Fleming Key Rentals
From $3665 per night (USD)VRBO
Spacious 2 BR Suite w\/ Living Area and Balcony | Onsite Parking Available
- Bedrooms:
- 1
- 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 $3665 per night (USD)VRBO
From $3513 per night (USD)VRBO
Two Bedrooms Family Suite with Balcony | Idyllic Resort w\/ Outdoor Pools
- Bedrooms:
- 1
- 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 $3513 per night (USD)VRBO
From $1242 per night (USD)VRBO
Waterfront Getaway | 2 Spacious Family Rooms w\/ Balcony | Old Town Best
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $1242 per night (USD)VRBO
From $829 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 $829 per night (USD)VRBO
From $1100 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 $1100 per night (USD)VRBO
From $947 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 $947 per night (USD)VRBO
From $1000 per night (USD)VRBO
Escape to Key West: Stylish Boutique Hotel by Duval Street | Pool & Breakfast
- Bedrooms:
- 1
- Bathrooms:
- 2
- 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 $1000 per night (USD)VRBO
From $801 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 $801 per night (USD)VRBO
From $880 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 $880 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 $832 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 $832 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 $785 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 $785 per night (USD)VRBO
From $849 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 $849 per night (USD)VRBO
From $914 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 $914 per night (USD)VRBO
From $799 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 $799 per night (USD)VRBO
From $823 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 $823 per night (USD)VRBO
From $1075 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 $1075 per night (USD)VRBO
From $796 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 $796 per night (USD)VRBO
From $956 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 $956 per night (USD)VRBO
From $810 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 $810 per night (USD)VRBO
From $218 per night (USD)Expedia
Island Time in Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Go back in “Island” Time, located in the historic Wilhelmina Harvey house, who was the "grand dame of Keys politics" as ...
From $218 per night (USD)Expedia
From $922 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 $922 per night (USD)VRBO
From $2610 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 $2610 per night (USD)VRBO
From $1018 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 $1018 per night (USD)VRBO
From $704 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 $704 per night (USD)VRBO
From $902 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 $902 per night (USD)VRBO
From $1104 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 $1104 per night (USD)VRBO
From $745 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 $745 per night (USD)VRBO
From $1194 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 $1194 per night (USD)VRBO
From $1018 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 $1018 per night (USD)VRBO
From $704 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 $704 per night (USD)VRBO
From $2322 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 $2322 per night (USD)VRBO
From $3601 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 $3601 per night (USD)VRBO
From $1545 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 $1545 per night (USD)VRBO
From $1009 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 $1009 per night (USD)VRBO
From $2382 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 $2382 per night (USD)VRBO
From $881 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 $881 per night (USD)VRBO
From $1250 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 $1250 per night (USD)VRBO
From $2049 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 $2049 per night (USD)VRBO
From $845 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 $845 per night (USD)VRBO
From $769 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 $769 per night (USD)VRBO
From $772 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 $772 per night (USD)VRBO
From $1170 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 $1170 per night (USD)VRBO
From $1024 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 $1024 per night (USD)VRBO
From $975 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 $975 per night (USD)VRBO
From $3169 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 $3169 per night (USD)VRBO
From $3601 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 $3601 per night (USD)VRBO
From $1063 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 $1063 per night (USD)VRBO
From $1874 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 $1874 per night (USD)VRBO
From $522 per night (USD)VRBO
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 $522 per night (USD)VRBO
From $212 per night (USD)Expedia
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 $212 per night (USD)Expedia
From $570 per night (USD)VRBO
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)VRBO
Click For PricingExpedia
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 PricingExpedia
From $258 per night (USD)VRBO
Book now for October and enjoy Fantasy Fest and the famous Goombay Festival.
- 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 $258 per night (USD)VRBO
From $600 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 $600 per night (USD)VRBO
From $381 per night (USD)VRBO
Boomerang Boathouse in Key West
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
NEW UNIT! Start up Discounts!“Richley individual” yet “classic Key West” are phrases that echo from Boomerang Boathouse, ...
