Top 10 Long-Term Rentals In Key West, Florida

long term rentals key west

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.

1. Spacious abode with a swimming pool (from USD 550)

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.

Forever Gem in Key West with outdoor Swimming Pool
Key West, Florida, United States
8 reviews  Wifi Available
Entire residential home 4 Beds 6 Guests 3 Bedrooms 1 Bathroom

Accommodates: 6

Top guest reviews
Amenities & Room:
the pool screen porch and kitchen are especially nice
anne & ea were excellent hosts
lovely home in an ideal location near the beach
you will love the location and ease of renting without any complications
anne & ea’s place is great
Read more reviews
Monthly discount: 63% off

2. Cozy home for a long-term stay (from USD 167)

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.

Historic Caroline St. w/Pool Dog-Friendly Sleeps 3
Key West, Florida, United States
8 reviews Superhost  Wifi Available
Entire rental unit 1 Bed 3 Guests 1 Bedroom 1 Bathroom

Accommodates: 3

Top guest reviews
lindsay is thoughtful host and responds quickly if you need anything
Read more reviews
Monthly discount: 10% off

3. Well-furnished bolthole with garden views (from USD 130)

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.

Old Town Key West Garden Apartment
Key West, Florida, United States
100 reviews  Wifi Available
Entire rental unit 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
the bicycles at the apartment were very useful
the bed was very comfortable and the deck and garden were beautiful
the apartment is cool slightly bohemian as much of key west
accommodation as described and very comfortable
we had a wonderful time in key west in large part to the ease and convenience of nicholas's apartment
the house was very clean and cozy
lights were on a/c had apartment comfortable towels were out generally environment was clean quiet and very private
the place was really cute and clean and had a beautiful back garden
the bed was really comfortable and the room was clean
the apartment was clean cozy and close to the center
our host nicholas made us feel very welcome
he was polite and kind and was eager to answer any questions we had
nicholas was a great host
nicholas was the perfect host
nicholas was the most wonderful host
what a great location
the location was perfect and a short bike to duval street
the location is close to everything and very comfortable
i very much enjoyed the ability to walk or ride a bike to everything
also very to close to multiple good restaurants and a bike rental place
Read more reviews
Monthly discount: 15% off

4. Beautiful townhouse with butterfly garden views (from USD 105)

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.

A Slice of Heaven
Key West, Florida, United States
21 reviews Superhost  Wifi Available
Entire townhouse 3 Beds 4 Guests 2 Bedrooms 1 Bathrooms

Accommodates: 4

Top guest reviews
Amenities & Room:
also the swimming pools are a pleasant addition to the complex
the home is clean and well appointed
the apartment was perfectly clean and had everything we needed for our whole stay
a real treat matt was our host & is awesome
he was a terrific host
great location close to everything without the noise
it’s great to be so close to key west but in a peaceful quiet location
good location pleasant surroundings easy access to airport easy availability to pool greatly equipped kitchen and great hosts
great place walking distance to the golf course clean close to the pool
we enjoyed the peaceful and beautiful location along with the warm swimming pool
Read more reviews
Monthly discount: 15% off

5. Charming haven with shared pool (from USD 389)

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.

Cozy, dog-friendly suite with balcony, shared hot tub/pool, and private parking!
39 reviews  Wifi Available
Entire condominium (condo) 3 Beds 6 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 6

Top guest reviews
everything was very clean & quiet
clean with a tropical feel
everything was clean and the apartment was well-stocked
the place was very clean and we loved the pool
very clean and spacious condo great for family trips loved our stay
good location in terms of access to downtown and harbour
it is in a great location
located in a quiet area of key west but easy drive to all sites and attractions
great location and a perfect setup for our small group trip
good location worked well for two couples with pets
Read more reviews

6. Exotic getaway with modern amenities (from USD 535)

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.

