Key West, an island city in the US, is a subtropical paradise and a most loved vacation hotspot. Palm-lined tracks, conch-style abodes, and impressive architecture make your head turn in admiration. The famed island city in the archipelago of Florida Keys is well-known for its beautiful coral reefs. Make sure that you enjoy snorkeling and scuba diving to discover underwater life. Key West Butterfly and Nature Conservatory, Mallory Square, and Ernest Hemingway Home and Museum are some prominent attractions here. Staying on this island paradise for a long period will help you make the best of your holidays. Eclectic festivals, pristine nature, and countless water adventures await you. Book one of these long-term rentals in Key West, Florida.
Popular picks in Key West
Nature enthusiasts can explore the remote Dry Tortugas National Park, which can be reached using a ferry. The 100-square-mile park houses Fort Jefferson, which was used as a prison during the Civil War. It also offers ample opportunities for birdwatching and scuba diving.
Check out The Oldest House Museum and Garden, which was built by Richard Cussans in 1826. At this Bahamian-style house, you can learn more about the construction of the house and see the original furnishings and period pieces.
We handpicked these listings carefully, considering (wherever possible) host status, recent guest reviews, location, accommodation type, prices, decor, availability of dates, and long-term stay rules and regulations. The image galleries get refreshed with the latest updates regularly. They were last updated on October 23, 2025.
1. Cozy home for a long-term stay (from USD 3264)
Whether you are a couple looking for a romantic getaway or a business traveler on a work trip in Key West, this well-furnished apartment is ideal for you to relax. The one-bedroom house lets you stay leisurely for a long span. Have your morning tea on the cozy front porch breathing in the fresh air. The fully equipped kitchen space lets you cook warm and healthy breakfast and meals. In the back of the apartment, there is a shared pool for you to enjoy a swim. The shared outdoor eating space lets you rest your weary feet and snack on refreshments after you return from a day-long excursion. While you’re here, you can go for a refreshing walk on the Key West Historic Seaport boardwalk, which is a block away.
Key West, Florida, United States
858 meters (0.6 ft) from The Hemingway Home and MuseumSuperhost
Accommodates: 3
Top guest reviews
Read more reviewsHost:
lindsay is thoughtful host and responds quickly if you need anythingMonthly discount: 10% off
2. Well-furnished bolthole with garden views (from USD 2984)
If you are a couple looking for long-term accommodation in Key West, this pleasant one-bedroom apartment awaits you. Wake up watching beautiful views of the lush green garden. The big outdoor deck is a lovely spot to enjoy your breakfast and reconnect with nature. The apartment provides you with web access to carry on your work conveniently. The well-equipped kitchen lets you cook delectable meals. Take time out to visit Mallory Square, which is six minutes away, to enjoy gorgeous sunset views.
Key West, Florida, United States
973 meters (0.7 ft) from The Hemingway Home and MuseumAccommodates: 2
Top guest reviews
Host:
our host nicholas made us feel very welcomehe was polite and kind and was eager to answer any questions we hadnicholas was a great hostnicholas was the perfect hostnicholas was the most wonderful hostLocation:
what a great locationthe location was perfect and a short bike to duval streetthe location is close to everything and very comfortablei very much enjoyed the ability to walk or ride a bike to everythingalso very to close to multiple good restaurants and a bike rental placeCleanliness:
the house was very clean and cozylights were on a/c had apartment comfortable towels were out generally environment was clean quiet and very privatethe place was really cute and clean and had a beautiful back gardenthe bed was really comfortable and the room was cleanthe apartment was clean cozy and close to the centerRead more reviewsAmenities & Room:
the bicycles at the apartment were very usefulthe bed was very comfortable and the deck and garden were beautifulthe apartment is cool slightly bohemian as much of key westaccommodation as described and very comfortablewe had a wonderful time in key west in large part to the ease and convenience of nicholas's apartmentMonthly discount: 15% off
3. Beautiful townhouse with butterfly garden views (from USD 5335)
Reconnect with nature by booking this lovely townhouse in Key West for your long vacation. The renovated two-story abode in Key West Golf Club Resort is ideal for a family or group of four individuals to relax. Whether you are solo adventurers or families with kids, the house offers you all the fun and comfort to make your long holidays memorable. Admire beautiful views of the butterfly garden from the living room. The screened-in porch is a fantastic spot to devour savory breakfast. Cook your favorite delicacies for the meals in the full kitchen. Take a dip in the outdoor heated pool and feel rejuvenated. You have access to the shared gymnasium to stay in shape during your long sabbatical. If you love golfing, take time out to play a game on the nearby golf course.
