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From $636 per night (USD)
VRBO
**THE OSPREY'S NEST @ SUNRISE SUITES** Condo & Pool + LAST KEY SERVICES…
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Want to be in ...
From $636 per night (USD)
VRBO
From $223 per night (USD)
Expedia
Poolside tropical paradise in Key West! The Salty Conch
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
The Salty Conch is tucked away in the gated community of The Key West Golf Club with 24/7 security for your peace of min ...
From $223 per night (USD)
Expedia
From $390 per night (USD)
VRBO
Craig & Cindy Key West Truman Annex Shipyard Condo with balcony at Mile Marker 0
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Partial list of rental amenities at Craig & Cindy's Truman Annex Shipyard Condos include: 2 bedrooms 1 bath {queen and ...
From $390 per night (USD)
VRBO
From $433 per night (USD)
Expedia
Our Piece of Paradise-
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Welcome to your ideal Key West getaway! Perfect for families and ideally situated between Old Town, New Town, and Duval ...
From $433 per night (USD)
Expedia
From $564 per night (USD)
VRBO
Midnight Cowboy by AvantStay | 3 Artistic Spaces
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
*Please note that this home is available for 28+ night stays only.* Midnight Cowboy is a one-of-a-kind Key West escape ...
From $564 per night (USD)
VRBO
From $201 per night (USD)
Expedia
Monkey House by AvantStay | Pool, by Duval Street
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
*Please note that this home is available for 28+ night stays only.* Monkey House is a two-bedroom Key West escape that ...
From $201 per night (USD)
Expedia
From $240 per night (USD)
VRBO
Tennessee Williams by AvantStay | Funky Design + Pool
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
*Please note that this home is available for 28+ night stays only.* Tennessee Williams is a one-of-a-kind Key West esca ...
From $240 per night (USD)
VRBO
From $384 per night (USD)
Expedia
Speakeasy Inn - 1C (1 Queen Bed & Sleeper Sofa)
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 $384 per night (USD)
Expedia
From $429 per night (USD)
VRBO
Speakeasy Inn - Room 1A (1 King Bed & 1 Single Sleeper Sofa)
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
The Speakeasy Inn is a quaint guesthouse located in an historic Key West conch style house. It is situated on upper Duva ...
From $429 per night (USD)
VRBO
$BE AS YOU ARE - 3 Bedroom \/ 3 Bathroom - Mid Town KEY WEST w\/ POOL$
From $653 per night (USD)
Expedia
BE AS YOU ARE - 3 Bedroom \/ 3 Bathroom - Mid Town KEY WEST w\/ POOL
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Elegantly renovated and furnished with guest comfort and enjoyment in mind we would like to welcome you to “Be as you ar ...
From $653 per night (USD)
Expedia
From $304 per night (USD)
VRBO
Hyatt Beach House, Two Bedroom
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
A tropical getaway in classic Key West style Hyatt Vacation Club at Beach House has 74 well-appointed luxury units off ...
From $304 per night (USD)
VRBO
From $497 per night (USD)
Expedia
1st year for this gorgeous 4Bd 4Ba all ensuite, 2 parking spots, backyard oasis!
Bedrooms:
5
Bathrooms:
4
Sleeps:
10
Welcome to Moveable Feast, a new monthly vacation rental in the heart of Bahama Village that sleeps 10 comfortably. Loca ...
From $497 per night (USD)
Expedia
From $925 per night (USD)
VRBO
KAMP | Rooftop Penthouse On Duval
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Stay in this one-of-a-kind penthouse and Jimmy Buffet's former Margaritaville Headquarters as well as David "Mr ...
From $925 per night (USD)
VRBO
$Key West Lighthouse Suite | Studio cottage w\/shared pool, half block from Duval Street$
From $720 per night (USD)
Expedia
Key West Lighthouse Suite | Studio cottage w\/shared pool, half block from Duval Street
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
The Key West Lighthouse Suite, one of five luxurious suites in the Lighthouse Suites Collection, is a 5-star stand-alone ...
From $720 per night (USD)
Expedia
$American Shoal Suite | 2 Bed, 1 Bath condo w\/share pool$
From $578 per night (USD)
VRBO
American Shoal Suite | 2 Bed, 1 Bath condo w\/share pool
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
The American Shoal Lighthouse Suite, one of five luxurious resident suites in the Lighthouse Suites Collection, is a 5-s ...
