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 $729 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 $729 per night (USD)
VRBO
From $1830 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 $1830 per night (USD)
VRBO
From $2052 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 $2052 per night (USD)
VRBO
From $1007 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 $1007 per night (USD)
VRBO
From $1373 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 $1373 per night (USD)
VRBO
$Snowbird-friendly condo with heated pool, patio lounge, water view, yard, & W\/D$
Click For Pricing
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 ...
Click For Pricing
Expedia
$Southard Retreat- 2 bed 2 bath townhome downtown w\/ pool, parking$
From $184 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 $184 per night (USD)
VRBO
From $1596 per night (USD)
VRBO
Old Town Key West Retreat | Seaport Paradise Room with Pool Access | 3 Rooms
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $1596 per night (USD)
VRBO
$Spacious Key West Room w\/ Balcony | Outdoor Pools | Seaport Proximity$
From $600 per night (USD)
VRBO
Spacious Key West Room w\/ Balcony | Outdoor Pools | Seaport Proximity
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 $600 per night (USD)
VRBO
$Family Old Town Key Getaway | Four Rooms w\/ Balcony & Outdoor Pools$
From $1939 per night (USD)
VRBO
Family Old Town Key Getaway | Four Rooms w\/ Balcony & Outdoor Pools
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $1939 per night (USD)
VRBO
$Vibrant Key West Stay w\/ Outdoor Pools | Four Rooms w\/ Balcony$
From $2124 per night (USD)
VRBO
Vibrant Key West Stay w\/ Outdoor Pools | Four Rooms w\/ Balcony
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $2124 per night (USD)
VRBO
$Two Relaxing Rooms w\/ Balcony | Waterfront Resort w\/ Access to Outdoor Pools$
From $1071 per night (USD)
VRBO
Two Relaxing Rooms w\/ Balcony | Waterfront Resort w\/ Access to Outdoor Pools
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 $1071 per night (USD)
VRBO
$2 BR Spacious Suite w\/ Living Area and Balcony | Outdoor Pools$
From $3121 per night (USD)
VRBO
2 BR Spacious Suite w\/ Living Area and Balcony | 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 $3121 per night (USD)
VRBO
From $1717 per night (USD)
VRBO
Seaport Paradise Room with Pools | Old Town Key West Retreat | 3 Rooms
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $1717 per night (USD)
VRBO
$Seaport Proximity | Resort w\/ Outdoor Pools | Spacious Key West Room w\/ Balcony$
From $636 per night (USD)
VRBO
Seaport Proximity | Resort w\/ Outdoor Pools | Spacious Key West Room w\/ Balcony
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 $636 per night (USD)
VRBO
$Spacious 2 BR Suite w\/ Living Area and Balcony | Onsite Parking Available$
From $2475 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 $2475 per night (USD)
VRBO
$Two Bedrooms Family Suite with Balcony | Idyllic Resort w\/ Outdoor Pools$
From $3121 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 $3121 per night (USD)
VRBO
$Waterfront Getaway | 2 Spacious Family Rooms w\/ Balcony | Old Town Best$
From $1144 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 $1144 per night (USD)
VRBO
From $422 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 $422 per night (USD)
VRBO
From $679 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 $679 per night (USD)
VRBO
$Quaint Bungalow w\/ Private Outdoor Space Near Duval Street | Free Breakfast$
From $453 per night (USD)
VRBO
Quaint Bungalow w\/ Private Outdoor Space Near Duval Street | Free Breakfast
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $453 per night (USD)
VRBO
From $573 per night (USD)
VRBO
Celebrate History in Key West: Tropical Bungalow Retreat Ideal for Relaxation
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $573 per night (USD)
VRBO
From $529 per night (USD)
VRBO
Spacious Bungalow with Patio | Near Ernest Hemingway Home – 7 Min Walk
Bedrooms:
1
Bathrooms:
1
Sleeps:
1
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $529 per night (USD)
VRBO
From $513 per night (USD)
VRBO
Serene Bungalow with Outdoor Pool Access | Near Historic Ernest Hemingway Museum
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $513 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 Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $465 per night (USD)
VRBO
From $714 per night (USD)
VRBO
Key West Oasis: Retreat in Historical Bungalows with Pool Paradise
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $714 per night (USD)
VRBO
From $673 per night (USD)
VRBO
Tropical Escape: Artistic-Vibe Bungalows with Balcony | Welcome Drinks Included
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $673 per night (USD)
VRBO
From $597 per night (USD)
VRBO
Enchanting Hideaway Perfect for Couples Seeking Romantic Bliss
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $597 per night (USD)
VRBO
From $457 per night (USD)
VRBO
Serene Bungalow in Key West: Poolside Refreshers & Relaxing Amenities
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $457 per night (USD)
VRBO
From $621 per night (USD)
VRBO
Couples' Retreat: Romantic Unit with Patio | Delicious Breakfast Included
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $621 per night (USD)
VRBO
$Tranquil Bungalow w\/ an Artistic Vibe in Vibrant Key West | Breakfast Included$
From $695 per night (USD)
VRBO
Tranquil Bungalow w\/ an Artistic Vibe in Vibrant Key West | Breakfast Included
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $695 per night (USD)
VRBO
$Stylish Room in the Heart of Old Town w\/ Access to Outdoor Pool | Free Breakfast$
From $463 per night (USD)
VRBO
Stylish Room in the Heart of Old Town w\/ Access to Outdoor Pool | Free Breakfast
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $463 per night (USD)
VRBO
From $543 per night (USD)
VRBO
Historical Charm in a Room Surrounded by Key West's Best: Complimentary Breakfas
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $543 per night (USD)
VRBO
From $635 per night (USD)
VRBO
Historic Inn: Romantic Couple Stay in Key West's Hidden Gem - Pools & Patio
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $635 per night (USD)
VRBO
From $458 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 $458 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 $360 per night (USD)
VRBO
Boomerang Boathouse in Key West
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Richley individual yet classic Key West are phrases that echo from Boomerang Boathouse, a 4 bedroom, 2.5 bath home with ...
