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From $360 per night (USD)
VRBO
Pool & Parking, & Pet Friendly - Hidden Oasis
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Hidden Oasis is a 28-night minimum rental, offering contemporary luxury in the heart of Midtown, Key West. It’s ...
From $360 per night (USD)
VRBO
From $291 per night (USD)
VRBO
Old Town Key West Live like a local
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Live like a local! This vacation flat is located at Mile marker 1, and sits nestled above the street right on Truman Av ...
From $291 per night (USD)
VRBO
$**ISLAND BLISS @ CASA MARINA** Spacious Home \/ Pool + LAST KEY SERVICES...$
From $374 per night (USD)
VRBO
**ISLAND BLISS @ CASA MARINA** Spacious Home \/ Pool + LAST KEY SERVICES...
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! ISLAND BLISS ...
From $374 per night (USD)
VRBO
From $465 per night (USD)
Expedia
Charming, updated home near Duval St. with enclosed patio & walkable location
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
The Coral Cove Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $465 per night (USD)
Expedia
From $339 per night (USD)
VRBO
THE GOOD LIFE ~ Charming 2nd Floor 1 Bedroom, 1 Bath Truman Annex Condo!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
COZY VALUE IN TRUMAN ANNEX… This 2nd Floor one bedroom, one bath condo is located in The Shipyard, a neighborhood of the ...
From $339 per night (USD)
VRBO
From $233 per night (USD)
Expedia
2 Bedroom Townhome on Key West Golf Club
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Escape to paradise with this spacious 2-bedroom townhome in Key West. Ideal for families and couples alike, this propert ...
From $233 per night (USD)
Expedia
$Experience Key West w\/ Poolside Bar, Private Terraces & Free Shuttle Service!$
From $807 per night (USD)
VRBO
Experience Key West w\/ Poolside Bar, Private Terraces & Free Shuttle Service!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Indulge in an island escape at this tropical haven. Wake up to Gulf of Mexico views, savoring breakfast on your private ...
From $807 per night (USD)
VRBO
From $1225 per night (USD)
VRBO
Ideal Family Stay in Great Location, 4 Pools, Shuttle Service, Near Airport!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Indulge in an island escape at this tropical haven. Wake up to Gulf of Mexico views, savoring breakfast on your private ...
From $1225 per night (USD)
VRBO
From $549 per night (USD)
VRBO
Beautiful Water Views! Minutes to Southernmost Point! Parking, Onsite Pools!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Indulge in an island escape at this tropical haven. Wake up to Gulf of Mexico views, savoring breakfast on your private ...
From $549 per night (USD)
VRBO
From $197 per night (USD)
Expedia
CASA DE CANAL ~ 3 BR, 2 Ba. Canal Front Home!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
KEY WEST BOATER'S BONANZA... This waterfront gem is a dream for boating and fishing enthusiasts. Indulge in all your nau ...
From $197 per night (USD)
Expedia
Click For Pricing
VRBO
Ocean view apartment on coconut resort
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Coconut Beach Resort once belonged to the late Senator John Spottswood. He originally purchased the property because of ...
Click For Pricing
VRBO
$Coconut Cottage | Colorful abode with a full kitchen, enclosed patio, AC, & W\/D$
From $297 per night (USD)
Expedia
Coconut Cottage | Colorful abode with a full kitchen, enclosed patio, AC, & W\/D
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Coconut Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $297 per night (USD)
Expedia
From $190 per night (USD)
VRBO
Charming + Circa 1889 Historic Eyebrow Home
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
28 Night Minimum. Welcome to "The Saltbox"! Featured in design magazines. 710 Ashe Street is a charming house circa 18 ...
From $190 per night (USD)
VRBO
$**MODERN MAJESTY @ THE ANNEX** Oceanside 3BR\/3.5BA Condo & Pool + LAST KEY SERVI$
From $505 per night (USD)
Expedia
**MODERN MAJESTY @ THE ANNEX** Oceanside 3BR\/3.5BA Condo & Pool + LAST KEY SERVI
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! MODERN MAJEST ...
