- Entire Home
- Listings where you have the whole place to yourself.
- Private Room
- Listings where you have your own room but share some common spaces.
- Shared Room
- Listings where you'll share your room or your room may be a common space.
- Room Type
- Social Connections
- Employee host
- Instant Book
- Property Type
- Host Language
173 Rentals · Key West
173 Rentals · Key West
Private 1 bedroom apt in prime location in Old Town Key West, with large deck on private garden. Ideal for a couple. We are seeking 30-day or 2 week rentals after May, but are now accepting weekly rentals. Learn More
You enter via a private walkway to the ground-floor rear apartment with your private garden. Inside, there is a bedroom with a Queen size bed, a living room/kitchen space, and a bathroom. Three separate doors lead to the outside deck. This big wooden deck has a dining table, and chairs to hang out, and gives on to the garden. There are two air conditioners, one in bedroom and one in living room. The apartment is equipped with wifi and premium cable television, with an HD flat screen TV a...
Brand new 5 room space 1 queen and 1 day bed /sofa, 1 airbed available. One bedroom, sleeping porch w/ sofa, living room, kitchenette, bath. High quality queen memory foam mattress / premium linens. Includes 2 bikes. Monthly rentals only. Learn More
One good sized bedroom with queen bed, sofa on the sunporch (see photos) which converts to a day bed, air mattress available. Sleeps 3 , 4 in a pinch.
Nicely furnished private room and bath in quiet, desirable neighborhood in Old Town Key West. A/C + Cable TV + WiFi + W/D. Access to an enchanting large pool/deck area with grill. Equipped with microwave and refrigerator. Parking. Certain pets OK. Learn More
The pool/deck ares is beautifully landscaped and available for your use. Conveniently located between the beaches and bustling Duval Street access to fabulous pool/deck area Peaceful, residential neighborhood in one of Key West's nicest areas Easy parking
Escape (the blues)! Plan your next vacation in the warm and sunny Florida Keys. You book your campground and we will set up your home away from home in an American icon. You'll love our restored 27' vintage 1974 Overlander. Learn More
A++ location -- private pool & parking Learn More
Perfect location and great for entertaining! In the heart of Old Town Key West just steps from restaurants, bars, theatres and shops, this sprawling six bedroom, seven bath compound has two private heated swimming pools, endless porches, terraces and a huge, fabulous roof deck that overlooks the action on Duval St. Comprised of two buildings—a luxurious Duval St. penthouse with 3 bedrooms and 2.5 baths, and a lovely 3 bedroom, 3.5 bath guest house. The two-story penthouse is designed af...
Beautiful piece of "Old Town" Key West livin' The Garden House is a bed & breakfast only 2 blocks from Duval St on the corner of Elizabeth and Eaton. The property has 12 rooms and features a heated pool, sun deck, and free breakfast every morning! Learn More
Guests have access to the pool and all common areas. We have a great staff that can always help and answer any questions you may have in order to enhance your stay. Located at 329 Elizabeth St, The Garden House is in the heart of "Old Town" Key West and walking distance to everywhere you will want to go I recommend renting bicycles, but you can walk to almost anywhere! Breakfast every morning. Free wifi. Cable TV. No pets allowed. We also have daily housekeeping that will replenish towe...
One week time-share at this incredible Hyatt hotel in Key West. Expect a two bedroom apartment with living room, dinning room, kitchen, one bathroom on each bedroom, hot tub, among other amenities. You can use all hotel facilities! Learn More
Original conch cottage restored in 2009 and impeccably maintained. We are 5 blocks from Duval but just far enough to enjoy peace and quiet. 2 bed, one bath plus outdoor shower. Property is fenced in for privacy. NO pets, NO smoking. Learn More
*PLEASE READ HOUSE RULES BEFORE REQUESTING A RESERVATION. The cottage which accommodates four adults was renovated with attention to detail in mind and features antiques, fine quality furniture and linens. The kitchen with a gas stove comes fully equipped with stainless cookware, small appliances and more. Each bedroom has a queen bed with doors leading to the outdoor area. The bedrooms share a large bathroom with an oversize shower. There is also an outdoor shower in the backyard. There a...
This little slice of paradise with private balcony is located off Truman Ave, in Old Town KW. A leisurely four scenic block walk to Duval St. This location is ideal for individuals looking to walk to most tourist attractions in Old Town Key West. Studio offers air conditioning, TV, cable, Wi-Fi internet, full bathroom with tub, no kitchen, microwave, coffee machine, and a small refrigerator with freezer on top. Learn More
This private studio apartment is ample enough to comfortably accommodate two people. The room offers a full size (a little smaller than a queen) bed. The bathroom has a tub and the room has a nice size closet. It does not have a kitchen (no sink) but includes small refrigerator, coffee maker and a microwave. The private and quiet balcony offers a great environment to enjoy reading. It is also a nice place to drink your coffee in the morning and cocktails in the evening before heading out fo...
