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$Old Town \Eleuthera\ • 2BR Waterfront Corner Condo$
From $717 per night (USD)
VRBO
Old Town \"Eleuthera\" • 2BR Waterfront Corner Condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Bring friends and family to this updated 1,350 sqft waterfront corner condo in historic downtown Key West! Just ...
From $717 per night (USD)
VRBO
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Expedia
Hyatt Residence Club Windward Pointe Key West 2br/2ba/6ppl
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Fantastic location!!! Sunday to Sunday 7 night rental at HYATT Windward Pointe. Sleeps 6 people. 2 bedrooms (1King/1Quee ...
Click For Pricing
Expedia
From $345 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 $345 per night (USD)
VRBO
From $306 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 $306 per night (USD)
Expedia
From $328 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 $328 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
From $991 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 $991 per night (USD)
VRBO
From $414 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 $414 per night (USD)
VRBO
From $602 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 $602 per night (USD)
VRBO
From $285 per night (USD)
Expedia
Coconut Cottage | Colorful abode with a full kitchen, enclosed patio, AC, & W/D
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Coconut Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $285 per night (USD)
Expedia
From $475 per night (USD)
VRBO
**MODERN MAJESTY @ THE ANNEX** Oceanside 3BR/3.5BA Condo & Pool + LAST KEY SERVI
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! MODERN MAJEST ...
From $475 per night (USD)
VRBO
From $394 per night (USD)
Expedia
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 $394 per night (USD)
Expedia
From $371 per night (USD)
VRBO
The Fleming Suite | 1 bed, 1 bath condo w/shared pool, monthly rental
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 $371 per night (USD)
VRBO
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Expedia
New Listing-Golf Course Charmer!
Bedrooms:
1
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 ...
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Expedia
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VRBO
Southern Skies, Stylish Home in Old Town Key West
Bedrooms:
2
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 ...
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VRBO
From $346 per night (USD)
Expedia
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 $346 per night (USD)
Expedia
From $359 per night (USD)
VRBO
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 $359 per night (USD)
VRBO
From $338 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 $338 per night (USD)
Expedia
From $357 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 $357 per night (USD)
VRBO
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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 ...
Click For Pricing
Expedia
From $155 per night (USD)
VRBO
Breezy Key West First-Floor Condo w/ Pool Access
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Experience your next seaside vacation in style at this 2-bedroom, 2-bathroom Key West vacation rental. This 1st-floor co ...
From $155 per night (USD)
VRBO
From $364 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 $364 per night (USD)
Expedia
From $227 per night (USD)
VRBO
Poolside tropical paradise in Key West! The Salty Conch
Bedrooms:
1
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)
VRBO
From $357 per night (USD)
Expedia
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 $357 per night (USD)
Expedia
From $437 per night (USD)
VRBO
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 $437 per night (USD)
VRBO
From $398 per night (USD)
Expedia
Midnight Cowboy by AvantStay | 3 Artistic Spaces
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
★ Recognized as one of our best. This home was a finalist in the 2025 AvantStay Awards, our annual celebration of top-ti ...
From $398 per night (USD)
Expedia
From $177 per night (USD)
VRBO
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 $177 per night (USD)
VRBO
From $207 per night (USD)
Expedia
Tennessee Williams by AvantStay | Funky Design + Pool
Bedrooms:
2
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 $207 per night (USD)
Expedia
From $359 per night (USD)
VRBO
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 $359 per night (USD)
VRBO
From $350 per night (USD)
Expedia
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 $350 per night (USD)
Expedia
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
From $451 per night (USD)
Expedia
Gorgeous Bahama Village 4Bd 4Ba all ensuite, 2x parking, pets, ideal location!
Bedrooms:
4
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 $830 per night (USD)
VRBO
Rooftop Penthouse, Walk to Duval - KAMP
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Stay in this one-of-a-kind penthouse and Jimmy Buffet's former Margaritaville Headquarters as well as David "Mr ...
From $830 per night (USD)
VRBO
From $633 per night (USD)
Expedia
Key West Lighthouse Suite
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Escape the Ordinary... The Key West Lighthouse Suite offers a cozy queen bungalow home with a unique queen loft and sle ...
From $633 per night (USD)
Expedia
From $575 per night (USD)
VRBO
American Shoal Light Suite
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Escape the Ordinary.... The American Shoal Lighthouse Suite offers separate King and Queen bedrooms and was completely ...
From $575 per night (USD)
VRBO
From $527 per night (USD)
Expedia
Tortugas Harbor Light Suite
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Escape the Ordinary... The Tortugas Harbor Lighthouse Suite offers a luxury king bedroom that can accommodate up to 4 g ...
