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$Downtown Key West 2BR/2BA•Pool, Dock, Pet \Aruba\$
From $535 per night (USD)
VRBO
Downtown Key West 2BR/2BA•Pool, Dock, Pet \"Aruba\"
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Enjoy true space in Key West! This 1,200 sq ft waterfront condo offers a full kitchen, dining area, living room ...
From $535 per night (USD)
VRBO
From $1717 per night (USD)
VRBO
St. Johns Waterfront 4BR Penthouse•Pool•Dock•Park
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
Summary: Bring the whole crew to this 2200 sqft waterfront penthouse—perfect for families & large groups! With 4 bedroom ...
From $1717 per night (USD)
VRBO
$Old Town \Eleuthera\ • 2BR Waterfront Corner Condo$
From $511 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 $511 per night (USD)
VRBO
Click For Pricing
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 $349 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 $349 per night (USD)
VRBO
From $301 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 $301 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 $982 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 $982 per night (USD)
VRBO
From $408 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 $408 per night (USD)
VRBO
From $607 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 $607 per night (USD)
VRBO
From $282 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 $282 per night (USD)
Expedia
From $476 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 $476 per night (USD)
VRBO
From $386 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 $386 per night (USD)
Expedia
From $363 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 $363 per night (USD)
VRBO
Click For Pricing
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 ...
Click For Pricing
Expedia
Click For Pricing
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 ...
Click For Pricing
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 $344 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 $344 per night (USD)
VRBO
From $332 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 $332 per night (USD)
Expedia
From $352 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 $352 per night (USD)
VRBO
Click For Pricing
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 $351 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 $351 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 $416 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 $416 per night (USD)
VRBO
From $398 per night (USD)
Expedia
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 $398 per night (USD)
Expedia
From $178 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 $178 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 $809 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 $809 per night (USD)
VRBO
From $648 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 $648 per night (USD)
Expedia
From $840 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 $840 per night (USD)
VRBO
From $525 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 $525 per night (USD)
Expedia
From $377 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 $377 per night (USD)
VRBO
From $510 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 $510 per night (USD)
Expedia
From $840 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 $840 per night (USD)
VRBO
From $861 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 $861 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 $459 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 $459 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 $289 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 $289 per night (USD)
Expedia
From $1187 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 $1187 per night (USD)
VRBO
From $357 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 $357 per night (USD)
VRBO
From $531 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 $531 per night (USD)
VRBO
From $396 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 $396 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 $776 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 $776 per night (USD)
VRBO
From $339 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 $339 per night (USD)
VRBO
From $585 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 $585 per night (USD)
VRBO
From $388 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 $388 per night (USD)
VRBO
From $381 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 $381 per night (USD)
VRBO
From $409 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 $409 per night (USD)
VRBO
From $669 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 $669 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 $361 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 $361 per night (USD)
VRBO
From $493 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 $493 per night (USD)
VRBO
From $206 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 $206 per night (USD)
Expedia
From $818 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 $818 per night (USD)
VRBO
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 $188 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 $188 per night (USD)
VRBO
From $260 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 $260 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 $485 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 $485 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 $200 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 $200 per night (USD)
Expedia
From $193 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 $193 per night (USD)
VRBO
From $189 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 $189 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
From $255 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 $255 per night (USD)
VRBO
From $255 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 $255 per night (USD)
VRBO
From $319 per night (USD)
VRBO
Balcony on Duval - The Green Pineapple
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Beautiful 3-bedroom, 2-bath monthly rental located on Key West's famous Duval Street. Guests enjoy easy access ...
From $319 per night (USD)
VRBO
From $678 per night (USD)
Expedia
Pool, Pet Friendly, & Near Duval - Coastal Rose
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Experience the charm of downtown Key West in this cozy 1-bedroom unit with an additional loft and a shared pool ...
From $678 per night (USD)
Expedia
From $491 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 $491 per night (USD)
VRBO
From $967 per night (USD)
Expedia
Pet Friendly, & Near Duval - Rose Key Cottage
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Escape to paradise with this luxurious Key West retreat, perfect for families and groups looking to unwind in s ...
From $967 per night (USD)
Expedia
From $301 per night (USD)
VRBO
An Island Siesta: 2 BR, 2 BA Townhouse in Key West, Sleeps 6
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This lovely, fully furnished, townhouse has two bedrooms that sleeps up to 6 and two full baths . The spacious upstairs ...
From $301 per night (USD)
VRBO
From $199 per night (USD)
Expedia
Tropical cottage with private pool, two blocks from Duval - near Hemingway House
Bedrooms:
2
Bathrooms:
1
Sleeps:
5
The Conch-Out Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $199 per night (USD)
Expedia
From $396 per night (USD)
VRBO
Boomerang Boathouse in Key West
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Richley individual yet classic Key West are phrases that echo from Boomerang Boathouse, a 4 bedroom, 2.5 bath home with ...
From $396 per night (USD)
VRBO
Click For Pricing
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 ...
Click For Pricing
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
From $325 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 $325 per night (USD)
Expedia
From $364 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 $364 per night (USD)
VRBO
From $244 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 $244 per night (USD)
Expedia
From $534 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 $534 per night (USD)
VRBO
From $566 per night (USD)
Expedia
Atlantis House's Palm Suite-voted top 25 in USA
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The Palm Suite is a stunning vacation rental property located in the heart of Key West. This luxurious suite is situated ...
From $566 per night (USD)
Expedia
From $343 per night (USD)
VRBO
HERE COMES THE SUN ~ 2 BR, 2 Ba Casa Marina Home with Pool!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CLASSIC CHARMER... Some of the best things come in small packages and this conch cutie is no exception. Nestled in the e ...
From $343 per night (USD)
VRBO
From $941 per night (USD)
Expedia
An Ocean Serenity in Truman Annex, Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
A luxury, ocean front, 2 bedroom, (king in master, queen in guest bedroom) 2.5 bath condo at Harbour Place in the award ...
From $941 per night (USD)
Expedia
From $465 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 $465 per night (USD)
VRBO
From $915 per night (USD)
Expedia
The Lighthouse Penthouse Suite
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Escape the Ordinary... The Lighthouse Penthouse Suite is a combination of two 1 BD/ 1 BA Suites delivering two luxury k ...
From $915 per night (USD)
Expedia
From $1204 per night (USD)
VRBO
The Lighthouse Group Suite
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
Escape the Ordinary... The Lighthouse Group Suite is a combination of two 2 BD/ 1 BA Suites delivering two luxury king ...
From $1204 per night (USD)
VRBO
From $456 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 $456 per night (USD)
VRBO

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