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From $379 per night (USD)
VRBO
Royal Palm in Key West
Bedrooms:
3
Bathrooms:
2
Sleeps:
5
End of Year Specials!There's no better way to experience island time - that slow shifting of hours that makes Key West s ...
From $379 per night (USD)
VRBO
$Mariner's Oasis at Sunset Marina- 2bed 2 bath condo w\/boat slip for rent$
From $266 per night (USD)
Expedia
Mariner's Oasis at Sunset Marina- 2bed 2 bath condo w\/boat slip for rent
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 $266 per night (USD)
Expedia
$Key West Home on Golf Course w\/ Patio & Grill!$
From $254 per night (USD)
VRBO
Key West Home on Golf Course w\/ Patio & Grill!
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Play a round of golf, snorkel the crystal-clear waters, and explore Key West’s bustling downtown when you stay at this l ...
From $254 per night (USD)
VRBO
From $723 per night (USD)
Expedia
A Gulfview Paradise in Key West - Call for more information!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Welcome to your dream vacation rental in Gulfview Pointe, Key West! This stunning property offers breathtaking waterfron ...
From $723 per night (USD)
Expedia
From $1643 per night (USD)
VRBO
NEW! The Delaney House - Private Pool & Remodeled
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Summary: Step into the classic conch cottage known as the Delaney House, situated just half a block from Duval Street. ...
From $1643 per night (USD)
VRBO
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Expedia
Located on a private beach along the shore, Casa Marina Key West ...
Bedrooms:
1
Bathrooms:
2
Sleeps:
2
Located on a private beach along the shore, Casa Marina Key West, Curio Collection by Hilton is a historic 1920s resort ...
Click For Pricing
Expedia
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VRBO
Located on a private beach along the shore, Casa Marina Key West ...
Bedrooms:
1
Bathrooms:
2
Sleeps:
2
Located on a private beach along the shore, Casa Marina Key West, Curio Collection by Hilton is a historic 1920s resort ...
Click For Pricing
VRBO
Click For Pricing
Expedia
Located on a private beach along the shore, Casa Marina Key West ...
Bedrooms:
1
Bathrooms:
2
Sleeps:
2
Located on a private beach along the shore, Casa Marina Key West, Curio Collection by Hilton is a historic 1920s resort ...
Click For Pricing
Expedia
From $318 per night (USD)
VRBO
Sunkissed Bungalow-B205
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
A perfect beach getaway in Key West! See the Sunset and stroll the sidewalks at this fabulous location away from the cr ...
From $318 per night (USD)
VRBO
From $315 per night (USD)
Expedia
Welcome to Kokomo Cottage-A311
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This beautifully renovated 3 bedroom, 2 bathroom beach getaway is waiting for your perfect escape. See the Sunset and s ...
From $315 per night (USD)
Expedia
From $311 per night (USD)
VRBO
Sandy Toes Retreat-A310
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This beautifully renovated 3 bedroom, 2 bathroom beach getaway is waiting for your perfect escape. See the Sunset and s ...
From $311 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 $247 per night (USD)
VRBO
Tropical cottage with private pool, two blocks from Duval - near Hemingway House
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
The Conch-Out Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $247 per night (USD)
VRBO
From $381 per night (USD)
Expedia
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)
Expedia
From $434 per night (USD)
VRBO
Key West King Escape, Fairfield Inn, Outdoor Swimming Pool | Near Mallory Square
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Explore Key West with us! Enjoy proximity to Historic Old Town, known for its rich history, vibrant culture, and stunnin ...
From $434 per night (USD)
VRBO
From $483 per night (USD)
VRBO
Key West Stay Ideal For Couple Close to Mallory Square | Outdoor Swimming Pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Explore Key West with us! Enjoy proximity to Historic Old Town, known for its rich history, vibrant culture, and stunnin ...
From $483 per night (USD)
VRBO
From $1069 per night (USD)
VRBO
Secluded and Private Monthly Tropical Modern Oasis with a Large Pool
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
Experience Key West like a local in this 4-bedroom house with a large saltwater pool. Step into your own private tropic ...
From $1069 per night (USD)
VRBO
$Newly Renovated Hotel w\/ Outdoor Pool | Short Drive to Historic Old Town$
From $510 per night (USD)
VRBO
Newly Renovated Hotel w\/ Outdoor Pool | Short Drive to Historic Old Town
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Explore Key West with us! Enjoy proximity to Historic Old Town, known for its rich history, vibrant culture, and stunnin ...
