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From $642 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 $642 per night (USD)
VRBO
From $1078 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 $1078 per night (USD)
VRBO
From $806 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 $806 per night (USD)
VRBO
From $616 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 $616 per night (USD)
VRBO
From $1748 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 $1748 per night (USD)
VRBO
From $3377 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 $3377 per night (USD)
VRBO
From $1145 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 $1145 per night (USD)
VRBO
From $1073 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 $1073 per night (USD)
VRBO
From $2220 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 $2220 per night (USD)
VRBO
From $712 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 $712 per night (USD)
VRBO
From $1126 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 $1126 per night (USD)
VRBO
From $2220 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 $2220 per night (USD)
VRBO
From $642 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 $642 per night (USD)
VRBO
From $712 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 $712 per night (USD)
VRBO
From $560 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 $560 per night (USD)
VRBO
From $1073 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 $1073 per night (USD)
VRBO
From $869 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 $869 per night (USD)
VRBO
From $1071 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 $1071 per night (USD)
VRBO
From $2493 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 $2493 per night (USD)
VRBO
From $3377 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 $3377 per night (USD)
VRBO
From $1078 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 $1078 per night (USD)
VRBO
From $1782 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 $1782 per night (USD)
VRBO
From $311 per night (USD)
VRBO
Old Town main house and guest house one block from Duval Street for the best of Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This luxury Old Town renovation is on a quiet end of Virginia street with no through traffic but located only one block ...
From $311 per night (USD)
VRBO
From $1043 per night (USD)
Expedia
**GARDEN OF EMMA @ THE ANNEX** Private Home & Pool + LAST KEY SERVICES…
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Tranquility. ...
From $1043 per night (USD)
Expedia
From $531 per night (USD)
VRBO
Bohemian Retreat with Pool in Old Town Key West | Free Breakfast Onsite!
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 $531 per night (USD)
VRBO
From $572 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 $572 per night (USD)
VRBO
From $337 per night (USD)
VRBO
Lofted 1 bedroom suite right off Duval St
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to sweet paradise! Located on Petronia Street, the Orange Blossom Suite is in close proximity to all the fun-fil ...
From $337 per night (USD)
VRBO
From $197 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 $197 per night (USD)
Expedia
From $278 per night (USD)
VRBO
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 $278 per night (USD)
VRBO
From $310 per night (USD)
Expedia
4 bed 2.5 bath home w/ ocean views, private pool oasis on Gulfview
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
AGE REQUIREMENT: Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their ...
From $310 per night (USD)
Expedia
From $294 per night (USD)
VRBO
Royal Palm in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
There's no better way to experience island time - that slow shifting of hours that makes Key West such an ideal vacation ...
From $294 per night (USD)
VRBO
From $250 per night (USD)
Expedia
Key West Home on Golf Course w/ Patio & Grill!
Bedrooms:
1
Bathrooms:
2
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 $250 per night (USD)
Expedia
Click For Pricing
VRBO
A Gulfview Paradise in Key West - Call for more information!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Welcome to your dream vacation rental in Gulfview Pointe, Key West! This stunning property offers breathtaking waterfron ...
Click For Pricing
VRBO
From $263 per night (USD)
Expedia
A 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 $263 per night (USD)
Expedia
From $181 per night (USD)
VRBO
A Kokomo Cottage: 3 BR, 2 BA in Key West, Sleeps 6
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 $181 per night (USD)
VRBO
From $233 per night (USD)
Expedia
A 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 $233 per night (USD)
Expedia
From $178 per night (USD)
VRBO
Tropical Cottage w/ Private Pool--Two blocks from Duval - Near Hemingway House!
Bedrooms:
2
Bathrooms:
1
Sleeps:
5
The Conch-Out Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $178 per night (USD)
VRBO
From $224 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 $224 per night (USD)
VRBO
From $224 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 $224 per night (USD)
VRBO
From $249 per night (USD)
VRBO
Newly Renovated Hotel w/ Outdoor Pool | Short Drive to Historic Old Town
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 $249 per night (USD)
VRBO
From $249 per night (USD)
VRBO
Relaxing Double Queen, Fairfield Inn, Breakfast Included, Near Downtown Key West
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 $249 per night (USD)
VRBO
From $355 per night (USD)
Expedia
Balcony on Duval - The Green Pineapple
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Beautiful 3-bedroom, 2-bath monthly rental located on Key West's famous Duval Street. Guests enjoy easy access ...
From $355 per night (USD)
Expedia
From $539 per night (USD)
VRBO
Pool, Pet Friendly, & Near Duval - Coastal Rose
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Experience the charm of downtown Key West in this cozy 1-bedroom unit with an additional loft and a shared pool ...
