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From $241 per night (USD)
VRBO
Comfortable Home with Private Pool, Central AC, WiFi, and Private Washer/Dryer
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Flagler Station Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $241 per night (USD)
VRBO
From $326 per night (USD)
Expedia
Heart of Old Town; 2 Bicycles, Grill, High Speed WiFi, 1st Floor, Pool!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Here in Key West we believe in One Human Family where everyone is welcome and treated like family. Our condo has always ...
From $326 per night (USD)
Expedia
From $320 per night (USD)
VRBO
MAJESTIC PARADISE @ Truman Annex - Heart of Old Town, Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
This wonderful 2 bedroom downstairs unit is owner's second home and has just been beautifully and professionally decorat ...
From $320 per night (USD)
VRBO
From $3062 per night (USD)
Expedia
~DREAMING ON DUVAL~ Grand 5 bedroom, 4.5 bath home with private pool/parking
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
THE PROPERTY: Dreams do come true in Key West! As you enter the front gate of this luxury property, you arrive in a priv ...
From $3062 per night (USD)
Expedia
From $535 per night (USD)
VRBO
Henry's Penthouse on the Ocean in Key West (weekly / nightly rentals)
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Spectacular ocean views from this condo located on the top floor with 1350 sq ft of fabulous living space and a 45 ft pr ...
From $535 per night (USD)
VRBO
From $442 per night (USD)
Expedia
**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)
Expedia
From $351 per night (USD)
VRBO
Craig & Cindy Key West Truman Annex Shipyard Condo with a deck at Mile Marker 0!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Partial list of rental amenities at Craig & Cindy's Truman Annex Shipyard Condos include: 2 bedrooms 1 bath {queen and ...
From $351 per night (USD)
VRBO
From $437 per night (USD)
Expedia
Craig & Cindy Truman Annex Foundry Townhouse 2 bedrooms 2.5 baths
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Craig & Cindy Truman Annex Foundry Townhouse is a 2 bedroom 2 1/2 bath townhouse in the best location in all of Key West ...
From $437 per night (USD)
Expedia
From $429 per night (USD)
VRBO
COCONUT in Old Town Key West
Bedrooms:
1
Bathrooms:
0
Sleeps:
4
The 'Coconut' as it's so lovingly referred to is the perfect Pied A Terre for your vacation in the Florida Keys. Open l ...
From $429 per night (USD)
VRBO
From $462 per night (USD)
Expedia
**COASTLINE COMFORT @ COCONUT MALLORY** Condo + LAST KEY SERVICES…
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! When your vac ...
From $462 per night (USD)
Expedia
From $463 per night (USD)
VRBO
**SET SAIL @ COCONUT MALLORY** Condo + LAST KEY SERVICES…
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! SET SAIL cele ...
From $463 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 $1101 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 $1101 per night (USD)
VRBO
From $192 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 $192 per night (USD)
Expedia
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 $591 per night (USD)
VRBO
**ENVY OF THE ISLAND @ OLD TOWN** Pristine Home & Pool + LAST KEY SERVICES...
Bedrooms:
7
Bathrooms:
5
Sleeps:
10
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! While Old Tow ...
From $591 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 $160 per night (USD)
Expedia
Ground-level getaway with free WiFi, private deck, & shared outdoor pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Louisa's Garden Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $160 per night (USD)
Expedia
Click For Pricing
VRBO
Hyatt Windward Pointe, Key West, Fl. - 2 Bedroom Unit - 1064 sq/ft
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
3rd floor (top level accessible by elevator or stairs) Balcony faces the Atlantic Ocean and gardens. 2 bedrooms (large m ...
Click For Pricing
VRBO
From $350 per night (USD)
Expedia
SOUTHERNMOST SWIM AND SOCIAL CLUB
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Look no further! You've found your home away from home. Where your family and friends can share their own piece of para ...
From $350 per night (USD)
Expedia
From $594 per night (USD)
VRBO
Treasure Cove- 2BDR/2.5BA Townhouse in Truman Annex
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
~~7 day minimum~~Experience the famous island city of Key West and stay at the Treasure Cove Townhouse in the private P ...