From $527 per night (USD)
Expedia
From $367 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 $367 per night (USD)
VRBO
From $456 per night (USD)
Expedia
Sombrero Reef Light Suite
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Escape the Ordinary... The Sombrero Reef Lighthouse Suite offers a luxury king bedroom that can accommodate up to 4 gue ...
From $456 per night (USD)
Expedia
From $633 per night (USD)
VRBO
Alligator Reef Light Suite
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Escape the Ordinary... The Alligator Reef Lighthouse Suite offers separate King and Queen bedrooms and was completely r ...
From $633 per night (USD)
VRBO
From $879 per night (USD)
Expedia
~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 $879 per night (USD)
Expedia
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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 ...
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VRBO
From $485 per night (USD)
Expedia
**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 $485 per night (USD)
Expedia
From $202 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 $202 per night (USD)
VRBO
From $297 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 $297 per night (USD)
Expedia
From $1226 per night (USD)
VRBO
**GARDEN OF EMMA @ THE ANNEX** Private Home & Pool + LAST KEY SERVICES…
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Tranquility. ...
From $1226 per night (USD)
VRBO
From $378 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 $378 per night (USD)
VRBO
From $561 per night (USD)
VRBO
Celebrate History in Key West: Tropical Free Breakfast and Pool Access!
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 $561 per night (USD)
VRBO
From $426 per night (USD)
VRBO
Serene Bungalow with Outdoor Pool Access | Free Breakfast Onsite!
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 $426 per night (USD)
VRBO
From $465 per night (USD)
VRBO
Romantic Getaway with Plush Turkish Robes & Inviting Pools! Free Breakfast
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 $768 per night (USD)
VRBO
Key West Oasis: Retreat in Historical Bungalows with Pool, Free Breakfast!
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 $768 per night (USD)
VRBO
From $366 per night (USD)
VRBO
Serene Bungalow in Key West: Poolside Refreshers & 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 $366 per night (USD)
VRBO
From $800 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 $800 per night (USD)
VRBO
From $415 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 $415 per night (USD)
VRBO
From $464 per night (USD)
VRBO
Historical Charm in a Room Surrounded by Key West's Best: 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 $464 per night (USD)
VRBO
From $478 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 $478 per night (USD)
VRBO
From $658 per night (USD)
Expedia
Palms and Pool Paradise
Bedrooms:
4
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 $658 per night (USD)
Expedia
From $295 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 $295 per night (USD)
VRBO
$Hemmingways Paradise \nJust a short stroll to all Key West has to offer.$
From $499 per night (USD)
Expedia
Hemmingways Paradise \nJust a short stroll to all Key West has to offer.
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
You will fall in love with this beautifully renovated old town historic home. Located on one of old towns coveted quiet ...
From $499 per night (USD)
Expedia
From $249 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 $249 per night (USD)
VRBO
From $244 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 $244 per night (USD)
Expedia
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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 ...
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VRBO
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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 ...
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VRBO
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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 ...
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VRBO
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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 ...
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VRBO
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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 ...
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VRBO
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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 ...
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VRBO
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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 ...
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VRBO
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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 ...
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VRBO
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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 ...
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VRBO
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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 ...
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VRBO
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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 ...
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VRBO
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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 ...
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VRBO
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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 ...
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VRBO
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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 ...
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VRBO
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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 ...
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VRBO
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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 ...
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VRBO
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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 ...
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VRBO
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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 ...
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VRBO
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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 ...
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VRBO
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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 ...
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VRBO
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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 ...
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VRBO
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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 ...
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VRBO
Click For Pricing
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 ...
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VRBO
Click For Pricing
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 ...
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VRBO
Click For Pricing
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 ...
Click For Pricing
VRBO
From $1128 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 $1128 per night (USD)
VRBO
Click For Pricing
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 ...
Click For Pricing
VRBO
From $456 per night (USD)
VRBO
Bohemian Retreat with Pool in Old Town Key West | Free Breakfast Onsite!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the heart of Old Town Key West! This hotel is located steps from Duval Street and Hemingway's home. Stroll to S ...
From $456 per night (USD)
VRBO
From $575 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 $575 per night (USD)
VRBO
From $188 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 $188 per night (USD)
Expedia
From $354 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 $354 per night (USD)
VRBO
From $261 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 $261 per night (USD)
Expedia
From $298 per night (USD)
VRBO
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 $298 per night (USD)
VRBO
From $505 per night (USD)
Expedia
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 $505 per night (USD)
Expedia
From $254 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 $254 per night (USD)
VRBO
From $392 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 $392 per night (USD)
Expedia
From $1114 per night (USD)
VRBO
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 $1114 per night (USD)
VRBO
From $209 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 $209 per night (USD)
Expedia
From $197 per night (USD)
VRBO
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 $197 per night (USD)
VRBO
From $196 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 $196 per night (USD)
Expedia

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