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.
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 April 09, 2024.
1. Spacious abode with a swimming pool
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
Amenities & Room:
the pool screen porch and kitchen are especially niceHost:
anne & ea were excellent hostsRead more reviewsLocation:
lovely home in an ideal location near the beachyou will love the location and ease of renting without any complicationsanne & ea’s place is great
2. Cozy home for a long-term stay (from USD 350)
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.
Top guest reviews
Read more reviewsHost:
lindsay is thoughtful host and responds quickly if you need anythingMonthly discount: 10% off
Superhost
3. Well-furnished bolthole with garden views (from USD 85)
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.
Top guest reviews
Amenities & 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 apartmentCleanliness:
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 centerHost:
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 hostRead more reviewsLocation:
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 placeMonthly discount: 15% off
4. Beautiful townhouse with butterfly garden views (from USD 125)
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.
Top guest reviews
Amenities & Room:
also the swimming pools are a pleasant addition to the complexCleanliness:
the home is clean and well appointedthe apartment was perfectly clean and had everything we needed for our whole stayRead more reviewsLocation:
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 poolMonthly discount: 15% off
5. Charming haven with shared pool (from USD 276)
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.
Top guest reviews
Cleanliness:
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 stayRead more reviewsLocation:
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 pets
6. Beachside condominium with a huge pool (from USD 556)
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.
Top guest reviews
Amenities & 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 patioCleanliness:
the condo was very clean and spaciousclean rooms and well furnishedvery nice clean and roomyclean comfortable highly recommendgreat clean place in key westHost:
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 reachRead more reviewsLocation:
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 gymMonthly discount: 12% off
7. Magnificent paradise with a private deck (from USD 279)
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.
Top guest reviews
Amenities & 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 urineCleanliness:
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 hostHost:
we would definitely stay again the host emails you check in instructions that are easy to followcommunication with the host was excellentRead more reviewsLocation:
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 relax
8. Pleasant apartment for families (from USD 574)
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.
Top guest reviews
Amenities & 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 kitchenCleanliness:
unit was very clean and spotlessvery clean and convenientvery clean and comfortable apartmentvery clean and spacious suitethe house was clean the linens were clean and smelled freshHost:
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 inRead more reviewsLocation:
great location and overall experiencegreat location right off duvalgreat 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 everythingMonthly discount: 54% off
9. Exotic getaway with modern amenities
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
Amenities & 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 everythingRead more reviewsLocation:
great location in the heart of old towngreat spot awesome location pictures give a great justice of hat you're getting
10. Lavish retreat with captivating water views (from USD 329)
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.
Top guest reviews
Amenities & Room:
amazing spacious apartment with fabulous views and great amenitieswe felt comfortable and felt at home with all of the amenities providedCleanliness:
beautiful condo and super cleanthe place was sparkling clean and had a full ocean view from every roomHost:
shannon made our trip i travel a lot and have never had someone so helpfulRead more reviewsLocation:
beautiful place and spot you can't beat it we'll worth the money
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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