From $505 per night (USD)
Expedia
$The Elizabeth Suite | 1 bed, 1 bath w\/shared pool$
From $398 per night (USD)
VRBO
The Elizabeth Suite | 1 bed, 1 bath w\/shared pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
We are pleased to introduce The Elizabeth Suite at The Bayview House, a nightly rental with shared pool. One of 4 units ...
From $398 per night (USD)
VRBO
$The Fleming Suite | 1 bed, 1 bath condo w\/shared pool$
From $398 per night (USD)
Expedia
The Fleming Suite | 1 bed, 1 bath condo w\/shared pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
We are pleased to introduce The Fleming Suite at The Bayview House, a 1-bedroom, 1-bathroom nightly rental with a shared ...
From $398 per night (USD)
Expedia
Click For Pricing
VRBO
New Listing-Golf Course Charmer!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
As you make your way into The Sweet Tee, an immediate sense of relaxation and vacation mode envelops you. The carefully ...
Click For Pricing
VRBO
Click For Pricing
Expedia
Southern Skies, Stylish Home in Old Town Key West
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
About this space Experience the paradise of Southern Skies, an elegant 3 bedroom and 2.5 bath home nestled in the heart ...
Click For Pricing
Expedia
From $401 per night (USD)
VRBO
The Speakeasy Inn - Room 1A (1 Queen Bed & 1 Single Bed)
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 $401 per night (USD)
VRBO
From $436 per night (USD)
Expedia
Room 2 (1 Queen Bed & Single 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 $436 per night (USD)
Expedia
$McCartney's Manor - Deluxe K Suite W\/Pvt. Spa!$
From $532 per night (USD)
VRBO
McCartney's Manor - Deluxe K Suite W\/Pvt. Spa!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Cool pastel, Caribbean inspired decor with original art throughout by Robin Hix. Bose speaker, Alexa Echo, full kitche ...
From $532 per night (USD)
VRBO
From $401 per night (USD)
Expedia
Speakeasy Inn -Room 1B-1 Queen Bed
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
The Speakeasy Inn is a quaint guesthouse located in an historic Key West conch style house. It is situated on upper Duva ...
From $401 per night (USD)
Expedia
$Starr's Suite - 2 person K Suite w\/Private Spa!$
From $508 per night (USD)
VRBO
Starr's Suite - 2 person K Suite w\/Private Spa!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Starr's Suite features a King Pillow-Top Memory Foam mattress. Renovated in 2010, it features a tumbled marble shower, ...
From $508 per night (USD)
VRBO
$**KESTRAL KOVE @ THE GOLF CLUB** Townhome w\/ Community Pool + LAST KEY SERVICES…$
From $253 per night (USD)
Expedia
**KESTRAL KOVE @ THE GOLF CLUB** Townhome w\/ Community Pool + LAST KEY SERVICES…
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Dreaming of va ...
From $253 per night (USD)
Expedia
$Breezy Key West First-Floor Condo w\/ Pool Access$
From $152 per night (USD)
VRBO
Breezy Key West First-Floor Condo w\/ Pool Access
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Experience your next seaside vacation in style at this 2-bedroom, 2-bathroom Key West vacation rental. This 1st-floor co ...
From $152 per night (USD)
VRBO
From $411 per night (USD)
Expedia
**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 $411 per night (USD)
Expedia
From $767 per night (USD)
VRBO
Key West Andros 2BR•Waterfront, Pool, Dock&Pet OK
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Time to fish & relax! Bring your family & friends to this 1350 sqft waterfront corner condo home. Boat slip a ...
From $767 per night (USD)
VRBO
$OASIS SOUTH~Stunning 5 BR\/3 Ba w\/ Pool!$
From $387 per night (USD)
Expedia
OASIS SOUTH~Stunning 5 BR\/3 Ba w\/ Pool!
