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From $764 per night (USD)
VRBO
Oceanfront King, Pier House, Stunning Ocean Views, Plush King Bed, Duval Locale
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $764 per night (USD)
VRBO
From $480 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 $480 per night (USD)
VRBO
From $791 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 $791 per night (USD)
VRBO
From $594 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 $594 per night (USD)
VRBO
From $486 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 $486 per night (USD)
VRBO
From $1256 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 $1256 per night (USD)
VRBO
From $2052 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 $2052 per night (USD)
VRBO
From $843 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 $843 per night (USD)
VRBO
From $655 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 $655 per night (USD)
VRBO
From $1405 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 $1405 per night (USD)
VRBO
From $568 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 $568 per night (USD)
VRBO
From $937 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 $937 per night (USD)
VRBO
From $1295 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 $1295 per night (USD)
VRBO
From $522 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 $522 per night (USD)
VRBO
From $596 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 $596 per night (USD)
VRBO
From $422 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 $422 per night (USD)
VRBO
From $711 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 $711 per night (USD)
VRBO
From $663 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 $663 per night (USD)
VRBO
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 $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 $318 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 $318 per night (USD)
VRBO
$Mariner's Oasis at Sunset Marina- 2bed 2 bath condo w\/boat slip for rent$
From $256 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 $256 per night (USD)
Expedia
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
$4 bed 2.5 bath home w\/ ocean views, private pool oasis on Gulfview$
From $298 per night (USD)
Expedia
4 bed 2.5 bath home w\/ ocean views, private pool oasis on Gulfview
Bedrooms:
3
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 $298 per night (USD)
Expedia
From $397 per night (USD)
VRBO
Royal Palm in Key West
Bedrooms:
3
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 $397 per night (USD)
VRBO
$Tropical Village: The Southern Cross - Quiet & gated. Pool\/Porch\/Pet friendly$
From $733 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 $733 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
From $1177 per night (USD)
VRBO
A contemporary island gem that was formerly used as a bottling plant,
Bedrooms:
3
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 $1177 per night (USD)
VRBO
$Key West Home on Golf Course w\/ Patio & Grill!$
From $244 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 $244 per night (USD)
VRBO
From $464 per night (USD)
Expedia
A Gulfview Paradise in Key West - Call for more information!
Bedrooms:
3
Bathrooms:
5
Sleeps:
8
Welcome to your dream vacation rental in Gulfview Pointe, Key West! This stunning property offers breathtaking waterfron ...
From $464 per night (USD)
Expedia
From $837 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 $837 per night (USD)
VRBO
From $1711 per night (USD)
Expedia
Private Parking & Pool - The Delaney House
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 $1711 per night (USD)
Expedia
$Spacious Townhome on Windsor Lane 3\/3.5$
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
From $313 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 $313 per night (USD)
VRBO
Click For Pricing
VRBO
ROBINSON CRUSOE COTTAGE - Quaint poolside cottage on Margaret St
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Robinson Crusoe Cottage is a one-bedroom cottage with a queen bed, sleeper sofa, kitchen, and private bath. The queen be ...
Click For Pricing
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
From $1248 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 $1248 per night (USD)
VRBO
$THALIA'S RETREAT @ Duval Square 2bd\/2ba townhome$
From $539 per night (USD)
VRBO
THALIA'S RETREAT @ Duval Square 2bd\/2ba townhome
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Lush and tropical gardens surround this beautiful development in the heart of historic Old Town. Private, secured parkin ...
From $539 per night (USD)
VRBO
From $1462 per night (USD)
VRBO
No secrets at Pilar's Secret - Just a great location!
Bedrooms:
2
Bathrooms:
4
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 $1462 per night (USD)
VRBO
From $314 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 $314 per night (USD)
VRBO
From $324 per night (USD)
Expedia
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 $324 per night (USD)
Expedia
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 $395 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 $395 per night (USD)
VRBO
$ALOHA - Large 1 level 4bd\/4ba Monthly Rental$
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
$Eyebrow Suite - 2bd\/1.5ba Suite off Duval$
From $550 per night (USD)
VRBO
Eyebrow Suite - 2bd\/1.5ba Suite off Duval
Bedrooms:
2
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 $550 per night (USD)
VRBO
$Life is a Breeze at Windward Breeze by RENT KEY WEST VACATIONS - 2\/2 townhome -$
From $577 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 $577 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
Click For Pricing
VRBO
ROYAL POINCIANA COTTAGE - Quaint Old Town location
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Royal Poinciana is a studio cottage with a queen bed, kitchen ,and private bath. The queen bed sleeps 2 people and the k ...