From $539 per night (USD)
VRBO
From $381 per night (USD)
Expedia
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 $381 per night (USD)
Expedia
From $1013 per night (USD)
VRBO
Pet Friendly, & Near Duval - Rose Key Cottage
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Escape to paradise with this luxurious Key West retreat, perfect for families and groups looking to unwind in s ...
From $1013 per night (USD)
VRBO
From $316 per night (USD)
Expedia
An Island Siesta: 2 BR, 2 BA in Key West, Sleeps 6
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This lovely, fully furnished, townhouse has two bedrooms that sleeps up to 6 and two full baths . The spacious upstairs ...
From $316 per night (USD)
Expedia
From $450 per night (USD)
VRBO
Boomerang Boathouse in Key West
Bedrooms:
2
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 $450 per night (USD)
VRBO
From $458 per night (USD)
Expedia
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 $458 per night (USD)
Expedia
From $554 per night (USD)
VRBO
Atlantis House's Palm Suite-voted top 25 in USA
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The Palm Suite is a stunning vacation rental property located in the heart of Key West. This luxurious suite is situated ...
From $554 per night (USD)
VRBO
Click For Pricing
Expedia
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 ...
Click For Pricing
Expedia
Click For Pricing
VRBO
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
VRBO
From $376 per night (USD)
Expedia
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 $376 per night (USD)
Expedia
From $436 per night (USD)
VRBO
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 $436 per night (USD)
VRBO
From $356 per night (USD)
Expedia
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 $356 per night (USD)
Expedia
From $326 per night (USD)
VRBO
HERE COMES THE SUN ~ 2 BR, 2 Ba Casa Marina Home with Pool!
Bedrooms:
2
Bathrooms:
2
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 $326 per night (USD)
VRBO
From $998 per night (USD)
Expedia
An Ocean Serenity in Truman Annex, Key West
Bedrooms:
2
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 $998 per night (USD)
Expedia
From $409 per night (USD)
VRBO
Modern Lodge w/ Outdoor Pool Access & Free Breakfast, Near Attractions!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This listing is for a room within a hotel. ✦ Your room is 420 sq. ft, equipped with complimentary toiletries, standard ...
From $409 per night (USD)
VRBO
From $805 per night (USD)
VRBO
2 Rooms for the whole family w/ Pool Access & Free Breakfast, Near Museums!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
This listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms. ✦ Each room is ...
From $805 per night (USD)
VRBO
From $668 per night (USD)
VRBO
2 Bedroom Suite w/ Outdoor Pool in Old Town Key West! Free Breakfast
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
This listing is for a room within a hotel. ✦ Your room is 800 sq. ft, equipped with complimentary toiletries, kitchen w ...
From $668 per night (USD)
VRBO
From $541 per night (USD)
VRBO
Stunning Key West Stay Perfect for a Romantic Escape! Pool, Free Breakfast
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 $541 per night (USD)
VRBO
From $186 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 $186 per night (USD)
VRBO
From $777 per night (USD)
Expedia
The Lighthouse Penthouse Suite
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Escape the Ordinary... The Lighthouse Penthouse Suite combines two 1 BD/1 BA suites into a spacious 2 BD/ 2 BA retreat ...
From $777 per night (USD)
Expedia
From $1178 per night (USD)
VRBO
The Lighthouse Group Suite
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
Escape the Ordinary... The Lighthouse Group Suite combines two 2 BD/1 BA units into a spacious 4 BD/ 2 BA retreat featu ...
From $1178 per night (USD)
VRBO
From $469 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 $469 per night (USD)
VRBO
From $198 per night (USD)
VRBO
Castaway Cove: Charming 2BR Townhome in New Town, Key West with Shared Pool, Private Patio & Kayaks!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
City of Key West zoning requires a minimum rental period of 30 days, and no exceptions can be made. Please review additi ...
From $198 per night (USD)
VRBO
From $269 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 $269 per night (USD)
Expedia
From $2495 per night (USD)
VRBO
Pool & Parking, & Near Duval - The Rigby House
Bedrooms:
6
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 $2495 per night (USD)
VRBO
From $733 per night (USD)
Expedia
NEW!!! Gorgeous! Beacon Terrace in the Truman Annex Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
"Beacon Terrace" in the Truman Annex is a beautifully renovated town home in the historic Foundry in the Truman Annex. ...
From $733 per night (USD)
Expedia
From $769 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 $769 per night (USD)
VRBO
From $3380 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 $3380 per night (USD)
VRBO
From $1540 per night (USD)
VRBO
Stunning 2 Floor Loft in Vibrant Key West Ideal for Romantic Weekends - Pool
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 $1540 per night (USD)
VRBO
From $719 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 $719 per night (USD)
VRBO
From $273 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 $273 per night (USD)
VRBO
From $169 per night (USD)
Expedia
Chic 1BR w/ Balcony in Old Town – Walk to Duval!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Galveston Porches – Stylish One-Bedroom in the Heart of Old Town Key West Welcome to Galveston Porches, your perfect ho ...
