Fleming Key, Florida Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Fleming Key, Florida on RentalSaver.com!

Fleming Key Rentals

From $548 per night (USD)
VRBO
The Bartlum | Luxury Studio In Prime Location!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Welcome to the Bartlum, a historic and luxurious studio apartment just steps to Duval Street. This studio, lo ...
From $548 per night (USD)
VRBO
$GOLDEN NUGGET ~ Adult Only, 1st Floor Queen Bedroom w\/ Shared Pool!$
From $390 per night (USD)
Expedia
GOLDEN NUGGET ~ Adult Only, 1st Floor Queen Bedroom w\/ Shared Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Beautiful 1st floor queen room just off the pool for easy access... DELIGHT IN OLD WORLD ALLURE... Bask in the charming ...
From $390 per night (USD)
Expedia
$NumberEleven ~ Charming Adult Only, 1 Bedroom, 1 Bath w\/ Shared Pool!$
From $402 per night (USD)
VRBO
NumberEleven ~ Charming Adult Only, 1 Bedroom, 1 Bath w\/ Shared Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Charming 1st Floor King for Convenience... DELIGHT IN OLD WORLD ALLURE... Bask in the charming ambience of the adults-o ...
From $402 per night (USD)
VRBO
$HONEY~ Adult Only, 2nd Floor 1 King Bedroom Unit w\/ Shared Pool!$
From $455 per night (USD)
Expedia
HONEY~ Adult Only, 2nd Floor 1 King Bedroom Unit w\/ Shared Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Gorgeous 2nd floor king room and ample balcony space... DELIGHT IN OLD WORLD ALLURE... Bask in the charming ambience of ...
From $455 per night (USD)
Expedia
$KEITT ~ Adult Only, 2nd Floor 1 Bedroom w\/ Shared Pool, Scarlet Mango Inn!$
From $399 per night (USD)
VRBO
KEITT ~ Adult Only, 2nd Floor 1 Bedroom w\/ Shared Pool, Scarlet Mango Inn!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Bright and airy 2nd floor king room... DELIGHT IN OLD WORLD ALLURE... Bask in the charming ambience of the adults-only ...
From $399 per night (USD)
VRBO
$JULIE ~ Adult Only, 1st Floor King Bedroom w\/ Shared Pool, Scarlet Mango Inn!$
From $390 per night (USD)
Expedia
JULIE ~ Adult Only, 1st Floor King Bedroom w\/ Shared Pool, Scarlet Mango Inn!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Lovely 1st floor king room steps from the pool for easy access... DELIGHT IN OLD WORLD ALLURE... Bask in the charming a ...
From $390 per night (USD)
Expedia
From $10013 per night (USD)
VRBO
Family Ready 1 BR Suite | Outdoor Pools | 4 Suites
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $10013 per night (USD)
VRBO
From $7904 per night (USD)
VRBO
Waterfront Room Retreat: Sparkling Pools | Three Spacious Rooms
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $7904 per night (USD)
VRBO
From $1449 per night (USD)
VRBO
Perfect Escape! Pools, Onsite 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 $1449 per night (USD)
VRBO
From $1610 per night (USD)
VRBO
Ultimate Vacation, 3 Pools, Tiki Bar, Bike Rentals, 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 $1610 per night (USD)
VRBO
From $1708 per night (USD)
VRBO
Tropical Hideaway: Room in Resort - Steps from Key West's Vibrance | 2 Units
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $1708 per night (USD)
VRBO
From $1470 per night (USD)
VRBO
Tropical Escape! 2 Spacious Units, 3 Pools!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $1470 per night (USD)
VRBO
From $7487 per night (USD)
VRBO
Resort Room with Direct Access to Water Adventures | 3 Suites Ideal for Family
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $7487 per night (USD)
VRBO
From $289 per night (USD)
VRBO
Topsail Cottage
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Topsail Cottage XXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXX ...
From $289 per night (USD)
VRBO
From $1465 per night (USD)
VRBO
A Palm Tree Haven in Key West
Bedrooms:
4
Bathrooms:
5
Sleeps:
8
This lovely single-family, two-story luxury home is in the prestigious Truman Annex gated community on a very private cu ...
From $1465 per night (USD)
VRBO
Click For Pricing
Expedia
Hyatt Residence Club Sunset Harbor-Old Town- Heart of Key West, Sleeps 4!
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 ...
