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From $350 per night (USD)
VRBO
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 alwa ...
From $350 per night (USD)
VRBO
From $350 per night (USD)
Expedia
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 $350 per night (USD)
Expedia
From $2347 per night (USD)
VRBO
~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 $2347 per night (USD)
VRBO
From $593 per night (USD)
Expedia
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 $593 per night (USD)
Expedia
From $648 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 $648 per night (USD)
VRBO
From $216 per night (USD)
Expedia
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 $216 per night (USD)
Expedia
From $294 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 $294 per night (USD)
VRBO
From $444 per night (USD)
Expedia
Craig & Cindy Truman Annex Foundry Townhouses (2 bedrooms 2 1/2 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 $444 per night (USD)
Expedia
From $462 per night (USD)
VRBO
**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)
VRBO
From $465 per night (USD)
Expedia
**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 $465 per night (USD)
Expedia
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 $429 per night (USD)
VRBO
COCONUT in Old Town Key West
Bedrooms:
1
Bathrooms:
2
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 $776 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 $776 per night (USD)
VRBO
From $196 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 $196 per night (USD)
Expedia
From $803 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 $803 per night (USD)
VRBO
From $722 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 $722 per night (USD)
VRBO
From $675 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 $675 per night (USD)
VRBO
From $1557 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 $1557 per night (USD)
VRBO
From $1383 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 $1383 per night (USD)
VRBO
From $741 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 $741 per night (USD)
VRBO
From $790 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 $790 per night (USD)
VRBO
From $184 per night (USD)
Expedia
Ground-level getaway with free WiFi, private deck, & shared outdoor pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Louisa's Garden Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $184 per night (USD)
Expedia
From $384 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 $384 per night (USD)
VRBO
From $151 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 $151 per night (USD)
Expedia
From $348 per night (USD)
VRBO
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 $348 per night (USD)
VRBO
From $352 per night (USD)
Expedia
Cayo Cruz Suite - Colorful Condo with Sunset View!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Paradise awaits you in this renovated, 2 bedroom/2 bathroom condo in the community of Sunrise Suites! The color ...
From $352 per night (USD)
Expedia
From $409 per night (USD)
VRBO
Martinique Suite- Family Friendly Condo #108!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: The Martinique Suite is set in the beautifully landscaped Sunrise Suites community, just 10 minutes away from a ...
From $409 per night (USD)
VRBO
From $613 per night (USD)
Expedia
2 bedroom accommodation in Key West
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 $613 per night (USD)
Expedia
From $234 per night (USD)
VRBO
IT'S A SALT LIFE AFTER ALL @ the Golf Club
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 $234 per night (USD)
VRBO
From $452 per night (USD)
VRBO
Conch home on a quiet lane. Walk to everything. Private swimspa. Dog friendly 🐶🐾
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Recently renovated home located on a quiet lane just 1 block from the iconic Green Parrot Bar and 2 blocks from world fa ...
From $452 per night (USD)
VRBO
From $462 per night (USD)
VRBO
Ultimate Beach Adventure! Pool, Restaurant, Bar, Bike Rental, Gym
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $462 per night (USD)
VRBO
From $325 per night (USD)
Expedia
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 ...
From $325 per night (USD)
Expedia
From $743 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 $743 per night (USD)
VRBO
From $336 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 $336 per night (USD)
Expedia
From $305 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 $305 per night (USD)
VRBO
From $450 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 $450 per night (USD)
Expedia
From $1246 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 $1246 per night (USD)
VRBO
Click For Pricing
Expedia
FIVE STAR RETREAT @ THE KEY WEST GOLF CLUB
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
28 Night Minimum Stay Required. New to the rental market February 2021. Step through the front door to this serene oas ...
Click For Pricing
Expedia
From $919 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 $919 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 $626 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 $626 per night (USD)
VRBO
From $1287 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 $1287 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 $1566 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 $1566 per night (USD)
VRBO
From $707 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 $707 per night (USD)
VRBO
From $1029 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 $1029 per night (USD)
VRBO
From $875 per night (USD)
VRBO
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 $875 per night (USD)
VRBO
From $1395 per night (USD)
Expedia
Sky Suites Retreat - 2 Stunning Condos On Duval St
Bedrooms:
5
Bathrooms:
4
Sleeps:
12
Summary: This elegant, elevated 2nd story loft with vaulted ceilings is made for your next dream Key West getaway. Taste ...
From $1395 per night (USD)
Expedia
From $521 per night (USD)
VRBO
ADMIRAL'S PARADISE Gorgeous Townhome in Truman Annex
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 $521 per night (USD)
VRBO
From $440 per night (USD)
Expedia
Waterfront Property - Marina Access - Spacious - Excellent Key West Condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Located just 2 miles from picturesque Smathers Beach, this well appointed 2 bedroom, 2 bath condo is ideally situated in ...
