Fleming Key Rentals
From $1074 per night (USD)VRBO
Rare Penthouse 2 bed/2bath additional King in loft
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Perfect vacation rental that allows you to enjoy breakfast on your private balcony, unwind and relax in the master bath ...
From $1074 per night (USD)VRBO
From $850 per night (USD)VRBO
The Galleon Resort in Beautiful Key West. Amazing Views! Over 500 Reviews!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
These are 7-night rentals, with check-in on Saturdays only. Overlooking the shimmering span of Gulf of Mexico in histor ...
From $850 per night (USD)VRBO
From $650 per night (USD)VRBO
BOTTOMS UP BUNGALOW - 2 Bedroom / 2 Bathroom With PRIVATE POOL
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Bottom’s Up Bungalow located The Meadows subdivision in Old Town Key West. This pristine Florida Bungalow ...
From $650 per night (USD)VRBO
From $965 per night (USD)VRBO
Rose Lane Villas - Villa Vista - 2 bedrooms - Downtown Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Nestled on a quiet lane in the heart of Old Town Key West, Rose Lane Villas is as close to the action as you'll get with ...
From $965 per night (USD)VRBO
From $2114 per night (USD)VRBO
BEACH HOUSE ~ Stunning 4B/4Ba Home with Private Pool in Truman Annex!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
PRESTIGIOUS TROPICAL RETREAT... Indulge in this spectacular two-story home situated in the premier gated community of hi ...
From $2114 per night (USD)VRBO
From $233 per night (USD)Expedia
Private Home in Heart of Old Town (Shared Pool!)
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Come escape to paradise in this newly updated and available home steps from Duval! Equipped with all the amenities for a ...
From $233 per night (USD)Expedia
From $442 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 $442 per night (USD)VRBO
From $766 per night (USD)VRBO
Key West Suites Hotel - Adam Scott Rote Suite
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Welcome to your charming private studio apartment right on Duval street! Built in 1919, it used to be called the Central ...
From $766 per night (USD)VRBO
From $233 per night (USD)VRBO
The Rex, a Key West Monthly Rental
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Enjoy a stylish experience at this centrally-located apartment. Just a short walk from some of Key West best restaurants ...
From $233 per night (USD)VRBO
From $287 per night (USD)Expedia
The Maria Luz, a Key West Monthly Rental
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The Maria Luz a is located in a Historic Conch house from the early 1900’s updated and decorated by its owner. Feature ...
From $287 per night (USD)Expedia
From $233 per night (USD)VRBO
The Gisela, a Key West Monthly Rental
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 1
The Gisela is located in the rear of an adorable Conch Cottage. Finished with a soft and neutral color scheme that will ...
From $233 per night (USD)VRBO
From $450 per night (USD)VRBO
Old Town Key West Condo - MONTHLY RENTALS ONLY
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Our condo is located is in the heart of Key West's Old Town. This neighborhood is filled with historic homes dating fro ...
From $450 per night (USD)VRBO
From $224 per night (USD)VRBO
Feel the Island Winds From Casita In The Clouds: 2 Bed/2 Bath - Monthly
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
WELCOME TO CASITA IN THE CLOUD! Your search for the perfect island getaway has ended! This large 3 story, two bedro ...
From $224 per night (USD)VRBO
From $314 per night (USD)VRBO
The Caribbean Suite - 2-K-bedroom /1 bath/ kitchenette/sleeps 6
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This deluxe "Key West Charmer" is a beautifully restored Victorian home built in the 1880's that was converted into indi ...
From $314 per night (USD)VRBO
From $200 per night (USD)VRBO
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)VRBO
From $688 per night (USD)VRBO
Hidden Treasure- 2 bedroom 2 bath with shared pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Hidden from sight, among a colony of freestanding conch cottages, surrounded by lush tropical landscaping, you will find ...
From $688 per night (USD)VRBO
From $326 per night (USD)VRBO
Caroline On My Mind-New Listing-Light, Bright and Airy!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This beautifully restored, remodeled second-floor 1933 Key West home on Caroline Street offers a unique and inviting exp ...
From $326 per night (USD)VRBO
From $1101 per night (USD)Expedia
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 $1101 per night (USD)Expedia
From $192 per night (USD)VRBO
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 $192 per night (USD)VRBO
From $599 per night (USD)VRBO
Rose Lane Villas - Villa Porta - 1 Bedroom - Downtown Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Nestled on a quiet lane in the heart of Old Town Key West, Rose Lane Villas is as close to the action as you'll get with ...