Click For Pricing
Expedia
From $262 per night (USD)
VRBO
Airy & Bright Home with Pool in Old Town
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
The perfect getaway for a long stay in Key West. A private pool and patio area lie behind a green gate on a quiet lane i ...
From $262 per night (USD)
VRBO
From $991 per night (USD)
Expedia
~ASHE HOUSE~ Renovated and relaxing with pool, porches, and privacy!
Bedrooms:
4
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 $991 per night (USD)
Expedia
Click For Pricing
VRBO
The Pinder House: Discover Key West Charm at Historic Eyebrow Home, Steps from Duval St & Seaport!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Welcome to The Pinder House, where modern comfort meets historic charm in the heart of Old Town Key West. This beautiful ...
Click For Pricing
VRBO
Click For Pricing
Expedia
DOWNTOWN KEY WEST 2BED OCEANFRONT!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This is a great OCEANFRONT unit with large balcony to watch sunsets. Hyatt Sunset Harbor is perfectly located in downtow ...
Click For Pricing
Expedia
From $1710 per night (USD)
VRBO
Conch House in Key West
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Quintessential Grand Key West Estate! The James J. Curtis House c. 1874 was acquired by the Navy in 1903 and the home b ...
From $1710 per night (USD)
VRBO
From $153 per night (USD)
Expedia
Cubana Casita in Key West
Bedrooms:
2
Bathrooms:
1
Sleeps:
2
Cubana Casita is an easy-access ground floor condo with one bedroom and 1½ baths. This special home's 'from the ground u ...
From $153 per night (USD)
Expedia
From $189 per night (USD)
VRBO
The Sea Glass Cottage in Historic Key West
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Spend time in beautiful Key West and live like a local in a true Conch Home! The Sea Glass Cottage is perfect for group ...
From $189 per night (USD)
VRBO
From $185 per night (USD)
VRBO
Adorable gated loft studio two blocks from Duval in Old Town - Location Location
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The Sanctuary is tucked away on a quiet street just two blocks off Duval St. in Old Town Key West. This hidden gem is on ...
From $185 per night (USD)
VRBO
From $1069 per night (USD)
VRBO
Stunning Views at The Galleon Resort in Beautiful Key West! Charming 2 Bed!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
<p>You'll find a boat, bicycles, and more on site at this beach condo. You're conveniently located within a 5-minute wal ...
From $1069 per night (USD)
VRBO
From $256 per night (USD)
Expedia
Ultimate Escape-2 bed 2 bath Old Town home, parking, open layout, Mid-century
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
AGE REQUIREMENT: Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their ...
From $256 per night (USD)
Expedia
From $654 per night (USD)
VRBO
**THE GILDED PINEAPPLE @ THE SEAPORT** Gorgeous Home & Pool + LAST KEY SERVICES…
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! THE GILDED PI ...
From $654 per night (USD)
VRBO
From $201 per night (USD)
Expedia
Casa Azul | Open Concept, Pool & Pets!
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
Summary: Casa Azul is a luxe modern cottage with an open-concept living area that ends up filled with natural sunlight. ...
From $201 per night (USD)
Expedia
From $2565 per night (USD)
VRBO
Your Private Key West Escape | 3 Family Ready Room, Near Duval Street Nightlife
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $2565 per night (USD)
VRBO
$Idyllic Key West Room w\/ Poolside Bar & Watersports | 2 Family Rooms$
From $5110 per night (USD)
VRBO
Idyllic Key West Room w\/ Poolside Bar & Watersports | 2 Family Rooms
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $5110 per night (USD)
VRBO
From $4876 per night (USD)
VRBO
Key West Room Retreat | Two Family Ready Suites Perfect For Long Stays
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $4876 per night (USD)
VRBO
$Perfect Location to Key West Action! Pool and Garden View Room w\/ Balcony$
From $678 per night (USD)
VRBO
Perfect Location to Key West Action! Pool and Garden View Room w\/ Balcony
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $678 per night (USD)
VRBO
From $702 per night (USD)
VRBO
Classic King at The Marker Waterfront Resort Key West
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 $702 per night (USD)
VRBO
$Tropical Escape! 2 Spacious Rooms w\/ Balcony$
From $1304 per night (USD)
VRBO
Tropical Escape! 2 Spacious Rooms w\/ Balcony
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $1304 per night (USD)
VRBO
$Relaxing Room w\/ Balcony & Breathtaking View$
From $885 per night (USD)
VRBO
Relaxing Room w\/ Balcony & Breathtaking View
