Key West long-term rentals

Call (888) 257-7970 for additional information about long-term bookings.

Take your time in the sunshine with an extended stay or monthly vacation rental.

Vacation homes with boat docks by the water in Key West, FL
How to travel alone

A long-term vacation to look forward to

Receive a discounted rate on many of our monthly rentals (displayed at check-out) and reductions in our usual fees. We also allow for partial payment if you book at least 45 days ahead of time. Call (888) 257-7970 for additional information about long-term bookings.

Plus, enjoy peace of mind with our simple cancellation policy and optional travel insurance.

Call us to learn more >

cartoon design of a home.
waterfront vacation rental with pool and lounge chairs in sugarloaf key

Key West monthly vacation rentals

Craving a longer stay in the sunshine? Take a snowbird retreat or an extended stay in the tropics of Key West. Bask in the warm weather beside the Gulf of Mexico’s turquoise waves, embark on a snorkeling adventure, sightsee through museums and botanical gardens, and of course, grab a slice of famous Key lime pie. Feel right at home with professional property management, pet-friendly vacation rentals, and amenities like fully-equipped kitchens, ocean views, private pools, beach access, and more. Savor your trip near the southernmost point with an extended stay or long-term rental.

The backyard area of a vacation rental in Key West.


Key To My Heart

5 Bed | 4 Bath

Make your extended stay one to remember with a luxurious waterfront rental. Fully relax with loved ones throughout the beautifully blended indoor/outdoor living spaces, backyard hammocks, and around the outdoor fire pit. As a pet-friendly home with plenty of room, the whole family can tag along to enjoy the outdoor kitchen, the kayak launch, and nearby beaches.

Long-term rentals with pools in Key West

When you want to bring the beach a little closer, enjoy the waves with access to a private pool.

The exterior of a home in Key West, Florida.


Old Town

Stay in the heart of the action in this historic part of the Florida Keys, which includes many of the area’s must-see landmarks, like the iconic Hemingway House and the Key West Lighthouse. The Old Town Trolley Tour is a great way to explore the neighborhood with kids, which you can take to get to the famous Southernmost Point (a perfect backdrop for a family photo) or shops in hunting down the right souvenir. Duval Street is a main hub in town, with popular restaurants serving conch fritters and clam chowder, and bars perfect for watching the sunset.

The pool area of a vacation rental in Key West, FL.

More long-term vacation destinations in Key West

The front deck with hammock overlooking a golf course at a vacation rental in Key West, Florida.


Putting In Paradise

2 Bed | 1.5 Bath

Bright, breezy, and built for relaxation, this charming townhouse rental serves as the perfect home base for a long-term vacation. Enjoy perks and amenities during your Florida retreat, like swimming pools, a butterfly garden, fitness centers, and golfing to your heart’s content at the nearby golf course.

Key West long-term dog-friendly rentals

Plan an adventure you and your pup will both love with a pet-friendly vacation rental. Play in the waves at Dog Beach, bring your pup for some paddle boarding, and grab a bite to eat at nearby dog-friendly restaurants.

The pool area of a vacation rental in Key West.


Last Minute

3 Bed | 2 Bath

Grab a long-term vacation rental where fun is never too far away. This sunny escape rests just a block away from the iconic Duval Street, so you can stay within walking distance of restaurants, shops, bars, and museums. Cool off with a dip in the private pool, whip up a family dinner in the fully-equipped kitchen, and rest up for another day of adventure.

The back deck area of a vacation rental overlooking the bay in Key West, Florida.


Bay Harbor View

5 Bed | 3 Bath

Enjoy ocean views for a month or longer on your long-term vacation. With stunning sapphire waves as your backdrop, you’ll have no trouble feeling right at home and making the most of your Florida adventure. Offering plenty of room for a large group, this home boasts a private pool, a dock, a patio, kayaks, and of course, waterfront access. Head out for a day of kayaking, plan a dinner al fresco in the outdoor dining area and watch the sunset, or feel the ocean breeze from the seating area on the deck. Your next great gathering place awaits.

Key West rentals with private docks

Fish, kayak, or live your dreams as a captain. Experience a Key West getaway like none other by staying at vacation rental with a private dock.

The view of a vacation rental with a dock as seen from a drone.


