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From $740 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 $740 per night (USD)
VRBO
From $1480 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 $1480 per night (USD)
VRBO
From $192 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 $192 per night (USD)
VRBO
From $441 per night (USD)
VRBO
Key West at Ocean’s Corner!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Whether you want to explore the historic sites, enjoy the nightlife, or relax in nature, you’ll find it all during your ...
From $441 per night (USD)
VRBO
From $394 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 $394 per night (USD)
VRBO
From $271 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 $271 per night (USD)
Expedia
From $367 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 $367 per night (USD)
VRBO
From $306 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 $306 per night (USD)
Expedia
From $234 per night (USD)
VRBO
Royal Palm in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Truman Annex Properties are going to Monthly (or longer) rentals beginning January 1, 2026 because of changing licensing ...
From $234 per night (USD)
VRBO
From $636 per night (USD)
VRBO
Tropical Village: The Southern Cross - Quiet & gated. Pool/Porch/Pet friendly
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
There are stars in the southern sky! The Southern Cross takes its name from the “crux” constellation that guided sailors ...
From $636 per night (USD)
VRBO
From $1305 per night (USD)
VRBO
The Caroline House Estate - 1 Block off Duval & Key West Historic Seaport
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
This gorgeous classical Key West Estate property is quite possibly the most stylish blend of historic Victorian-Caribbea ...
From $1305 per night (USD)
VRBO
From $1254 per night (USD)
VRBO
A contemporary island gem that was formerly used as a bottling plant,
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
A contemporary island gem that was formerly used as a bottling plant, this modern and spacious home is now a desirable t ...
From $1254 per night (USD)
VRBO
From $245 per night (USD)
VRBO
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 $245 per night (USD)
VRBO
From $387 per night (USD)
Expedia
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 ...
From $387 per night (USD)
Expedia
From $466 per night (USD)
VRBO
Escape to the wonderful Cuban Paradise!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Built in 1917 as a “club” for Cuban cigar makers and their families as their home-away-from-home, this building soon bec ...
From $466 per night (USD)
VRBO
From $821 per night (USD)
VRBO
Spacious Townhome on Windsor Lane 3/3.5
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Welcome to Windsor Townhomes #3! Once you enter this beautifully decorated oasis…your vacation begins. This townhome has ...
From $821 per night (USD)
VRBO
From $256 per night (USD)
VRBO
ESPERANZA SUITE Monthly Rental close to Duval
Bedrooms:
2
Bathrooms:
1
Sleeps:
4
Esperanza Suite is a bi-level suite with a very spacious upstairs king bedroom with a writing desk and chair and a color ...
From $256 per night (USD)
VRBO
From $821 per night (USD)
VRBO
Windsor Townhomes #6 - Large pool 3B/3.5 bath, 3 blocks to Duval
Bedrooms:
3
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 $821 per night (USD)
VRBO
From $1454 per night (USD)
VRBO
MERMAID COVE - A collection of four units on Duval
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Mermaid Cove features four separate units (two cottages and two apartments), each with a private entrance and all decora ...
From $1454 per night (USD)
VRBO
From $580 per night (USD)
Expedia
THALIA'S RETREAT @ Duval Square 2bd/2ba townhome
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Lush and tropical gardens surround this beautiful development in the heart of historic Old Town. Private, secured parkin ...
From $580 per night (USD)
Expedia
From $1420 per night (USD)
VRBO
No secrets at Pilar's Secret - Just a great location!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Pilar’s Secret is hidden away in the heart of Old Town Key West just half a block off the famous Duval Street. This secl ...
From $1420 per night (USD)
VRBO
From $332 per night (USD)
VRBO
Deckside Suite - Efficiency at its finest!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Efficiency at its finest! The Deckside Suite is the perfect vacation rental in Key West for those who are trying to get ...