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $885 per night (USD)
VRBO
$Spacious Suite w\/ Terrace & Scenic Harbor View$
From $2003 per night (USD)
VRBO
Spacious Suite w\/ Terrace & Scenic Harbor View
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $2003 per night (USD)
VRBO
From $1907 per night (USD)
VRBO
Best Spot Near Duval Street Nightlife! Suite ScenicHarbor View and Terrace
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $1907 per night (USD)
VRBO
From $2571 per night (USD)
VRBO
Your Waterfront Hideaway in the Heart of Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $2571 per night (USD)
VRBO
$Breathtaking Waterfront Retreat | Spacious 1BR Suite w\/ Living Area$
From $2392 per night (USD)
VRBO
Breathtaking Waterfront Retreat | Spacious 1BR Suite w\/ Living Area
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $2392 per night (USD)
VRBO
$Chic Waterfront Room | 1BR Suite w\/ Balcony | Outdoor Pools$
From $2437 per night (USD)
VRBO
Chic Waterfront Room | 1BR Suite w\/ Balcony | Outdoor Pools
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $2437 per night (USD)
VRBO
$Harbor front Hideaway w\/ Pools & Seaside Dining | 1BR Spacious Suite$
From $2523 per night (USD)
VRBO
Harbor front Hideaway w\/ Pools & Seaside Dining | 1BR Spacious Suite
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $2523 per night (USD)
VRBO
From $9539 per night (USD)
VRBO
4 Family Ready Suites | Spacious and Near Duval Street Nightlife
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $9539 per night (USD)
VRBO
Click For Pricing
VRBO
Best Location in Key West-Hyatt Sunset Harbor with water view
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
LISTING is ONLY available January 29 to Feb 5. Best location in town. Only 1.5 blocks to Duvall Street but quiet. Key We ...
Click For Pricing
VRBO
$Waterfront Resort w\/ Outdoor Pools | Spacious Room w\/ Scenic View$
From $792 per night (USD)
VRBO
Waterfront Resort w\/ Outdoor Pools | Spacious Room w\/ Scenic View
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $792 per night (USD)
VRBO
$Scenic Old Town Key West Retreat w\/ Pool Access$
From $651 per night (USD)
VRBO
Scenic Old Town Key West Retreat w\/ Pool Access
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $651 per night (USD)
VRBO
$Waterfront Stay in Duval St. Room w\/ Pool Access$
From $821 per night (USD)
VRBO
Waterfront Stay in Duval St. Room w\/ Pool Access
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $821 per night (USD)
VRBO
$Escape to Key West w\/ Exclusive Waterfront Stay & Pool Access | 4 Family Rooms$
From $3513 per night (USD)
VRBO
Escape to Key West w\/ Exclusive Waterfront Stay & Pool Access | 4 Family Rooms
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $3513 per night (USD)
VRBO
From $664 per night (USD)
VRBO
Tropical Getaway! Refreshing Pools: 2 Blocks Away from Duval Street
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $664 per night (USD)
VRBO
From $849 per night (USD)
VRBO
Romantic Key West Getaway | Scenic Pool View Room
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $849 per night (USD)
VRBO
From $1001 per night (USD)
VRBO
Paradise Escape! 3 Pools, Restaurant with Latin Cuisine, Tiki Bar, Cycling!
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 $1001 per night (USD)
VRBO
From $1251 per night (USD)
VRBO
Harbor Oasis Room: Tranquil Seaport & Water Fun
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $1251 per night (USD)
VRBO
From $951 per night (USD)
VRBO
Perfect Key West Escape! Scenic Harbor View Room Ideal for Romantic Stay
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $951 per night (USD)
VRBO
$Relaxing Room w\/ Water View | Pool Access$
From $1020 per night (USD)
VRBO
Relaxing Room w\/ Water View | Pool Access
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $1020 per night (USD)
VRBO
From $522 per night (USD)
Expedia
Underwater Cabana at Custom House Inn | On Duval!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Welcome to Underwater Cabana at the Custom House Inn! Each apartment in our five unit complex is uniquely desig ...
From $522 per night (USD)
Expedia
From $364 per night (USD)
VRBO
Citrus Queen at Custom House Inn | On Duval St!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Welcome to Citrus Queen at the Custom House Inn! Each apartment in our five unit complex is uniquely designed a ...
From $364 per night (USD)
VRBO
From $426 per night (USD)
Expedia
Chicken Run at Custom House Inn | On Duval St!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Welcome to Chicken Run at the Custom House Inn! Each apartment in our five unit complex is uniquely designed an ...