From $510 per night (USD)
VRBO
From $510 per night (USD)
VRBO
Relaxing Double Queen, Fairfield Inn, Breakfast Included, Near Downtown Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Explore Key West with us! Enjoy proximity to Historic Old Town, known for its rich history, vibrant culture, and stunnin ...
From $510 per night (USD)
VRBO
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Expedia
Southernmost Beach Resort provides flawless service and all the necessary facilities for ...
Bedrooms:
1
Bathrooms:
2
Sleeps:
2
Southernmost Beach Resort provides flawless service and all the necessary facilities for visitors. Stay connected with y ...
Click For Pricing
Expedia
From $1219 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 $1219 per night (USD)
VRBO
From $611 per night (USD)
Expedia
New! The Green Pineapple - Balcony on Duval!
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Summary: Beautiful 4-bedroom, 3-bath monthly rental located on Key West's famous Duval Street. Guests enjoy easy access ...
From $611 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 $310 per night (USD)
Expedia
New Property! An Island Siesta
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This lovely, fully furnished, townhouse has two bedrooms that sleeps up to 6 and two full baths . The spacious upstairs ...
From $310 per night (USD)
Expedia
From $611 per night (USD)
VRBO
Atlantis House's Banyan Suite-voted top 25 in USA
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
The Banyan Suite is a stunning vacation rental property located in the heart of Key West. This luxurious suite is situat ...
From $611 per night (USD)
VRBO
From $741 per night (USD)
Expedia
Atlantis House's Palm Suite-voted top 25 in USA
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
The Palm Suite is a stunning vacation rental property located in the heart of Key West. This luxurious suite is situated ...
From $741 per night (USD)
Expedia
From $343 per night (USD)
VRBO
Keys to Paradise by AvantStay | Balcony, Pool, Golf
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This home is available for stays of 28 nights or longer. Welcome to Keys to Paradise, your Key West sanctuary nestled r ...
From $343 per night (USD)
VRBO
Click For Pricing
Expedia
Upgraded 2-Bedroom Condo-Olympic size Pool- Fitness room-Beach-on Atlantic Ocean
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Beautiful upgraded condo features vaulted ceilings and spacious living room, two bedrooms and a office/den for your use. ...
Click For Pricing
Expedia
$SATISFY MY SOUL ~ 3 BR, 3.5 Ba Newly Renovated Mid Town Home w\/ Pool!$
From $384 per night (USD)
VRBO
SATISFY MY SOUL ~ 3 BR, 3.5 Ba Newly Renovated Mid Town Home w\/ Pool!
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
AUTHENTIC KEY WEST AMBIENCE... This fully renovated mid-century jewel pairs modern allure with classic White Street Gall ...
From $384 per night (USD)
VRBO
From $460 per night (USD)
Expedia
Speakeasy Inn-Room 3B- 2 Queen Beds
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The Speakeasy Inn is a quaint guesthouse located in an historic Key West conch style house. It is situated on upper Duva ...
From $460 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 $373 per night (USD)
Expedia
HERE COMES THE SUN ~ 2 BR, 2 Ba Casa Marina Home with Pool!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
CLASSIC CHARMER... Some of the best things come in small packages and this conch cutie is no exception. Nestled in the e ...
From $373 per night (USD)
Expedia
From $915 per night (USD)
VRBO
An Ocean Serenity in Truman Annex, Key West
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
A luxury, ocean front, 2 bedroom, (king in master, queen in guest bedroom) 2.5 bath condo at Harbour Place in the award ...
From $915 per night (USD)
VRBO
$Romantic Stay in Historic Key West: 1BR Suite w\/ King Bed & Pool$
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
$Key West Paradise: Minimalist King Room w\/ Balcony or Terrace! Enjoy the Breeze$
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 $1038 per night (USD)
Expedia
Tortugas Harbor-Sombrero Reef Suites: Traveling with a group? Share these 2 condos
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
The Tortugas Harbor and Sombrero Reef Lighthouse Suites are two separate and NON-Connecting suites on the same level tha ...
From $1038 per night (USD)
Expedia
From $1038 per night (USD)
VRBO
Alligator Reef & American Shoal Suites: Traveling with a group? Share these 2 condos
Bedrooms:
2
Bathrooms:
6
Sleeps:
12
The Alligator Reef and American Shoal Lighthouse Suites are two separate and NON-Connecting suites on the same level tha ...
