Vacation Rentals & House Rentals in Key West

Updating...

age 0-16
32 Results

Relevance

Price: low to high

Price: high to low

Reviews

32 house rentals

NEW LISTING! 40’ Luxury Catamaran Yacht!

Key West yacht

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

Match: Bicycles available Boat available

All filters match

Price per night from

$1,950

“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

Match: Bicycles available Boat available

All filters match

Price per night from

$287

SEAPORT SERENITY in Old Town—Beach-Pool-BBQ-Hot Tub

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Bicycles available Boat available

All filters match

Price per night from

$912

These homes match some but not all of your filters. Clear all filters

One-bedroom time share suite in the heart of Old Key West

Key West condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 26 minutes

1 of 2 match: Boat available, Bicycles available

1 of 2 filters match

Price per night from

$339

New Listing Family Friendly

Key West townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Boat available, Bicycles available

1 of 2 filters match

Price per night from

$367

Cozy Key West Hideaway with a Pool, Digital Workspace, and Privacy

Key West house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Boat available, Bicycles available

1 of 2 filters match

Price per night from

$345

SEAPORT SAILING—Beach-Pool-BBQ-55”TV-HotTub

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Boat available, Bicycles available

1 of 2 filters match

Price per night from

$976

Studio Blue

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Boat available, Bicycles available

1 of 2 filters match

Price per night from

$331

KEY WEST and 3 Bikes or Walk Everywhere! 2 Porches, Pool, Parking & WIFI

Key West condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Boat available, Bicycles available

1 of 2 filters match

Price per night from

$342

1 of 2 match: Boat available, Bicycles available

1 of 2 filters match

Price per night from

$155

Ohana Paradise At Historic Seaport ,Old Town, Key West. Private Home.

Key West house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Boat available, Bicycles available

1 of 2 filters match

Price per night from

$258

Moveable Feast

Key West house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

1 of 2 match: Boat available, Bicycles available

1 of 2 filters match

Price per night from

$430

1 of 2 match: Boat available, Bicycles available

1 of 2 filters match

Price per night from

$912

Single Family Home, 3 Bedroom, 2 Baths, and Pool. Great Value!

Key West house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Boat available, Bicycles available

1 of 2 filters match

Price per night from

$166

Tee by the Sea - Luxury 2/2 1/2, WIFI, pool, parking, Bikes, 3 night min.

Key West townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

“Absolutely Perfect!!!” I chose this place to rent because it looked nice and it was affordable. I knew going in that it was not located on the Key West island, which was fine considering the condo came with bikes you could ride onto the island...What I experienced during my stay here is nothing short of Perfect!!! The entire condo was clean and spacious, everything inside the condo worked, the beds and all furniture were clean and comfortable, plenty of towels and linens, the showers, water presure and plumbing were excellent, the pool was clean, relaxing and private, the nights were quiet for sleeping and the gated community within the condo were friendly and fun. The bikes were the best part...10-15 minutes and you were on Duval Street, or the Southernmost Point, or Fort Zachery beach with no hassles what so ever, and I got some good exercise!!! I will definately stay here again!!!

1 of 2 match: Boat available, Bicycles available

1 of 2 filters match

Price per night from

$344

Best Downtown Location Monthly Rental Open Nov 2023- Jan 2024

Key West apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Bicycles available, Boat available

1 of 2 filters match

Price per night from

$382

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: Bicycles available, Boat available

1 of 2 filters match

Price per night from

$478

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: Bicycles available, Boat available

1 of 2 filters match

Price per night from

$1,718

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

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Bicycles available, Boat available

1 of 2 filters match

Price per night from

$859

Top floor Ocean Views, Spacious 2 Bedroom Condo, Views from every room

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Bicycles available, Boat available

1 of 2 filters match

Price per night from

$974

Botanical Island Delight Key West fantastic discounts for Summer & Fall

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Bicycles available, Boat available

1 of 2 filters match

Price per night from

$745

Poolside Breeze a Tropical Retreat has a wrap around Balcony best location

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Bicycles available, Boat available

1 of 2 filters match

Price per night from

$859

Anchor Drop modern elegance upgrades throughout views of Atlantic Ocean

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Bicycles available, Boat available

1 of 2 filters match

Price per night from

$1,374

Our Nautical Home in Key West is available for amazing prices Summer of 2023

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Bicycles available, Boat available

1 of 2 filters match

Price per night from

$859

Great rentals within 20 miles that match your search

Match: Bicycles available Boat available

All filters match

Price per night from

$263

Hyatt Sunset Harbor

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Bicycles available Boat available

All filters match

Price per night from

$496

Hyatt Sunset Harbor

Stock Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Bicycles available Boat available

All filters match

Price per night from

$445

Coconut Mallory Resort and Marina

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Bicycles available Boat available

All filters match

Price per night from

$346

Hyatt Windward Pointe

Stock Island apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Bicycles available Boat available

All filters match

Price per night from

$525

Hyatt Beach House! Quiet Key West Location!

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Bicycles available Boat available

All filters match

Price per night from

$471

Hyatt Windward Pointe

Stock Island apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Bicycles available Boat available

All filters match

Price per night from

$525

Hyatt Windward Pointe

Stock Island apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Bicycles available Boat available

All filters match

Price per night from

$484

×

Also consider