From $360 per night (USD)
VRBO
From $652 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 $652 per night (USD)
Expedia
From $474 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 $474 per night (USD)
VRBO
From $1128 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 $1128 per night (USD)
Expedia
From $229 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 $229 per night (USD)
VRBO
$Relax in Romantic Lodge w\/ Pool Minutes from Vibrant Duval Street$
From $690 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 $690 per night (USD)
VRBO
$Modern Lodge w\/ Outdoor Pool Near Attractions Ideal for Family Fun$
From $435 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 $435 per night (USD)
VRBO
$2 Rooms for the whole family w\/ Pool access! Near Duval St. and Museums$
From $883 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 $883 per night (USD)
VRBO
$2 Bedroom Suite w\/ Outdoor Pool in Old Town Key West$
From $794 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 $794 per night (USD)
VRBO
From $516 per night (USD)
Expedia
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 $516 per night (USD)
Expedia
From $2315 per night (USD)
VRBO
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 $2315 per night (USD)
VRBO
$Charming 2 room guest house, access to Pool, A\/C, & WiFi, Key West, near Duval$
From $1179 per night (USD)
VRBO
Charming 2 room guest house, access to Pool, A\/C, & WiFi, Key West, near Duval
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Key West is waiting for you at this clean & spacious 2-bedroom guest house. Good for up to 6 people. This cozy retreat o ...
From $1179 per night (USD)
VRBO
From $2443 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
Short walk to Duval Street. Central location. Restaurants nearby. Surrounded by charm of Key West. Explore the city the ...
From $2443 per night (USD)
VRBO
From $153 per night (USD)
Expedia
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 $153 per night (USD)
Expedia
From $1145 per night (USD)
VRBO
Charming Bungalow Perfect for Families and Couples': Escape in Old Town
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $1145 per night (USD)
VRBO
From $407 per night (USD)
Expedia
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 $407 per night (USD)
Expedia
From $203 per night (USD)
VRBO
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)
VRBO
From $462 per night (USD)
Expedia
**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 $462 per night (USD)
Expedia
From $125 per night (USD)
VRBO
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)
VRBO
From $513 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 $513 per night (USD)
VRBO
From $219 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 $219 per night (USD)
VRBO
From $363 per night (USD)
Expedia
Palm Isle: Tropical 2nd-Floor Unit, Shared Heated Pool, Near Duval St, Historic Seaport & Beaches
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to Palm Isle! A tropical 2nd-floor condo in the charming Meadows area of Key West. Relax on your private front ...
From $363 per night (USD)
Expedia
From $195 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 $195 per night (USD)
VRBO
From $2319 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 $2319 per night (USD)
Expedia
From $425 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 $425 per night (USD)
VRBO
From $685 per night (USD)
Expedia
~Hibiscus Cottage~ Adults Only cottage near Duval with shared pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
THE PROPERTY: Welcome to your private rocking chair front porch and tropical, Adult Only setting! As you enter your quai ...
From $685 per night (USD)
Expedia
$WASTIN' A WAYLAND ~ Renovated 2 BR\/2 Ba Home in Old Town!$
From $242 per night (USD)
VRBO
WASTIN' A WAYLAND ~ Renovated 2 BR\/2 Ba Home in Old Town!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
OLD TOWN GEM... This 2 bedroom, 2 bathroom cutie resides down a charming lane surrounded by historic residences and is a ...
From $242 per night (USD)
VRBO
From $1389 per night (USD)
Expedia
**The Three Mermaids @ Solaris Hill** New Construction Compound + Last Key Servi
Bedrooms:
5
Bathrooms:
5
Sleeps:
12
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Finding a com ...
From $1389 per night (USD)
Expedia
From $265 per night (USD)
VRBO
Cozy on Caroline - Key West Seaport
Bedrooms:
2
Bathrooms:
1
Sleeps:
4
Experience the quintessential Key West lifestyle in this charming one-bedroom, two-bathroom apartment that perfectly bal ...
