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 $343 per night (USD)Expedia
From $1338 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 $1338 per night (USD)VRBO
From $1404 per night (USD)Expedia
**THE COMMODORE'S MANOR @ THE BIGHT** Waterfront Home & Pool + LAST KEY SERVICES
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 14
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! THE COMMODORE ...
From $1404 per night (USD)Expedia
From $2239 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 $2239 per night (USD)VRBO
From $1054 per night (USD)Expedia
Fabulous home in a great neighborhood
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
So Close to Everything in Old Town but far enough away to be able to relax on quiet on one of the best Streets in Key W ...
From $1054 per night (USD)Expedia
From $804 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 $804 per night (USD)VRBO
From $1588 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 $1588 per night (USD)Expedia
From $348 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 $348 per night (USD)VRBO
From $1157 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 $1157 per night (USD)Expedia
From $750 per night (USD)VRBO
ROOFTOP PENTHOUSE- Luxury Penthouse in prime Downtown location
- 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 $750 per night (USD)VRBO
From $205 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 $205 per night (USD)VRBO
From $334 per night (USD)VRBO
Dog-Friendly Oasis with Patio, Central AC, Private Pool, and Walkable Locale
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Mermaid Manor Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $334 per night (USD)VRBO
From $244 per night (USD)Expedia
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 $244 per night (USD)Expedia
From $225 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 $225 per night (USD)VRBO
From $144 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 $144 per night (USD)Expedia
From $127 per night (USD)VRBO
Dog-friendly home with central AC, fast WiFi, washer/dryer, and private hot tub
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Seafoam Escape Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $127 per night (USD)VRBO
From $249 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 $249 per night (USD)Expedia
From $400 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 $400 per night (USD)VRBO
From $145 per night (USD)Expedia
**MARA-VILLA @ OLD TOWN** Private Conch Home & Hot Tub + LAST KEY SERVICES...
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! MARA-VILLA is ...
From $145 per night (USD)Expedia
From $375 per night (USD)VRBO
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 ...
From $375 per night (USD)VRBO
From $352 per night (USD)Expedia
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 $352 per night (USD)Expedia
From $183 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 $183 per night (USD)VRBO
From $226 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 $226 per night (USD)Expedia
From $176 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 $176 per night (USD)VRBO
From $106 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 $106 per night (USD)Expedia
From $121 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 $121 per night (USD)VRBO
From $250 per night (USD)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 ...
From $250 per night (USD)Expedia
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 $565 per night (USD)Expedia
Duval Dream Loft- Pvt. Balcony Overlooking 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 $565 per night (USD)Expedia
From $533 per night (USD)VRBO
The Collins- Two Story Loft w/ Balcony on Duval St
- 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 $533 per night (USD)VRBO
From $222 per night (USD)Expedia
**CARSTEN CONCH COTTAGE @ OLD TOWN** Quaint Cottage + LAST KEY SERVICE…
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! CARSTEN CONCH ...
From $222 per night (USD)Expedia
From $1073 per night (USD)VRBO
Duval Duo- Two Premier Lofts w/ Pvt Balconies!
- 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 D ...
From $1073 per night (USD)VRBO
From $260 per night (USD)Expedia
Clean/stylish Old Town Key West- Walk to Duval
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
This 1 bedroom/1.5 bathroom Key West cottage has all the comforts of home and is the perfect place to relax and enjoy is ...
From $260 per night (USD)Expedia
From $245 per night (USD)VRBO
Old Town- Walk to everything- Banyan tree view
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
This 1 bedroom/1.5 bathroom Key West cottage has all the comforts of home and is the perfect place to relax and enjoy is ...
From $245 per night (USD)VRBO
From $300 per night (USD)Expedia
NEW! Completely Renovated | Close to Everything | Private Courtyard
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
La Cala is a Newly Renovated Historic Home Situated on a Corner Lot within Walking Distance to Everything you want to Se ...
From $300 per night (USD)Expedia
From $155 per night (USD)VRBO
NEW MONTHLY RENTAL, Old Town, Duplex, private backyard, summer open $4500/mo
- 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 $155 per night (USD)VRBO
From $159 per night (USD)Expedia
NEW Conch Cottage- SunFilled with 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 ...
From $159 per night (USD)Expedia
From $607 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 $607 per night (USD)VRBO
From $359 per night (USD)Expedia
Yellow Room at Grand Maloney Hotel with Pool!
- 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 $306 per night (USD)VRBO
Blue Room at Grand Maloney Hotel with Pool!
- 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 $306 per night (USD)VRBO
From $504 per night (USD)Expedia
Green Room at Grand Maloney Hotel with Pool!
- 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 $504 per night (USD)Expedia
From $389 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 $389 per night (USD)VRBO
From $349 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 $349 per night (USD)Expedia