From $426 per night (USD)
Expedia
$Priced to book! 2 Bdr\/2Ba Walking distance to Duval St., Mallory Square, Trolley$
Click For Pricing
VRBO
Priced to book! 2 Bdr\/2Ba Walking distance to Duval St., Mallory Square, Trolley
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Great location in Key West. The Galleon is Walking distance to shopping, bars, dining, trolley, marina, Duval st., Mallo ...
Click For Pricing
VRBO
From $432 per night (USD)
Expedia
Sunshine State at Custom House Inn | On Duval!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Summary: Welcome to Sunshine at the Custom House Inn! Each apartment in our five unit complex is uniquely designed and t ...
From $432 per night (USD)
Expedia
$The Caroline Suite | 1 bed, 1 bath condo w\/shared pool$
From $656 per night (USD)
Expedia
The Caroline Suite | 1 bed, 1 bath condo w\/shared pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The Caroline Suite is in The Bayview House, a completely remodeled historic house built in 1928. The 4 units and shared ...
From $656 per night (USD)
Expedia
From $159 per night (USD)
Expedia
Truman's Treasure: Beautifully Updated 2nd Floor Condo, Perfectly Convenient to Duval St & Beaches!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to "Truman's Treasure," where you can fully embrace the vibrant and unique Key West lifestyle. This beautifully ...
From $159 per night (USD)
Expedia
From $433 per night (USD)
VRBO
The Cozy Little Cottage!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Welcome to The Cozy Little Cottage !!! A REAL ISLAND GATAWAY IN KEY WEST!!! Nested in the heart of Key West, The Cozy L ...
From $433 per night (USD)
VRBO
$\Big Blu\ is a 5-bed, 4-bath home with a heated pool in downtown Key West.$
From $1696 per night (USD)
Expedia
\"Big Blu\" is a 5-bed, 4-bath home with a heated pool in downtown Key West.
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
NEW ON THE RENTAL MARKET - Big Blu is a recently renovated five-bedroom, four-bathroom traditional shotgun house with a ...
From $1696 per night (USD)
Expedia
From $391 per night (USD)
VRBO
Beautiful Old Town 2 bedroom Cottage on a Private Lane
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Located in the heart of Key West's historic district on a quiet lane with parking directly in front of the private gated ...
From $391 per night (USD)
VRBO
From $426 per night (USD)
Expedia
Spend your Holidays at Frogmore on Fleming in Downtown Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to your dream residence in the heart of Key West, Florida! Nestled in a prime location, this 2-bedroom apartment ...
From $426 per night (USD)
Expedia
From $374 per night (USD)
VRBO
Hot tin roof on Olivia Street, Key West Florida
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Located right across from the cemetery in the heart of old town Key West this property is in the perfect location to the ...
From $374 per night (USD)
VRBO
From $448 per night (USD)
VRBO
Old Town Key West Hideaway with Poolside Fun
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover Old Town charm, plunge into vibrant Duval Street life, and dive deep into Key West's treasures. We're footsteps ...
From $448 per night (USD)
VRBO
From $468 per night (USD)
VRBO
Romantic Key West Lodge with Outdoor Pool & Stunning Amenities
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover Old Town charm, plunge into vibrant Duval Street life, and dive deep into Key West's treasures. We're footsteps ...
From $468 per night (USD)
VRBO
From $814 per night (USD)
VRBO
Heart of Key West: Unique Stay with Outdoor Pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Enjoy vibrant Key West: steps to Duval Street's nightlife, historic sites, and serene beaches. Perfect for culture and s ...
From $814 per night (USD)
VRBO
From $1550 per night (USD)
VRBO
2-Bedroom Suite at a 4⭐️ Hotel
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Approximately 1,200 square feet, King bed in Master, Queen bed in second bedroom, Living area with Queen sleeper sofa an ...
From $1550 per night (USD)
VRBO
From $1550 per night (USD)
Expedia
2-Bedroom Suite at a 4⭐️ Hotel
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Approximately 1,200 square feet, King bed in Master, Queen bed in second bedroom, Living area with Queen sleeper sofa an ...
From $1550 per night (USD)
Expedia
From $231 per night (USD)
VRBO
Large 1 bedroom condo in the historic area of Key West!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Enjoy your Key West vacation in this spacious 623 square foot condo located on the second floor of this classical reviva ...
