
Key West Rentals

- From $656 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 $656 per night (USD)VRBO
- From $1615 per night (USD)
Expedia
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 $1615 per night (USD)Expedia
- From $650 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 $650 per night (USD)VRBO
- From $321 per night (USD)
Expedia
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 $321 per night (USD)Expedia
- Click For Pricing
VRBO
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 PricingVRBO
- From $353 per night (USD)
Expedia
**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 $353 per night (USD)Expedia
- From $312 per night (USD)
VRBO
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 $312 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 $981 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 $981 per night (USD)VRBO
- From $379 per night (USD)
Expedia
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 $379 per night (USD)Expedia
- From $632 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 $632 per night (USD)VRBO
- From $286 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 $286 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 $376 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 $376 per night (USD)Expedia
- From $396 per night (USD)
VRBO
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 $396 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 PricingExpedia
- 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 PricingVRBO
- From $356 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 $356 per night (USD)Expedia
- From $368 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 $368 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 PricingExpedia
- From $158 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 $158 per night (USD)VRBO
- From $339 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 $339 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 $361 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 $361 per night (USD)Expedia
- From $406 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 $406 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 $180 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 $180 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 $355 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 $355 per night (USD)VRBO
- From $607 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 $607 per night (USD)Expedia
- From $451 per night (USD)
VRBO
Gorgeous Bahama Village 4Bd 4Ba ensuite, parking, backyard oasis, perf locale!
- 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)VRBO
- From $904 per night (USD)
Expedia
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 $904 per night (USD)Expedia
- From $389 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 $389 per night (USD)VRBO
- From $625 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 $625 per night (USD)Expedia
- From $552 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 $552 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 $430 per night (USD)
VRBO
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 $430 per night (USD)VRBO
- From $657 per night (USD)
Expedia
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 $657 per night (USD)Expedia
- From $709 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 $709 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 PricingExpedia
- From $411 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 $411 per night (USD)VRBO
- From $203 per night (USD)
Expedia
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 $203 per night (USD)Expedia
- 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 $1043 per night (USD)
Expedia
**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 $1043 per night (USD)Expedia
- From $370 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 $370 per night (USD)VRBO
- From $515 per night (USD)
Expedia
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 $515 per night (USD)Expedia
- From $386 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 $386 per night (USD)VRBO
- From $465 per night (USD)
Expedia
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)Expedia
- From $774 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 $774 per night (USD)VRBO
- From $358 per night (USD)
Expedia
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 $358 per night (USD)Expedia
- From $455 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 $455 per night (USD)VRBO
- From $386 per night (USD)
Expedia
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 $386 per night (USD)Expedia
- From $394 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 $394 per night (USD)VRBO
- From $416 per night (USD)
Expedia
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 $416 per night (USD)Expedia
- From $643 per night (USD)
VRBO
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 $643 per night (USD)VRBO
- From $295 per night (USD)
Expedia
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)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 $389 per night (USD)
Expedia
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 $389 per night (USD)Expedia
- From $509 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 $509 per night (USD)VRBO
- From $198 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 $198 per night (USD)Expedia
- From $861 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 $861 per night (USD)VRBO
- From $184 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 $184 per night (USD)Expedia
- From $319 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 $319 per night (USD)VRBO
- From $256 per night (USD)
Expedia
Mariner's Oasis at Sunset Marina- 2bed 2 bath condo w/boat slip for rent
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
AGE REQUIREMENT: Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their ...
From $256 per night (USD)Expedia
- From $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 $438 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 $438 per night (USD)Expedia
- From $258 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 $258 per night (USD)VRBO
- From $398 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 $398 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 $190 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 $190 per night (USD)Expedia
- From $183 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 $183 per night (USD)VRBO
- From $180 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 $180 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 $227 per night (USD)
Expedia
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 $227 per night (USD)Expedia
- 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)
Expedia
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)Expedia
- From $316 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 $316 per night (USD)VRBO
- From $534 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 $534 per night (USD)Expedia
- From $462 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 $462 per night (USD)VRBO
- From $819 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 $819 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 $197 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 $197 per night (USD)Expedia
- From $281 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 $281 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 PricingExpedia
- 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 PricingVRBO
- From $327 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 $327 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 $229 per night (USD)
Expedia
Casa Tranquila - Fully-Renovated 2-bedroom Townhome in Old Town Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Casa Tranquila! This 2-bedroom townhome is perfect for your escape to Key West. Located in Old Town just five ...
From $229 per night (USD)Expedia
- From $264 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 $264 per night (USD)VRBO
- From $935 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 $935 per night (USD)Expedia
- From $294 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 $294 per night (USD)VRBO
- From $377 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 $377 per night (USD)Expedia
- From $447 per night (USD)
VRBO
Modern Lodge w/ Outdoor Pool Near Attractions Ideal for Family Fun
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Discover Old Town charm, plunge into vibrant Duval Street life, and dive deep into Key West's treasures. We're footsteps ...
From $447 per night (USD)VRBO
- From $903 per night (USD)
Expedia
2 Rooms for the whole family w/ Pool access! Near Duval St. and Museums
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Discover Old Town charm, plunge into vibrant Duval Street life, and dive deep into Key West's treasures. We're footsteps ...
From $903 per night (USD)Expedia
- From $740 per night (USD)
VRBO
2 Bedroom Suite w/ Outdoor Pool in Old Town Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Discover Old Town charm, plunge into vibrant Duval Street life, and dive deep into Key West's treasures. We're footsteps ...
From $740 per night (USD)VRBO
- From $403 per night (USD)
Expedia
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 $403 per night (USD)Expedia
- From $186 per night (USD)
VRBO
Charming 2-bedroom House in Historic Key West with Pool
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Embrace the Enchantment of Old Key West Charm! Escape to the enchanting world of Key West Hideaway, where history meets ...
From $186 per night (USD)VRBO
- From $1060 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 $1060 per night (USD)Expedia
- From $1066 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 $1066 per night (USD)VRBO
- From $411 per night (USD)
Expedia
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 $411 per night (USD)Expedia