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 $784 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 $784 per night (USD)
VRBO
From $880 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 $880 per night (USD)
VRBO
From $902 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 $902 per night (USD)
VRBO
From $820 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 $820 per night (USD)
VRBO
From $854 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 $854 per night (USD)
VRBO
From $1048 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 $1048 per night (USD)
VRBO
From $892 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 $892 per night (USD)
VRBO
From $915 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 $915 per night (USD)
VRBO
From $882 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 $882 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 $900 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 $900 per night (USD)
VRBO
From $2506 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 $2506 per night (USD)
VRBO
From $951 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 $951 per night (USD)
VRBO
From $812 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 $812 per night (USD)
VRBO
From $975 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 $975 per night (USD)
VRBO
From $1127 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 $1127 per night (USD)
VRBO
From $781 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 $781 per night (USD)
VRBO
From $1299 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 $1299 per night (USD)
VRBO
From $951 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 $951 per night (USD)
VRBO
From $814 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 $814 per night (USD)
VRBO
From $2016 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 $2016 per night (USD)
VRBO
From $3376 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 $3376 per night (USD)
VRBO
From $1480 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 $1480 per night (USD)
VRBO
From $1149 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 $1149 per night (USD)
VRBO
From $2243 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 $2243 per night (USD)
VRBO
From $861 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 $861 per night (USD)
VRBO
From $1547 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 $1547 per night (USD)
VRBO
From $2301 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 $2301 per night (USD)
VRBO
From $758 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 $758 per night (USD)
VRBO
From $882 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 $882 per night (USD)
VRBO
From $737 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 $737 per night (USD)
VRBO
From $1119 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 $1119 per night (USD)
VRBO
From $951 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 $951 per night (USD)
VRBO
From $1099 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 $1099 per night (USD)
VRBO
From $2156 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 $2156 per night (USD)
VRBO
From $3376 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 $3376 per night (USD)
VRBO
From $1333 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 $1333 per night (USD)
VRBO
From $2335 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 $2335 per night (USD)
VRBO
$Snowbird-friendly condo with heated pool, patio lounge, water view, yard, & W\/D$
From $934 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 $934 per night (USD)
VRBO
$Southard Retreat- 2 bed 2 bath townhome downtown w\/ pool, parking$
From $205 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 $205 per night (USD)
Expedia
From $738 per night (USD)
VRBO
Two Suites on Duval - Custom House Inn
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 $738 per night (USD)
VRBO
From $736 per night (USD)
Expedia
Two Suites on Duval - Custom House Inn
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 $736 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 Pricing
Expedia
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 Pricing
Expedia
From $263 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 $263 per night (USD)
VRBO
From $592 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 $592 per night (USD)
VRBO
From $1226 per night (USD)
VRBO
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 $1226 per night (USD)
VRBO
From $664 per night (USD)
Expedia
Pool, Pet Friendly, & Near Duval - Coastal Rose
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 $664 per night (USD)
Expedia
From $407 per night (USD)
VRBO
Pet Friendly, Near Duval - Rose Petal Petite Suite
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 $407 per night (USD)
VRBO
From $955 per night (USD)
Expedia
Pet Friendly, & Near Duval - Rose Key Cottage
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 $955 per night (USD)
Expedia
From $247 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 $247 per night (USD)
VRBO
$Romantic Stay in Historic Key West: 1BR Suite w\/ King Bed & Pool$
From $1113 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 $1113 per night (USD)
VRBO
$Key West Paradise: Minimalist King Room w\/ Balcony or Terrace! Enjoy the Breeze$
From $804 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 $804 per night (USD)
VRBO
From $940 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 $940 per night (USD)
VRBO
From $241 per night (USD)
VRBO
Charming 2-bedroom House in Historic 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 $241 per night (USD)
VRBO
$Relax in Romantic Lodge w\/ Pool Minutes from Vibrant Duval Street$
From $911 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 $911 per night (USD)
VRBO
$Modern Lodge w\/ Outdoor Pool Near Attractions Ideal for Family Fun$
From $691 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 $691 per night (USD)
VRBO
$2 Rooms for the whole family w\/ Pool access! Near Duval St. and Museums$
From $1382 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 $1382 per night (USD)
VRBO
$2 Bedroom Suite w\/ Outdoor Pool in Old Town Key West$
From $1045 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 $1045 per night (USD)
VRBO
$Beautiful Room w\/ Outdoor Pool & Close to Duval St. Restaurants$
From $646 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 $646 per night (USD)
VRBO
From $541 per night (USD)
VRBO
Heron Hideaway - Charming 1st-Floor Unit, Shared Pool, Private Hot Tub, Near Duval St & Beaches
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Welcome to Heron Hideaway, a charming 1st-floor condo nestled in the desirable Meadows area of Key West. Just six blocks ...
