Fleming Key Rentals
From $974 per night (USD)VRBO
Custom House Inn | Two 2nd Floor Suites On Duval!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Summary: Located right in the heart of the World Famous Duval Street, enjoy a true downtown Key West experience at the o ...
From $974 per night (USD)VRBO
From $916 per night (USD)Expedia
Custom House Inn | Two Suites On Duval St
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Summary: Located right in the heart of the World Famous Duval Street, enjoy a true downtown Key West experience at the o ...
From $916 per night (USD)Expedia
From $264 per night (USD)VRBO
A quiet Paradise sanctuary on a dead-end street overlooking Florida Bay.
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Greet the day with a sunrise over the bay. Situated on a peaceful, quiet dead-end street. Located within a 2 mile radius ...
From $264 per night (USD)VRBO
From $570 per night (USD)Expedia
Delancey Hall in Old Town with a pool and privacy!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Live like a local and walk or bike to town. Enjoy your large furnished front porch or your own private back porch by the ...
From $570 per night (USD)Expedia
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Studio Unit in quiet resort adjacent to Old Town Key West!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
With a coveted location in the heart of Old Town and magnificent views of the Gulf of Mexico, Sunset Harbor is the ultim ...
Click For PricingVRBO
From $1794 per night (USD)VRBO
Island Retreat: Daily Housekeeping, 3 Pools, Fitness Center Access
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $1794 per night (USD)VRBO
From $605 per night (USD)VRBO
Island Paradise: Modern Unit, Latin Cuisine, Poolside Cocktails
- 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 $605 per night (USD)VRBO
From $2392 per night (USD)VRBO
Key West Sanctuary: Daily Housekeeping, Tiki Bar, Fitness Center
- 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 $2392 per night (USD)VRBO
From $3028 per night (USD)VRBO
Island Oasis: New Property, Poolside Cocktails, Latin Cuisine On-Site
- Bedrooms:
- 2
- 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 $3028 per night (USD)VRBO
From $4249 per night (USD)VRBO
Key West Getaway: Private Balcony, 3 Pools, Fitness Center Access
- Bedrooms:
- 2
- 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 $4249 per night (USD)VRBO
From $2153 per night (USD)VRBO
Duval Street Gem: Ocean-View Balcony, On-Site Dining, 3 Pools
- 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 $2153 per night (USD)VRBO
From $1196 per night (USD)VRBO
Key West Hideaway: Private Balcony, Tiki Bar, On-Site Restaurant
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $1196 per night (USD)VRBO
From $2285 per night (USD)VRBO
Oceanfront Escape: Modern Design, 3 Pools, Bicycle Rentals
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $2285 per night (USD)VRBO
From $1614 per night (USD)VRBO
Coastal Haven: Modern Unit, Poolside Cocktails, Latin Cuisine
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $1614 per night (USD)VRBO
From $544 per night (USD)VRBO
Ocean Oasis: Daily Housekeeping, On-Site Dining, Fitness Center
- 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 $544 per night (USD)VRBO
From $832 per night (USD)VRBO
Tropical Escape: Ocean-View Balcony, Tiki Bar, 3 Pools
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $832 per night (USD)VRBO
From $530 per night (USD)VRBO
Bohemian Retreat with Pool in Old Town Key West | Walk to Duval Street
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the heart of Old Town Key West! This hotel is located steps from Duval Street and Hemingway's home. Stroll to S ...
From $530 per night (USD)VRBO
From $652 per night (USD)VRBO
Stylish and Modern 2BR Suite Near Old Town | Pool + Patio
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Discover the heart of Old Town Key West! This hotel is located steps from Duval Street and Hemingway's home. Stroll to S ...
From $652 per night (USD)VRBO
From $627 per night (USD)VRBO
Romantic Key West Getaway with Heated Pool, Patio & Breakfast | Near Sunset Pier
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the heart of Old Town Key West! This hotel is located steps from Duval Street and Hemingway's home. Stroll to S ...
From $627 per night (USD)VRBO
From $710 per night (USD)VRBO
Escape to Key West: Stylish Boutique Hotel by Duval Street | Pool & Breakfast
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the heart of Old Town Key West! This hotel is located steps from Duval Street and Hemingway's home. Stroll to S ...
From $710 per night (USD)VRBO
From $496 per night (USD)VRBO
Historic Haven w\/ Unique Rooms, Afternoon Refreshers & Steps from Duval St
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the charm of Old Town in our vibrant retreat, steps away from Duval's delights. Dive into history at Hemingway' ...
