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1,000 Rentals In Key West
United States
Florida
Monroe Area
Florida Keys
Key West
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Key West
(102)
Fleming Key
(26)
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Amenities
Pool
Internet
Washer
Fishing
FirePlace
Wheelchair Access
Non Smoking
Yard
TV
Balcony
Patio
Parking
AC
Microwave
No Pets
Jacuzzi
Pet Allowed
Dishwasher
Kitchen
Sauna
Crib
Smoking Allowed
Grill
Heart of Old Town; 2 Bicycles, Grill, High Speed WiFi, 1st Floor, Pool!
2
1.0
4
Key West fl Condo
From $275 per night
(USD)
MAJESTIC PARADISE @ Truman Annex - Heart of Old Town, Key West
2
1.0
5
Key West Florida Condo
From $310 per night
(USD)
~DREAMING ON DUVAL~ Grand 5 bedroom, 4.5 bath home with private pool\/parking
5
5.0
10
Key West Florida Private vacation home
From $2050 per night
(USD)
Henry's Penthouse on the Ocean in Key West (weekly \/ nightly rentals)
2
2.0
5
Key West Florida Condo
From $470 per night
(USD)
**OLD TOWN OASIS @ THE ANNEX** Oceanside 2BR\/2BA Condo & Pool + LAST KEY SERVICE
2
2.0
6
Key West Florida Condo
From $605 per night
(USD)
Comfortable Home with Private Pool, Central AC, WiFi, and Private Washer\/Dryer
3
2.0
6
Key West Florida Private vacation home
From $243 per night
(USD)
Craig & Cindy Key West Truman Annex Shipyard Condo with a deck at Mile Marker 0!
2
1.0
4
Key West Florida Condo
From $287 per night
(USD)
Craig & Cindy Truman Annex Foundry Townhouse 2 bedrooms 2.5 baths
2
3.0
6
Key West Florida Private vacation home
From $401 per night
(USD)
**COASTLINE COMFORT @ COCONUT MALLORY** Condo + LAST KEY SERVICES…
2
2.0
6
Key West Florida Condo
From $289 per night
(USD)
**SET SAIL @ COCONUT MALLORY** Condo + LAST KEY SERVICES…
2
2.0
6
Key West Florida Condo
From $291 per night
(USD)
Cozy studio cottage in Old Town Key West
1
1.0
4
Key West Florida Cottage
From $200 per night
(USD)
COCONUT Adorable cottage in Old Town
1.0
4
Key West Florida Private vacation home
From $329 per night
(USD)
Heart of Key West - 2BR Waterfront at the Galleon Resort
2
2.0
6
Key West Florida Condo
From $709 per night
(USD)
Little Casita: Key West Monthly rental Close to Duval - RealKeyWest
1
1.0
2
Key West Florida Apartment
From $145 per night
(USD)
Welcome to the Shady Palms - Private Pool - RealKeyWest
2
3.0
6
Key West Florida Private vacation home
From $311 per night
(USD)
Old Town Getaway
1
1.0
4
Key West Florida Private vacation home
From $155 per night
(USD)
Perfect Location to Key West Action! Garden View, Pool, Bike Rental!
1
1.0
2
Key West Florida Guest house
From $556 per night
(USD)
Wonderful Stay, Amazing Location! 3 Pools, Bar, Pets Allowed!
1
1.0
2
Key West Florida Guest house
From $463 per night
(USD)