From $332 per night (USD)
VRBO
From $350 per night (USD)
VRBO
Rent at PORCHSIDE PARADISE - Steps to Duval
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Porchside Paradise is located in the front section of the Conch Republic Cottages. This beautiful home-away-from-home fe ...
From $350 per night (USD)
VRBO
From $373 per night (USD)
VRBO
Half block to Duval @ Mango Hideaway -studio apt
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
The Mango Hideaway is comfortable junior suite, with sofa sitting area with adjoining king bedroom. The suite features ...
From $373 per night (USD)
VRBO
From $439 per night (USD)
VRBO
ALOHA - Large 1 level 4bd/4ba Monthly Rental
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Aloha is a stunning private residence on corner lot in the Casa Marina District. Updated 2 years ago, this beautiful hom ...
From $439 per night (USD)
VRBO
From $545 per night (USD)
VRBO
Eyebrow Suite - 2bd/1.5ba Suite off Duval
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Eyebrow Suite is a spacious two-bedroom suite with one of the best locations on the island. Its large front porch and pa ...
From $545 per night (USD)
VRBO
From $575 per night (USD)
VRBO
Life is a Breeze at Windward Breeze by RENT KEY WEST VACATIONS - 2/2 townhome -
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Windward Breeze is part of the Windward Park gated community just off Simonton Street, one block from Duval Street. Ther ...
From $575 per night (USD)
VRBO
From $921 per night (USD)
VRBO
Relax in Style at Windsor Townhomes #4
Bedrooms:
3
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 $921 per night (USD)
VRBO
From $319 per night (USD)
VRBO
Oceanfront Splendor @ the Key West Beach Club
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
29 NIGHT MINIMUM RENTAL ... This property is not allowed to accept pets. Enjoy endless views of the tranquil waters of ...
From $319 per night (USD)
VRBO
From $234 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 $234 per night (USD)
Expedia
From $216 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 $216 per night (USD)
VRBO
From $240 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 $240 per night (USD)
Expedia
From $481 per night (USD)
VRBO
Helluva Happy Place | Escape to Old Town Key West - 3 bed/2.5 bath townhome with private pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Escape to Old Town Key West and indulge in a monthly retreat at our charming 3-bedroom, 2.5-bathroom townhome. Nestled i ...
From $481 per night (USD)
VRBO
From $191 per night (USD)
Expedia
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 $191 per night (USD)
Expedia
From $399 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 $399 per night (USD)
VRBO
From $507 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 $507 per night (USD)
Expedia
From $575 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 $575 per night (USD)
VRBO
From $222 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 $222 per night (USD)
VRBO
From $222 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 $222 per night (USD)
VRBO
From $248 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 $248 per night (USD)
VRBO
From $247 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 $247 per night (USD)
VRBO
From $291 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 $291 per night (USD)
Expedia
From $476 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 $476 per night (USD)
VRBO
From $406 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 $406 per night (USD)
Expedia
From $1044 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 $1044 per night (USD)
VRBO
From $308 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 $308 per night (USD)
Expedia
Click For Pricing
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 ...
Click For Pricing
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
From $495 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 $495 per night (USD)
VRBO
From $373 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 $373 per night (USD)
Expedia
From $319 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 $319 per night (USD)
VRBO
From $812 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 $812 per night (USD)
VRBO
From $331 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 $331 per night (USD)
VRBO
From $977 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 $977 per night (USD)
Expedia
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 Florida Charming 1-bedroom resort with WiFi, AC
Bedrooms:
1
Bathrooms:
1
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 $5625 per night (USD)
VRBO
Hyatt Beach House Resort Key West 2-bedroom with WiFi, AC
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to your private sanctuary in the lush landscape of Key West. Imagine old-fashioned screen-enclosed porches, gard ...
From $5625 per night (USD)
VRBO
From $527 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 $527 per night (USD)
VRBO
From $205 per night (USD)
Expedia
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 $205 per night (USD)
Expedia
From $863 per night (USD)
VRBO
The Lighthouse Penthouse Suite
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Escape the Ordinary... The Lighthouse Penthouse Suite is a combination of two 1 BD/1 BA Suites delivering two luxury ki ...