From $578 per night (USD)
VRBO
$Tortugas Harbor Suite | 1 Bed, 1 Bath condo w\/shared pool$
From $514 per night (USD)
Expedia
Tortugas Harbor Suite | 1 Bed, 1 Bath condo w\/shared pool
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
The Tortugas Harbor Light Suite, one of five luxurious residences in the Lighthouse Suites Collection, is a 5-star, 1 be ...
From $514 per night (USD)
Expedia
From $578 per night (USD)
VRBO
Sombrero Suite | 1 Bed, 1 Bath
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
The Sombrero Reef Light Suite, one of five luxurious resident suites in the Lighthouse Suites Collection, is a 5-star, 1 ...
From $578 per night (USD)
VRBO
From $636 per night (USD)
Expedia
Alligator Reef Suite | 2 Bed, 1 Bath
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
The Alligator Reef Lighthouse Suite, one of five luxurious suites in the Lighthouse Suites Collection, is a 5-star, 2 be ...
From $636 per night (USD)
Expedia
From $382 per night (USD)
VRBO
L'Attitude Adjustment | 3 Bed, 2 Bath with pool in Key West
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Your Dream Getaway in Key West! Discover the ultimate monthly vacation rental in Key West. This stunning hom ...
From $382 per night (USD)
VRBO
$Romantic Retreat - 2 person K Suite, Pvt deck\/Spa!$
From $716 per night (USD)
VRBO
Romantic Retreat - 2 person K Suite, Pvt deck\/Spa!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Romantic Retreat is an Historic, free standing cottage which, in the 1800's, was the cistern for the Cigar Maker cottage ...
From $716 per night (USD)
VRBO
Click For Pricing
VRBO
~CALIFORNIA DREAMING~ Enjoy an extended vacation in this posh home and pool.
Bedrooms:
3
Bathrooms:
4
Sleeps:
7
MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local ...
Click For Pricing
VRBO
From $736 per night (USD)
Expedia
Custom House Inn | Two 2nd Floor Suites On Duval!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Summary: Located right in the heart of the World Famous Duval Street, enjoy a true downtown Key West experience at the o ...
From $736 per night (USD)
Expedia
From $918 per night (USD)
VRBO
Custom House Inn | Two Suites On Duval St
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Summary: Located right in the heart of the World Famous Duval Street, enjoy a true downtown Key West experience at the o ...
From $918 per night (USD)
VRBO
From $570 per night (USD)
Expedia
Delancey Hall in Old Town with a pool and privacy!
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
Live like a local and walk or bike to town. Enjoy your large furnished front porch or your own private back porch by the ...
From $570 per night (USD)
Expedia
Click For Pricing
VRBO
Studio Unit in quiet resort adjacent to Old Town Key West!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
With a coveted location in the heart of Old Town and magnificent views of the Gulf of Mexico, Sunset Harbor is the ultim ...
Click For Pricing
VRBO
From $444 per night (USD)
Expedia
NEW! Atlantic Oasis | Pool, Hot Tub & Near Beach!
Bedrooms:
4
Bathrooms:
3
Sleeps:
10
Summary: Atlantic Oasis is a true Key West "Conch Style" townhome consisting of over 1900 sq. ft. of beautiful living sp ...
From $444 per night (USD)
Expedia
From $1007 per night (USD)
VRBO
**THE COZY STARFISH @ THE ANNEX** Condo Near Duval & Beach + LAST KEY SERVICES…
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! THE COZY STAR ...
From $1007 per night (USD)
VRBO
From $258 per night (USD)
Expedia
Book now for October and enjoy Fantasy Fest and the famous Goombay Festival.
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Greet the day with a sunrise over the bay. Situated on a peaceful, quiet dead-end street. Located within a 2 mile radius ...
From $258 per night (USD)
Expedia
From $304 per night (USD)
VRBO
Beautifully Renovated Paradise with Pool and Tropical Gardens in Old Town
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Step into paradise in this clean and impeccably appointed 2 bedroom, 2 bathroom house in Old Town. Located just 2 blocks ...