**ENVY OF THE ISLAND @ OLD TOWN** Pristine Home & Pool + LAST KEY SERVICES...
5
7.0
10
Key West Florida Private vacation home
From $506 per night
(USD)
Amazing Stay, Great Location! Bike Rental, Pools, Onsite Bar
1
1.0
2
Key West Florida Guest house
From $528 per night
(USD)
Luxurious Vacation! Pools, Tiki Bar, Bike Rental
1
1.0
2
Key West Florida Guest house
From $637 per night
(USD)
Ground-level getaway with free WiFi, private deck, & shared outdoor pool
1
1.0
2
Key West Florida Condo
From $147 per night
(USD)
SOUTHERNMOST SWIM AND SOCIAL CLUB
3
2.0
6
Key West Florida Private vacation home
From $400 per night
(USD)
Hyatt Windward Pointe, Key West, Fl. - 2 Bedroom Unit - 1064 sq\/ft
2
2.0
6
Key West Florida Condo
Click For Pricing
Treasure Cove- 2BDR\/2.5BA | 2 Bed, 2.5 Bath
2
3.0
6
Key West Florida Private vacation home
Click For Pricing
Rarely Available! Quiet Lane in the Heart of Old Town, Sleeps 4 + 🐶🐾
2
2.0
6
Key West Florida Private vacation home
From $180 per night
(USD)
ISLAND TIME - 5 Bed\/3 Bath OldTown Complex - MONTHLY - Private pool
5
3.0
12
Key West Florida Private vacation home
From $676 per night
(USD)
TROPICAL PROPERTIES VACATION RENTAL - KEY WEST
3
2.0
8
Key West Florida Private vacation home
From $307 per night
(USD)
Tropical Jewel: Historic Seaport Oldtown - 2BR\/2BA - Pool - RealKeyWest
2
2.0
6
Key West Florida Cottage
From $228 per night
(USD)
MAJESTIC PARADISE II Luxury living in Truman Annex. Downtown, pool, 2 blks
2
3.0
6
Key West Florida Private vacation home
From $400 per night
(USD)
**JASMINE JEWEL @ THE ANNEX** Lush Private Home & Pool + LAST KEY SERVICES…
2
3.0
6
Key West Florida Private vacation home
From $970 per night
(USD)
Tropical Getaway! 3 Pools, Bike Rental, Pets Allowed!
1
1.0
2
Key West Florida Private vacation home
From $415 per night
(USD)
Wonderful Beach Vacation! 3 Pools, Tiki Bar, Bike Rentals, Pets Allowed, Dining!
1
1.0
4
Key West Florida Guest house
From $477 per night
(USD)
Amazing Vacation! 4 Spacious Units! 3 Pools, Tiki Bar, Bike Rental!
4
4.0
8
Key West Florida Guest house
Click For Pricing
Family and Friends Vacation! Pet-friendly!
1
1.0
4
Key West Florida Guest house
From $514 per night
(USD)
ADMIRAL'S PARADISE in Key West
2
3.0
4
Key West Florida Private vacation home
From $489 per night
(USD)
Sky Suites Retreat by Brightwild–2 Stunning Condos
4
5.0
12
Key West Florida Apartment
From $978 per night
(USD)
Tortuga Suite | Heated Pool & Hot Tub!
2
2.0
6
Key West Florida Condo
From $307 per night
(USD)
Waterfront Property - Marina Access - Spacious - Excellent Key West Condo
2
2.0
6
Key West Florida Condo
From $455 per night
(USD)
Key West's Crown Jewel
2
2.0
6
Key West Florida Condo
From $640 per night
(USD)
Beautiful & Relaxing 2 bed 2 bath condo
2
2.0
6
Key West Florida Hotel resort
Click For Pricing
Southernmost Retreat: 2 Blocks from Duval in Old Town.
3
2.0
6
Key West Florida Cottage
From $500 per night
(USD)
Casa Verde - Perfection in a monthly rental - private pool - RealKeyWest
3
4.0
6
Key West Florida Private vacation home
From $345 per night
(USD)
**SEAPORT SENSATION @ OLD TOWN VILLAS** Condo & Pool + LAST KEY SERVICES...
3
4.0
8
Key West Florida Private vacation home
From $345 per night
(USD)