Bedrooms:
3
Bathrooms:
7
Sleeps:
14
BRING THE WHOLE GANG... If you and your large band of loved ones are looking for the perfect gathering in southernmost ...
From $387 per night (USD)
Expedia
$BE AS YOU ARE - 3 Bedroom \/ 3 Bathroom - Mid Town KEY WEST w\/ POOL$
From $607 per night (USD)
VRBO
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 $607 per night (USD)
VRBO
$SWEET LIKE SUMMERTIME ~ 3 BR\/2Ba Home w\/ Pool and Yard!$
From $484 per night (USD)
Expedia
SWEET LIKE SUMMERTIME ~ 3 BR\/2Ba Home w\/ Pool and Yard!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
CLASSIC CHARMER... Welcome to this beautifully renovated 3 bedroom 2 bath pool home, located in Bahama Village. This cla ...
From $484 per night (USD)
Expedia
From $1279 per night (USD)
VRBO
Waterfront Sunset Harbor Resort Near Old Town+Amenities: 2BR FindingMeili
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to FindingMeili🌴 Experience Paradise at Hyatt Vacation Club at Sunset Harbor! An Additional Savings from $500 ...
From $1279 per night (USD)
VRBO
From $227 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 $227 per night (USD)
Expedia
From $362 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 $362 per night (USD)
VRBO
From $405 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 $405 per night (USD)
Expedia
From $461 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 $461 per night (USD)
VRBO
From $219 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 $219 per night (USD)
Expedia
From $213 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 $213 per night (USD)
VRBO
From $431 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 $431 per night (USD)
Expedia
From $499 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 $499 per night (USD)
VRBO
$THE NEST ~ Charming Conch Cottage Close to the Beach and Duval w\/ Pool!$
From $310 per night (USD)
Expedia
THE NEST ~ Charming Conch Cottage Close to the Beach and Duval w\/ Pool!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
HIDDEN GEM... The perfect location for guests who want to walk and bike to everything Key West has to offer. Modern cot ...
From $310 per night (USD)
Expedia
From $520 per night (USD)
VRBO
POCKETFUL OF SUNSHINE ~ 5 BR Near Beach and Prime Fireworks Watching!
Bedrooms:
6
Bathrooms:
5
Sleeps:
10
EXQUISITE MODERN FAMILY COMPOUND... If a large home with all the modern luxuries is a must for your next island getaway, ...
From $520 per night (USD)
VRBO
From $451 per night (USD)
Expedia
Gorgeous Bahama Village 4Bd 4Ba ensuite, parking, backyard oasis, perf locale!
Bedrooms:
5
Bathrooms:
4
Sleeps:
10
Welcome to Moveable Feast, a dreamy home in the heart of Bahama Village that sleeps 10 comfortably. Located on a quiet, ...
From $451 per night (USD)
Expedia
From $962 per night (USD)
VRBO
Rooftop Penthouse, Walk to Duval - KAMP
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 $962 per night (USD)
VRBO
$Romantic Retreat - 2 person K Suite, Pvt deck\/Spa!$
From $545 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 $545 per night (USD)
VRBO
From $717 per night (USD)
VRBO
Key West Lighthouse Suite
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The Key West Lighthouse Suite offers a cozy queen bungalow home with a unique queen loft and sleeps up to 4 guests, comp ...
From $717 per night (USD)
VRBO
From $982 per night (USD)
Expedia
American Shoal Light Suite
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
The American Shoal Lighthouse Suite offers separate King and Queen bedrooms and was completely refurbished in 2024 that ...
From $982 per night (USD)
Expedia
From $713 per night (USD)
VRBO
Tortugas Harbor Light Suite
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
The Tortugas Harbor Lighthouse Suite offers a luxury king bedroom that can accommodate up to 4 guests and was completely ...
From $713 per night (USD)
VRBO
From $717 per night (USD)
Expedia
Sombrero Reef Light Suite
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
The Sombrero Reef Lighthouse Suite offers a luxury king bedroom that can accommodate up to 4 guests and was completely r ...