From $541 per night (USD)
VRBO
From $3156 per night (USD)
Expedia
Pool & Parking, & Near Duval - The Rigby House
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 $3156 per night (USD)
Expedia
$Charming 2-bedroom guest house with Pool, A\/C, & WiFi in Key West, near Duval St$
From $1260 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 $1260 per night (USD)
VRBO
From $2687 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 $2687 per night (USD)
VRBO
From $198 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 $198 per night (USD)
VRBO
From $1749 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 $1749 per night (USD)
VRBO
From $511 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 $511 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 $709 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 60 days prior to your arrival! SOUTHERN STAR ...
From $709 per night (USD)
VRBO
Click For Pricing
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 ...
Click For Pricing
Expedia
From $381 per night (USD)
VRBO
Boomerang Boathouse in Key West
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
MARCH Still Open!“Richley individual” yet “classic Key West” are phrases that echo from Boomerang Boathouse, a 4 bedroom ...
From $381 per night (USD)
VRBO
From $1023 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 $1023 per night (USD)
Expedia
From $1961 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 $1961 per night (USD)
VRBO
From $555 per night (USD)
Expedia
Palm Isle: Tropical 2nd-Floor Unit, Shared Heated Pool, Near Duval St, Historic Seaport & Beaches
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Welcome to Palm Isle, a tropical 2nd-floor condo in the charming Meadows area of Key West. Relax on your private front p ...
From $555 per night (USD)
Expedia
From $294 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 $294 per night (USD)
VRBO
From $3345 per night (USD)
Expedia
Meadows Manor | Elegant Oasis with Private Pool & Parking! Weekly 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 $3345 per night (USD)
Expedia
From $550 per night (USD)
VRBO
Poolside Hide-Away @ Palm Gardens offered by Rent Key West Vacations
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Poolside Hide-Away is a first floor one bedroom, one bath historic condo, that can accommodate up to 4 people, with wrap ...
From $550 per night (USD)
VRBO
From $2916 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 $2916 per night (USD)
VRBO
From $155 per night (USD)
VRBO
Charming 1-bedroom apartment in Key West with AC, WiFi. Enjoy
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Your cozy getaway awaits in Key West at this brilliant apartment. This marvelous space features 1 bedroom with a queen b ...
From $155 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 $1424 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 $1424 per night (USD)
VRBO
From $3110 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 $3110 per night (USD)
VRBO
From $1521 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 $1521 per night (USD)
VRBO
From $1223 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 $1223 per night (USD)
VRBO
From $2961 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 $2961 per night (USD)
VRBO
From $2005 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 $2005 per night (USD)
VRBO
From $991 per night (USD)
VRBO
𝐅𝐢𝐧𝐝𝐢𝐧𝐠𝐌𝐞𝐢𝐥𝐢 Near Duval Street, Waterfront Sunset Harbor Resort. 2BR
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to 𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢🌴 Experience Paradise at Hyatt Vacation Club at Sunset Harbor! 🌅 Nestled in the he ...
From $991 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 $452 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 $452 per night (USD)
VRBO
$Spacious Townhome on Windsor Lane 3\/3.5$
From $1570 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 $1570 per night (USD)
VRBO
$Windsor Townhomes #6 - Large pool 3B\/3.5 bath, 3 blocks to Duval$
From $1686 per night (USD)
VRBO
Windsor Townhomes #6 - Large pool 3B\/3.5 bath, 3 blocks to Duval
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 $1686 per night (USD)
VRBO
$ANNA MARIA HAVEN - Renovated 3bd\/3ba Conch Monthly rental$
From $284 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 $284 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
$Mid Town 2\/1 TREE HOUSE RETREAT$
From $564 per night (USD)
VRBO
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 ...
From $564 per night (USD)
VRBO
$Mid Town Affordable 3bd\/2.5ba 3 story Townhome$
From $766 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 $766 per night (USD)
Expedia
From $1651 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 $1651 per night (USD)
VRBO
From $2086 per night (USD)
VRBO
Key West, Galleon Resort, Marina, In Town, Pool, Hot Tub
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to The Galleon Resort in Key West, where paradise meets luxury at the southernmost tip of the United States. In ...
From $2086 per night (USD)
VRBO
$Escape to \Casa Escondida\$
From $636 per night (USD)
VRBO
Escape to \"Casa Escondida\"
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Escape to the enchanting "Casa Escondida," a historic Conch Style home with a modern twist, nestled on a tranquil, seclu ...
From $636 per night (USD)
VRBO
From $2320 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 $2320 per night (USD)
Expedia

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