From $304 per night (USD)
VRBO
From $2360 per night (USD)
VRBO
Old Town Key West Retreat | Seaport Paradise Room with Pool Access | 3 Rooms
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $2360 per night (USD)
VRBO
$Spacious Key West Room w\/ Balcony | Outdoor Pools | Seaport Proximity$
From $780 per night (USD)
VRBO
Spacious Key West Room w\/ Balcony | Outdoor Pools | Seaport Proximity
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $780 per night (USD)
VRBO
$Family Old Town Key Getaway | Four Rooms w\/ Balcony & Outdoor Pools$
From $3249 per night (USD)
VRBO
Family Old Town Key Getaway | Four Rooms w\/ Balcony & Outdoor Pools
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $3249 per night (USD)
VRBO
From $7265 per night (USD)
VRBO
Key West Getaway: Private Balcony, 3 Pools, Fitness Center Access
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $7265 per night (USD)
VRBO
$Vibrant Key West Stay w\/ Outdoor Pools | Four Rooms w\/ Balcony$
From $2484 per night (USD)
VRBO
Vibrant Key West Stay w\/ Outdoor Pools | Four Rooms w\/ Balcony
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $2484 per night (USD)
VRBO
$Two Relaxing Rooms w\/ Balcony | Waterfront Resort w\/ Access to Outdoor Pools$
From $1566 per night (USD)
VRBO
Two Relaxing Rooms w\/ Balcony | Waterfront Resort w\/ Access to Outdoor Pools
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $1566 per night (USD)
VRBO
$2 BR Spacious Suite w\/ Living Area and Balcony | Outdoor Pools$
From $3513 per night (USD)
VRBO
2 BR Spacious Suite w\/ Living Area and Balcony | Outdoor Pools
Bedrooms:
1
Bathrooms:
2
Sleeps:
8
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $3513 per night (USD)
VRBO
From $1863 per night (USD)
VRBO
Seaport Paradise Room with Pools | Old Town Key West Retreat | 3 Rooms
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $1863 per night (USD)
VRBO
$Seaport Proximity | Resort w\/ Outdoor Pools | Spacious Key West Room w\/ Balcony$
From $605 per night (USD)
VRBO
Seaport Proximity | Resort w\/ Outdoor Pools | Spacious Key West Room w\/ Balcony
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $605 per night (USD)
VRBO
$Spacious 2 BR Suite w\/ Living Area and Balcony | Onsite Parking Available$
From $3665 per night (USD)
VRBO
Spacious 2 BR Suite w\/ Living Area and Balcony | Onsite Parking Available
Bedrooms:
1
Bathrooms:
2
Sleeps:
8
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $3665 per night (USD)
VRBO
$Two Bedrooms Family Suite with Balcony | Idyllic Resort w\/ Outdoor Pools$
From $3513 per night (USD)
VRBO
Two Bedrooms Family Suite with Balcony | Idyllic Resort w\/ Outdoor Pools
Bedrooms:
1
Bathrooms:
2
Sleeps:
8
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $3513 per night (USD)
VRBO
$Waterfront Getaway | 2 Spacious Family Rooms w\/ Balcony | Old Town Best$
From $1242 per night (USD)
VRBO
Waterfront Getaway | 2 Spacious Family Rooms w\/ Balcony | Old Town Best
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $1242 per night (USD)
VRBO
From $272 per night (USD)
Expedia
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 $272 per night (USD)
Expedia
From $1018 per night (USD)
VRBO
**GARDEN OF EMMA @ THE ANNEX** Private Home & Pool + LAST KEY SERVICES…
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Tranquility. ...
From $1018 per night (USD)
VRBO
$Seaside Serenity-2BD 2BA condo w\/ pool, parking, tennis courts, near beaches$
From $250 per night (USD)
Expedia
Seaside Serenity-2BD 2BA condo w\/ pool, parking, tennis courts, near beaches
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 $250 per night (USD)
Expedia
From $628 per night (USD)
VRBO
Updated Old Town condo with pool & parking 5 min walk to Duval and Truman Park
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This gorgeous 2-bedroom, 2-bathroom unit offers a slice of Key West paradise within a gated property, ensuring security ...
