We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Key West Vacation Rentals

Destination
Revenue impacts this sort order. Learn more

Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 mi
633 rentals in Key West.
The Local's favorite spot., vacation rental in Key West
The Local's favorite spot., vacation rental in Key West
The Local's favorite spot., vacation rental in Key West

The Local's favorite spot.

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Pure Bliss, vacation rental in Key West
Pure Bliss, vacation rental in Key West
Pure Bliss, vacation rental in Key West

Pure Bliss

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Charming 'Boho Breeze' Retreat w/ Pool Access, vacation rental in Key West
Charming 'Boho Breeze' Retreat w/ Pool Access, vacation rental in Key West
Charming 'Boho Breeze' Retreat w/ Pool Access, vacation rental in Key West

Charming 'Boho Breeze' Retreat w/ Pool Access

Rental Home
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Atlantis House's Palm Suite-voted top 25 in USA, vacation rental in Key West
Atlantis House's Palm Suite-voted top 25 in USA, vacation rental in Key West
Atlantis House's Palm Suite-voted top 25 in USA, vacation rental in Key West

Atlantis House's Palm Suite-voted top 25 in USA

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Crystal blue seas, Island Breezes, Morning Sunrises & Key West Island days., vacation rental in Key West
Crystal blue seas, Island Breezes, Morning Sunrises & Key West Island days., vacation rental in Key West
Crystal blue seas, Island Breezes, Morning Sunrises & Key West Island days., vacation rental in Key West

Crystal blue seas, Island Breezes, Morning Sunrises & Key West Island days.

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Ocean View Balcony King Room at Oceans Edge, Panoramic Water Views, Pets Welcome, vacation rental in Key West
Ocean View Balcony King Room at Oceans Edge, Panoramic Water Views, Pets Welcome, vacation rental in Key West
Ocean View Balcony King Room at Oceans Edge, Panoramic Water Views, Pets Welcome, vacation rental in Key West

Ocean View Balcony King Room at Oceans Edge, Panoramic Water Views, Pets Welcome

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
By the Beautiful Sea - Key West Beach Front Condo - w Pool Access, vacation rental in Key West
By the Beautiful Sea - Key West Beach Front Condo - w Pool Access, vacation rental in Key West
By the Beautiful Sea - Key West Beach Front Condo - w Pool Access, vacation rental in Key West

By the Beautiful Sea - Key West Beach Front Condo - w Pool Access

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Designer Octagon House of Key West - w Private Pool - Blocks off Duval, vacation rental in Key West
Designer Octagon House of Key West - w Private Pool - Blocks off Duval, vacation rental in Key West
Designer Octagon House of Key West - w Private Pool - Blocks off Duval, vacation rental in Key West

Designer Octagon House of Key West - w Private Pool - Blocks off Duval

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Bayview South: 4 Bedroom 3 Bath Waterfront Condo at Bayfront Suites & Marina, vacation rental in Key West
Bayview South: 4 Bedroom 3 Bath Waterfront Condo at Bayfront Suites & Marina, vacation rental in Key West
Bayview South: 4 Bedroom 3 Bath Waterfront Condo at Bayfront Suites & Marina, vacation rental in Key West

Bayview South: 4 Bedroom 3 Bath Waterfront Condo at Bayfront Suites & Marina

Condo/Apartment
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
No secrets at Pilar's Secret - Just a great location!, vacation rental in Key West
No secrets at Pilar's Secret - Just a great location!, vacation rental in Key West
No secrets at Pilar's Secret - Just a great location!, vacation rental in Key West

No secrets at Pilar's Secret - Just a great location!

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
~ CASABLANCA TOO ~Chicly updated home with hot tub in a quiet location., vacation rental in Key West
~ CASABLANCA TOO ~Chicly updated home with hot tub in a quiet location., vacation rental in Key West
~ CASABLANCA TOO ~Chicly updated home with hot tub in a quiet location., vacation rental in Key West

~ CASABLANCA TOO ~Chicly updated home with hot tub in a quiet location.