Sunset Bay

4 Bed | 3 Bath

Keep fun on the water at your fingertips. This bayfront bungalow is the perfect escape for anglers, water sports enthusiasts, and large groups. Get your fill of fishing and boating with the home’s dock, kayaks, and stand-up paddle boards. Your family and friends will experience a getaway to remember with easy access to waves and Florida’s nearly-endless sunshine.

Key West long-term stays FAQ

In many cases, yes. If your reservation is eligible for a discount, you’ll see that reflected in the price when you book. Our long-term reservation sales specialists can also help answer any questions about discounts. Call (888) 257-7970 or email

You don't have to pay all at once. In fact, you’ve got a couple of different options to pay in installments. First, you can make monthly payments (over 3, 6, or 12 months) on most reservations through our partnership with Affirm. It’s easy, too—just select “Pay later with Affirm” when completing your vacation purchase.

If you book at least 45 days before your trip, your other option is to split your trip into just two payments. If the cost of your reservation is between $2,000 and $9,999, 50% is due at the time of booking. If the cost of your reservation is over $10,000, 25% is due at the time of booking. If you choose to make two payments, you must make your second payment 30 days before the start of your trip.

Explore all long-term rentals in Key West >

Beautiful beaches, warm Gulf of Mexico waves, and a relaxing tropical climate, Key West offers a full itinerary of family fun. Kick up the adrenaline with water sports or savor a slower pace with museum tours, restful beach days, and sightseeing. Find activities and attractions for all ages, like:

  • Snorkeling
  • Parasailing
  • Southernmost point
  • Duval Street
  • Mallory Square
  • Hunting down the perfect slice of Key lime pie
  • Old West Trolley Tours
  • Hemingway House and Museum
  • Key West Butterfly and Nature Conservatory
  • Key West Aquarium
  • Historic Key West
  • Key West Lighthouse
  • Smathers Beach
  • Charter fishing tours
  • Fort Zachary Taylor Historic State Park
  • Key West Tropical Forest & Botanical Garden
  • Key West Golf Club

Long-term vacation inspiration

California licenses
Vacasa Seasonals Inc.
California DRE #02160171

Vacation Palm Springs Real Estate, Inc.
California DRE #01523013

Vacasa offers property management and other real estate services directly through Vacasa LLC and through Vacasa LLC's licensed subsidiaries. Click here for more information about Vacasa's licensed real estate brokerage/property manager in your state. Vacasa’s licensed real estate brokerages/property managers include: Vacasa Alabama LLC; Vacasa Arizona LLC; Vacasa of Arkansas LLC; Vacasa Colorado LLC (Micah Victory); Vacasa Delaware LLC, 302-541-8999; Vacasa Florida LLC; Vacasa Illinois LLC 481.014072, Micah Victory Managing Broker Lic# 471.021837; Vacasa Louisiana LLC, Dana MacCord, Principal Broker, ph 504.252.0155 (Licensed in LA); Vacasa Michigan LLC, 602-330-9934; Vacasa Missouri LLC, Vicki Lyn Brown, Designated Broker; Vacasa Nevada LLC; Vacasa New Hampshire LLC,45 NH-25, Meredith, NH 03253, Susan Scanlon, Broker of Record; Vacasa Minnesota, Broker: Micah Victory, license #40877637; Vacasa New Mexico LLC, 503-345-9399; Vacasa New York LLC, 888-433-0068, Susan Scanlon, Real Estate Broker; Vacasa North Carolina LLC; Vacasa Oregon LLC; Vacasa Pennsylvania LLC; Vacation Palm Springs Real Estate, Inc., California DRE #01523013, Mark Graham, California DRE #00700720; Vacasa Real Estate LLC (licensed in Texas, Debra Brock, Designated Broker); Vacasa Real Estate LLC (licensed in Washington, Robert Brush, Designated Broker); Vacasa Seasonals Inc., California DRE #02160171, Lisa Renee Stevens, California DRE #01485234; Vacasa South Carolina LLC; Vacasa South Dakota LLC; Vacasa Tennessee LLC; Vacasa Vacation Rentals of Hawaii LLC, 69-201 Waikoloa Beach Dr. Ste. #2F17, Waikoloa, HI 96738; Vacasa Vacation Rentals of Montana LLC, Terah M. Young, Licensed Property Manager; Vacasa Virginia LLC; Vacasa Wisconsin LLC; Vacasa Wyoming LLC. In Canada, this advertisement is provided by Vacasa Canada ULC, CPBC lic. number 75826, 172 Asher Rd. V1X 3H6 Kelowna, BC.