Key West, Florida, United States
6.55 km (4.1 mi) from The Hemingway Home and MuseumAccommodates: 4
Top guest reviews
Location:
great location close to everything without the noiseit’s great to be so close to key west but in a peaceful quiet locationgood location pleasant surroundings easy access to airport easy availability to pool greatly equipped kitchen and great hostsgreat place walking distance to the golf course clean close to the poolwe enjoyed the peaceful and beautiful location along with the warm swimming poolCleanliness:
the home is clean and well appointedthe apartment was perfectly clean and had everything we needed for our whole stayRead more reviewsAmenities & Room:
also the swimming pools are a pleasant addition to the complexMonthly discount: 15% off
4. Beachside condominium with a huge pool (from USD 1081)
Get a true island experience by retreating into this exquisite abode in Key West. The two-bedroom house welcomes a family of six individuals on long holidays. Wake up to the sound of lapping waves of the ocean. You can enjoy your morning coffee, relaxing on the balcony while appreciating the beautiful garden. Spend a relaxing time in the cool waters of the large outdoor swimming pool. The property also features three tennis courts for your outdoor recreation. You can visit Smather’s Beach, which is in the vicinity, to enjoy some seaside fun.
Key West, Florida, United States
2.43 km (1.6 mi) from The Hemingway Home and MuseumAccommodates: 6
Top guest reviews
Host:
very good management service with quick and informative answersthis host was very responsive and helpfulwonderful hosts and a great private 2 bedroom condowe definitely recommend peggy and jim as hosts they were very courteous and quick to answer any questionsjim and peggy are excellent hosts and so easy to reachLocation:
very comfortable close to everythinggreat place near higgs beachthe location was beautiful close to duval street but far enough away to be quiet and privateplace was great perfect locationexcellent location and great pool and gymCleanliness:
the condo was very clean and spaciousclean rooms and well furnishedvery nice clean and roomyclean comfortable highly recommendgreat clean place in key westRead more reviewsAmenities & Room:
loved the pool area with ocean views and sandy beach steps awaybeautiful property with lush courtyard and a fantastic large poolnice pool area secure lush garden courtyard and quietlots of room big balcony clean close to beachloved the sliding doors from each bedroom and living room to the patioMonthly discount: 12% off
5. Magnificent paradise with a private deck (from USD 481)
If you wish to spend a long vacation in the tropical Key West with your family and furry friend, book this pet-friendly elegant home. The well-furnished, two-bedroom retreat welcomes a family or group of six guests. Start your day by relishing a soul-satisfying breakfast on the private deck while watching spectacular nature views. Soothe your muscles in the bubbling hot tub after a day-long excursion. The full kitchen inspires you to cook delicious meals for your loved ones. Make sure that you spend time exploring exotic tropical gardens here. Reconnect with nature by exploring exotic tropical gardens.
Key West, Florida, United States
4.93 km (3.1 mi) from The Hemingway Home and MuseumAccommodates: 6
Top guest reviews
Host:
we would definitely stay again the host emails you check in instructions that are easy to followcommunication with the host was excellentLocation:
great location away from down town key westthe place that we stayed in was so cute and gave such an island feelvery good place to relaxCleanliness:
everything was clean insideclean spacious quieteasy check in clean & comfortablethe apartment is excellent - very clean and nicely set upbathrooms very clean and kitchen well supplied great communication with hostRead more reviewsAmenities & Room:
the sofa bed was surprisingly comfortable toolike it was cooler outside of the pool than actually in itthe beds were super comfortable and the kitchen with full size appliances and barstool seating was nicethe pool was great and where we spent most of our daysthe pool was so hot it felt like swimming in urine
6. Lavish retreat with captivating water views (from USD 2292)
If you are a big family or group of eight individuals on a long vacation in Key West, choose to unwind in this exotic abode. The beachfront house features beautiful interiors and spellbinding outdoors. Sunlight floods the living room as you enjoy your breakfast on the table. Relax on the balcony and take in mesmerizing views of the Atlantic Ocean. Please your loved ones by preparing their favorite delicacies in the full kitchen. The outdoor dining space on the balcony lets you enjoy your meals together. Step in the refreshing waters of the large outdoor hot tub and rejuvenate your mind and body. Explore the walking path from the pool that takes you to the exotic beach.
Key West, Florida, United States
2.5 km (1.6 mi) from The Hemingway Home and MuseumAccommodates: 8
Top guest reviews
Host:
shannon made our trip i travel a lot and have never had someone so helpfulLocation:
beautiful place and spot you can't beat it we'll worth the moneyCleanliness:
beautiful condo and super cleanthe place was sparkling clean and had a full ocean view from every roomRead more reviewsAmenities & Room:
amazing spacious apartment with fabulous views and great amenitieswe felt comfortable and felt at home with all of the amenities provided
7. Pleasant apartment for families (from USD 277)
If you are planning family holidays to Key West, opt to stay in this lovely two-bedroom accommodation. The fully furnished apartment is a half-block away from the well-known Duval Street and is ideal for a family of six individuals. Pleasant décor graces the interiors of the house. The rental offers you a well-equipped kitchen to whip up delicious meals for your loved ones. The dedicated workspace and web access let you work peacefully during your long holidays here. You can also go for a beach excursion at South Beach, which is nearby.