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Stunning 2 Floor Loft in Vibrant Key West Ideal for Romantic Weekends - Pool, vacation rental in Key West
Stunning 2 Floor Loft in Vibrant Key West Ideal for Romantic Weekends - Pool, vacation rental in Key West
Stunning 2 Floor Loft in Vibrant Key West Ideal for Romantic Weekends - Pool, vacation rental in Key West

Stunning 2 Floor Loft in Vibrant Key West Ideal for Romantic Weekends - Pool

Rental Home
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Charming, spacious monthly home w/large pool in the Meadows Old Town Key West, vacation rental in Key West
Charming, spacious monthly home w/large pool in the Meadows Old Town Key West, vacation rental in Key West
Charming, spacious monthly home w/large pool in the Meadows Old Town Key West, vacation rental in Key West

Charming, spacious monthly home w/large pool in the Meadows Old Town Key West

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Two Bedroom Residence, vacation rental in Key West
Two Bedroom Residence, vacation rental in Key West
Two Bedroom Residence, vacation rental in Key West

Two Bedroom Residence

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Exclusive Key West Beach Front - 3BR Luxury Condo w/Gym and Pool Access, vacation rental in Key West
Exclusive Key West Beach Front - 3BR Luxury Condo w/Gym and Pool Access, vacation rental in Key West
Exclusive Key West Beach Front - 3BR Luxury Condo w/Gym and Pool Access, vacation rental in Key West

Exclusive Key West Beach Front - 3BR Luxury Condo w/Gym and Pool Access

Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Panoramic Ocean View! Amazing Room w/ King Bed, Outdoor Swimming Pool, vacation rental in Key West
Panoramic Ocean View! Amazing Room w/ King Bed, Outdoor Swimming Pool, vacation rental in Key West
Panoramic Ocean View! Amazing Room w/ King Bed, Outdoor Swimming Pool, vacation rental in Key West

Panoramic Ocean View! Amazing Room w/ King Bed, Outdoor Swimming Pool

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Sunshine, beaches, and ocean breezes at Ocean Vista (La Brisa #403E), vacation rental in Key West
Sunshine, beaches, and ocean breezes at Ocean Vista (La Brisa #403E), vacation rental in Key West
Sunshine, beaches, and ocean breezes at Ocean Vista (La Brisa #403E), vacation rental in Key West

Sunshine, beaches, and ocean breezes at Ocean Vista (La Brisa #403E)

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Amelia Street Retreat: Updated 3BR Key West Home, 2 Blocks to Duval St, vacation rental in Key West
Amelia Street Retreat: Updated 3BR Key West Home, 2 Blocks to Duval St, vacation rental in Key West
Amelia Street Retreat: Updated 3BR Key West Home, 2 Blocks to Duval St, vacation rental in Key West

Amelia Street Retreat: Updated 3BR Key West Home, 2 Blocks to Duval St

Rental Home
3 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Uptown quiet cottage close to beaches, restaurant & shopping., vacation rental in Key West
Uptown quiet cottage close to beaches, restaurant & shopping., vacation rental in Key West
Uptown quiet cottage close to beaches, restaurant & shopping., vacation rental in Key West

Uptown quiet cottage close to beaches, restaurant & shopping.

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
3 Island-Chic Rooms Offering Private White Sand Beach on Duval St. in Key West, vacation rental in Key West
3 Island-Chic Rooms Offering Private White Sand Beach on Duval St. in Key West, vacation rental in Key West
3 Island-Chic Rooms Offering Private White Sand Beach on Duval St. in Key West, vacation rental in Key West

3 Island-Chic Rooms Offering Private White Sand Beach on Duval St. in Key West

Rental Home
3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Waterfront Resort, New Year’s Eve, 7 Nights, Sleeps 6, Pool, Hot Tub, Beach, vacation rental in Key West
Waterfront Resort, New Year’s Eve, 7 Nights, Sleeps 6, Pool, Hot Tub, Beach, vacation rental in Key West
Waterfront Resort, New Year’s Eve, 7 Nights, Sleeps 6, Pool, Hot Tub, Beach, vacation rental in Key West

Waterfront Resort, New Year’s Eve, 7 Nights, Sleeps 6, Pool, Hot Tub, Beach

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Fantastic Land and Sea Vacation! Amazing Ocean View Room w/ King Bed, Pool, vacation rental in Key West
Fantastic Land and Sea Vacation! Amazing Ocean View Room w/ King Bed, Pool, vacation rental in Key West
Fantastic Land and Sea Vacation! Amazing Ocean View Room w/ King Bed, Pool, vacation rental in Key West

Fantastic Land and Sea Vacation! Amazing Ocean View Room w/ King Bed, Pool

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Charming 3-bedroom townhome with WiFi, AC in fantastic Key West Golf Course, vacation rental in Key West
Charming 3-bedroom townhome with WiFi, AC in fantastic Key West Golf Course, vacation rental in Key West
Charming 3-bedroom townhome with WiFi, AC in fantastic Key West Golf Course, vacation rental in Key West