Key West home w/shared pool and just steps from historic Old Town
9 reviews  Wifi Available
Entire townhouse 4 Beds 5 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 5

Top guest reviews
Amenities & Room:
comfortable rooms great family space and amenities
we enjoyed our stay comfortable living areas air conditioning worked great (and we needed it) very walkable to everything
great location in the heart of old town
great spot awesome location pictures give a great justice of hat you're getting
Read more reviews

7. Beachside condominium with a huge pool (from USD 406)

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 Beachside 1400sf, 2 Bedroom Condo
Key West, Florida, United States
87 reviews Superhost  Wifi Available
Entire rental unit 2 Beds 6 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 6

Top guest reviews
Amenities & Room:
loved the pool area with ocean views and sandy beach steps away
beautiful property with lush courtyard and a fantastic large pool
nice pool area secure lush garden courtyard and quiet
lots of room big balcony clean close to beach
loved the sliding doors from each bedroom and living room to the patio
the condo was very clean and spacious
clean rooms and well furnished
very nice clean and roomy
clean comfortable highly recommend
great clean place in key west
very good management service with quick and informative answers
this host was very responsive and helpful
wonderful hosts and a great private 2 bedroom condo
we definitely recommend peggy and jim as hosts they were very courteous and quick to answer any questions
jim and peggy are excellent hosts and so easy to reach
very comfortable close to everything
great place near higgs beach
the location was beautiful close to duval street but far enough away to be quiet and private
place was great perfect location
excellent location and great pool and gym
Read more reviews
Monthly discount: 12% off

8. Lavish retreat with captivating water views (from USD 439)

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.

22 reviews Superhost  Wifi Available
Entire condominium (condo) 4 Beds 8 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 8

Top guest reviews
Amenities & Room:
amazing spacious apartment with fabulous views and great amenities
we felt comfortable and felt at home with all of the amenities provided
beautiful condo and super clean
the place was sparkling clean and had a full ocean view from every room
shannon made our trip i travel a lot and have never had someone so helpful
beautiful place and spot you can't beat it we'll worth the money
Read more reviews

9. Magnificent paradise with a private deck (from USD 401)

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.

Cozy dog-friendly condo w/ shared pool, hot tub, private deck, and parking
53 reviews  Wifi Available
Entire condominium (condo) 3 Beds 6 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 6

Top guest reviews
Amenities & Room:
the sofa bed was surprisingly comfortable too
like it was cooler outside of the pool than actually in it
the beds were super comfortable and the kitchen with full size appliances and barstool seating was nice
the pool was great and where we spent most of our days
the pool was so hot it felt like swimming in urine
everything was clean inside
clean spacious quiet
easy check in clean & comfortable
the apartment is excellent - very clean and nicely set up
bathrooms very clean and kitchen well supplied great communication with host
we would definitely stay again the host emails you check in instructions that are easy to follow
communication with the host was excellent
great location away from down town key west
the place that we stayed in was so cute and gave such an island feel
very good place to relax
Read more reviews

10. Pleasant apartment for families (from USD 390)

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.

Old Town Suites - 2 Bedroom Suite #2
141 reviews  Wifi Available
Entire rental unit 2 Beds 6 Guests 2 Bedrooms 1 Bathroom

Accommodates: 6

Top guest reviews
Amenities & Room:
the sitting room is a good size with comfortable furniture
great amenities spacious and super clean two bedroom apartment scooter rentals and cvs right across the street
beds were comfortable
this apartment was perfect for two couples visiting key west for a wedding
comfortable space and beds with a great kitchen
unit was very clean and spotless
very clean and convenient
very clean and comfortable apartment
very clean and spacious suite
the house was clean the linens were clean and smelled fresh
the host was wonderful
hosts were very nice and quick to reply
host was very responsive and accommodating
hosts were very accomodating and responsive
the owner was great with letting us store the luggage prior to check in
great location and overall experience
great location right off duval
great place and location on the "duval strip"
great location right in the heart of downtown
location is great; out of the hustle and bustle but close to everything
Read more reviews
Monthly discount: 54% off

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.

Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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Manjiri Kochrekar is a travel blogger from India. She loves exploring and learning various destinations, their history, culture, and peculiarities. Writing is her passion, which means she enjoys...Read more

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