Key West, Florida, United States
246 meters (0.2 ft) from The Hemingway Home and MuseumAccommodates: 6
Top guest reviews
Host:
the host was wonderfulhosts were very nice and quick to replyhost was very responsive and accommodatinghosts were very accomodating and responsivethe owner was great with letting us store the luggage prior to check inLocation:
great location right off duvalgreat location and overall experiencegreat place and location on the "duval strip"great location right in the heart of downtownlocation is great; out of the hustle and bustle but close to everythingCleanliness:
very clean and comfortable apartmentvery clean and convenientunit was very clean and spotlessthe house was clean the linens were clean and smelled freshvery clean and spacious suiteRead more reviewsAmenities & Room:
the sitting room is a good size with comfortable furnituregreat amenities spacious and super clean two bedroom apartment scooter rentals and cvs right across the streetbeds were comfortablethis apartment was perfect for two couples visiting key west for a weddingcomfortable space and beds with a great kitchenMonthly discount: 54% off
8. Studio apartment near Bayview Park (from USD 394)
Due to its location, you probably do not require a car to get around since bikes are provided. However, should you decide to drive, there is free on-street parking available. This studio apartment has a queen-size bed right beside the living area. It’s a small space, great for singles or couples. The full bathroom has a bathtub that is a vintage clawfoot soaking tub. Bayview Park is the nearest park for your exercise needs.
Key West, Florida, United States
1.15 km (0.8 mi) from The Hemingway Home and MuseumAccommodates: 2
Top guest reviews
Host:
shawn is an excellent hostshawn was friendly and helpfull hostshawn was very helpful and quick to respondshawn and romi were amazing hosts will definitely recommend to everyoneshawn was very thoughtful and responsiveLocation:
a great locationgreat little spot close to everythinglocation is great with everything needed within walking distance and an easy bike ride to duval stthis is an ideal location for exploring key westmuch better location than chain hotels can walk to everythingCleanliness:
very clean and cozyefficiency apartment was very clean and beautifully decoratedhouse was clean and well equippedstudio was clean and cozyfound the apartment to be very clean and comfortableRead more reviewsAmenities & Room:
went to the coffee shop that was recommended & had an awesome breakfast to start the day alsoyou will enjoy this quaint private room in a quiet settingfound the space to be just as described and very comfortablethe studio is well prepared with a very cool kitchen and bedther could be more windows in the room but the mirror does a good job tooMonthly discount: 10% off
9. Bayliner boat experience in Stock Island Marina Village (from USD 1245)
This is a wonderful chance to stay in a Bayliner boat in Stock Island Marina Village. There is a queen-size bed that fits two adults and a v-berth that can accommodate another adult or two children. You will have access to the stove, microwave, and refrigerator. Feel free to use the waterfront swimming pool. You will also enjoy complimentary WiFi access, a 24-hour fitness center, and laundry facilities. It’s recommended that you head to the nearby Marina Bath House for showers and to use the bathroom.
Key West, Florida, United States
6.3 km (4.0 mi) from The Hemingway Home and MuseumAccommodates: 4
Top guest reviews
Host:
thanks to the owner for the good servicehost was easy to communicate with and prompt in responsesthe host is a super great guy who was always on handsteve was an awesome hostthe host is very quick & responsive & helped accommodate our stayLocation:
a great place to stay with close ammenitieswonderful experience beautiful boat and locationthe bath facilities are a short walk away and the perry hotel facilities are wonderfulwhat a great placethere are toilets and bathroom close by that are nice and cleanCleanliness:
very clean public bathhousesbathhouses were clean and convenientclean and quiet we didn’t use the pool but it was gorgeousclean and sufficient size for two people for a weekend stayhis boat was clean and had nice touches like fresh towels and shampoo availableRead more reviewsAmenities & Room:
great amenities with access to beautiful pools bars and restaurantsafter about 5 minutes in he was sold he’s 6’6 and actually fit great in the bedMonthly discount: 20% off
10. Homey one-bedroom apartment overlooking Duval Street (from USD 193)
This one-bedroom apartment overlooking Duval Street reminds us of home. The bedroom has a king-size bed for two persons and the common space has one sofa bed for one. Pets, infants, and children are not allowed in the property. The bathroom has a bathtub and shower with sliding doors. You will be at a walking distance to Key West Lighthouse and The Ernest Hemingway Home and Museum.