From $496 per night (USD)VRBO
From $498 per night (USD)VRBO
Celebrate History in Key West: Relaxing Bungalows with Resort-Like Amenities
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Discover the charm of Old Town in our vibrant retreat, steps away from Duval's delights. Dive into history at Hemingway' ...
From $498 per night (USD)VRBO
From $1878 per night (USD)VRBO
4 Traditional Two Queen, Pier House Resort, Island Elegance, Duval St. Access
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $1878 per night (USD)VRBO
From $763 per night (USD)VRBO
One Bedroom Suite Queens, Pier House, Roomy Elegance, Beachside Bliss, Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $763 per night (USD)VRBO
From $486 per night (USD)VRBO
Serene Resort Room with Private Beach & Spa - Perfect Key West Escape
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $486 per night (USD)VRBO
From $763 per night (USD)VRBO
One Bedroom Suite King, Pier House, Spacious Comfort, Spa Access, Ocean Breeze
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $763 per night (USD)VRBO
From $831 per night (USD)VRBO
Oceanfront King, Pier House, Stunning Ocean Views, Plush King Bed, Duval Locale
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $831 per night (USD)VRBO
From $468 per night (USD)VRBO
Family-Friendly Key West Resort with Private Beach on Duval St.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $468 per night (USD)VRBO
From $889 per night (USD)VRBO
Inviting Key West Paradise Perfect for Couples - Spa & Oceanfront Views
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $889 per night (USD)VRBO
From $763 per night (USD)VRBO
Relaxing Key West Haven with Full-Service Spa and Legendary Dining
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $763 per night (USD)VRBO
From $486 per night (USD)VRBO
Lanai Two Queen, Pier House, Tropical Views, Beachfront Access, Key West Charm
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $486 per night (USD)VRBO
From $1368 per night (USD)VRBO
3 Traditional Two Queen, Pier House Resort, Fine Dining, Near Mallory Square
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $1368 per night (USD)VRBO
From $2478 per night (USD)VRBO
3 Charming Resort Stays with Private Beach & Spa Treatments - Key West Retreat
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $2478 per night (USD)VRBO
From $911 per night (USD)VRBO
2 Traditional Two Queen, Pier House Resort, Beachside, Key West Vibe
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $911 per night (USD)VRBO
From $881 per night (USD)VRBO
Oceanfront Two Queen, Pier House, Beach Panorama, Custom Decor, Pet-Friendly
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $881 per night (USD)VRBO
From $1653 per night (USD)VRBO
2 Oceanfront Two Queen, Pier House Resort, Beach Access, Pet-Friendly, Duval St.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $1653 per night (USD)VRBO
From $576 per night (USD)VRBO
Key West Beachfront Accommodation - Ideal for Family Vacation Fun!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $576 per night (USD)VRBO
From $936 per night (USD)VRBO
2 Serene Beachside Accommodations with Enhanced Spa Experience in Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $936 per night (USD)VRBO
From $1751 per night (USD)VRBO
2 Sophisticated Resort Rooms Perfect for Family Relaxation! Spa Access
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $1751 per night (USD)VRBO
From $453 per night (USD)VRBO
Traditional King, Pier House, Classic Island Style, Fine Dining, Duval Street Proximity
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $453 per night (USD)VRBO
From $692 per night (USD)VRBO
Pure Wellness Spa Junior Suite, Pier House, Private Beach Access, Duval St.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $692 per night (USD)VRBO
From $445 per night (USD)VRBO
Beachfront Bliss with Water Activities & Next to Vibrant Nightlife Attractions
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $445 per night (USD)VRBO
From $822 per night (USD)VRBO
Unique Island-Style Rooms with Custom Furniture & Art in Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $822 per night (USD)VRBO
From $657 per night (USD)VRBO
Pet-Friendly Coastal Retreat in Key West with Private Beach Access
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $657 per night (USD)VRBO
From $780 per night (USD)VRBO
Chic Beachfront Stays - Enjoy Ocean Views & Private Sand in Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $780 per night (USD)VRBO