From $594 per night (USD)
VRBO
From $208 per night (USD)
VRBO
IT'S A SALT LIFE AFTER ALL at the Golf Club in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This 2 bedroom 2 bath town-home is just what you are looking for. *****PLEASE NOTE THIS IS A MINIMUM MONTHLY RENTAL ONL ...
From $208 per night (USD)
VRBO
From $468 per night (USD)
VRBO
Conch home on a quiet lane. Walk to everything. Private swimspa. Dog friendly 🐶🐾
Bedrooms:
3
Bathrooms:
2
Sleeps:
2
Recently renovated home located on a quiet lane just 1 block from the iconic Green Parrot Bar and 2 blocks from world fa ...
From $468 per night (USD)
VRBO
From $599 per night (USD)
VRBO
Ultimate Beach Adventure! Pool, Restaurant, Bar, Bike Rental, Gym
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $599 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 $495 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 $495 per night (USD)
Expedia
From $237 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 $237 per night (USD)
VRBO
From $400 per night (USD)
Expedia
MAJESTIC PARADISE II Luxury living in Truman Annex. Downtown, pool, 2 blks
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Featured in The Key West Citizen Home of the Week. Perfect location, and newly renovated with fresh paint, new kitchen w ...
From $400 per night (USD)
Expedia
From $822 per night (USD)
VRBO
**JASMINE JEWEL @ THE ANNEX** Lush Private Home & Pool + LAST KEY SERVICES…
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Hidden amongs ...
From $822 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 Pricing
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 ...
Click For Pricing
VRBO
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 Pricing
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 ...
Click For Pricing
VRBO
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 Pricing
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 ...
Click For Pricing
VRBO
From $538 per night (USD)
Expedia
ADMIRAL'S PARADISE in Key West
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
Newly renovated town home located on a charming lane in the Truman Annex. The generous open floor plan features 10 foot ...
From $538 per night (USD)
Expedia
From $975 per night (USD)
VRBO
Sky Suites Retreat by Brightwild–2 Stunning Condos
Bedrooms:
5
Bathrooms:
4
Sleeps:
12
Summary: This elegant, elevated 2nd story loft with vaulted ceilings has been designed for your next dream Key West geta ...
From $975 per night (USD)
VRBO
From $338 per night (USD)
Expedia
Tortuga Suite | Heated Pool & Hot Tub!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: - Welcome to the quiet & relaxing Sunrise Suites community located on the southeast side of Key West. - Just 1 ...
From $338 per night (USD)
Expedia
From $381 per night (USD)
VRBO
Waterfront Property - Marina Access - Spacious - Excellent Key West Condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Located just two miles from picturesque Smathers Beach, this well appointed two bedroom, two bath condo is ideally situa ...
From $381 per night (USD)
VRBO
From $760 per night (USD)
VRBO
Key West's Crown Jewel
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Key West's Crown Jewel is a penthouse condominium at 1800 Atlantic Condominium development with two-bedroom, two-bath wi ...
From $760 per night (USD)
VRBO
Click For Pricing
VRBO
Beautiful & Relaxing 2 bed 2 bath condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This is a large 2 bed 2 bath condo with a separate living room, kitchen, and private balcony at the Hyatt Resort. It off ...
Click For Pricing
VRBO
From $425 per night (USD)
Expedia
Southernmost Retreat: 2 Blocks from Duval in Old Town.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Located just 2 short blocks from Duval and in the center of downtown, the Southernmost Retreat is a recently renovated a ...
From $425 per night (USD)
Expedia
From $777 per night (USD)
VRBO
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)
VRBO
From $426 per night (USD)
Expedia
**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)
Expedia
From $438 per night (USD)
VRBO
**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)
VRBO
From $350 per night (USD)
VRBO
Flirty Flamingo Key West
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
Flirty Flamingo is luxurious and in a prime Key West location. Built in 1998 and meticulously cared for this spacious 3 ...