From $717 per night (USD)
Expedia
From $974 per night (USD)
VRBO
Alligator Reef Light Suite
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
The Alligator Reef Lighthouse Suite offers separate King and Queen bedrooms and was completely refurbished in 2024, slee ...
From $974 per night (USD)
VRBO
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
From $1361 per night (USD)
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 ...
From $1361 per night (USD)
VRBO
Click For Pricing
Expedia
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
Expedia
$Escape to \Casa Escondida\$
From $439 per night (USD)
VRBO
Escape to \"Casa Escondida\"
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Escape to the enchanting "Casa Escondida," a historic Conch Style home with a modern twist, nestled on a tranquil, seclu ...
From $439 per night (USD)
VRBO
From $452 per night (USD)
Expedia
Private Pool & Parking - Atlantic Oasis
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 $452 per night (USD)
Expedia
From $593 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 $593 per night (USD)
VRBO
From $2140 per night (USD)
VRBO
Key West, Galleon Resort, Marina, In Town, Pool, Hot Tub
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to The Galleon Resort in Key West, where paradise meets luxury at the southernmost tip of the United States. In ...
From $2140 per night (USD)
VRBO
From $1189 per night (USD)
VRBO
Sunset Harbor Resort & Spa, In Town, Marina, Hot Tub.
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Discover this relaxing oasis in the heart of Key West's famed Old Town. Lush, verdant foliage surrounds the grounds and ...
From $1189 per night (USD)
VRBO
From $1664 per night (USD)
VRBO
Sunset Harbor Resort & Spa, Hot Tub, Pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Discover this relaxing oasis in the heart of Key West's famed Old Town. Lush, verdant foliage surrounds the grounds and ...
From $1664 per night (USD)
VRBO
From $397 per night (USD)
VRBO
Last Mango Beach Retreat
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Experience the allure of La Brisa Penthouse! Step into this captivating two-bedroom, two-bathroom condo nestled within t ...
From $397 per night (USD)
VRBO
From $610 per night (USD)
VRBO
Beach Club #112 - Unique Oceanfront living
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Unique oceanfront living only 65 feet from the Atlantic! The Key West Beach Club is a quiet, peaceful residential build ...
From $610 per night (USD)
VRBO
From $201 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 $201 per night (USD)
VRBO
From $1596 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 $1596 per night (USD)
VRBO
$Spacious Key West Room w\/ Balcony | Outdoor Pools | Seaport Proximity$
From $600 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 $600 per night (USD)
VRBO
$Family Old Town Key Getaway | Four Rooms w\/ Balcony & Outdoor Pools$
From $1939 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 $1939 per night (USD)
VRBO
$Vibrant Key West Stay w\/ Outdoor Pools | Four Rooms w\/ Balcony$
From $2124 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 $2124 per night (USD)
VRBO
$Two Relaxing Rooms w\/ Balcony | Waterfront Resort w\/ Access to Outdoor Pools$
From $1071 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 $1071 per night (USD)
VRBO
$2 BR Spacious Suite w\/ Living Area and Balcony | Outdoor Pools$
From $3121 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 $3121 per night (USD)
VRBO
From $1717 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 $1717 per night (USD)
VRBO
$Seaport Proximity | Resort w\/ Outdoor Pools | Spacious Key West Room w\/ Balcony$
From $636 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 $636 per night (USD)
VRBO
$Spacious 2 BR Suite w\/ Living Area and Balcony | Onsite Parking Available$
From $2475 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 $2475 per night (USD)
VRBO
$Two Bedrooms Family Suite with Balcony | Idyllic Resort w\/ Outdoor Pools$
From $3121 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 $3121 per night (USD)
VRBO
$Waterfront Getaway | 2 Spacious Family Rooms w\/ Balcony | Old Town Best$
From $1144 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 $1144 per night (USD)
VRBO
From $286 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 $286 per night (USD)
VRBO
From $1393 per night (USD)
Expedia
**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 $1393 per night (USD)
Expedia
From $422 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 $422 per night (USD)
VRBO
From $679 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 $679 per night (USD)
VRBO
$Escape to \Oasis on 18th\ w\/ PRIVATE HEATED Pool in the KW Golf Club Sanctuary!$
From $354 per night (USD)
VRBO
Escape to \"Oasis on 18th\" w\/ PRIVATE HEATED Pool in the KW Golf Club Sanctuary!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Escape to your own private paradise at "Oasis on 18th," a luxurious three-bedroom, three-bathroom haven nestled within t ...