From $599 per night (USD)VRBO
From $284 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 $284 per night (USD)VRBO
From $261 per night (USD)Expedia
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 $261 per night (USD)Expedia
From $1251 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 $1251 per night (USD)VRBO
From $1422 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 $1422 per night (USD)VRBO
From $1535 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 $1535 per night (USD)VRBO
From $1535 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 $1535 per night (USD)VRBO
From $754 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 $754 per night (USD)VRBO
From $754 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 $754 per night (USD)VRBO
From $335 per night (USD)VRBO
Island Style- 1 bedroom 1 bath in old town Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Resort-style accommodations at an affordable price! Nestled among a colony of freestanding Conch style cottages, amid lu ...
From $335 per night (USD)VRBO
From $266 per night (USD)VRBO
TRANQUILITY - Meadows Monthly Rental - Private Pool - 3BDR/3BA - RealKeyWest
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Tranquility, a luxurious vacation rental nestled in a tropical setting. This stunning 3 bedroom, 3 bathroom h ...
From $266 per night (USD)VRBO
From $268 per night (USD)VRBO
SERENITY ~ Relax in Ultimate Luxury and Comfort in Old Town Key West!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
LOCAL LIVING.... Spend time relaxing in Paradise in the perfect home. Serenity is a beautifully decorated, 4 bedroom ho ...
From $268 per night (USD)VRBO
From $395 per night (USD)VRBO
CONCH COTTAGE: Old Town - Hot Tub - 1 Block from Duval - 1BD/1BA RealKeyWest
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
WELCOME TO CONCH COTTAGE! In the 20th century many residents of Key West began referring to themselves as “Conchs”, no ...
From $395 per night (USD)VRBO
From $762 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 $762 per night (USD)VRBO
From $337 per night (USD)VRBO
Heavenly Hideaway-Monthly 3BD 2.5BA Private Pool - RealKeyWest
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
HEAVENLY HIDEAWAY! Welcome to our Heavenly Hideaway, a serene oasis nestled in the heart of Key West. This enchanting 3 ...
From $337 per night (USD)VRBO
From $495 per night (USD)VRBO
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 $495 per night (USD)VRBO
From $237 per night (USD)Expedia
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 $237 per night (USD)Expedia
From $679 per night (USD)VRBO
Rose Lane Villas - Villa Rosa - 1 Bedroom - Downtown Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Nestled on a quiet lane in the heart of Old Town Key West, Rose Lane Villas is as close to the action as you'll get wit ...
From $679 per night (USD)VRBO
From $911 per night (USD)VRBO
Old Town Key West Compound with Pool, Parking and Privacy One Block Off Duval!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Down a hidden lane in the heart of Old Town Key West you will find Loco Court. The compound is located one block off Duv ...
From $911 per night (USD)VRBO
From $368 per night (USD)VRBO
Dog-friendly downtown home + guest home with private pool, grill, deck, AC
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Sunny Corner Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $368 per night (USD)VRBO
From $1545 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 $1545 per night (USD)VRBO
Click For PricingVRBO
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 ...
Click For PricingVRBO
From $1492 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 $1492 per night (USD)VRBO
From $732 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 $732 per night (USD)VRBO
From $1854 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 $1854 per night (USD)VRBO
Click For PricingVRBO
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 ...
Click For PricingVRBO
From $1854 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 $1854 per night (USD)VRBO
Click For PricingVRBO
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 ...
Click For PricingVRBO
From $446 per night (USD)VRBO
THE FICUS HOUSE ~ Adult Only, Lush 3 BR, 2.5 Ba Gem with Pool and Cottage!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
VINTAGE ISLAND PARADISE... Tucked within luxuriant foliage lies this timeless, adult only, tropical sanctuary in the mid ...
From $446 per night (USD)VRBO
Click For PricingVRBO
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 ...
Click For PricingVRBO
From $783 per night (USD)Expedia
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 $783 per night (USD)Expedia
From $766 per night (USD)VRBO
PURA VIDA ~ 3 Bed/3.5 Bath Home on Quaint Old Town Lane!
- Bedrooms:
- 4
- 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 $766 per night (USD)VRBO
From $417 per night (USD)VRBO
Miami Vice Sailboat Near Downtown Key West North Fleming Key
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
*Our business is growing with new natural setting stay at our moorings in quiet secluded area in Key West Harbor!” We h ...