**COASTAL LOVING @ OLD TOWN** Chic 4BR Home & Pool + LAST KEY SERVICES...
4
3.0
8
Key West Florida Private vacation home
From $355 per night
(USD)
Flirty Flamingo Key West
3
4.0
8
Key West Florida Private vacation home
From $350 per night
(USD)
Runaway Bills | 3 Bed, 1 Bath
3
1.0
6
Key West Florida Private vacation home
Click For Pricing
Henry's Piece of Paradise on the Ocean in Key West - Weekly \/ Nightly
2
2.0
5
Key West Florida Condo
From $435 per night
(USD)
Sunset South: First Floor 2 Bedroom 1 Bath Condo at Bayfront Suites & Marina
2
1.0
4
Key West Florida Condo
From $495 per night
(USD)
Sunset views at the Galleon
2
2.0
6
Key West Florida Condo
Click For Pricing
Upper Bayview North: Waterfront 4 Bedroom Condo at Bayfront Suites & Marina
4
4.0
8
Key West Florida Condo
From $1800 per night
(USD)
Upscale Townhouse with Golf and Lake Views, Shared Pool, WiFi, and AC - Dogs OK
3
3.0
6
Key West Florida Private vacation home
From $207 per night
(USD)
Middle Sunset: 3 Bedroom 3 Bath Luxury Condo at Bayfront Suites & Marina
3
3.0
6
Key West Florida Condo
From $882 per night
(USD)
Bayview North One: Waterfront 4 Bedroom 4 Bath Condo at Bayfront Suites
4
4.0
8
Key West Florida Condo
From $1808 per night
(USD)
Sunset North: Luxury 4 Bedroom 4.5 Bath Condo at Bayfront Suites & Marina
4
4.0
8
Key West Florida Condo
From $917 per night
(USD)
Upper Sunset South: Luxury 3 Bedroom Condo at Bayfront Suites & Marina
3
3.0
6
Key West Florida Condo
From $877 per night
(USD)
Bayview South: 4 Bedroom 3 Bath Waterfront Condo at Bayfront Suites & Marina
4
3.0
8
Key West Florida Condo
From $1827 per night
(USD)
Upper Sunset North: Luxury 4 Bedroom Condo at Bayfront Suites & Marina
4
5.0
8
Key West Florida Condo
From $993 per night
(USD)
Bayview Middle: Waterfront 3 Bedroom Condo at Bayfront Suites & Marina
3
2.0
6
Key West Florida Condo
From $895 per night
(USD)
Hidden Gem-Key West 3/2 wading pool home with parking -RealKeyWest
3
2.0
6
Key West Florida Private vacation home
From $489 per night
(USD)
Upper Bayview South: Waterfront 4 Bedroom Condo at Bayfront Suites & Marina
4
3.0
8
Key West Florida Condo
From $1895 per night
(USD)
~HORSE CONCH~ Amazing location with shared pool and covered balcony!
1
1.0
4
Key West Florida Apartment
From $309 per night
(USD)
coral stone
1
1.0
2
Key West Florida Condo
From $106 per night
(USD)
WASTIN AWAY IN MARGARITAVILLE! HYATT RESIDENCE CLUB JEWEL IN HEART OF KEY WEST
2
2.0
4
KEY WEST Florida Hotel resort
From $700 per night
(USD)
~Serene Lily~ Luxurious 2 bed, 2.5 bath home in the upscale Truman Annex
2
3.0
6
Key West Florida Private vacation home
From $645 per night
(USD)
Paradise found at the Key West Golf Club!
2
2.0
4
Key West Florida Private vacation home
From $163 per night
(USD)
NEW YEAR - NEW CRAZY LOW DEALS ON FANTASTIC HOME
2
1.0
6
Key West Florida Condo
From $558 per night
(USD)
Lush Gardens-Pool-Jacuzzi-No Contact Check-In
3
2.0
6
Key West Florida Private vacation home
From $196 per night
(USD)
FANTASY WEEK
2
2.0
6
Key West Florida Condo
Click For Pricing
Petite Pearl! Spacious 1 Bedroom, 1 Bath Pool Condo- RealKeyWest
1
1.0
2
Key West Florida Condo
From $179 per night
(USD)
Old Town Key West - Historic & Charming - 2 Blks From Duval
2
1.0
5
Key West Florida Private vacation home
From $819 per night
(USD)
The Sylvia Gwynn, Key West Southernmost Point monthly vacation rental
1
1.0
2
Key West Florida Apartment
From $145 per night
(USD)
La Casita
2
2.0
6
Key West Florida Private vacation home
From $606 per night
(USD)
**COLORS OF THE KEYS @ THE FOUNDRY** Villa Near Duval & Beach + LAST KEY SERVICE
2
3.0
6
Key West Florida Private vacation home
From $552 per night
(USD)
The Key West Bougain Villa, a Monthly Vacation Rental
2
2.0
6
Key West Florida Private vacation home
From $412 per night
(USD)
~FISH CAMP!~ Family friendly, canal front, monthly rental.