With 2 swimming pools, a hot tub, tiki bar, BBQ grills, & a kitchen you can enjoy the lush private surroundings & still be close to the heart of Key West, Mallory Square, Hemingway House, Sloppy Joes, only 1 block off Duval w/concierge service. Learn More
Surrounded by a large single banyan tree which grows over the driveway & on all sides of the resort, you feel the lush tropical flavor of Key West, FL only a block from the entertainment district of Duval St and close to the world-renowned Mallory Square Sunset Celebration in downtown Key West. With two swimming pools, a hot tub, Tiki Bar, barbecue grills, and a kitchenette in each room you can enjoy the lush private surroundings and still be close to the heart of Key West. - Same Street as...
Look for the lightning bolt for faster booking
Queen size bed, with private bathroom. Full use of kitchen, Living room , and Balcony, with lovely view, I have lived in Key west for over 20 years. Will guide you to all the local hotspots, and make your stay in Paradise perfect. No Cleaning fee Learn More
I have a personal Concierge that will assist you with all your Land and Sea Activities and Recommend the Best Restaurants Paradise has to offer.
Come stay for a night, or two, or more in my comfortable and inviting townhouse. I am located on Stock Island, which is separated from Key West by Cow Key Channel. It is a ten to fifteen minute drive to "old town", or you can bike. Learn More
The room is bright with a nice view of the surrounding area as it is on the second floor of a stilt townhouse. The room has a comfortable queen bed and also a private bath. Use of the washer and dryer is also included, as well as use of the kitchen. Coffee is provided. I am located on Stock Island, which is a 10-15 minute drive downtown, or a 20-30 minute bike ride. I can connect you with nearby bike rentals if you chose to bike. I can also recommend many fun things to do. I work in a resta...
Queen sized canopy bedroom suite (bathroom w/shower). TV. Wi-Fi. Door to fenced-in backyard & heated pool. Located in New Town area of Key West (2.5 miles from Duval Street). Plentiful free street parking. No smoking in the house or yard. Learn More
Your staying here gives you full access to the pool (heated in winter) and backyard. My husband and I are living in the house and available at all times (you'll have our contact information if we are at work or out for the evening). If you don't have your own car you might want to rent a bike. My home is 2.5 miles from downtown Key West. This is a quiet residential neighborhood and you can come and go as you like but please be respectful. As in no loud motorcycles noise or yelling late...
Look for the lightning bolt for faster booking
Hyatt Beach House Resort comprises 74 fully furnished, 2-bedroom units facing the blue-green waters of the Gulf of Mexico. In a style reminiscent of Old Florida,this resort rests on Florida Bay and Cow Key Channel,which has direct access to the ocean Learn More
10%OFF= ONLY $1573. WK/OCT! Rent this Hemingway inspired villa at the REDUCED MO RATE & feel free to only stay 2 wks of your mo ( no transient license to rent it out wkly) & only pay the price of a 2 wk rental! (ex-$3146 =2 wk stay of your Oct mo ) Learn More
Our Hemingway inspired villa is a monthly rental since we do not have a transient license to rent it out for less than 28 nights. ( all monthly rates based on 28 nights-4 wks) However, if you cannot stay the entire month, we can offer you a much lower monthly rate and you are welcome to come and stay here for your special event, or your vacation, etc. At our reduced monthly rate ( cheaper than some other weekly rates!) you can afford to rent it for the month and just enjoy the time you hav...
Oceanfront 3Bed/2BA home, acre of gorgeously lush tropical grounds, heated pool, oceanside sandy area, 60' Dock, 15 min Key West - private heated pool, ping pong table, gas barbecue, indoor dining oroutdoor dining up on the porch or poolside. Learn More
Cudjoe Key (15 minutes from Key West OR Bahia Honda State Park) 3 bedroom, 2 bath newer home with master suite having a double sink, handmade tiles,walk-in closet. Two king size and one queen size bedded room, (queen size pull out couch in master bedroom, pack n play, 1 twin mattress for the floor and queen sized air bed) give gorgeous, comfortable quarters to each guest decorated in Laura Ashley comforters, Claire Murray hand-made throw rugs, and lots of handmade Spencer & Spencer pottery...
Enjoy breathtaking sights and sounds from our penthouse condo, just 5 mi. outside of Key West. Our 672 sq. ft. efficient condo is the sole unit on the 3rd floor of Bldg. 3 of the Bayside Condos. Recently remodeled & with beautiful decor, we offer 2 bedrooms, a full kitchen and bathroom that both boast fresh granite/tile work, new appliances, free WIFI, laundry unit & a private sun deck with an outdoor shower. The master bedroom has one queen size bed and the second bedroom has two twin beds...
Renting out my entire house for Labor Day Weekend! You'll be able to walk to all the bars, restaurants, and shopping on Duval Street, as well as the beach! The bedroom has a Queen sized tempurpedic bed, and a full sized tempurpedic bed can be set up in the living room. The house has a full kitchen, very large shower, and a nice patio. Wifi is included. My indoor VERY FRIENDLY cat will be home to hold down the fort, so, if you have pet allergies, this is not the right place for you. Learn More
The house is located two short blocks from Duval Street and a couple long blocks (about a 10 minute walk) to Higgs Beach and the dog park. There's a patio with a privacy fence out front. You'll have access to the entire house. I'll be away, but you will have the contact information of my personal assistant. If you need anything, you'll be able to call her. You can call or text me, but I will be out of the state. The key will be hidden on the patio for you.
Book without waiting for your reservation to be accepted