From $1824 per night (USD)VRBO
4 Key West Stays with Spa, Private Beach & Culinary Delights - On Duval St.
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $1824 per night (USD)VRBO
From $2478 per night (USD)VRBO
3 Oceanfront Two Queen, Pier House Resort, Beachfront Leisure, Key West Sunset
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $2478 per night (USD)VRBO
From $1100 per night (USD)VRBO
Oceanfront Suite, Pier House, Serene Waterfront, Elegant Dining, Island Life
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $1100 per night (USD)VRBO
From $1409 per night (USD)VRBO
3 Island-Chic Rooms Offering Private White Sand Beach on Duval St. in Key West
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $1409 per night (USD)VRBO
From $244 per night (USD)Expedia
Snowbird-friendly condo with heated pool, patio lounge, water view, yard, & W\/D
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The Key to Tranquility Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $244 per night (USD)Expedia
From $196 per night (USD)VRBO
Southard Retreat- 2 bed 2 bath townhome downtown w\/ pool, parking
- 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 $196 per night (USD)VRBO
From $529 per night (USD)VRBO
Garden-Set Bungalows Featuring Poolside Bliss- Near Duval Street
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 1
Discover the charm of Old Town in our vibrant retreat, steps away from Duval's delights. Dive into history at Hemingway' ...
From $529 per night (USD)VRBO
From $508 per night (USD)VRBO
Romantic Getaway: Sun-Drenched Bungalows near Duval Street
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the charm of Old Town in our vibrant retreat, steps away from Duval's delights. Dive into history at Hemingway' ...
From $508 per night (USD)VRBO
From $465 per night (USD)VRBO
Romantic Getaway with Plush Turkish Robes & Inviting Pools Near Duval Street
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 1
Discover the charm of Old Town in our vibrant retreat, steps away from Duval's delights. Dive into history at Hemingway' ...
From $465 per night (USD)VRBO
From $546 per night (USD)VRBO
Key West Oasis: Retreat in Historical Bungalows with Pool Paradise
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Discover the charm of Old Town in our vibrant retreat, steps away from Duval's delights. Dive into history at Hemingway' ...
From $546 per night (USD)VRBO
From $542 per night (USD)VRBO
Tropical Escape: Artistic-Vibe Bungalows Steps from Duval Street
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the charm of Old Town in our vibrant retreat, steps away from Duval's delights. Dive into history at Hemingway' ...
From $542 per night (USD)VRBO
From $584 per night (USD)VRBO
Enchanting Hideaway Perfect for Couples Seeking Romantic Bliss
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the charm of Old Town in our vibrant retreat, steps away from Duval's delights. Dive into history at Hemingway' ...
From $584 per night (USD)VRBO
From $455 per night (USD)VRBO
Serene Bungalow in Key West: Poolside Refreshers & Relaxing Amenities
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the charm of Old Town in our vibrant retreat, steps away from Duval's delights. Dive into history at Hemingway' ...
From $455 per night (USD)VRBO
From $517 per night (USD)VRBO
Unwind in Paradise: Playful Historic Bungalows with Resort-Like Amenities
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the charm of Old Town in our vibrant retreat, steps away from Duval's delights. Dive into history at Hemingway' ...
From $517 per night (USD)VRBO
From $798 per night (USD)VRBO
Coastal Bliss: Tranquil Bungalows with an Artistic Vibe in Vibrant Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Discover the charm of Old Town in our vibrant retreat, steps away from Duval's delights. Dive into history at Hemingway' ...
From $798 per night (USD)VRBO
From $531 per night (USD)VRBO
Seaside Retreat: Inviting Bungalows with Turkish Robes and Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the charm of Old Town in our vibrant retreat, steps away from Duval's delights. Dive into history at Hemingway' ...
From $531 per night (USD)VRBO
From $624 per night (USD)VRBO
Stunning Hideaway: Charming Bungalows near Ernest Hemingway Home
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the charm of Old Town in our vibrant retreat, steps away from Duval's delights. Dive into history at Hemingway' ...
From $624 per night (USD)VRBO
From $521 per night (USD)VRBO
Historic Inn: Romantic Stay in Key West's Hidden Gem - Pools & Patio
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the charm of Old Town in our vibrant retreat, steps away from Duval's delights. Dive into history at Hemingway' ...
From $521 per night (USD)VRBO
From $151 per night (USD)Expedia
Island Time in Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
NEW UNIT! Summer and Fall DiscountsGo back in “Island” Time, located in the historic Wilhelmina Harvey house, who was th ...