From $440 per night (USD)
Expedia
From $706 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 $706 per night (USD)
VRBO
From $368 per night (USD)
Expedia
Tortuga Suite 301 - Pool, Hot Tub, Private Balcony
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Take in the sunset from your beautiful private balcony and enjoy the beautiful amenities this resort has to off ...
From $368 per night (USD)
Expedia
From $280 per night (USD)
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 ...
From $280 per night (USD)
VRBO
From $575 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 $575 per night (USD)
Expedia
From $831 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 $831 per night (USD)
VRBO
From $331 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 $331 per night (USD)
Expedia
From $487 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 $487 per night (USD)
VRBO
From $300 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 $300 per night (USD)
VRBO
From $525 per night (USD)
VRBO
3 bedroom accommodation in Key West
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 $525 per night (USD)
VRBO
From $208 per night (USD)
Expedia
★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 $208 per night (USD)
Expedia
From $536 per night (USD)
VRBO
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 $536 per night (USD)
VRBO
From $562 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 $562 per night (USD)
Expedia
From $3750 per night (USD)
VRBO
Sailing Catamaran in Key West with Captain and Chef/Hostess
Bedrooms:
4
Bathrooms:
4
Sleeps:
6
Dedicated to providing the most perfect hospitality and sailing experience one could find in Key West, Elizabeth, Charte ...
From $3750 per night (USD)
VRBO
From $385 per night (USD)
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 ...
From $385 per night (USD)
Expedia
From $226 per night (USD)
VRBO
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 $226 per night (USD)
VRBO
From $1299 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 $1299 per night (USD)
Expedia
From $454 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 $454 per night (USD)
VRBO
From $1178 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 $1178 per night (USD)
Expedia
From $1029 per night (USD)
VRBO
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 $1029 per night (USD)
VRBO
From $1299 per night (USD)
Expedia
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 $1299 per night (USD)
Expedia
From $1277 per night (USD)
VRBO
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 $1277 per night (USD)
VRBO
From $987 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 $987 per night (USD)
Expedia
From $1225 per night (USD)
VRBO
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 $1225 per night (USD)
VRBO
From $1349 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 $1349 per night (USD)
Expedia
From $1149 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 $1149 per night (USD)
VRBO
From $454 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 $454 per night (USD)
Expedia
From $798 per night (USD)
VRBO
**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)
VRBO
From $195 per night (USD)
Expedia
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 $195 per night (USD)
Expedia
From $700 per night (USD)
VRBO
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)
VRBO
From $141 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 $141 per night (USD)
Expedia
From $350 per night (USD)
VRBO
2023 IS HERE - BOOK NOW & SAVE BIG!!!
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 $350 per night (USD)
VRBO
From $140 per night (USD)
Expedia
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 $140 per night (USD)
Expedia
From $500 per night (USD)
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 ...
From $500 per night (USD)
VRBO
From $216 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 $216 per night (USD)
Expedia
From $1040 per night (USD)
VRBO
Old Town Key West - Historic & Charming - 2 Blks From Duval
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
A few words about the 'damn'pandemic… The health and safety of our guests and employees is our top priority. Our homes ...
From $1040 per night (USD)
VRBO
From $705 per night (USD)
Expedia
~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 $705 per night (USD)
Expedia
From $241 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 $241 per night (USD)
VRBO
From $201 per night (USD)
Expedia
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 $201 per night (USD)
Expedia
From $688 per night (USD)
VRBO
**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 $688 per night (USD)
VRBO
From $242 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 $242 per night (USD)
VRBO
From $381 per night (USD)
VRBO
~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 $381 per night (USD)
VRBO
From $321 per night (USD)
Expedia
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 $321 per night (USD)
Expedia
From $248 per night (USD)
VRBO
Open July & August 2022 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 $248 per night (USD)
VRBO
From $521 per night (USD)
Expedia
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 $521 per night (USD)
Expedia
From $153 per night (USD)
VRBO
parking and private pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Monthly rental nestled on one of Key West's charming lanes just steps to the world famous Duval Street. Arrival is easy ...
From $153 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 $267 per night (USD)
Expedia
*New Listing* 2/2 luxurious waterfront condo located at Sunset Marina
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
2 bedroom 2 bathroom luxurious waterfront condominium located at Sunset Marina Waterfront Residences. Sunset Marina is a ...
From $267 per night (USD)
Expedia
From $558 per night (USD)
VRBO
Key West On My Mind: 2 BR, 2 BA Condominium in Key West, Sleeps 6
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 $558 per night (USD)
VRBO
From $489 per night (USD)
Expedia
Atlantic Oasis on the Ocean: 2 BR, 2 BA Condominium in Key West, Sleeps 6
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 $489 per night (USD)
Expedia

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