From $863 per night (USD)
VRBO
From $1061 per night (USD)
Expedia
The Lighthouse Group Suite
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
Escape the Ordinary... The Lighthouse Group Suite is a combination of two 2 BD/ 1 BA Suites delivering one luxury king ...
From $1061 per night (USD)
Expedia
From $552 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 $552 per night (USD)
VRBO
From $250 per night (USD)
Expedia
3 Bedroom 2 Bathroom Near Beaches and Art Galleries
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Spacious 3-Bedroom, 2-Bathroom Retreat in Key West Escape to paradise in this charming Key West rental, perfectly situa ...
From $250 per night (USD)
Expedia
From $477 per night (USD)
VRBO
Modern Lodge w/ Outdoor Pool Access & Free Breakfast, Near Attractions!
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 $477 per night (USD)
VRBO
From $926 per night (USD)
VRBO
2 Rooms for the whole family w/ Pool Access & Free Breakfast, Near 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 $926 per night (USD)
VRBO
From $792 per night (USD)
VRBO
2 Bedroom Suite w/ Outdoor Pool in Old Town Key West! Free Breakfast
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Discover Old Town charm, plunge into vibrant Duval Street life, and dive deep into Key West's treasures. We're footsteps ...
From $792 per night (USD)
VRBO
From $1069 per night (USD)
VRBO
𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢 Dream Getaway at the Beach House Resort+Amenities. 2BR
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to 𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢🌴 Experience Key West Paradise at the Beach House Resort Retreat! 🏖️ Additional $ ...
From $1069 per night (USD)
VRBO
From $195 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 $195 per night (USD)
VRBO
From $258 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 $258 per night (USD)
Expedia
From $3403 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 $3403 per night (USD)
VRBO
From $728 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 $728 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 $2245 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 $2245 per night (USD)
VRBO
From $1228 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 $1228 per night (USD)
VRBO
From $747 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 $747 per night (USD)
VRBO
From $523 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 $523 per night (USD)
VRBO
From $1069 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 $1069 per night (USD)
VRBO
From $171 per night (USD)
VRBO
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 $171 per night (USD)
VRBO
From $433 per night (USD)
Expedia
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 $433 per night (USD)
Expedia
From $1316 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 $1316 per night (USD)
VRBO
From $1168 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 $1168 per night (USD)
VRBO
From $348 per night (USD)
VRBO
Discover this cozy retreat in the charm of Old Town Key West at Poorhouse Lane!
Bedrooms:
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)
VRBO
From $182 per night (USD)
VRBO
Island Oasis-2 Bedroom Townhouse in the Gated Community of the Key West Golf Club
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Step into our Island Oasis! A very spacious 2-bedroom, 1 1/2 -bathroom home, perfect for your island getaway, in the cov ...
From $182 per night (USD)
VRBO
From $253 per night (USD)
VRBO
2 Bedroom Townhome in the Key West Golf Club
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
**Beautiful 2-Bedroom Townhome in Key West Golf Club** Welcome to this charming 2-bedroom, 2.5-bathroom townhome locate ...
From $253 per night (USD)
VRBO
From $467 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 $467 per night (USD)
Expedia
From $491 per night (USD)
VRBO
**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 $491 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 $773 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 $773 per night (USD)
VRBO
From $823 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 $823 per night (USD)
Expedia
From $686 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 $686 per night (USD)
VRBO
From $1420 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 $1420 per night (USD)
Expedia
From $362 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 $362 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 $423 per night (USD)
VRBO
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 $423 per night (USD)
VRBO
From $218 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 $218 per night (USD)
Expedia
From $179 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 $179 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 $435 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 $435 per night (USD)
VRBO
From $456 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 $456 per night (USD)
Expedia

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