Click For Pricing
VRBO
From $428 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 $428 per night (USD)
VRBO
From $187 per night (USD)
VRBO
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 $187 per night (USD)
VRBO
From $178 per night (USD)
Expedia
A Kokomo Cottage: 3 BR, 2 BA Condominium 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 $178 per night (USD)
Expedia
From $178 per night (USD)
VRBO
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 $178 per night (USD)
VRBO
$Helluva Happy Place | Escape to Old Town Key West - 3 bed\/2.5 bath townhome with private pool$
From $307 per night (USD)
VRBO
Helluva Happy Place | Escape to Old Town Key West - 3 bed\/2.5 bath townhome with private pool
Bedrooms:
3
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 $307 per night (USD)
VRBO
From $248 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 $248 per night (USD)
VRBO
From $360 per night (USD)
Expedia
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)
Expedia
From $583 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 $583 per night (USD)
VRBO
From $672 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 $672 per night (USD)
Expedia
From $228 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 $228 per night (USD)
VRBO
From $228 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 $228 per night (USD)
VRBO
$Newly Renovated Hotel w\/ Outdoor Pool | Short Drive to Historic Old Town$
From $258 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 $258 per night (USD)
VRBO
From $258 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 $258 per night (USD)
VRBO
From $359 per night (USD)
VRBO
Balcony on Duval - The Green Pineapple
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Summary: Beautiful 3-bedroom, 2-bath monthly rental located on Key West's famous Duval Street. Guests enjoy easy access ...
From $359 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 $298 per night (USD)
VRBO
An Island Siesta: 2 BR, 2 BA Townhouse in Key West, Sleeps 6
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 $298 per night (USD)
VRBO
From $385 per night (USD)
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 ...
From $385 per night (USD)
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
$SATISFY MY SOUL ~ 3 BR, 3.5 Ba Newly Renovated Mid Town Home w\/ Pool!$
From $551 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 $551 per night (USD)
Expedia
From $431 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 $431 per night (USD)
VRBO
From $229 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 $229 per night (USD)
Expedia
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 $335 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 $335 per night (USD)
Expedia
From $919 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 $919 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 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 $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 $1461 per night (USD)
Expedia
The Lighthouse Penthouse Suite
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
The Lighthouse Penthouse Suite is a combination of two 1 BD/ 1 BA Suites delivering two luxury king bedrooms with two lu ...
From $1461 per night (USD)
Expedia
From $2128 per night (USD)
VRBO
The Lighthouse Group Suite
Bedrooms:
2
Bathrooms:
6
Sleeps:
12
The Lighthouse Group Suite is a combination of two 2 BD/ 1 BA Suites delivering two luxury king bedrooms and two luxury ...
From $2128 per night (USD)
VRBO
$Stylish Boutique Room w\/ 2 Queen Beds - Access Pool & Poolside Bar$
From $519 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 $519 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 $809 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 $809 per night (USD)
VRBO
From $199 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
City of Key West zoning requires a minimum rental period of 30 days, and no exceptions can be made. Please review additi ...
From $199 per night (USD)
Expedia
From $516 per night (USD)
VRBO
Heron Hideaway - Charming 1st-Floor Unit, Shared Pool, Private Hot Tub, Near Duval St & Beaches
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Welcome to Heron Hideaway, a charming 1st-floor condo nestled in the desirable Meadows area of Key West. Just six blocks ...
From $516 per night (USD)
VRBO
$Ocean Oasis at Sunset Marina-2 bed 2 bath oceanfront condo w\/boat slip rental$
From $225 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 $225 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
From $681 per night (USD)
Expedia
NEW!!! Gorgeous! Beacon Terrace in the Truman Annex Key West
Bedrooms:
3
Bathrooms:
3
Sleeps:
5
"Beacon Terrace" in the Truman Annex is a beautifully renovated town home in the historic Foundry in the Truman Annex. ...
From $681 per night (USD)
Expedia

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