From $354 per night (USD)
VRBO
$Quaint Bungalow w\/ Private Outdoor Space Near Duval Street | Free Breakfast$
From $453 per night (USD)
VRBO
Quaint Bungalow w\/ Private Outdoor Space Near Duval Street | Free Breakfast
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $453 per night (USD)
VRBO
From $573 per night (USD)
VRBO
Celebrate History in Key West: Tropical Bungalow Retreat Ideal for Relaxation
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $573 per night (USD)
VRBO
From $529 per night (USD)
VRBO
Spacious Bungalow with Patio | Near Ernest Hemingway Home – 7 Min Walk
Bedrooms:
1
Bathrooms:
1
Sleeps:
1
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $529 per night (USD)
VRBO
From $513 per night (USD)
VRBO
Serene Bungalow with Outdoor Pool Access | Near Historic Ernest Hemingway Museum
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $513 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 Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $465 per night (USD)
VRBO
From $714 per night (USD)
VRBO
Key West Oasis: Retreat in Historical Bungalows with Pool Paradise
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $714 per night (USD)
VRBO
From $673 per night (USD)
VRBO
Tropical Escape: Artistic-Vibe Bungalows with Balcony | Welcome Drinks Included
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $673 per night (USD)
VRBO
From $597 per night (USD)
VRBO
Enchanting Hideaway Perfect for Couples Seeking Romantic Bliss
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $597 per night (USD)
VRBO
From $457 per night (USD)
VRBO
Serene Bungalow in Key West: Poolside Refreshers & Relaxing Amenities
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $457 per night (USD)
VRBO
From $621 per night (USD)
VRBO
Couples' Retreat: Romantic Unit with Patio | Delicious Breakfast Included
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $621 per night (USD)
VRBO
$Tranquil Bungalow w\/ an Artistic Vibe in Vibrant Key West | Breakfast Included$
From $695 per night (USD)
VRBO
Tranquil Bungalow w\/ an Artistic Vibe in Vibrant Key West | Breakfast Included
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $695 per night (USD)
VRBO
$Stylish Room in the Heart of Old Town w\/ Access to Outdoor Pool | Free Breakfast$
From $463 per night (USD)
VRBO
Stylish Room in the Heart of Old Town w\/ Access to Outdoor Pool | Free Breakfast
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $463 per night (USD)
VRBO
From $543 per night (USD)
VRBO
Historical Charm in a Room Surrounded by Key West's Best: Complimentary Breakfas
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $543 per night (USD)
VRBO
From $635 per night (USD)
VRBO
Historic Inn: Romantic Couple Stay in Key West's Hidden Gem - Pools & Patio
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $635 per night (USD)
VRBO
From $458 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 $458 per night (USD)
VRBO
From $660 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 $660 per night (USD)
VRBO
From $370 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 $370 per night (USD)
VRBO
From $306 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 $306 per night (USD)
VRBO
$Seaside Serenity-2BD 2BA condo w\/ pool, parking, tennis courts, near beaches$
From $196 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 $196 per night (USD)
Expedia
From $1674 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 $1674 per night (USD)
VRBO
From $594 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 $594 per night (USD)
VRBO
From $486 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 $486 per night (USD)
VRBO
From $610 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 $610 per night (USD)
VRBO

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