From $151 per night (USD)Expedia
From $619 per night (USD)VRBO
Bohemian Key West Boutique Inn with Pool & Free Breakfast | Near Sunset Pier
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the heart of Old Town Key West! This hotel is located steps from Duval Street and Hemingway's home. Stroll to S ...
From $619 per night (USD)VRBO
From $2226 per night (USD)VRBO
Oceanfront Retreat: Daily Housekeeping, Fitness Center Access, Latin Cuisine
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $2226 per night (USD)VRBO
From $2285 per night (USD)VRBO
Tropical Paradise: Daily Housekeeping, Tiki Bar, On-Site Restaurant
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $2285 per night (USD)VRBO
From $1593 per night (USD)VRBO
Island Serenity: Private Balcony, On-Site Dining, 3 Pools
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $1593 per night (USD)VRBO
From $536 per night (USD)VRBO
Green Turtle Cottage KW 1 Block from Mile Marker 0 in Gated Truman Annex
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
This 2 bedroom 2.5 bath private home in a secluded section of the gated community of Truman Annex quietly sits among pre ...
From $536 per night (USD)VRBO
From $619 per night (USD)Expedia
Hyatt Residence 1 bedroom in a coveted location in the heart of Old Town.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Unwind in Key West at this lovely Villa. Nestled in the heart of the city, this enchanting property offers a cozy retrea ...
From $619 per night (USD)Expedia
From $354 per night (USD)VRBO
Boomerang Boathouse in Key West
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
NEW UNIT! Summer and Fall Discounts“Richley individual” yet “classic Key West” are phrases that echo from Boomerang Boat ...
From $354 per night (USD)VRBO
From $965 per night (USD)Expedia
Luxurious Gated Key West Oasis: 3 Bed + 4th Floor Sleeper, Elevator, & Golf Cart
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Immerse yourself in the heart of Old Town Key West and discover a luxurious retreat where island living meets modern com ...
From $965 per night (USD)Expedia
From $483 per night (USD)VRBO
New! Coastal Rose - Bright Loft with High Ceilings!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Experience the charm of downtown Key West in this cozy 1-bedroom unit with an additional loft and a shared pool ...
From $483 per night (USD)VRBO
From $255 per night (USD)Expedia
New! Rose Petal Petite Suite - Pool & Parking!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Located in downtown Key West, the 'Rose Petal Petite Suite' offers a cozy and charming accommodation experience ...
From $255 per night (USD)Expedia
From $915 per night (USD)VRBO
New! Rose Retreat - Pool & Parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Escape to paradise with this luxurious Key West retreat, perfect for families and groups looking to unwind in s ...
From $915 per night (USD)VRBO
From $657 per night (USD)VRBO
Relax in Romantic Lodge w\/ Pool Minutes from Vibrant Duval Street
- 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 $657 per night (USD)VRBO
From $486 per night (USD)VRBO
Modern Lodge w\/ Outdoor Pool Near Attractions Ideal for Family 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 $486 per night (USD)VRBO
From $993 per night (USD)VRBO
2 Rooms for the whole family w\/ Pool access! Near Duval St. and Museums
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Discover Old Town charm, plunge into vibrant Duval Street life, and dive deep into Key West's treasures. We're footsteps ...
From $993 per night (USD)VRBO
From $792 per night (USD)VRBO
2 Bedroom Suite w\/ Outdoor Pool in Old Town Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Discover Old Town charm, plunge into vibrant Duval Street life, and dive deep into Key West's treasures. We're footsteps ...
From $792 per night (USD)VRBO
From $393 per night (USD)VRBO
Beautiful Room w\/ Outdoor Pool & Close to Duval St. Restaurants
- 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 $393 per night (USD)VRBO
From $475 per night (USD)VRBO
Heron Hideaway - Charming 1st Floor Condo, Private Spa\/Shared Pool, Near Duval Street & Beaches!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to Heron Hideaway, a charming 1st-floor condo nestled in the desirable Meadows area of Key West. Just six blocks ...
From $475 per night (USD)VRBO
From $3004 per night (USD)Expedia
NEW! The Rigby House - Pvt Pool, Amazing Location!
- Bedrooms:
- 7
- Bathrooms:
- 6
- Sleeps:
- 12
Summary: Escape to paradise with this stunning 6-bedroom, 6.5 bathroom home nestled in the heart of historic Key West. W ...
From $3004 per night (USD)Expedia
From $761 per night (USD)VRBO
Charming 2-bedroom guest house with AC & WiFi in brilliant Key West, near Duval
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Key West is waiting for you at this clean and spacious 2-bedroom guest house. With 2 queen beds and 3 bathrooms equippe ...