From $169 per night (USD)
Expedia
From $425 per night (USD)
VRBO
Atlantis House- beautiful residence close to beaches
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to the Atlantis House, a beautiful vacation rental located in the heart of the charming island town of Key West. ...
From $425 per night (USD)
VRBO
From $1105 per night (USD)
VRBO
Charming Bungalow Perfect for Families! Free Breakfast and Pool Access
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 $1105 per night (USD)
VRBO
From $1015 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 $1015 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:
2
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 $791 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 $791 per night (USD)
VRBO
From $758 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 $758 per night (USD)
Expedia
From $649 per night (USD)
VRBO
Coco's Poolside Retreat
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Coco’s Poolside Retreat is a cheerful three-story townhome tucked inside a private, gated mini-compound in Old Town Key ...
From $649 per night (USD)
VRBO
From $1457 per night (USD)
Expedia
The Flower Power House - Boho Beautiful
Bedrooms:
4
Bathrooms:
5
Sleeps:
13
When you enter the gate next to the painted 1306 sign, you’ll find yourself immersed in this one-of-a-kind tropical wond ...
From $1457 per night (USD)
Expedia
From $386 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 $386 per night (USD)
VRBO
From $408 per night (USD)
VRBO
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 $408 per night (USD)
VRBO
From $467 per night (USD)
VRBO
**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 $467 per night (USD)
VRBO
From $564 per night (USD)
Expedia
**SOUTHERN STAR @ THE MEADOWS** Private Home & Pool + LAST KEY SERVICES...
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! SOUTHERN STAR ...
From $564 per night (USD)
Expedia
From $115 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 $115 per night (USD)
VRBO
From $380 per night (USD)
Expedia
Garden of Roses | Private Hot Tub, Prime Key West Location! - Monthly Rental
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Garden of Roses | Private Hot Tub, Prime Key West Location! Experience the essence of Key West living at Garden of Rose ...
From $380 per night (USD)
Expedia
From $203 per night (USD)
VRBO
Cabana at the Golf Club-Monthly Rental Charming 2-Bedroom Golf Course Retreat
Bedrooms:
1
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 $203 per night (USD)
VRBO
From $286 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 $286 per night (USD)
Expedia
From $391 per night (USD)
VRBO
Duval Hideaway | Dog-Friendly Home w/ Shared Hot Tub, Patio & Prime Location
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Duval Hideaway | Dog-Friendly Home with Shared Hot Tub, Patio & Prime Location Duval Hideaway is the perfect home base ...
From $391 per night (USD)
VRBO
From $391 per night (USD)
Expedia
Duval Street Retreat | Dog-Friendly Home w/ Hot Tub, Patio, & Parking
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Duval Street Retreat | Dog-Friendly Home with Hot Tub, WiFi, & Private Parking Duval Street Retreat is your ideal Key W ...
From $391 per night (USD)
Expedia
From $1872 per night (USD)
VRBO
Meadows Manor | Elegant Oasis with Private Pool & Parking!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Meadows Manor | Elegant Oasis with Private Pool & Parking --- 3-Night Minimum Stay Required --- Discover the perfect b ...
From $1872 per night (USD)
VRBO
From $509 per night (USD)
Expedia
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 $509 per night (USD)
Expedia
From $769 per night (USD)
VRBO
Southernmost Retreat | On Duval! With Hot Tub, Patio, & Private Parking
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
Southernmost Retreat | Two Dog-Friendly Homes with Hot Tubs, WiFi, & Private Parking Southernmost Retreat is the perfec ...
From $769 per night (USD)
VRBO
From $319 per night (USD)
Expedia
Kingfish Keep | Lively Escape on Duval! Balcony!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Kingfish Keep | Lively Escape on Duval! Balcony! Kingfish Keep is the perfect escape in the heart of the historic distr ...
From $319 per night (USD)
Expedia
From $264 per night (USD)
VRBO
Yellowfin Ledge | Inviting Getaway On Duval! Balcony!
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Yellowfin Ledge | Inviting Getaway On Duval! Balcony! Yellowfin Ledge is the ideal choice for your Key West adventure! ...
From $264 per night (USD)
VRBO
From $247 per night (USD)
Expedia
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 $247 per night (USD)
Expedia
From $767 per night (USD)
VRBO
Pescado Penthouse | Vibrant Retreat Overlooking Duval Street!
Bedrooms:
3
Bathrooms:
3
Sleeps:
9
Pescado Penthouse | Vibrant Retreat Overlooking Duval Street! Pescado Penthouse is the ultimate getaway for families or ...
From $767 per night (USD)
VRBO
From $448 per night (USD)
Expedia
Palm Isle: Tropical 2nd-Floor Unit, Shared Heated Pool, Near Duval St, Historic Seaport & 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 ...
From $448 per night (USD)
Expedia

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