From $417 per night (USD)VRBO
From $355 per night (USD)VRBO
ISLAND PEARL - Cozy Nightly Rental just off Duval RealKeyWest
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
WELCOME TO ISLAND PEARL This nightly rental located in sought after Old Town Key West is just steps from the famous D ...
From $355 per night (USD)VRBO
From $777 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 $777 per night (USD)Expedia
From $426 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 $426 per night (USD)VRBO
From $438 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 $438 per night (USD)Expedia
From $404 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 $404 per night (USD)VRBO
From $1138 per night (USD)VRBO
Casa Margarita- 3 bedrooms | 3 baths | sleeps up to 8 | large heated pool & hot
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Casa Margarita is the perfect luxury retreat if you are looking for a peaceful place that also is in the heart of Old To ...
From $1138 per night (USD)VRBO
From $482 per night (USD)VRBO
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 $482 per night (USD)VRBO
Click For PricingExpedia
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 PricingExpedia
From $1204 per night (USD)VRBO
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 $1204 per night (USD)VRBO
From $519 per night (USD)VRBO
Town Home with King Bed, Full Kitchen, and Pullout Sofa
- Bedrooms:
- 0
- Bathrooms:
- 0
- Sleeps:
- 4
This is a two-story Victorian Town Home with 1st and 2nd floor private verandas overlooking historic Fleming Street. It ...
From $519 per night (USD)VRBO
From $895 per night (USD)VRBO
Downtown Retreat - A++ Location W/ Private Heated Pool/Hot Tub
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Location, location, location! Brand new and beautiful, this spacious house is conveniently located on a quiet street in ...
From $895 per night (USD)VRBO
From $180 per night (USD)VRBO
Just Restored One Bedroom Hideaway with Garden and Hot Tub 5 No Need For A Car
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This one bedroom apartment on the ground floor is completely restored with a full kitchen and laundry. This unit has eve ...
From $180 per night (USD)VRBO
From $261 per night (USD)VRBO
~ VILLA AZUL ~ Enjoy this historic home with pool house and parking.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local ...
From $261 per night (USD)VRBO
From $525 per night (USD)VRBO
~ROOSTER CONCH~ Amazing location with shared pool and covered balcony!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
THE PROPERTY: Enjoy your stay in the tropics at Rooster Conch, part of the highly touted "Queen Conch" complex, which in ...
From $525 per night (USD)VRBO
From $861 per night (USD)VRBO
SEA CONCH~ Amazing location with shared pool, deck, and parking!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
THE PROPERTY: Enjoy your stay in the tropics at Sea Conch, part of the highly touted "Queen Conch" complex, which includ ...
From $861 per night (USD)VRBO
From $534 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 $534 per night (USD)Expedia
From $1734 per night (USD)VRBO
~QUEEN CONCH ~ Amazing location with pool and room for family and friends!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 14
THE PROPERTY: Enjoy your stay in the tropics at the highly touted "Queen Conch" complex, which includes 3 separate renta ...
From $1734 per night (USD)VRBO
From $1063 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 $1063 per night (USD)Expedia
From $600 per night (USD)VRBO
Galleon Resort Efficiency Historic District
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
$25,00 Renovation completed end of 2016/beginning of 2017!! Different than ANY other Efficiency at the Galleon!! You w ...
From $600 per night (USD)VRBO
From $1199 per night (USD)VRBO
Rose Lane Villas - Villa Grande - 3 bedrooms - Downtown Key West
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Nestled on a quiet lane in the heart of Old Town Key West, Rose Lane Villas is as close to the action as you'll get with ...
From $1199 per night (USD)VRBO
From $625 per night (USD)VRBO
Historic "Old Town" Charm
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
* We are activally cleaning and sanitizing this rental with extra sanitation methods with each stay. LUXURY IN OLD TOWN ...