From $628 per night (USD)
VRBO
From $315 per night (USD)
Expedia
Dog-friendly duplex with a furnished patio & fast WiFi - near beaches
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Tropical Treat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $315 per night (USD)
Expedia
From $2610 per night (USD)
VRBO
4 Traditional Two Queen, Pier House Resort, Island Elegance, Duval St. Access
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 $2610 per night (USD)
VRBO
From $1018 per night (USD)
VRBO
One Bedroom Suite Queens, Pier House, Roomy Elegance, Beachside Bliss, 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 $1018 per night (USD)
VRBO
From $704 per night (USD)
VRBO
Serene Resort Room with Private Beach & Spa - Perfect Key West Escape
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 $704 per night (USD)
VRBO
From $902 per night (USD)
VRBO
One Bedroom Suite King, Pier House, Spacious Comfort, Spa Access, Ocean Breeze
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 $902 per night (USD)
VRBO
From $1104 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 $1104 per night (USD)
VRBO
From $745 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 $745 per night (USD)
VRBO
From $1194 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 $1194 per night (USD)
VRBO
From $1018 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 $1018 per night (USD)
VRBO
From $704 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 $704 per night (USD)
VRBO
From $2322 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 $2322 per night (USD)
VRBO
From $3601 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 $3601 per night (USD)
VRBO
From $1545 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 $1545 per night (USD)
VRBO
From $1009 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 $1009 per night (USD)
VRBO
From $2382 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 $2382 per night (USD)
VRBO
From $881 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 $881 per night (USD)
VRBO
From $1250 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 $1250 per night (USD)
VRBO
From $2049 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 $2049 per night (USD)
VRBO
From $845 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 $845 per night (USD)
VRBO
From $769 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 $769 per night (USD)
VRBO
From $772 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 $772 per night (USD)
VRBO
From $1170 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 $1170 per night (USD)
VRBO
From $1024 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 $1024 per night (USD)
VRBO
From $975 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 $975 per night (USD)
VRBO
From $3169 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 $3169 per night (USD)
VRBO
From $3601 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 $3601 per night (USD)
VRBO
From $1063 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 $1063 per night (USD)
VRBO
From $1874 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 $1874 per night (USD)
VRBO
$Snowbird-friendly condo with heated pool, patio lounge, water view, yard, & W\/D$
From $522 per night (USD)
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 ...
From $522 per night (USD)
Expedia
$Historic Haven w\/ Unique Rooms, Afternoon Refreshers & Steps from Duval St$
From $801 per night (USD)
VRBO
Historic Haven w\/ Unique Rooms, Afternoon Refreshers & Steps from Duval St
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the charm of Old Town in our vibrant retreat, steps away from Duval's delights. Dive into history at Hemingway' ...
From $801 per night (USD)
VRBO
From $880 per night (USD)
VRBO
Celebrate History in Key West: Relaxing Bungalows with Resort-Like Amenities
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Discover the charm of Old Town in our vibrant retreat, steps away from Duval's delights. Dive into history at Hemingway' ...
From $880 per night (USD)
VRBO
From $529 per night (USD)
VRBO
Garden-Set Bungalows Featuring Poolside Bliss- Near Duval Street
Bedrooms:
1
Bathrooms:
1
Sleeps:
1
Discover the charm of Old Town in our vibrant retreat, steps away from Duval's delights. Dive into history at Hemingway' ...
From $529 per night (USD)
VRBO
From $832 per night (USD)
VRBO
Romantic Getaway: Sun-Drenched Bungalows near Duval Street
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the charm of Old Town in our vibrant retreat, steps away from Duval's delights. Dive into history at Hemingway' ...
From $832 per night (USD)
VRBO
From $465 per night (USD)
VRBO
Romantic Getaway with Plush Turkish Robes & Inviting Pools Near Duval Street
Bedrooms:
1
Bathrooms:
1
Sleeps:
1
Discover the charm of Old Town in our vibrant retreat, steps away from Duval's delights. Dive into history at Hemingway' ...
From $465 per night (USD)
VRBO
From $785 per night (USD)
VRBO
Key West Oasis: Retreat in Historical Bungalows with Pool Paradise
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Discover the charm of Old Town in our vibrant retreat, steps away from Duval's delights. Dive into history at Hemingway' ...
From $785 per night (USD)
VRBO
From $849 per night (USD)
VRBO
Tropical Escape: Artistic-Vibe Bungalows Steps from Duval Street
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the charm of Old Town in our vibrant retreat, steps away from Duval's delights. Dive into history at Hemingway' ...
