Vacation Rentals & House Rentals in Key West

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Wireless Internet
Swimming pool
Private pool
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Private indoor pool
Balcony or terrace
Washing machine
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Private tennis court
Cot available
Sea view
Safe
Dishwasher
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Children's pool
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Pool or snooker table
Games room
Fax machine
Shared indoor pool
Clothes dryer
Private outdoor pool (unheated)
Private outdoor pool (heated)
Shared outdoor pool (unheated)
Shared outdoor pool (heated)
Cribs
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Video player
Climbing frame
Boat available
Stove
Solarium or roof terrace
TV
Central heating
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Kettle
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Iron
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Staffed property
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Linen provided
Towels provided
Bicycles available
Swing set or jungle gym
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Private fishing lake or river
Housekeeping Included

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Pets
Pets allowed
Parking
Car not required

Children under 5
Smoking allowed
Non-Smoking property
Smoking - Ask
Wheelchair adapted
Wheelchair accessible
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Beach or lakeside relaxation
City breaks
Skiing – property near ski resort
Walking trips

Tennis in town
Nightlife
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Horse riding
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Cycling trips
Golf course on site or within 15 min walk
Beach or lakeside relaxation
Golf within 30mins drive
Lakefront
Waterfront

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38 house rentals

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Luxury Oceanview Pool Eco-friendly Villa Near Key West

Summerland Key villa

4 bedrooms
2 bathrooms

sleeps 12

Match: Boat available Private outdoor pool (unheated)

All filters match

Price per night from

$701

Lobster Lagoon

Stock Island house

4 bedrooms
4 bathrooms

sleeps 9

1 of 2 match: Boat available, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$976

Paradise Point: Your Luxurious Waterfront Getaway with Pool, Tiki, Dockage, and

Sugarloaf house

4 bedrooms
4 bathrooms

sleeps 10

Responds fast! avg. 2 hours 34 minutes

1 of 2 match: Private outdoor pool (unheated), Boat available

1 of 2 filters match

Price per night from

$458

The Hideaway: Discover and Lose Yourself! Newly Decorated Canal Front Home, Dock

Summerland Key house

2 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 2 hours 34 minutes

1 of 2 match: Private outdoor pool (unheated), Boat available

1 of 2 filters match

Price per night from

$144

Luxury Condominium in Old Town | Monthly Rental at Steamplant Key West

Key West condo

3 bedrooms
4 bathrooms

sleeps 8

1 of 2 match: Boat available, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$316

Harbor Walk Hideaways

Key West b&b

4 bedrooms
3 bathrooms

sleeps 8

“Location, Location, Location” We were a group of 8 and rented the entire compound! The place was in an amazing location that was easily accessible to everything. We had everything we needed onsite and if we had any questions, Phyllis was always just a phone call away. The music and talking at night from the cigar lounge was a bit loud, but nothing we couldn't tolerate. The only suggestion I'd make is to buy an ionizer for the first two units to help with the cigar smell....again, nothing intolerable, but could make a world of difference. Can't wait to come back for another visit! THANK YOU!

1 of 2 match: Boat available, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$1,303

$145 per night for months of Sep-Nov on Canal (fits 25-28 ft boat) and Pool.

Cudjoe Key house

3 bedrooms
2 bathrooms

sleeps 8

1 of 2 match: Boat available, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$259

Key West House

Key West house

2 bedrooms
3 bathrooms

sleeps 6

1 of 2 match: Boat available, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$689

Island Time on Cudjoe Key! 20 miles from Key West. Quick open water access.

Cudjoe Key house

4 bedrooms
4 bathrooms

sleeps 8

1 of 2 match: Boat available, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$517

NEW LISTING! 40’ Luxury Catamaran Yacht!