From $350 per night (USD)
VRBO
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 $461 per night (USD)
Expedia
Henry's Piece of Paradise on the Ocean in Key West - Weekly / Nightly
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Thirteen-hundred-fifty square feet of fabulous living space located on the second floor with garden and partial ocean vi ...
From $461 per night (USD)
Expedia
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 Pricing
Expedia
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 Pricing
Expedia
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 $209 per night (USD)
Expedia
Upscale Townhouse with Golf and Lake Views, Shared Pool, WiFi, and AC - Dogs OK
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
The Tipsy Mermaid Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $209 per night (USD)
Expedia
From $534 per night (USD)
VRBO
~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)
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 $1021 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 $1021 per night (USD)
VRBO
From $1199 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 $1199 per night (USD)
Expedia
From $989 per night (USD)
VRBO
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)
VRBO
From $981 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 $981 per night (USD)
Expedia
From $1232 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 $1232 per night (USD)
VRBO
From $1018 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 $1018 per night (USD)
Expedia
From $1229 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 $1229 per night (USD)
VRBO
From $489 per night (USD)
Expedia
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)
Expedia
From $115 per night (USD)
VRBO
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)
VRBO
From $700 per night (USD)
Expedia
WASTIN AWAY IN MARGARITAVILLE! HYATT RESIDENCE CLUB JEWEL IN HEART OF KEY WEST
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
ONLY AVAILABLE 2/20-2/27: PRIME REAL ESTATE IN THE HEART OF KEY WEST. HYATT RESIDENCE CLUB COVETED RESORT SUNSET HARBOR ...
From $700 per night (USD)
Expedia
From $680 per night (USD)
VRBO
~Serene Lily~ Luxurious 2 bed, 2.5 bath home in the upscale Truman Annex
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
WEEKLY RENTAL: This property has a 7 night minimum stay. THE PROPERTY: Located where the Gulf meets the Atlantic, this ...
From $680 per night (USD)
VRBO
From $164 per night (USD)
Expedia
Paradise found at the Key West Golf Club!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
We selected the best of everything to create paradise in Key West. Enjoy tropical breezes as you sip your morning coffee ...
From $164 per night (USD)
Expedia
From $300 per night (USD)
VRBO
FANTASTIC FALL SPECIAL
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
City of Key West Business License # 28224 We hope you will enjoy this home where Ernest Hemingway and Jimmy Buffet memo ...
From $300 per night (USD)
VRBO
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
Click For Pricing
VRBO
FANTASY WEEK
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Set along the Atlantic Ocean, Hyatt Windward Pointe Resort blends the laid-back Key West style with a modern, upscale re ...
Click For Pricing
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 $980 per night (USD)
VRBO
Old Town Key West - Historic & Charming - 2 Blks From Duval
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
OVERVIEW The Turtle House is a 100+ year old recently completely renovated “Conch” house. The house can be described as ...
From $980 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 $342 per night (USD)
VRBO
The Sylvia Gwynn, Key West Southernmost Point monthly vacation rental
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Just 1 block from the action of Duval Street lies our newest space located at 1307 Whitehead Street. The Sylvia Gwynn is ...
From $342 per night (USD)
VRBO
From $455 per night (USD)
Expedia
**COLORS OF THE KEYS @ THE FOUNDRY** Villa Near Duval & Beach + 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! COLORS OF THE ...
From $455 per night (USD)
Expedia
From $412 per night (USD)
VRBO
The Key West Bougain Villa, a Monthly Vacation Rental
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The Bougain Villa is found on Whitehead Street. Reserve a stay in this home located in the heart of historic Old Town Ke ...
From $412 per night (USD)
VRBO
From $255 per night (USD)
Expedia
~FISH CAMP!~ Family friendly, canal front, monthly rental.
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local ...
From $255 per night (USD)
Expedia
From $329 per night (USD)
VRBO
La Casita
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This beautiful, fully furnished 2BD/2BA single family home is located in the prestigious Casa Marina neighborhood. Speci ...