From $625 per night (USD)VRBO
From $1021 per night (USD)Expedia
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 $1021 per night (USD)Expedia
From $1199 per night (USD)VRBO
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 $1199 per night (USD)VRBO
From $989 per night (USD)Expedia
Sunset North: Luxury 4 Bedroom 4.5 Bath Condo at Bayfront Suites & Marina
- Bedrooms:
- 4
- Bathrooms:
- 1
- Sleeps:
- 8
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $989 per night (USD)Expedia
From $981 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 $981 per night (USD)VRBO
From $1232 per night (USD)Expedia
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 $1232 per night (USD)Expedia
From $1018 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 $1018 per night (USD)VRBO
From $1229 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 $1229 per night (USD)Expedia
From $489 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 $489 per night (USD)VRBO
From $115 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 $115 per night (USD)Expedia
From $261 per night (USD)VRBO
Dog-friendly Conch cottage with private yard, plunge pool, deck, & grill
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Casa Azul Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $261 per night (USD)VRBO
From $226 per night (USD)Expedia
Cozy Key West Hideaway in Old Town with Pool
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Your Key West Hideaway home is located in the heart of Old Town. Key West landmarks, attractions, Duval St, restaurants, ...
From $226 per night (USD)Expedia
From $193 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 $193 per night (USD)VRBO
From $223 per night (USD)Expedia
Petite Pearl! Spacious 1 Bedroom, 1 Bath Pool Condo- RealKeyWest
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to Petite Pearl, your hidden gem nestled in the heart of the coveted Meadows district in Key West. A stone's thr ...
From $223 per night (USD)Expedia
From $395 per night (USD)VRBO
Key West Harbor 44ft Morgan Catalina Sailboat Wild Thing
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
*Our business model has changed. We are excited to share our moorings at North Fleming Key for the Adventurous vacatione ...
From $395 per night (USD)VRBO
From $250 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 $250 per night (USD)VRBO
From $942 per night (USD)VRBO
Hyatt Residence Club, Sunset Harbor - Amazing Resort -Come Enjoy Key West!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Tropical Key West welcomes you to a classic Florida condominium, offering a one bedroom unit with plush queen bed, fully ...
From $942 per night (USD)VRBO
From $483 per night (USD)VRBO
LOVE LANDING ~ Charming 3 Bedroom, 3 Bathroom Home w/ Pool and Parking!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
MARITIME-INSPIRED LIVING… Come unwind in this desirable retreat, tucked in a quiet and private lane just a stone's throw ...
From $483 per night (USD)VRBO
From $259 per night (USD)VRBO
The Hollinsed House "Victorian Delights" - Large 1 Bedroom
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Mingle with other guests around the tropical gardens surrounding the heated pool and sundeck creating the perfect settin ...
From $259 per night (USD)VRBO
From $828 per night (USD)VRBO
~ CASABLANCA GRANDE ~ Old Town quiet duplex with pool, hot tub, and parking!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
THE PROPERTY: Enjoy fresh air and sunshine from your front porch, private pool or hot tub at Casablanca Grande. You are ...
From $828 per night (USD)VRBO
From $811 per night (USD)VRBO
~ POINCIANA PARADISE ~ Casual duplex 2 blocks from Duval Street with hot tub!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
THE PROPERTY: This comfortably furnished duplex home comes with Key West charm and contemporary touches. Walkable to man ...
From $811 per night (USD)VRBO
From $721 per night (USD)VRBO
Mango Cottage- 2 bedroom 2 bath with private pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This historic Conch house is an excellent vacation home which has been thoughtfully remodeled to provide the best in mod ...
From $721 per night (USD)VRBO
From $249 per night (USD)VRBO
Hollinsed House Poolside / King 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 $249 per night (USD)VRBO
From $850 per night (USD)VRBO
Namaste 'The Spirit Within Me Salutes The Spirit Within You'
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
Tucked away in an inviting compound you'll find a blissful retreat called Namaste; a tranquil and relaxing one bedroom B ...
From $850 per night (USD)VRBO
From $793 per night (USD)VRBO
Heavenly Hideout at Rainbow's End
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to the end (and the beginning) of the road. There aren’t many places in the world where you can say you’re both ...
From $793 per night (USD)VRBO
From $550 per night (USD)VRBO
Old Town Bali Hideaway For 2, Just Steps From Duval
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 2
Perfect for two, this Bali style, studio cottage has it all... COMFORT and LOCATION. Located on an Ann Street compound j ...
From $550 per night (USD)VRBO
From $231 per night (USD)VRBO
ORCHID ESCAPE~ 2 bedroom 2 bath set in Old Town with private dip pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
CLASSIC OLD KEY WEST HOME... This home is boasting a rare combination of location and character. A mix of historic detai ...
From $231 per night (USD)VRBO
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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 ...
Click For PricingExpedia