From $381 per night (USD)VRBO
From $1219 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 $1219 per night (USD)Expedia
From $950 per night (USD)VRBO
New! Coastal Rose - Bright Loft with High Ceilings!
- Bedrooms:
- 1
- Bathrooms:
- 2
- 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 $950 per night (USD)VRBO
From $380 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 $380 per night (USD)Expedia
From $948 per night (USD)VRBO
New! Rose Key Cottage- Pool & Parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Escape to paradise with this luxurious Key West retreat, perfect for families and groups looking to unwind in s ...
From $948 per night (USD)VRBO
From $728 per night (USD)VRBO
Relax in Romantic Lodge w\/ Pool Minutes from Vibrant Duval Street
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
Discover Old Town charm, plunge into vibrant Duval Street life, and dive deep into Key West's treasures. We're footsteps ...
From $728 per night (USD)VRBO
From $494 per night (USD)VRBO
Modern Lodge w\/ Outdoor Pool Near Attractions Ideal for Family Fun
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Discover Old Town charm, plunge into vibrant Duval Street life, and dive deep into Key West's treasures. We're footsteps ...
From $494 per night (USD)VRBO
From $990 per night (USD)VRBO
2 Rooms for the whole family w\/ Pool access! Near Duval St. and Museums
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Discover Old Town charm, plunge into vibrant Duval Street life, and dive deep into Key West's treasures. We're footsteps ...
From $990 per night (USD)VRBO
From $886 per night (USD)VRBO
2 Bedroom Suite w\/ Outdoor Pool in Old Town Key West
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Discover Old Town charm, plunge into vibrant Duval Street life, and dive deep into Key West's treasures. We're footsteps ...
From $886 per night (USD)VRBO
From $494 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 $494 per night (USD)VRBO
From $587 per night (USD)VRBO
Heron Hideaway - Charming 1st-Floor Unit, Shared Pool, Spa, Pet-Friendly, Near Duval St & Beaches
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Heron Hideaway, a charming 1st-floor condo nestled in the desirable Meadows area of Key West. Just six blocks ...
From $587 per night (USD)VRBO
From $2424 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 $2424 per night (USD)Expedia
From $734 per night (USD)VRBO
Charming 2-bedroom guest house with Pool, A\/C, & WiFi in Key West, near Duval St
- 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 $734 per night (USD)VRBO
From $2800 per night (USD)VRBO
Spacious 5-bdrm 5 bathroom house in charming Key West with AC, WiFi, Plunge Pool
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Located in Key West and about 6 blocks away from Duval Street, enjoy what this 5-bedroom house has to offer. This beauti ...
From $2800 per night (USD)VRBO
From $239 per night (USD)VRBO
Contemporary Hideaway in the Heart of Old Town Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Galveston Porches Stylish one bedroom apartment in the heart of Old Town. Totally renovated and beautifully decorated. E ...
From $239 per night (USD)VRBO
From $1043 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 $1043 per night (USD)VRBO
From $853 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 $853 per night (USD)VRBO
From $873 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 $873 per night (USD)VRBO
From $244 per night (USD)VRBO
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)VRBO
From $2105 per night (USD)VRBO
Celebrate History in Key West! 2 Relaxing Units, Outdoor Pools, Pets Allowed!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Discover the charm of Old Town in our vibrant retreat, steps away from Duval's delights. Dive into history at Hemingway' ...
From $2105 per night (USD)VRBO
From $348 per night (USD)VRBO
Discover this cozy retreat in the charm of Old Town Key West at Poorhouse Lane!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This 3-bedroom house is perfect for your escape to Key West. This cozy retreat offers prime location near all the action ...
From $348 per night (USD)VRBO
From $203 per night (USD)Expedia
Charming 1-bedroom apartment with WiFi, AC in delightful Key West Old Town
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Your Key West adventure begins at this fabulous 1-bedroom apartment. The cozy bedroom features a queen bed, perfect for ...
From $203 per night (USD)Expedia
From $688 per night (USD)VRBO
**SOUTHERN STAR @ THE MEADOWS** Private Home & Pool + LAST KEY SERVICES...
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! SOUTHERN STAR ...