Charming 3-bedroom townhome with WiFi, AC in fantastic Key West Golf Course

Rental Home
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Romantic Stay in Historic Key West: 1BR Suite w/ King Bed & Pool, vacation rental in Key West
Romantic Stay in Historic Key West: 1BR Suite w/ King Bed & Pool, vacation rental in Key West
Romantic Stay in Historic Key West: 1BR Suite w/ King Bed & Pool, vacation rental in Key West

Romantic Stay in Historic Key West: 1BR Suite w/ King Bed & Pool

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Speakeasy Inn  - Room 1A (1 King Bed & 1 Single Sleeper Sofa), vacation rental in Key West
Speakeasy Inn  - Room 1A (1 King Bed & 1 Single Sleeper Sofa), vacation rental in Key West
Speakeasy Inn  - Room 1A (1 King Bed & 1 Single Sleeper Sofa), vacation rental in Key West

Speakeasy Inn - Room 1A (1 King Bed & 1 Single Sleeper Sofa)

Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Old Town Key West Hideaway with Poolside Fun, vacation rental in Key West
Old Town Key West Hideaway with Poolside Fun, vacation rental in Key West
Old Town Key West Hideaway with Poolside Fun, vacation rental in Key West

Old Town Key West Hideaway with Poolside Fun

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Villa Paradiso: A unique mid-town paradise, vacation rental in Key West
Villa Paradiso: A unique mid-town paradise, vacation rental in Key West
Villa Paradiso: A unique mid-town paradise, vacation rental in Key West

Villa Paradiso: A unique mid-town paradise

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Room in Coastal Resort w/ Oceanview - Six Pools & Pvt Oceanview Balcony, vacation rental in Key West
Room in Coastal Resort w/ Oceanview - Six Pools & Pvt Oceanview Balcony, vacation rental in Key West
Room in Coastal Resort w/ Oceanview - Six Pools & Pvt Oceanview Balcony, vacation rental in Key West

Room in Coastal Resort w/ Oceanview - Six Pools & Pvt Oceanview Balcony

Rental Home
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
South Street Cottage: Bright & Sunny with Pool, Patio & Hot Tub, vacation rental in Key West
South Street Cottage: Bright & Sunny with Pool, Patio & Hot Tub, vacation rental in Key West
South Street Cottage: Bright & Sunny with Pool, Patio & Hot Tub, vacation rental in Key West

South Street Cottage: Bright & Sunny with Pool, Patio & Hot Tub

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Casa Atlantica: A one bedroom condo on the Atlantic shore of Key West, vacation rental in Key West
Casa Atlantica: A one bedroom condo on the Atlantic shore of Key West, vacation rental in Key West
Casa Atlantica: A one bedroom condo on the Atlantic shore of Key West, vacation rental in Key West

Casa Atlantica: A one bedroom condo on the Atlantic shore of Key West

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
3| Galleon | Marina | Spa | Hot Tub | Pool, vacation rental in Key West
3| Galleon | Marina | Spa | Hot Tub | Pool, vacation rental in Key West
3| Galleon | Marina | Spa | Hot Tub | Pool, vacation rental in Key West

3| Galleon | Marina | Spa | Hot Tub | Pool

Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Snowbird-friendly downtown Key West studio with patio, full kitchen, partial AC, vacation rental in Key West
Snowbird-friendly downtown Key West studio with patio, full kitchen, partial AC, vacation rental in Key West
Snowbird-friendly downtown Key West studio with patio, full kitchen, partial AC, vacation rental in Key West

Snowbird-friendly downtown Key West studio with patio, full kitchen, partial AC

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
NEW! The Rigby House - Pvt Pool, Amazing Location!, vacation rental in Key West
NEW! The Rigby House - Pvt Pool, Amazing Location!, vacation rental in Key West
NEW! The Rigby House - Pvt Pool, Amazing Location!, vacation rental in Key West

NEW! The Rigby House - Pvt Pool, Amazing Location!

