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
857 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
The Flower Power House - Boho Beautiful
More info
Check-in
Check-out
As seen on
Key West Oasis 2 blocks from White Street Pier
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
**A BEACHY VIEW * THE TRUMAN ANNEX IN KEY WEST**
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Peaceful Setting Amongst The Active Island Life Style
More info
Check-in
Check-out
As seen on
Perfect for Groups! 2 Pet-friendly Units, Free Breakfast, Outdoor Pool!
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
As seen on
THE HEMINGWAY SUITE ~ 2nd Floor King Suite * Inn on Fleming w/ Shared Pool!
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
As seen on
Glimmer Glass oceanfront condo by Rent Key West Hideaways
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Sublime Sunsets Waterfront Condo at The Truman Annex in Key West
More info
Check-in
Check-out
As seen on
Coconut Cabana: A restored Old Town home with charm & tropical ambience
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Penthouse in Paradise!
More info
Check-in
Check-out
As seen on
Southernmost Serenity - 3 Bedroom / 2.5 Bathroom With Pool & Outdoor Bar
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 7
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
Sleeps 6 | Lux Resort | Hot Tub | Pool | Concierge
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Room 2 (1 Queen Bed & Single Sleeper Sofa)
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Charter a Luxury Yacht and Anchor off Sunset Key overnight.
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check-in
Check-out
As seen on
Key West Stay Ideal For Couple Close to Mallory Square | Outdoor Swimming Pool
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
As seen on
Bayview Retreat: Spacious Luxury Waterfront Home with Private Pool and Dock!
More info
Check-in
Check-out
As seen on
New Listing-Golf Course Charmer!
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Excellent Choice! Three Family-friendly Rooms, Fantastic View, Outdoor Pool
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out
As seen on
Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Key West Home on Deep Water Canal with Pool at Mile Marker 5, Fisherman's Dream
More info
Check-in
Check-out
As seen on
Beautiful, private, bright one bedroom cottage walk to Duval, Truman
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Private Island Oasis Getaway, A Dream Vacation
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Key West Golf Club 2 Bedroom Spa Home in the sanctuary
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
3 Bedroom Key West Home with Perfect Location & Private Pool
More info
Check-in
Check-out
As seen on
Sundial Luxurious 2 Bedroom Ocean View Condominium- Quality at its Best.
More info
Check-in
Check-out
As seen on
Margarita Cottage ~ Popular island retreat
More info
Check-in
Check-out
As seen on
Southernmost Sanctuary | Vibrant Oasis Near Duval! Perfect for Groups!
Holiday Rental House
6 bedrooms
6 bathrooms
Sleeps 24
Match: Sleeps
More info
Check-in
Check-out
As seen on
3 Island-Chic Rooms Offering Private White Sand Beach on Duval St. in Key West
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out
As seen on
Panoramic Ocean View! Amazing Room w/ King Bed, Outdoor Swimming Pool
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
As seen on
������� ����� Dream Getaway at the Beach House Resort+Amenities. 2BR
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
BONITA EN ROSA ~ Charming 2 Bedroom, 1 Bathroom Home w/ Pool!
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Spacious Key West Room w/ Balcony | Outdoor Pools | Seaport Proximity
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
As seen on
Combined Bayview Manor and Bayview Retreat, accommodating up to 22 guests!
Holiday Rental House
9 bedrooms
7 bathrooms
Sleeps 22
Match: Sleeps
More info
Check-in
Check-out
As seen on
Jimmy Buffet Getaway in Old Town Key West
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
As seen on
Fantastic Land and Sea Vacation! 3 Relaxing Spaces, Outdoor Pool
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out
As seen on
PATHWAY TO PARADISE ~ 2 BR/2.5 Ba Townhome w/ Shared Pool!
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
2 BR Charmer w/ Pool, Old Town, Key West - "A Stone's Throw"
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Sunset Harbor Resort & Spa, Hot Tub, Pool
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Poolside Paradise Monthly Rental 1800 Atlantic -June - Sep $5250 monthly
More info
Check-in
Check-out
As seen on
**HARBORSIDE HARMONY * TRUMAN ANNEX** Waterfront Condo + LAST KEY SERVICES…
Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Best Place to Stay in Key West! 4 Stylish Units, Pool! Parking & EV Charger
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
More info
Check-in
Check-out
As seen on
Two Relaxing Rooms w/ Balcony | Waterfront Resort w/ Access to Outdoor Pools
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Sailfish Suite on Duval
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Casa Papa Del Mar Ocean Front 1800 Atlantic spectacular view and Island charm
More info
Check-in
Check-out
As seen on
Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
205E La Brisa-2BR 2BA beachfront condo w/parking, shared pool, grills
More info
Check-in
Check-out
As seen on
Blue Moonshine upgrades throughout modern finishes, close to Smathers Beach
More info
Check-in
Check-out
As seen on
**SOUTHERN STAR * THE MEADOWS** Private Home & Pool + LAST KEY SERVICES...
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
As seen on
Showing results 1-50 of 857
Frequently Asked Questions about Key West
- Yes, here are some popular holiday rentals in Key West that have a pool:
- Pool, Laundry, and grilling area
- Key West Hyatt Charming 2-bedroom resort with WiFi, AC
- Key West Home on Deep Water Canal with Pool at Mile Marker 5, Fisherman's Dream
- Yes, here are some popular holiday rentals in Key West that have internet access:
- Pool, Laundry, and grilling area
- Key West Hyatt Charming 2-bedroom resort with WiFi, AC
- Key West Home on Deep Water Canal with Pool at Mile Marker 5, Fisherman's Dream
- The best pet friendly rentals in Key West are:
- Key West Home on Deep Water Canal with Pool at Mile Marker 5, Fisherman's Dream
- Perfect Staycation! Close to Local Attractions! Deluxe Room w/ Pool View
- Short Drive to the Nearest Beach! Amazing Deluxe Room w/ Amazing Pool View
- Some of the most popular kid friendly rentals in Key West are:
- Key West Hyatt Charming 2-bedroom resort with WiFi, AC
- Key West Home on Deep Water Canal with Pool at Mile Marker 5, Fisherman's Dream
- Perfect Staycation! Close to Local Attractions! Deluxe Room w/ Pool View
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
Affordable Hotels in Key WestKey West Hotels with SaunaKey West Hotels with Breakfast BuffetKey West Hotels with Heated PoolKey West Hotels with Rooftop PoolKey West Hotels with Rooftop BarKey West Adventure HotelsKey West Hotels with Banquet HallKey West Resorts with BoatsKey West Hotels with Bridal Suite
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