From $1038 per night (USD)
VRBO
$Relax in Romantic Lodge w\/ Pool Minutes from Vibrant Duval Street$
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
$Modern Lodge w\/ Outdoor Pool Near Attractions Ideal for Family Fun$
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
$2 Rooms for the whole family w\/ Pool access! Near Duval St. and Museums$
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
$2 Bedroom Suite w\/ Outdoor Pool in Old Town Key West$
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
$Beautiful Room w\/ Outdoor Pool & Close to Duval St. Restaurants$
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
$Stylish Boutique Room w\/ 2 Queen Beds - Access Pool & Poolside Bar$
From $800 per night (USD)
VRBO
Stylish Boutique Room w\/ 2 Queen Beds - Access Pool & Poolside Bar
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Explore, dine, and relax in downtown Key West! We're steps from the Hemingway Home, Duval Street nightlife, and Southern ...
From $800 per night (USD)
VRBO
From $341 per night (USD)
Expedia
Castaway Cove: Charming 2BR Townhome in New Town, Key West with Shared Pool, Private Patio & Kayaks!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to Castaway Cove! Nestled in the vibrant New Town area of Key West, Castaway Cove is your perfect home away from ...
From $341 per night (USD)
Expedia
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
$Ocean Oasis at Sunset Marina-2 bed 2 bath oceanfront condo w\/boat slip rental$
From $260 per night (USD)
Expedia
Ocean Oasis at Sunset Marina-2 bed 2 bath oceanfront condo w\/boat slip rental
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 $260 per night (USD)
Expedia
$Outstanding Room w\/ King Bed & Patio just steps from Duval St - Key West Bliss$
From $929 per night (USD)
VRBO
Outstanding Room w\/ King Bed & Patio just steps from Duval St - Key West Bliss
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Explore, dine, and relax in downtown Key West! We're steps from the Hemingway Home, Duval Street nightlife, and Southern ...
From $929 per night (USD)
VRBO
$1BR Suite w\/ Spacious Living Area and Access to Heated Pool, Near Duval St$
From $1097 per night (USD)
VRBO
1BR Suite w\/ Spacious Living Area and Access to Heated Pool, Near Duval St
Bedrooms:
1
Bathrooms:
2
Sleeps:
2
Explore, dine, and relax in downtown Key West! We're steps from the Hemingway Home, Duval Street nightlife, and Southern ...
From $1097 per night (USD)
VRBO
$Welcoming 2 Queen Room w\/ Patio- Heart of Key West$
From $890 per night (USD)
VRBO
Welcoming 2 Queen Room w\/ Patio- Heart of Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Explore, dine, and relax in downtown Key West! We're steps from the Hemingway Home, Duval Street nightlife, and Southern ...
From $890 per night (USD)
VRBO
$Room w\/ Queen Bed w\/ Patio in the Heart of Key West - Duval St steps away$
From $826 per night (USD)
VRBO
Room w\/ Queen Bed w\/ Patio in the Heart of Key West - Duval St steps away
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Explore, dine, and relax in downtown Key West! We're steps from the Hemingway Home, Duval Street nightlife, and Southern ...
From $826 per night (USD)
VRBO
From $2557 per night (USD)
VRBO
Stunning 2 Floor Loft in Vibrant Key West Ideal for Romantic Weekends - Pool
Bedrooms:
1
Bathrooms:
2
Sleeps:
2
Explore, dine, and relax in downtown Key West! We're steps from the Hemingway Home, Duval Street nightlife, and Southern ...
From $2557 per night (USD)
VRBO
From $1146 per night (USD)
VRBO
Vibrant 2 Floor Loft Ideal for Relaxing Escape in Key West - Near Duval St
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Explore, dine, and relax in downtown Key West! We're steps from the Hemingway Home, Duval Street nightlife, and Southern ...
From $1146 per night (USD)
VRBO
$Elegant Boutique Room w\/ Private Patio & Garden - Duval Street steps away$
From $952 per night (USD)
VRBO
Elegant Boutique Room w\/ Private Patio & Garden - Duval Street steps away
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Explore, dine, and relax in downtown Key West! We're steps from the Hemingway Home, Duval Street nightlife, and Southern ...
From $952 per night (USD)
VRBO
From $1181 per night (USD)
Expedia
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 $1181 per night (USD)
Expedia
From $2424 per night (USD)
VRBO
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)
VRBO
From $774 per night (USD)
Expedia
NEW!!! UNDER RENOVATION!!! - Beacon Terrace in the Truman Annex Key West
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
"Beacon Terrace" at the Truman Annex is a beautifully renovated town home in the historic Foundry. The living area is th ...