From $761 per night (USD)VRBO
From $1807 per night (USD)Expedia
Spacious 5-bedroom house in charming Key West with AC, WiFi, Plunge Pool
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Located in Key West and just blocks away from Duval Street, enjoy what this 5-bedroom house has to offer. This beautiful ...
From $1807 per night (USD)Expedia
From $646 per night (USD)VRBO
Romantic Stay in Historic Key West: 1BR Suite w\/ King Bed & 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 $646 per night (USD)VRBO
From $592 per night (USD)VRBO
Key West Paradise: Minimalist King Room w\/ Balcony or Terrace! Enjoy the Breeze
- 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 $592 per night (USD)VRBO
From $724 per night (USD)VRBO
Stunning Key West Stay Perfect for a Romantic Escape! Outdoor Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Enjoy vibrant Key West: steps to Duval Street's nightlife, historic sites, and serene beaches. Perfect for culture and s ...
From $724 per night (USD)VRBO
From $244 per night (USD)Expedia
Charming 2-bedroom house in Key West with Pool
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Embrace the Enchantment of Old Key West Charm! Escape to the enchanting world of Key West Hideaway, where history meets ...
From $244 per night (USD)Expedia
From $374 per night (USD)VRBO
Casa Tranquila - Fully-Renovated 2-bedroom Townhome in Old Town Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Casa Tranquila! This 2-bedroom townhome is perfect for your escape to Key West. Located in Old Town just five ...
From $374 per night (USD)VRBO
From $5625 per night (USD)VRBO
Key West Hyatt Charming 2-bedroom resort with WiFi, AC
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Experience a serene oasis nestled in the heart of Key West’s historic Old Town. Surrounded by lush greenery, this retrea ...
From $5625 per night (USD)VRBO
From $5625 per night (USD)VRBO
Key West Studio Charming resort with WiFi, AC, fitness room
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Experience a serene oasis nestled in the heart of Key West’s historic Old Town. Surrounded by lush greenery, this retrea ...
From $5625 per night (USD)VRBO
From $288 per night (USD)VRBO
In the heart of Old Town lies the HAVEN HOUSE
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
Haven House provides the perfect home base to be near the center of everything but be able to retreat to home and watch ...
From $288 per night (USD)VRBO
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Mid Town 2\/1 TREE HOUSE RETREAT
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Tree House Retreat is located on the second floor of Amanda's Garden Getaway. It offers a large living room with french ...
Click For PricingVRBO
From $1155 per night (USD)Expedia
Amanda's Garden Getaway - Mid Town 3\/2 cottage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Lush tropical grounds and large shared pool are just outside the doors of the Garden Getaway. Expansive covered porch, l ...
From $1155 per night (USD)Expedia
Click For PricingVRBO
Mid Town Affordable 3bd\/2.5ba 3 story Townhome
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Coco's Hideaway is a 3-level townhome that is part of a mini-compound complete with lush tropical gardens and a huge sha ...
Click For PricingVRBO
From $1160 per night (USD)VRBO
Relax in Style at Windsor Townhomes #4
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Elegance and modern sophistication are apparent as you enter any one of these six conveniently located townhomes in a q ...
From $1160 per night (USD)VRBO
From $582 per night (USD)VRBO
The Hideout! Where Luxury Meets Location. Fully Renovated, with Pool.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to The Hideout, where luxury meets location. Look no further than "The Hideout" for upscale luxury and single- ...
From $582 per night (USD)VRBO
From $1883 per night (USD)Expedia
The Caroline House Estate - 1 Block off Duval & Key West Historic Seaport
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
This gorgeous classical Key West Estate property is quite possibly the most stylish blend of historic Victorian-Caribbea ...
From $1883 per night (USD)Expedia
From $1185 per night (USD)VRBO
Spacious Townhome on Windsor Lane 3\/3.5
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Windsor Townhomes #3! Once you enter this beautifully decorated oasis…your vacation begins. This townhome has ...
From $1185 per night (USD)VRBO
From $269 per night (USD)VRBO
ANNA MARIA HAVEN - Renovated 3bd\/3ba Conch Monthly rental
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This newly remodeled Conch house is located on Olivia Street in Old Town Key West just two and a half blocks from World ...
From $269 per night (USD)VRBO