From $688 per night (USD)VRBO
From $125 per night (USD)Expedia
Serene Key West Studio with Poolside Peace
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Studio Apartment for Rent in Key West This cozy studio apartment is located in a quiet, gated community on Grinnell Str ...
From $125 per night (USD)Expedia
From $285 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 $285 per night (USD)VRBO
From $852 per night (USD)Expedia
Coco's Poolside Retreat
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Coco's Poolside Retreat is a 3-story Key West vacation rental townhouse situated in a one-of-a-kind private tropical poo ...
From $852 per night (USD)Expedia
From $2269 per night (USD)VRBO
The Flower Power House - Boho Beautiful
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 13
Boho beautiful, the free-spirited presence of the Key West Flower Power House vacation rental, has much more in common w ...
From $2269 per night (USD)VRBO
From $585 per night (USD)Expedia
Palm Isle: Tropical 2nd-Floor Unit, Shared Pool, Private Spa, Pet-Friendly, Near Duval St & Beaches
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to Palm Isle, a tropical 2nd-floor condo in the charming Meadows area of Key West. Relax on your private front p ...
From $585 per night (USD)Expedia
From $319 per night (USD)VRBO
Gypsyginny's Hideaway in downtown Key West
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Set in the heart of Key West's vibrant Meadows district, this delightful 3-bedroom vacation rental on iconic White Stree ...
From $319 per night (USD)VRBO
From $2242 per night (USD)Expedia
Meadows Manor | Elegant Oasis with Private Pool & Parking! Monthly Rental
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Meadows Manor | Elegant Oasis with Private Pool & Parking Discover the perfect blend of luxury and tranquility at the M ...
From $2242 per night (USD)Expedia
From $2761 per night (USD)VRBO
3| Galleon | Marina | Spa | Hot Tub | Pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
The Galleon Resort is a premier destination in Key West, Florida, offering an unbeatable combination of luxury, comfort, ...
From $2761 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 $1207 per night (USD)VRBO
Sunset Harbor | Marina | Hot Tub | Pool | Concierge
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to your serene oasis in the heart of Key West’s iconic Old Town, where lush greenery and contemporary design cre ...
From $1207 per night (USD)VRBO
From $1234 per night (USD)VRBO
The Banyan | Concierge | Beach Access | Pool
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Located in the heart of historic Old Town Key West, The Banyan Resort is a charming escape set on a mid-1800s estate ste ...
From $1234 per night (USD)VRBO
From $2727 per night (USD)VRBO
Galleon | Hot Tub | Marina | Lux Resort | Concierge
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Galleon Resort is a premier destination in Key West, Florida, offering an unbeatable combination of luxury, comfort, ...
From $2727 per night (USD)VRBO
From $1502 per night (USD)VRBO
Sunset Harbor | Hyatt | Hot Tub | Pool | Marina | Lux Resort
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to your serene oasis in the heart of Key West’s iconic Old Town, where lush greenery and contemporary design cre ...
From $1502 per night (USD)VRBO
From $1009 per night (USD)VRBO
Galleon | Marina | Lux Resort | Pool | Hot Tub
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The Galleon Resort is a premier destination in Key West, Florida, offering an unbeatable combination of luxury, comfort, ...
From $1009 per night (USD)VRBO
From $2903 per night (USD)VRBO
Galleon | Marina | Concierge | Hot Tub | Spa
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Nestled along the sparkling Gulf of Mexico in historic Old Town, The Galleon Resort places you in the heart of Key West’ ...
From $2903 per night (USD)VRBO
From $1951 per night (USD)VRBO
Sunset Harbor | Hyatt | Marina | Concierge | Pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your serene oasis in the heart of Key West’s iconic Old Town, where lush greenery and contemporary design cre ...
From $1951 per night (USD)VRBO
From $233 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 $233 per night (USD)VRBO
Click For PricingExpedia
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 PricingExpedia
From $1155 per night (USD)VRBO
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)VRBO
From $791 per night (USD)Expedia
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 ...
From $791 per night (USD)Expedia