From $849 per night (USD)
VRBO
From $914 per night (USD)
VRBO
Enchanting Hideaway Perfect for Couples Seeking Romantic Bliss
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the charm of Old Town in our vibrant retreat, steps away from Duval's delights. Dive into history at Hemingway' ...
From $914 per night (USD)
VRBO
From $799 per night (USD)
VRBO
Serene Bungalow in Key West: Poolside Refreshers & Relaxing Amenities
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the charm of Old Town in our vibrant retreat, steps away from Duval's delights. Dive into history at Hemingway' ...
From $799 per night (USD)
VRBO
From $823 per night (USD)
VRBO
Unwind in Paradise: Playful Historic Bungalows with Resort-Like Amenities
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the charm of Old Town in our vibrant retreat, steps away from Duval's delights. Dive into history at Hemingway' ...
From $823 per night (USD)
VRBO
From $1075 per night (USD)
VRBO
Coastal Bliss: Tranquil Bungalows with an Artistic Vibe in Vibrant Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Discover the charm of Old Town in our vibrant retreat, steps away from Duval's delights. Dive into history at Hemingway' ...
From $1075 per night (USD)
VRBO
From $796 per night (USD)
VRBO
Seaside Retreat: Inviting Bungalows with Turkish Robes and Pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the charm of Old Town in our vibrant retreat, steps away from Duval's delights. Dive into history at Hemingway' ...
From $796 per night (USD)
VRBO
From $956 per night (USD)
VRBO
Stunning Hideaway: Charming Bungalows near Ernest Hemingway Home
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the charm of Old Town in our vibrant retreat, steps away from Duval's delights. Dive into history at Hemingway' ...
From $956 per night (USD)
VRBO
From $810 per night (USD)
VRBO
Historic Inn: Romantic Stay in Key West's Hidden Gem - Pools & Patio
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the charm of Old Town in our vibrant retreat, steps away from Duval's delights. Dive into history at Hemingway' ...
From $810 per night (USD)
VRBO
From $218 per night (USD)
VRBO
Island Time in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Go back in “Island” Time, located in the historic Wilhelmina Harvey house, who was the "grand dame of Keys politics" as ...
From $218 per night (USD)
VRBO
From $922 per night (USD)
VRBO
Bohemian Key West Boutique Inn with Pool & Free Breakfast | Near Sunset Pier
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the heart of Old Town Key West! This hotel is located steps from Duval Street and Hemingway's home. Stroll to S ...
From $922 per night (USD)
VRBO
From $840 per night (USD)
VRBO
Palms and Pool Paradise
Bedrooms:
5
Bathrooms:
4
Sleeps:
10
Welcome to our luxurious Key West retreat in the heart of midtown! This spacious house boasts a private pool, soothing h ...
From $840 per night (USD)
VRBO
From $691 per night (USD)
VRBO
Escape to the Keys! Modern Pet-friendly Unit! EV Charger and Parking! Pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $691 per night (USD)
VRBO
From $524 per night (USD)
VRBO
Tropical Dream! Pool, Restaurant, Bar, Gym, Bike Rental, Parking!
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $524 per night (USD)
VRBO
From $829 per night (USD)
VRBO
Bohemian Retreat with Pool in Old Town Key West | Walk to Duval Street
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the heart of Old Town Key West! This hotel is located steps from Duval Street and Hemingway's home. Stroll to S ...
From $829 per night (USD)
VRBO
From $1100 per night (USD)
VRBO
Stylish and Modern 2BR Suite Near Old Town | Pool + Patio
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Discover the heart of Old Town Key West! This hotel is located steps from Duval Street and Hemingway's home. Stroll to S ...
From $1100 per night (USD)
VRBO
From $947 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 $947 per night (USD)
VRBO
From $1000 per night (USD)
VRBO
Escape to Key West: Stylish Boutique Hotel by Duval Street | Pool & Breakfast
Bedrooms:
1
Bathrooms:
2
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 $1000 per night (USD)
VRBO
$Southard Retreat- 2 bed 2 bath townhome downtown w\/ pool, parking$
From $212 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 $212 per night (USD)
Expedia
From $460 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 $460 per night (USD)
VRBO
$4 bed 2.5 bath home w\/ ocean views, private pool oasis on Gulfview$
From $579 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 $579 per night (USD)
Expedia

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