3
3.0
8
Key West Florida Private vacation home
From $232 per night
(USD)
Seaport Walkabout- the best location in town
2
1.0
6
Key West Florida Private vacation home
From $317 per night
(USD)
2bed 2bath luxe condo w\/ ocean views, dock space, waterfront pool\/hot tub
2
2.0
4
Key West Florida Condo
From $223 per night
(USD)
Key West On My Mind, Ocean Views, Renovated Kitchen, Last minute deals
2
2.0
6
Key West Florida Condo
From $479 per night
(USD)
Key West Affordable Ocean View Condo. Clean priced well on the Atlantic
2
2.0
6
Key West Florida Condo
From $499 per night
(USD)
Free Island Sprint has been transformed- Wonderful Renovation done in Fall 21
2
2.0
4
Key West Florida Condo
From $150 per night
(USD)
Casa Papa Del Mar formerly Ocean Extravaganza - Totally Renovated in 2022.
2
2.0
6
Key West Florida Condo
From $598 per night
(USD)
Moonlight Paradise Upgraded Family oasis Tropical views expansive balcony
2
2.0
6
Key West Florida Condo
From $457 per night
(USD)
Ocean Front Key West Oasis Island Tones Charming Historical Downtown area
2
2.0
6
Key West Florida Condo
From $175 per night
(USD)
Key West Paradise, Conch Hideaway, Island Vibrations, Balmy Ocean Breezes KWF
2
2.0
6
Key West Florida Condo
Click For Pricing
~POINCIANA GARDEN~ Casual 1st floor duplex 2 blocks from Duval Street!
1
1.0
3
Key West Florida Private vacation home
From $307 per night
(USD)
Key West Beachfront Luxury 2\/2 Condo A212
2
2.0
6
Key West Florida Condo
From $450 per night
(USD)
Vibrant Island retreat, Expansive private balcony, Enjoy the Coastal Breezes
2
2.0
4
Key West Florida Condo
From $146 per night
(USD)
Salty Sea Breezes, Exquisite Morning Sunrises, Luxurious Condo. Fall Specials
3
2.0
8
Key West Florida Condo
From $280 per night
(USD)
Casa Coastal East, Morning sunrises, Evening night time vibes An Island home.
2
2.0
4
Key West Florida Condo
From $185 per night
(USD)
Amazingly Transformed in 2022 Luxurious renovation Fantastic Ocean View
2
2.0
6
Key West Florida Condo
From $569 per night
(USD)
Key Wes't Best- Upgraded condo 5 mins to Smathers Beach Fantastic value
2
2.0
6
Key West Florida Condo
From $556 per night
(USD)
~ HARRY TRUMAN SUITE ~ Walk to Duval Street from this beautiful property!
2
1.0
5
Key West Florida Apartment
Click For Pricing
Paradise Found in Key West upgrades throughout 5 minutes to Smathers Beach
2
2.0
6
Key West Florida Condo
From $462 per night
(USD)
Best Downtown Location Monthly Rental Open Nov 2023- Jan 2024
2
1.0
4
Key West Florida Apartment
From $147 per night
(USD)
Carolina to Keys Ocean view dream Monthly pricing Best pool on the Island
2
2.0
4
Key West Florida Condo
From $175 per night
(USD)
Anchor Drop modern elegance upgrades throughout views of Atlantic Ocean
2
2.0
6
Key West Florida Condo
From $549 per night
(USD)
Tropical Paradise Key West - Upgraded Master Bath - Best Value Discounts
2
2.0
6
Key West Florida Condo
From $389 per night
(USD)
Joan's Caribbean Hideaway
2
2.0
4
Key West Florida Private vacation home
From $134 per night
(USD)
Key West Morning reflections, Balmy Ocean Breezes, Downtown family fun
2
2.0
4
Key West Florida Condo
From $150 per night
(USD)
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