0+ Beds for 1+ Guests
Price  $10 - $1000+

Key West Vacation Rentals and Short Term Rentals

Tripping.com is the world's top vacation rental search engine, rated 9.6 out of 10 based on 50 user reviews. Compare Key West vacation homes and short term rentals from 9 rental sites including HomeAway, VRBO, FlipKey and more, ranging from $52 to $4,667 a night. 
Showing 1,767 personalized results
    $289 / night
    Historic Landmark, Key West, Florida
    Historic Landmark, Key West, Florida
    1 bed / 1 bath
    Key West, FL
    $750 / night
    By The Beautiful Sea ~ Weekly Rental
    By The Beautiful Sea ~ Weekly Rental
    4 bed / 3 bath
    Key West, FL
    $250 / night
    Ultra 2 BR, 2 bath for Jan 24-Jan 31
    Ultra 2 BR, 2 bath for Jan 24-Jan 31
    2 bed / 2 bath
    Key West, FL
    $185 / night
    Port Side Perfection ~ Monthly Rental
    Port Side Perfection ~ Monthly Rental
    2 bed / 2 bath
    Key West, FL
    $743 / night
    Ocean Paradise
    Ocean Paradise
    3 bed / 4 bath
    Key West, FL
    $200 / night
    Luxurious Manor ~ Monthly Rental
    Luxurious Manor ~ Monthly Rental
    3 bed / 3 bath
    Key West, FL
    $214 / night
    The Banyan Resort at Key West
    The Banyan Resort at Key West
    2 bed / 1 bath
    Key West, FL
    $4500 / night
    Lighthouse View Cigar Makers Cottage Key West
    Lighthouse View Cigar Makers Cottage Key West
    2 bed / 1 bath
    Key West, FL
    $283 / night
    Key West~Indies ~ Monthly Rental
    Key West~Indies ~ Monthly Rental
    4 bed / 3 bath
    Key West, FL

    Information about Key West

    About Key West

    Key West is proud to be the southernmost city in the continental US. With such a prominent claim to fame, Key West has become a destination for those seeking a budget beach vacation. Off the tip of mainland Florida and hooked into the Gulf of Mexico, the climate is nearly tropical with mild winters and warm summers. A multitude of activities for everyone in the family makes Key West a wonderful place for anyone to travel to.

    Things to Do in Key West

    For pride’s sake, the first thing to do is check out the “Southernmost Point” buoy that marks Key West’s distinct location. After that, you can move on to attractions like the house of Ernest Hemingway or the Key West Aquarium on Mallory Square. Dry Tortugas Park has really cool marine life and for divers the Vandenberg Wreck is an underwater wonder. As with any Gulf of Mexico vacation destination, fishing and golfing activities are abundant! The location historically has been an important naval center, so for navy brats and Civil War buffs the Key West Naval Station and Fort Zachary Taylor State Park are the go to locations.

    Key West Accommodations

    In Key West, staying somewhat off the main streets will avoid the noise coming from the energetic nightlife crowd. You can find a lot of Key West vacation rentals that are situated right on the beach, sometimes even on a private beach. Criteria should be focused on amenities. You’ll want air conditioning to cool off, beach towels to bring to the beach, and a barbeque for your freshly caught fish.

    Vacation Rentals In Key West

    Save hundreds with a Tripping.com vacation rental and forget about the expensive hotel room. For the ultimate getaway trip, Key West offers 1,639 vacation home rentals for an affordable price to match your budget and accommodation needs. Book one now for an average price of $235 a night, or a long-term rental for an average price of $3,465 a month.

    These homes offer a range of amenities, giving you more bang for your buck. For those looking to stay in a corporate rental, 1,341 of Key West’s rentals offer high speed internet so you can easily keep in touch with your company or team. Go for a swim at one of the 1,201 properties complete with pool or jacuzzi, or relax with a night of cable TV in any of our 1,395 cozy homes.

    Search properties from 9 rental sites in Key West where the top providers in that area are HomeAway, VRBO, and FlipKey. There are 874 HomeAway rentals, 404 VRBO short term rentals and 164 FlipKey vacation rentals.

    Traveling with pets? Choose from 590 pet-friendly rentals in Key West for a quality experience. Tripping.com’s home rentals offer far more room and comfort than a hotel, providing a safe and spacious place for you and your furry buddy. Book instantly with properties marked “Instabook”, and check out our other listings now to find the perfect vacation home for you.