Rental Home
6 bedrooms
7 bathrooms
Sleeps 12
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
A Siesta Bay by AvantStay | Key West Walkable | Gated Community, Shared Pool, vacation rental in Key West
A Siesta Bay by AvantStay | Key West Walkable | Gated Community, Shared Pool, vacation rental in Key West
A Siesta Bay by AvantStay | Key West Walkable | Gated Community, Shared Pool, vacation rental in Key West

A Siesta Bay by AvantStay | Key West Walkable | Gated Community, Shared Pool

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Key West dream townhouse * Sleeps 6 * Like new! Old Town * Perfect location, vacation rental in Key West
Key West dream townhouse * Sleeps 6 * Like new! Old Town * Perfect location, vacation rental in Key West
Key West dream townhouse * Sleeps 6 * Like new! Old Town * Perfect location, vacation rental in Key West

Key West dream townhouse * Sleeps 6 * Like new! Old Town * Perfect location

Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
HERE COMES THE SUN ~ 2 BR, 2 Ba Casa Marina Home with Pool!, vacation rental in Key West
HERE COMES THE SUN ~ 2 BR, 2 Ba Casa Marina Home with Pool!, vacation rental in Key West
HERE COMES THE SUN ~ 2 BR, 2 Ba Casa Marina Home with Pool!, vacation rental in Key West

HERE COMES THE SUN ~ 2 BR, 2 Ba Casa Marina Home with Pool!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
SWEET DREAMS ARE MADE OF 'THE KEYS' ~ Bahama Village 2 BR/2 Ba Home w/ Pool!, vacation rental in Key West
SWEET DREAMS ARE MADE OF 'THE KEYS' ~ Bahama Village 2 BR/2 Ba Home w/ Pool!, vacation rental in Key West
SWEET DREAMS ARE MADE OF 'THE KEYS' ~ Bahama Village 2 BR/2 Ba Home w/ Pool!, vacation rental in Key West

SWEET DREAMS ARE MADE OF 'THE KEYS' ~ Bahama Village 2 BR/2 Ba Home w/ Pool!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
~MISS SUNSHINE~Pool, privacy and palms abound at this 3B/3BA sensation!, vacation rental in Key West
~MISS SUNSHINE~Pool, privacy and palms abound at this 3B/3BA sensation!, vacation rental in Key West
~MISS SUNSHINE~Pool, privacy and palms abound at this 3B/3BA sensation!, vacation rental in Key West

~MISS SUNSHINE~Pool, privacy and palms abound at this 3B/3BA sensation!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
3 Traditional Two Queen, Pier House Resort, Fine Dining, Near Mallory Square, vacation rental in Key West
3 Traditional Two Queen, Pier House Resort, Fine Dining, Near Mallory Square, vacation rental in Key West
3 Traditional Two Queen, Pier House Resort, Fine Dining, Near Mallory Square, vacation rental in Key West

3 Traditional Two Queen, Pier House Resort, Fine Dining, Near Mallory Square

Rental Home
3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
The Secret Grotto, vacation rental in Key West
The Secret Grotto, vacation rental in Key West
The Secret Grotto, vacation rental in Key West

The Secret Grotto

Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
1 block to the beach, vacation rental in Key West
1 block to the beach, vacation rental in Key West
1 block to the beach, vacation rental in Key West

1 block to the beach

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Sunkissed Bungalow-B205, vacation rental in Key West
Sunkissed Bungalow-B205, vacation rental in Key West
Sunkissed Bungalow-B205, vacation rental in Key West

Sunkissed Bungalow-B205

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Relaxing Double Queen, Fairfield Inn, Breakfast Included, Near Downtown Key West, vacation rental in Key West
Relaxing Double Queen, Fairfield Inn, Breakfast Included, Near Downtown Key West, vacation rental in Key West
Relaxing Double Queen, Fairfield Inn, Breakfast Included, Near Downtown Key West, vacation rental in Key West

Relaxing Double Queen, Fairfield Inn, Breakfast Included, Near Downtown Key West

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
High Tide awaits your next visit upgraded condo close to Smathers Beach, vacation rental in Key West
High Tide awaits your next visit upgraded condo close to Smathers Beach, vacation rental in Key West
High Tide awaits your next visit upgraded condo close to Smathers Beach, vacation rental in Key West

High Tide awaits your next visit upgraded condo close to Smathers Beach

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Shipyard Truman Annex; 620 Thomas St. 1st Floor - AVAILABLE  JULY & SEPT 2025, vacation rental in Key West
Shipyard Truman Annex; 620 Thomas St. 1st Floor - AVAILABLE  JULY & SEPT 2025, vacation rental in Key West
Shipyard Truman Annex; 620 Thomas St. 1st Floor - AVAILABLE  JULY & SEPT 2025, vacation rental in Key West

Shipyard Truman Annex; 620 Thomas St. 1st Floor - AVAILABLE JULY & SEPT 2025

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Poinciana Place Garden: First Floor, Hot Tub, Walk to Beach & Downtown!, vacation rental in Key West
Poinciana Place Garden: First Floor, Hot Tub, Walk to Beach & Downtown!, vacation rental in Key West
Poinciana Place Garden: First Floor, Hot Tub, Walk to Beach & Downtown!, vacation rental in Key West

Poinciana Place Garden: First Floor, Hot Tub, Walk to Beach & Downtown!

Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
������������ Near Duval Street, Waterfront Sunset Harbor Resort. 2BR, vacation rental in Key West
������������ Near Duval Street, Waterfront Sunset Harbor Resort. 2BR, vacation rental in Key West
������������ Near Duval Street, Waterfront Sunset Harbor Resort. 2BR, vacation rental in Key West

������������ Near Duval Street, Waterfront Sunset Harbor Resort. 2BR

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Key West Dream! 2 Awesome Units, Pool, Restaurant, Bar, Bike Rentals, Parking!, vacation rental in Key West
Key West Dream! 2 Awesome Units, Pool, Restaurant, Bar, Bike Rentals, Parking!, vacation rental in Key West
Key West Dream! 2 Awesome Units, Pool, Restaurant, Bar, Bike Rentals, Parking!, vacation rental in Key West

Key West Dream! 2 Awesome Units, Pool, Restaurant, Bar, Bike Rentals, Parking!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
La Brisa Monthly Rental across the street from Smathers Beach, vacation rental in Key West
La Brisa Monthly Rental across the street from Smathers Beach, vacation rental in Key West
La Brisa Monthly Rental across the street from Smathers Beach, vacation rental in Key West

La Brisa Monthly Rental across the street from Smathers Beach

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Penthouse Beach Ocean Views-  Live the Dream, vacation rental in Key West
Penthouse Beach Ocean Views-  Live the Dream, vacation rental in Key West
Penthouse Beach Ocean Views-  Live the Dream, vacation rental in Key West

Penthouse Beach Ocean Views- Live the Dream

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
…
Showing results 1-50 of 633
Frequently Asked Questions about Key West






Key West Vacation Rentals and Condos
Browse through the list of beachfront house rentals in the Florida Keys and you’ll start to feel the warm breeze. You’ll sense the cool sand under your feet and taste the spike of a margarita. Everyone and everything on the island of Key West seems to go at its own pace, which makes it a wondrous vacation destination for families and friends of all ages. House and condo rentals abound – penthouse beach villas on the sandy shoreline, inland cottages in the bustling Old Town district, even fully equipped yachts are available for stay!
Where To Rent a Vacation Home in Key West
Vacation rentals in Key West can be found all over town, but knowing what each area offers will help you decide on the perfect place. Condo rentals in Old Town will put you in the center of the action – steps from the famous Duval Street, with numerous restaurants, bars, boutiques, souvenir shops and major attractions. Luxurious, modern house rentals on the beach offer more privacy and relaxation. No matter where you make your home base, if you rent a moped or scooter in Key West, you’ll find it easy to get around without a rental car.
Many House Rentals Near Attractions and Activities For All Ages
Key West vacation rentals scatter the whole island, so you’ll always be close to family fun and adventure. Fury Water Adventures offers jet skis, kayaking, parasailing, boating and some of the best snorkeling and diving excursions you’ll ever find. Fishermen will marvel at the eclectic aquatic life in the crystal-blue waters, while families can take the kids to the Florida Keys Eco-Discovery Center, with interactive and dynamic sea exhibits – all just steps away from the island’s spacious, family-friendly condo rentals. Enjoy the romance of paradise on a sunset dinner cruise to wind down from a busy day on the beach or in town.
Key West Bars and Restaurants
Bustling nightlife and gastronomy surround the house rentals in the Historic Seaport neighborhood. Start your night with frozen daiquiris at the famous Lazy Gecko before moving to the award-winning Italian restaurant La Trattoria on the legendary Duval Street. A visit to Key West wouldn’t be complete without trying the conch fritters. And we recommend you indulge in as many different versions of key lime pie as possible. Parrotheads (you know who you are) should make a beeline to Jimmy Buffet’s Margaritaville Café, where you can order up your very own Cheeseburger in Paradise.
Book a Key West Vacation Rental For Your Next Trip
Vacation rentals in Key West are the perfect way to experience the island like a local. Traipse down Duval Street to take in the culture, enjoy the family-friendly attractions with your children and loved ones and relax on the white-sand beaches with a margarita in hand. Whichever way you vacation, TripAdvisor has the best deals on house rentals, condo rentals, and beach homes in Key West.
Things to DoRestaurantsFlightsTravel StoriesCruisesRental Cars