Key West yacht

3 bedrooms
3 bathrooms

sleeps 7

1 of 2 match: Private outdoor pool (unheated), Boat available

1 of 2 filters match

Price per night from

$1,950

80' luxury yacht

Stock Island house

3 bedrooms
4 bathrooms

sleeps 6

1 of 2 match: Private outdoor pool (unheated), Boat available

1 of 2 filters match

Price per night from

$4,016

LA DOLCE VITA, OLD TOWN KEY WEST!! STEPS TO DUVAL!! SLEEPS 2-4, 3 BLKS TO BEACH

Key West apartment

1 bedroom
1 bathroom

sleeps 4

“Fantastic Stay!” My husband and two sons (21 & 24) stayed in this condo over Christmas. This was our first stay in Key West and we wanted to be close to everything, but yet not right on Duval St. This location was perfect; literally a stones throw away from Duval St. The unit inside was decorated very lovely and had all the amenities one would need. I found the owners were nice to do business with, especially Deb who I mostly communicated with. My family and I enjoyed our stay in Key West immensely, we had so much fun! We met many very friendly people out and about town. We would love to visit again, if we do, we would like to stay in this condo or the Bella Vita, the owner's other condo.

Responds fast! avg. 14 minutes

1 of 2 match: Private outdoor pool (unheated), Boat available

1 of 2 filters match

Price per night from

$287

All-Inclusive Yacht Margarita Flaca: Marina OR Anchor on the Ocean: Free Charter

Stock Island yacht

1 bedroom
1 bathroom

sleeps 6

1 of 2 match: Private outdoor pool (unheated), Boat available

1 of 2 filters match

Price per night from

$263

Coconut Mallory Resort and Marina

Stock Island condo

2 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Private outdoor pool (unheated), Boat available

1 of 2 filters match

Price per night from

$347

Hyatt Sunset Harbor

Stock Island condo

2 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Private outdoor pool (unheated), Boat available

1 of 2 filters match

Price per night from

$497

Hyatt Sunset Harbor

Stock Island condo

1 bedroom
1 bathroom

sleeps 4

1 of 2 match: Private outdoor pool (unheated), Boat available

1 of 2 filters match

Price per night from

$524

Mar Y Sol a spectacular Ocean Front Oasis 10 minutes to Historic District

Key West apartment

3 bedrooms
2 bathrooms

sleeps 8

1 of 2 match: Private outdoor pool (unheated), Boat available

1 of 2 filters match

Price per night from

$1,718

Best Downtown Location Monthly Rental Open Nov 2023- Jan 2024

Key West apartment

2 bedrooms
1 bathroom

sleeps 4

1 of 2 match: Private outdoor pool (unheated), Boat available

1 of 2 filters match

Price per night from

$382

Caribbean Conch 5 Minutes to Smathers Beach & 10 minute Bike Downtown - Value

Stock Island condo

2 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Private outdoor pool (unheated), Boat available

1 of 2 filters match

Price per night from

$859

Leaward Isle close to the Ocean' & a short bike downtown. Best value at 1800

Stock Island condo

2 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Private outdoor pool (unheated), Boat available

1 of 2 filters match

Price per night from

$859

Ocean Hideaway a Key West Nature retreat close to Smathers & 15 to Duval

Stock Island condo

2 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Private outdoor pool (unheated), Boat available

1 of 2 filters match

Price per night from

$859

Casa Coastal East, Morning sunrises, Evening night time vibes An Island home.

Key West apartment

2 bedrooms
2 bathrooms

sleeps 4

1 of 2 match: Private outdoor pool (unheated), Boat available

1 of 2 filters match

Price per night from

$478

6 bedroom Duval Street Compound - Pool, Hot Tub, 2 parking spots - A++ Location

Key West villa

6 bedrooms
7 bathrooms

sleeps 16

1 of 2 match: Boat available, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$2,008

Ocean View Estate with Private Pool 15 minutes from Key West

Cudjoe Key house

4 bedrooms
2 bathrooms

sleeps 10

“This vacation home has everything you need.” This home has all the amenities you could possibly need inside and out. Very quiet and secure with a great covered porch where we spent much of our time (we had 7 in our group). Plenty of towels and miscellaneous supplies. It was very easy to book and communicate with the owners. They responded promptly to any questions.

Responds fast! avg. 59 minutes

1 of 2 match: Boat available, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$545