From $265 per night (USD)
VRBO
From $287 per night (USD)
Expedia
Seaport Serenity Cottage - Quiet and Quaint
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This charming 2BR/2BA rental is located in the Historic Seaport District offering off-street parking and a prime locatio ...
From $287 per night (USD)
Expedia
From $512 per night (USD)
VRBO
Tropical Island Retreat Near Florida Beaches with Pool & Views
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 $512 per night (USD)
VRBO
From $604 per night (USD)
VRBO
Charming Hideaway with Pool – Walk to Duval St & Local Attractions
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 $604 per night (USD)
VRBO
From $535 per night (USD)
VRBO
Cozy Key West Escape – Near Shops, Bars & Famous Duval Street
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $535 per night (USD)
VRBO
From $728 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 $728 per night (USD)
Expedia
From $1558 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 $1558 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 $1824 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 $1824 per night (USD)
VRBO
From $2236 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 $2236 per night (USD)
VRBO
From $1941 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 $1941 per night (USD)
VRBO
From $11524 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 $11524 per night (USD)
VRBO
From $2236 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 $2236 per night (USD)
VRBO
From $1839 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 $1839 per night (USD)
VRBO
From $1839 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 $1839 per night (USD)
VRBO
From $863 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 $863 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 $258 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 $258 per night (USD)
VRBO
From $1140 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 $1140 per night (USD)
VRBO
From $1823 per night (USD)
VRBO
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 $1823 per night (USD)
VRBO
$Spacious Townhome on Windsor Lane 3\/3.5$
From $1122 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 $1122 per night (USD)
VRBO
$ANNA MARIA HAVEN - Renovated 3bd\/3ba Conch Monthly rental$
From $378 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 $378 per night (USD)
VRBO
$Windsor Townhomes #6 - Large pool 3B\/3.5 bath, 3 blocks to Duval$
From $922 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 $922 per night (USD)
VRBO
$Escape to \Casa Escondida\$
From $439 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 $439 per night (USD)
VRBO
From $2140 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 $2140 per night (USD)
VRBO
From $615 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 $615 per night (USD)
VRBO
From $767 per night (USD)
Expedia
Key West Andros 2BR•Waterfront, Pool, Dock&Pet OK
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Time to fish & relax! Bring your family & friends to this 1350 sqft waterfront corner condo home. Boat slip a ...
From $767 per night (USD)
Expedia
From $190 per night (USD)
VRBO
Charming + Circa 1889 Historic Eyebrow Home
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
28 Night Minimum. Welcome to "The Saltbox"! Featured in design magazines. 710 Ashe Street is a charming house circa 18 ...
From $190 per night (USD)
VRBO
From $154 per night (USD)
Expedia
ANCHORS AWAY ~ Cheerful 1 BR, 1 Ba Condo with Private Hot Tub in The Meadows!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
CLASSIC AND COZY... Exhale your worries away as you approach this delightful condo, one of four that are situated insid ...
From $154 per night (USD)
Expedia
From $291 per night (USD)
VRBO
Old Town Key West Live like a local
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Live like a local! This vacation flat is located at Mile marker 1, and sits nestled above the street right on Truman Av ...
From $291 per night (USD)
VRBO
From $524 per night (USD)
Expedia
JUST OFF DUVAL~ 2nd Floor Condo in Center of Duval St. with Parking Space!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
STEPS TO DUVAL ST… Take advantage of this premier opportunity to indulge in all your desired Key West bucket list items ...
From $524 per night (USD)
Expedia
From $868 per night (USD)
VRBO
Rose Lane Villas - Villa Aqua - 2 King Bedrooms - Downtown Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Nestled on a quiet lane in the heart of Old Town Key West, Rose Lane Villas is as close to the action as you'll get with ...
From $868 per night (USD)
VRBO
From $142 per night (USD)
Expedia
CABIN FEVER ~ First Floor 1 Bedroom, 1 Bathroom with Full Kitchen and Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
SIMPLISTIC ELEGANCE... Enjoy easy island living in this quaint and cozy Key West gem located in the attractive community ...
From $142 per night (USD)
Expedia
From $132 per night (USD)
VRBO
Mango Tree Key West Cottage
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
True Key West flavor! 1 Bedroom 1 Bathroom apartment newly remodeled and updated Conch House located on White St.with h ...
From $132 per night (USD)
VRBO
$Location In Down Town Key West W\/ 2 Pools, Huge Private Roof Deck & Parking$
From $2064 per night (USD)
Expedia
Location In Down Town Key West W\/ 2 Pools, Huge Private Roof Deck & Parking
Bedrooms:
7
Bathrooms:
7
Sleeps:
16
Perfect location and great for entertaining! In the heart of Old Town Key West just steps from restaurants, bars, theate ...
From $2064 per night (USD)
Expedia

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