Holiday Rentals in Key West
Destination
Revenue impacts this sort order. Learn more
Bedrooms
Bathrooms
Amenities
Suitability
Property type
Distinctive Features
Distance from
5 km
855 rentals in Key West.
Pool, Laundry, and grilling area
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Oceanfront Resort, Thanksgiving Week, Infinity Pool, Hot Tub, Sleeps 6, Hyatt
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
524 Elizabeth St. #2
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
As seen on
Tropical cottage with private pool, two blocks from Duval - near Hemingway House
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
As seen on
Triple Crown Villa- Boaters Paradise with Pool
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
As seen on
Key West/Surrounded by The Atlantic Ocean Includes 42 Ft Dock Space
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Key West Escape
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
As seen on
THE GEIGER ROOM ~ 3rd Floor 2 Bedroom Suite * Inn on Fleming w/ Shared Pool!
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Island living 3-bed oasis w large pool, lush deck, cabana, outdoor shower
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Amelia Street Retreat: Updated 3BR Key West Home, 2 Blocks to Duval St
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
As seen on
Your Private Key West Escape | 3 Family Ready Room, Near Duval Street Nightlife
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out
As seen on
Tropical Escape: Artistic-Vibe Bungalows Steps from Duval Street
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
As seen on
Waterfront Stay in Duval St. Room w/ Pool Access
More info
Check-in
Check-out
As seen on
Oceanfront King, Pier House, Stunning Ocean Views, Plush King Bed, Duval Locale
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
As seen on
**SOUTHARD PEARL * OLD TOWN** Condo & Community Pool + LAST KEY SERVICES…
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
As seen on
Pool View Three Bedroom Residence
Condo/Apartment
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
As seen on
ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!
More info
Check-in
Check-out
As seen on
The Mermaids House - Old Town, Yearly Rental ! Historic Bahama Conch House
More info
Check-in
Check-out
As seen on
Tropical getaway with pool & sundeck - 1 block to Duval St, 2 blocks to beach
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
La Casa de Luna - 1 Bd/1B condo just off upper Duval
More info
Check-in
Check-out
As seen on
MOONDANCE condo at La Brisa across Smather's Beach
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Coconut Beach | Hot Tub | Lux Resort | Pool | Concierge
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
As seen on
Tropical Tee Time Villa
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Ocean's Edge | Lux Resort | Concierge | Marina
Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
As seen on
Perfect Beach Getaway! Four Convenient Rooms, Driving Distance to the Beach!
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
More info
Check-in
Check-out
As seen on
Ocean View Balcony 2 Queen Suite at Oceans Edge Resort, Marina Access, 6 Pools
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
NEW listing!! Luxurious Island Pearl, 2 Bed/2 Bath Home near Duval - Pool
More info
Check-in
Check-out
As seen on
Spacious Key West Condo at Coconut Mallory Resort & Marina
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Tropical Village: 12BD/9BA Enclave for Large Groups. Gated. Pool/Hot
Holiday Rental House
12 bedrooms
9 bathrooms
Sleeps 30
Match: Sleeps
More info
Check-in
Check-out
As seen on
2 Bedroom Suite w/ Outdoor Pool in Old Town Key West
Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Spacious 5-bdrm 5 bathroom house in charming Key West with AC, WiFi, Plunge Pool
Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
As seen on
Atocha Cottage at Harbor Walk Hideaways | 2 Blocks From Duval! Shared Pool
Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Charming 2-bedroom house with AC, WiFi, and private pool in tranquil Key West
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
4 Traditional Two Queen, Pier House Resort, Island Elegance, Duval St. Access
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
More info
Check-in
Check-out
As seen on
**SEA BREEZE VILLA * GRINNELL GARDENS** Modern Townhome & Pool + LAST KEY SERVIC
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Tropical Cottage - Entire house in the center of Key West
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Ocean Hideaway a Key West Nature retreat close to Smathers & 15 to Duval
More info
Check-in
Check-out
As seen on
JUST OFF DUVAL~ 2nd Floor Condo in Center of Duval St. with Parking Space!
More info
Check-in
Check-out
As seen on
Beach Club #103 - Unique oceanfront living with breathtaking views
More info
Check-in
Check-out
As seen on
Charming catamaran sailboat with AC, pool in stock island yacht club, Key West.
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check-in
Check-out
As seen on
Oceanfront Two Queen, Pier House, Beach Panorama, Custom Decor, Pet-Friendly
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
HERE COMES THE SUN ~ 2 BR, 2 Ba Casa Marina Home with Pool!
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
LA CASA CUBANA * Cuban Club Suites
More info
Check-in
Check-out
As seen on
Perfect Key West Escape! Scenic Harbor View Room Ideal for Romantic Stay
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
As seen on
Sleeps 6 | Hyatt | Lux Resort | Concierge | Pool | Spa
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Carey’s Corner | Updated Studio with Heated Pool
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
As seen on
WINTER WEEK - KEY WEST - 2 Bedroom 2 Bathrooms Sleeps 6
More info
Check-in
Check-out
As seen on
**NEPTUNE'S PENTHOUSE * THE BEACH** Oceanfront Condo / Pool + LAST KEY SERVICE.
More info
Check-in
Check-out
As seen on
You Found it! Amazing Room w/ 2 Queen Beds, Outdoor Swimming Pool
More info
Check-in
Check-out
As seen on
Charming 2-bedroom guest house with Pool, A/C, & WiFi in Key West, near Duval
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Showing results 1-50 of 855
Key West TourismKey West HotelsKey West Guest HouseKey West Holiday HomesKey West FlightsKey West RestaurantsKey West AttractionsKey West Travel ForumKey West PhotosKey West MapKey West Visitors Guide
All Key West HotelsKey West Hotel DealsLast Minute Hotels in Key West
Things to DoRestaurantsFlightsKey West MotelsKey West CampsitesKey West HostelsFamily Hotels in Key WestBusiness Hotels in Key WestKey West Green HotelsRomantic Hotels in Key WestResorts in Key WestLuxury Hotels in Key WestKey West Beach HotelsSpa Resorts in Key West
Curio Collection by Hilton Hotels in Key WestMarriott Hotels in Key WestFairfield (Marriott Bonvoy) Hotels in Key WestHyatt Holiday Club Hotels in Key WestAutograph Collection (Marriott Bonvoy) Hotels in Key WestKey West Hotels in Key WestHyatt Hotels in Key WestHilton Hotels in Key West
Holiday Rentals near Mallory SquareHoliday Rentals near Smathers BeachHoliday Rentals near Fort Zachary Taylor Historic State ParkHoliday Rentals near Key West CemeteryHoliday Rentals near Duval StreetHoliday Rentals near Truman Little White HouseHoliday Rentals near The Ernest Hemingway Home and MuseumHoliday Rentals near Southernmost PointHoliday Rentals near Higgs BeachHoliday Rentals near Sunset Pier