
Key West Rentals

- 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
- 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 PricingExpedia
- 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 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 $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 PricingExpedia
- 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 PricingVRBO
- 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
- 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 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 $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