From $231 per night (USD)
VRBO
$PAGITT HOUSE - 3\/ 2 - OLD TOWN KEY WEST WITH POOL$
From $1451 per night (USD)
Expedia
PAGITT HOUSE - 3\/ 2 - OLD TOWN KEY WEST WITH POOL
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
NEW LISTINGS APRIL - 2024! Welcome to the Pagitt House built in 1933 and located on Elizabeth Street just steps to all ...
From $1451 per night (USD)
Expedia
$NEW listing!! Luxurious Island Pearl, 2 Bed\/2 Bath Home near Duval - Pool$
From $1208 per night (USD)
VRBO
NEW listing!! Luxurious Island Pearl, 2 Bed\/2 Bath Home near Duval - Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to Island Pearls, an embodiment of sophistication and luxury in the heart of Key West on Fleming Street. This to ...
From $1208 per night (USD)
VRBO
From $597 per night (USD)
Expedia
Cozy home with private pool, BBQ, central AC, enclosed yard
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Key to Paradise Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $597 per night (USD)
Expedia
$Charming, spacious monthly home w\/large pool in the Meadows Old Town Key West$
From $977 per night (USD)
VRBO
Charming, spacious monthly home w\/large pool in the Meadows Old Town Key West
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Welcome to this charming 1896 Conch house nestled within the lushly landscaped grounds of the Meadows in Old Town Key We ...
From $977 per night (USD)
VRBO
$Conch Cove - 3br\/3ba with private heated pool and private parking$
From $1251 per night (USD)
Expedia
Conch Cove - 3br\/3ba with private heated pool and private parking
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Conch Cove | Heated Pool & Prime Location! Conch Cove is your private oasis in Old Town Key West! This 3-bedroom, 3-bat ...
From $1251 per night (USD)
Expedia
$Charming 1-bedroom\/1-bath apartment in historical home with pool in Key West, FL$
From $146 per night (USD)
VRBO
Charming 1-bedroom\/1-bath apartment in historical home with pool in Key West, FL
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Your cozy getaway awaits in Key West at this amazing apartment. Nestled in a beautiful private historical home in the he ...
From $146 per night (USD)
VRBO
From $509 per night (USD)
Expedia
~SUNNY DAZE COTTAGE~ A private, newly designed home in a fantastic location.
Bedrooms:
2
Bathrooms:
2
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 $509 per night (USD)
Expedia
From $1225 per night (USD)
VRBO
“Wandering Conchs” Luxury home with private pool, separate cottage, and parking!
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
“Wandering Conchs” – A new luxury home with private pool, cottage, and parking! Nestled in the heart of Key West’s hist ...
From $1225 per night (USD)
VRBO
From $718 per night (USD)
Expedia
4-bedroom New Construction house with private pool in Key West
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
Experience Island Living In The Treetops… Welcome to your luxurious oasis in Key West, where modern comfort meets tropic ...
From $718 per night (USD)
Expedia
$ISLAND DREAMIN' ~ Exceptional 4 BR\/3.5 Ba Home w\/ Pool!$
From $579 per night (USD)
VRBO
ISLAND DREAMIN' ~ Exceptional 4 BR\/3.5 Ba Home w\/ Pool!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
MODERN MEETS CLASSIC KEY WEST STYLE... Located on the perfect corner of White and Petronia Streets, this understated bea ...
From $579 per night (USD)
VRBO
From $389 per night (USD)
Expedia
African Queen | Perfect Suite Near Historic Seaport, Shared Pool!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to African Queen Cottage, a charming retreat within the serene Harbor Walk Hideaways complex in Key West's Histo ...
From $389 per night (USD)
Expedia
From $495 per night (USD)
VRBO
Atocha Cottage at Harbor Walk Hideaways | 2 Blocks From Duval! Shared Pool
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Atocha Cottage at Harbor Walk Hideaways Welcome to Atocha Cottage, a serene getaway nestled within the charming Harbor ...
From $495 per night (USD)
VRBO
$Pilar Cottage | Spectacular Studio w\/ Shared Pool$
From $388 per night (USD)
Expedia
Pilar Cottage | Spectacular Studio w\/ Shared Pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to Pilar Cottage, a charming studio located within the peaceful Harbor Walk Hideaways complex in Key West's Hist ...
From $388 per night (USD)
Expedia
From $1386 per night (USD)
VRBO
Harbor Walk Hideaways | Group Compound In Old Town!
Bedrooms:
3
Bathrooms:
7
Sleeps:
14
Welcome to Harborwalk Hideaways! Overview: Discover Harbor Walk Hideaways, a beautifully renovated vacation rental comp ...