From $774 per night (USD)
Expedia
From $219 per night (USD)
VRBO
Tropical Tee Time Villa
Bedrooms:
4
Bathrooms:
2
Sleeps:
4
Escape to a stunning vacation rental in Key West, nestled on a picturesque golf course within an amazing resort. This pr ...
From $219 per night (USD)
VRBO
$Charming 2-bedroom guest house with Pool, A\/C, & WiFi in Key West, near Duval St$
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)
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 $239 per night (USD)
Expedia
From $872 per night (USD)
VRBO
Stunning 2BD Oceanfront Escape, Breathtaking Views - pool, hot tub and more
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to Côte du Bonheur, your oceanfront retreat located in Key West. This 3rd Floor-level unit in the prestigious 18 ...
From $872 per night (USD)
VRBO
From $567 per night (USD)
Expedia
Atlantis House- beautiful residence close to beaches
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Welcome to the Atlantis House, a beautiful vacation rental located in the heart of the charming island town of Key West. ...
From $567 per night (USD)
Expedia
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 $1101 per night (USD)
VRBO
2 Family-friendly Units, Complimentary Breakfast, Outdoor Pool!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Explore, dine, and relax in downtown Key West! We're steps from the Hemingway Home, Duval Street nightlife, and Southern ...
From $1101 per night (USD)
VRBO
From $1883 per night (USD)
VRBO
Perfect for Groups! 2 Pet-friendly Units, Free Breakfast, Outdoor Pool!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Explore, dine, and relax in downtown Key West! We're steps from the Hemingway Home, Duval Street nightlife, and Southern ...
From $1883 per night (USD)
VRBO
From $348 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 $348 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 $520 per night (USD)
Expedia
**A BEACHY VIEW @ THE TRUMAN ANNEX IN KEY WEST**
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Come and relax in this 2-bedroom 1 bath, first floor with 3 flat screen TV's, custom kitchen, backyard tropical paradise ...
From $520 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 $660 per night (USD)
VRBO
3-bedroom townhome in Key West with fitness room, WiFi
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Your cozy getaway awaits in Key West at this lovely townhome. With 3 bedrooms including 2 king beds and 2 queen beds, th ...
From $660 per night (USD)
VRBO
From $1185 per night (USD)
Expedia
Atlantis House Suites
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Nestled within the serene enclave of the Atlantis House Compound, the Palm and Banyan Suites offer a tropical oasis for ...
From $1185 per night (USD)
Expedia
From $852 per night (USD)
VRBO
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)
VRBO
From $2269 per night (USD)
Expedia
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)
Expedia
$VIRGINIA VISTA - Steps from Duval, 2B\/R, 2 Bath Retreat with Pool & Large Porch$
From $334 per night (USD)
VRBO
VIRGINIA VISTA - Steps from Duval, 2B\/R, 2 Bath Retreat with Pool & Large Porch
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Just a few houses off Duval on Virginia Street, VIRGINIA VISTA occupies the upper level of an almost 100-year-old home i ...
From $334 per night (USD)
VRBO
$VIRGINIA VERANDA, Stylish Old Town 2 B\/R, 2Bath, with Pool, Steps from Duval$
From $340 per night (USD)
Expedia
VIRGINIA VERANDA, Stylish Old Town 2 B\/R, 2Bath, with Pool, Steps from Duval
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Just a few houses off Duval, this wonderful 2 Bedroom, 2 Bath retreat occupies the ground level of an almost 100-year-ol ...
From $340 per night (USD)
Expedia
From $299 per night (USD)
VRBO
A slice of paradise in the Florida Keys
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
About this space As seen on My Tiny Home (reality tv) this is the pefect getaway for a romantic night in Key West. The s ...
From $299 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:
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 p ...
From $585 per night (USD)
Expedia
From $375 per night (USD)
VRBO
Garden of Roses | Private Hot Tub, Prime Key West Location! - Monthly Rental
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Garden of Roses | Private Hot Tub, Prime Key West Location! Experience the essence of Key West living at Garden of Rose ...
From $375 per night (USD)
VRBO
From $268 per night (USD)
Expedia
Cabana at the Golf Club-Monthly Rental Charming 2-Bedroom Golf Course Retreat
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Charming 2-Bedroom Retreat with Golf Course Views | Key West Golf Club Community Nestled in the picturesque Key West Go ...