From $329 per night (USD)
VRBO
From $300 per night (USD)
Expedia
Open Feb 23rd 2023 for Monthly rent in the Heart of Old Town Key West.
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Echo's retreat is a 3 Bedroom 2 bath Apartment right in the heart of the Historic district in downtown Key West. 2 off ...
From $300 per night (USD)
Expedia
From $516 per night (USD)
VRBO
Spacious Truman Annex End Unit Townhouse /Side Courtyard
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
IN 2005 FEATURED ON HGTV NATIONAL OPEN HOUSE MILLION DOLLAR PROPERTY Located in one of Key West's most prestigious gate ...
From $516 per night (USD)
VRBO
Click For Pricing
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 ...
Click For Pricing
Expedia
From $223 per night (USD)
VRBO
2bed 2bath luxe condo w/ ocean views, dock space, waterfront pool/hot tub
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
2 bedroom 2 bathroom luxurious waterfront condominium located at Sunset Marina Waterfront Residences. Sunset Marina is a ...
From $223 per night (USD)
VRBO
From $661 per night (USD)
Expedia
Key West On My Mind, Ocean Views, Renovated Kitchen, Last minute deals
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Stunning 2 bedroom ocean-view oasis vacation rental at the fabulous 1800 Atlantic in Key West. Our family owned unit has ...
From $661 per night (USD)
Expedia
From $535 per night (USD)
VRBO
Key West Affordable Ocean View Condo. Clean priced well on the Atlantic
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Penthouse property with vaulted ceilings at the famous 1800 Atlantic. Both bedrooms and the living room have access to y ...
From $535 per night (USD)
VRBO
From $176 per night (USD)
Expedia
Free Island Sprint has been transformed- Wonderful Renovation done in Fall 21
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Lovely 3rd floor interior courtyard view monthly rental. Enjoy the serenity of this bright and airy unit. This unit offe ...
From $176 per night (USD)
Expedia
From $982 per night (USD)
VRBO
Casa Papa Del Mar formerly Ocean Extravaganza - Totally Renovated in 2022.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Casa Papa Del Mar Two Bedroom Premiere Ocean View With a complete 2023 renovation, the décor is inspired by the life and ...
From $982 per night (USD)
VRBO
From $488 per night (USD)
Expedia
Moonlight Paradise Upgraded Family oasis Tropical views expansive balcony
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Moonlight" is a freshly renovated condo that is located at 1800 Atlantic Blvd on the beach, with sunset views right from ...
From $488 per night (USD)
Expedia
From $191 per night (USD)
VRBO
Ocean Front Key West Oasis Island Tones Charming Historical Downtown area
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Beautiful 2 bedroom 2 bath unit, with a lovely view of the Atlantic Ocean. This unit is an extra large floor plan with a ...
From $191 per night (USD)
VRBO
From $156 per night (USD)
Expedia
Key West Paradise, Conch Hideaway, Island Vibrations, Balmy Ocean Breezes KWF
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This property features an extra large floor plan from the popular B building at 1800 Atlantic. Enjoy the flow through br ...
From $156 per night (USD)
Expedia
From $498 per night (USD)
VRBO
~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 $498 per night (USD)
VRBO
From $223 per night (USD)
Expedia
Best Downtown Location Monthly Rental Open Nov 2023- Jan 2024
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This delightful 2 Bedroom Cigar Maker's Cottage at 1008 Whitehead was built in the 1880's, where there was once a Cigar ...
From $223 per night (USD)
Expedia
From $601 per night (USD)
VRBO
Key West Beachfront Luxury 2/2 Condo A212
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This Luxury unit is 1375 sq ft of breath taking beachfront living space in this tropical complex. Great views from the 4 ...
From $601 per night (USD)
VRBO
From $150 per night (USD)
Expedia
Vibrant Island retreat, Expansive private balcony, Enjoy the Coastal Breezes
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Fabulous top floor ocean-view penthouse condo. Available during the Spring/Summer Season. Enjoy the Ocean-breeze's from ...
From $150 per night (USD)
Expedia

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