From $1386 per night (USD)
VRBO
From $1230 per night (USD)
VRBO
Fantastic Location, Old Town Waterfront Galleon Resort+Amenities, 2-Bedroom
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to 𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢 !! Our Galleon Resort accommodations in Historic Old Town-Key West, Florida – Where ...
From $1230 per night (USD)
VRBO
From $1700 per night (USD)
VRBO
2 Hyatt Sunset Harbor Resort, In Town, Marina
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This stylish place is close to must-see destinations. Discover this relaxing oasis in the heart of Key West's famed Old ...
From $1700 per night (USD)
VRBO
From $3577 per night (USD)
VRBO
Key West, Galleon Resort, Marina, In Town, Pool, Hot Tub
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Enjoy the glamour of this stylish, upscale place. Overlooking the shimmering span of Gulf of Mexico in historic Old Tow ...
From $3577 per night (USD)
VRBO
From $305 per night (USD)
VRBO
Adorable Key West cottage!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This pristine condo has two bedrooms, two full bathrooms and is perfect for two couples and visitors. The primary bed ...
From $305 per night (USD)
VRBO
From $735 per night (USD)
VRBO
FLEMING-O (Flamingo) Cottage is the perfect getaway
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Fleming-O (pronounced “flamingo”) is located on one-way Fleming Street in the middle of historic Old Town Key West and o ...
From $735 per night (USD)
VRBO
From $1538 per night (USD)
VRBO
Modern Elegance at Windsor Townhomes #5
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
These beautiful villas boast over 1700 sq ft. on two levels for your vacation destination, with it’s own private garden ...
From $1538 per night (USD)
VRBO
From $1757 per night (USD)
VRBO
CASA MARGARITA Steps to the Historic Seaport
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Casa Margarita is the ideal for outdoor dining, relaxing, and entertaining, with its spacious covered patio, ample seati ...
From $1757 per night (USD)
VRBO
From $683 per night (USD)
VRBO
Find your zen at HIDDEN TREASURE
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Hidden from sight, among a colony of freestanding conch cottages and surrounded by lush tropical landscaping, you will f ...
From $683 per night (USD)
VRBO
From $658 per night (USD)
Expedia
Get your ISLAND STLYE on!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This quaint property offers resort-style accommodations at an affordable price! Nestled among a colony of freestanding C ...
From $658 per night (USD)
Expedia
From $486 per night (USD)
VRBO
HIDDEN OASIS 3 blocks from Duval
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Tucked among a colony of freestanding Conch style cottages and lush tropical landscaping sits the newly renovated Hidden ...
From $486 per night (USD)
VRBO
From $975 per night (USD)
VRBO
𝐅𝐢𝐧𝐝𝐢𝐧𝐠𝐌𝐞𝐢𝐥𝐢 Waterfront Sunset Harbor Resort, DUVAL STREET+Amenities
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to 𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢🌴 Experience Paradise at Hyatt Vacation Club at Sunset Harbor! Additional $500-$1 ...
From $975 per night (USD)
VRBO
From $829 per night (USD)
VRBO
SEAPORT PANORAMA at Galleon Resort near Mallory Square—King Suite-Beach-Pool-BBQ
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
GALLEON RESORT LUXURY OCEANFRONT CONDO RENTAL 45 FT FROM THE WATER WITH BREATHTAKING 180 DEGREE FRONT & CORNER BALCONY V ...
From $829 per night (USD)
VRBO
$KALI ZOI HOUSE ~ Charming 3 BR\/3 Ba Home in Old Town w\/ Pool!$
From $328 per night (USD)
Expedia
KALI ZOI HOUSE ~ Charming 3 BR\/3 Ba Home in Old Town w\/ Pool!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
THE GOOD LIFE AWAITS... Kali Zoi is Greek for 'good life" and that is what you'll experience in this island retreat in t ...
From $328 per night (USD)
Expedia
From $186 per night (USD)
VRBO
THE HIDDEN GEM ~ Charming Renovated Studio with Large Community Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
HIDDEN GARDEN STUDIO… This charming 340 sq.ft. escape in the exclusive Lionsgate Condominium community will delight your ...
From $186 per night (USD)
VRBO
From $355 per night (USD)
Expedia
524 Elizabeth St. #2
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Enjoy a stylish experience at this centrally-located place. Located just blocks from duval and many of it's restaurants ...
From $355 per night (USD)
Expedia

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