From $268 per night (USD)
Expedia
From $263 per night (USD)
VRBO
Key West vibes, 2-bedroom townhome with AC, WiFi in marvelous Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Nestled in Key West, this delightful townhome boasts 2 bedrooms with a king bed and a full bed, perfect for a small grou ...
From $263 per night (USD)
VRBO
From $319 per night (USD)
Expedia
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)
Expedia
From $309 per night (USD)
VRBO
Hyatt Windward Pointe, 2 bedroom Waterfront Condo, 2 Night Stay in December
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Whether you choose to spend your days simply relaxing by the infinity pool or setting off on a dive adventure, Key West ...
From $309 per night (USD)
VRBO
$Duval Hideaway | Dog-Friendly Home w\/ Shared Hot Tub, Patio & Prime Location$
From $749 per night (USD)
Expedia
Duval Hideaway | Dog-Friendly Home w\/ Shared Hot Tub, Patio & Prime Location
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Duval Hideaway | Dog-Friendly Home with Shared Hot Tub, Patio & Prime Location Duval Hideaway is the perfect home base ...
From $749 per night (USD)
Expedia
$Duval Street Retreat | Dog-Friendly Home w\/ Hot Tub, Patio, & Parking$
From $754 per night (USD)
VRBO
Duval Street Retreat | Dog-Friendly Home w\/ Hot Tub, Patio, & Parking
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Duval Street Retreat | Dog-Friendly Home with Hot Tub, WiFi, & Private Parking Duval Street Retreat is your ideal Key W ...
From $754 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 $198 per night (USD)
VRBO
Salt Pond Hideaway | Comfortable Condo with Pool, Hot Tub, Close to Beach!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Salt Pond Hideaway | Comfortable Condo with Pool, Hot Tub, and Close to Beach! Salt Pond Hideaway is your ideal retreat ...
From $198 per night (USD)
VRBO
From $1421 per night (USD)
Expedia
Southernmost Retreat | On Duval! With Hot Tub, Patio, & Private Parking
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
Southernmost Retreat | Two Dog-Friendly Homes with Hot Tubs, WiFi, & Private Parking Southernmost Retreat is the perfec ...
From $1421 per night (USD)
Expedia
From $364 per night (USD)
VRBO
Kingfish Keep | Lively Escape on Duval! Balcony!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Kingfish Keep | Lively Escape on Duval! Balcony! Kingfish Keep is the perfect escape in the heart of the historic distr ...
From $364 per night (USD)
VRBO
From $353 per night (USD)
Expedia
Yellowfin Ledge | Inviting Getaway On Duval! Balcony!
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
Yellowfin Ledge | Inviting Getaway On Duval! Balcony! Yellowfin Ledge is the ideal choice for your Key West adventure! ...
From $353 per night (USD)
Expedia
From $346 per night (USD)
VRBO
Wahoo Way | Charming Hideaway On Duval Street!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Wahoo Way | Charming Hideaway On Duval Street! Escape to Wahoo Way for an unforgettable couple’s retreat in Key West! T ...
From $346 per night (USD)
VRBO
From $1046 per night (USD)
Expedia
Pescado Penthouse | Vibrant Retreat Overlooking Duval Street!
Bedrooms:
3
Bathrooms:
5
Sleeps:
9
Pescado Penthouse | Vibrant Retreat Overlooking Duval Street! Pescado Penthouse is the ultimate getaway for families or ...
From $1046 per night (USD)
Expedia
From $1192 per night (USD)
VRBO
Coconut Beach | Hot Tub | Lux Resort | Pool | Concierge
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Coconut Beach Resort transports you to your very own private oasis, where the charm of old island architecture meets lus ...
From $1192 per night (USD)
VRBO
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 $2537 per night (USD)
VRBO
Sleeps 6 | Lux Resort | Hot Tub | Pool | Concierge
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to your private sanctuary at Hyatt Beach House Resort, where the lush landscapes of Key West meet unparalleled l ...
From $2537 per night (USD)
VRBO
From $402 per night (USD)
VRBO
Island Oasis-2 Bedroom Townhouse in the Gated Community of the Key West Golf Club
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Step into this spacious 2-bedroom, 1 1/2 -bathroom home, perfect for your island getaway, in the gated community of the ...
From $402 per night (USD)
VRBO

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