Key West, Florida, United States
284 meters (0.2 ft) from The Hemingway Home and MuseumAccommodates: 3
Top guest reviews
Host:
tom is a great hosttom was an amazing hosttom is a wonderful hosttom is a great host tootom is a great hostLocation:
great location with everything within walking distancethe location is amazingthe location is amazingbest location in key westeverything was walking distance or even better a quick bike ride awayCleanliness:
very clean & spacious for twoit was clean with beautiful decortom has some wonderful clean apartmentsthe vacation rental is very clean and spaciousbedding was very comfortable everything was clean well stocked kitchenRead more reviewsAmenities & Room:
great a/c and an upstairs patio overlooking duval st) a/c in both rooms can be controlled separately- very responsive and strongperfect location everything is provided: plenty of towels pillows coffee dishes cable & wifi and private balconybut there is a bar in front of the apartment if you want a good sleep you may need earplugsking bed and sofa bed perfect alternative to doing 2 overpriced hotel rooms further away from downtownMonthly discount: 8% off
11. Exotic getaway with modern amenities (from USD 414)
Enjoy a fun-filled tropical retreat in Key West by booking this lovely house for your long holidays. The well-furnished abode lets you stay with your entire family of five leisurely. A spectacular stone figurine of an alligator welcomes you at the entrance of this beautiful home. Have your morning breakfast on the airy outdoor deck before you head out for a day-long excursion. You can splash in the cool waters of the shared swimming pool with your kids and make memories. The house features a well-equipped kitchen to let you prepare a variety of culinary delights for meals. Stream a good movie on the large flat-screen television for your family as you relax in the living room. You can take your kids to the Florida Keys Eco-Discovery Center to show them fantastic exhibits of native animals and plants.
530 meters (0.4 ft) from The Hemingway Home and MuseumAccommodates: 5
Top guest reviews
Location:
great location in the heart of old towngreat spot awesome location pictures give a great justice of hat you're gettingRead more reviewsAmenities & Room:
comfortable rooms great family space and amenitieswe enjoyed our stay comfortable living areas air conditioning worked great (and we needed it) very walkable to everything
12. Spacious abode with a swimming pool (from USD 800)
The large three-bedroom house near Higgins Beach is the perfect option to relax during your long vacations in Key West. Beautiful outdoors and modern interiors make it an inviting haven for a long-term stay. You can start your day by going for a refreshing stroll on the landscaped lawn. The elegant outdoor swimming pool is ideal to splash in the water with your kids. You don’t have to miss homemade food, as the well-furnished kitchen is available here to let your prepare culinary delights. You can enjoy your meals together in the outdoor dining area and make memories. In the evening, you can roast a hot dog on the outdoor grill and relish it leisurely.
Key West, Florida, United States
2.02 km (1.3 mi) from The Hemingway Home and MuseumAccommodates: 6
Top guest reviews
Host:
anne & ea were excellent hostsLocation:
lovely home in an ideal location near the beachyou will love the location and ease of renting without any complicationsanne & ea’s place is greatRead more reviewsAmenities & Room:
the pool screen porch and kitchen are especially niceMonthly discount: 63% off
13. Charming haven with shared pool (from USD 309)
Make your long vacation in Key West unforgettable by reserving this elegant abode to unwind. A family or group of six individuals can enjoy a relaxing stay in this two-bedroom abode. Beautiful décor and furnishing grace the interiors of the house. Have your morning breakfast on the airy balcony as you feel the gentle breeze and watch trees sway. You do not have to miss your beloved pet, as the vacation rental is pet-welcoming with some extra fees. Enjoy your long vacations in Key West with your furry friend around. Step in the pleasant waters of the outdoor pool and feel relaxed. You can also explore nearby beaches and shopping venues.
Key West, Florida, United States
4.92 km (3.1 mi) from The Hemingway Home and MuseumAccommodates: 6
Top guest reviews
Location:
good location in terms of access to downtown and harbourit is in a great locationlocated in a quiet area of key west but easy drive to all sites and attractionsgreat location and a perfect setup for our small group tripgood location worked well for two couples with petsRead more reviewsCleanliness:
everything was very clean & quietclean with a tropical feeleverything was clean and the apartment was well-stockedthe place was very clean and we loved the poolvery clean and spacious condo great for family trips loved our stay
A mesmerizing tropical island escape
Key West is a spellbinding tropical island that boasts beautiful beaches and fabulous attractions. Kayaking, surfing, sailing, and swimming are some exciting activities that you can enjoy. Staying here for long can help you make your holidays full of fun and memories. Head out for a long vacation, and book one of these long-term rentals in the area.
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