16 Best Long-Term Rentals In Florida Keys, Florida - Updated 2022

Gabby
Gabby 
Updated

If you feel like you need some time off from your hectic daily schedule, then it might be time for you to plan your next vacation. The beach is the perfect place to unwind. If you still do not know where to go, Florida Keys has one of the most beautiful coasts in the United States, making it the perfect getaway destination. For the outdoorsy, you can visit Bahia Honda State Park and Dry Tortugas National Park, where you can enjoy outdoor activities such as swimming, fishing, and camping. If you are planning a long vacation, check out the best long-term rentals in Florida Keys, Florida, for a convenient stay.

1. Immaculate retreat in Coral Lagoon

A stay in this immaculate retreat means admiring amazing bay views all day. Located in a point lot in Coral Lagoon, Marathon, this waterfront property allows you to experience the cool breeze and views from its two covered decks and side yard where the kids can play. On its main floor, you’ll find a bright and airy living room with cable TV and Wi-Fi, a six-seater dining table, and a fully stocked kitchen. Upstairs are three coastal-themed bedrooms equipped with beds ranging from twin-size to king-size—any group of six will find it comfortable.

There’s also a community pool on-site as well as a marina with facilities such as a boat ramp, slip, and cleaning spaces for your fishing and boating adventures. Parking for three cars comes in handy during check-in and after exploring nearby beaches, restaurants, and activities in town.

3 Bed/ 2.5 Bath Home - Sleeps 6, Amazing Views, Finest Location Boat Slip!
Marathon, FL, US
6 Guests 3 Bedrooms 3 Bathrooms

2. Cozy studio in Lion's Lair community (from USD 160)

Fishing and boating enthusiasts will adore the location of this fully furnished studio in Lion’s Lair, a private community in Grassy Key, Marathon. It has access to many fishing sites, including the jetty, and a protected marina lagoon that can accommodate boats up to 25 feet (7.6 meters), with a dock fee of 15 USD per day.

During your idle days, you can simply relax in the unit’s tropical front yard that comes with a picnic table and an umbrella. Alternatively, you can hang out indoors and stream your favorite shows through the smart TV and high-speed WiFi. The air-conditioned property also has a fully equipped kitchen to help with your meal plans during your extended stay. For refreshing moments under the sun, don’t miss out on the nearby community pool.

Fully furnished studio, 50 yards from ocean, shared pool, fishing-jetty
Marathon, FL, US
studio 2 Guests 0 Bedrooms 1 Bathroom

3. "Kelly’s Cabin" in Summerland Key (from USD 275)

Come and unwind for a week or two at Kelly’s Cabin, a quiet and vibrant cottage in the sunny community of Summerland Key. The place features a serene back patio overlooking a lush mangrove area. In this outdoor space, you can prepare and enjoy your fresh catch of the day as it is equipped with a fish cleaning station, charcoal grill, and dining table. The indoor space is equally adorable as the beautifully decorated retreat offers the conveniences of a smart TV with cable services, WiFi, and a fully equipped kitchen.

There is ample parking for multiple vehicles and a boat on the property. If you wish to skip driving when touring nearby areas, you can easily take the public transportation conveniently accessible next to the cottage.

Kelly’s Kabin - Adorable Private Summerland Key Cottage
61 reviews  Wifi Available
cottage 5 Guests 1 Bedroom 1 Bathroom

Accommodates: 5
Minimum Nights: 1
Refund Policy : 100% refund if you cancel at least 30 days before check-in.

Top guest reviews
Amenities & Room:
it is roomy the kitchen is nicely renovated and the entire place well appointed
if you are looking for a great breakfast i highly recommend the galley grill
Cleanliness:
clean & comfortable place to vacation
the place was clean quiet and comfortable
really a nice clean and comfortable place
the house was very clean stocked well even for a family of 5
we spent 8 days at the spotlessly clean comfortable adorable kabin
Host:
very communicative and helpful hosts
the owners communicated with us prior to arrival so we could easily access the house
host is also great with communication
lori and tom were responsive and helpful
bahia-honda park was very nice too owners were prompt and very easy to work with
Location:
loved the location and the cabin
for us the location was perfect
great location away from crowds but close to restaurants and fishing
it was in a nice quiet location
adorable little place within in perfect driving distance to key west for our 1/2 marathon this past january
Read more reviews

4. Cottage inside a gated community (from USD 180)

Located in a secure, gated community, this two-bedroom cottage boldly states that it is a “Florida lover’s paradise”. Stay a while and relax as it features a queen-sized bed, flat-screen TV, hot tub, outdoor swimming pool, ping pong table, and a pool table. Decoration-wise, the cottage features a colorful island vibe that creates, according to the owners, a feeling of being in paradise.

Finally, the cottage is only 3.2 mi (5.1 km) from Upper Sugarloaf Key, 5.9 mi (9.4 km) from Sugarloaf Beach, 6.3 mi (10.1 km) from Cook Island, and 7.3 mi (11.7 km) from the Florida Keys Wilderness. Please note, an additional 107.50 USD is levied at the gate - this is not included in eh price nor charged by the owner.

We know you need a vacation after this year!
81 reviews
cottage 6 Guests 2 Bedrooms 1 Bathroom

Accommodates: 6
Minimum Nights: 4
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
Amenities & Room:
the main bedroom was comfortable but i wouldn’t want anyone to sleep in the back bedroom
Host:
everyone was friendly neighbors and staff
had a few questions and the owner was quick and responsive with our needs
thank you to such wonderful owners who rent out the really family friendly home to stay
i'm sure the owner felt this review coming
the community the property is on is very quiet and everyone was friendly
Location:
a great location on cudjoe key close to stores and restaurants
location is excellent not too far away from key west or marathon
the location of the property is great
Read more reviews

5. Oceanfront rental by a private beach (from USD 175)

Directly located by a private sandy beach, this one-bedroom oceanfront beach rental offers a scenic place for groups of up to eight people to enjoy a beachside vacation. The nearby sandbar proudly showcases beautiful views of the sunrise, sunset, and the Atlantic Ocean itself.

The rental features a king-sized bed, sofa bed, smart TV, DVD player, fireplace, fire pit, air conditioning, and a kitchen with a stove, blender, and oven. There are also kayaks available if you’re in the mood to swim in the ocean. Guests planning to stay for more than 28 days will be happy to know that there is a monthly discount.

Oceanfront Sandy Beach Vacation Rental Unit 1
78 reviews  Wifi Available
Apartment 8 Guests 1 Bedroom 1 Bathroom

Accommodates: 8
Minimum Nights: 7
Refund Policy :

Top guest reviews
Amenities & Room:
great ocean view and very comfortable units fully stocked with everything for a beach vacation
Cleanliness:
very clean and relaxing
the kitchen was well stocked king size bed was great all was clean and comfortable
house had everything you could possibly need and was spotlessly clean
Host:
the owner made sure you had everything you needed to have the perfect vacation
overall great property with a great owner (rhonda was great too )
Location:
it's a great location being midway to visit all of the keys and the attractions
this location is private and the views are amazing a plus was watching the iguanas
andy was very easy to work with rhonda had great ideas for things to do and places to go
we stayed overnight so we could enjoy duval street in full but the whole place is great
Read more reviews

6. Two-bedroom private house with kayaks and bikes (from USD 279)

Featuring crown molding, bamboo wood floors, and a gourmet kitchen, this two-bedroom private house offers many luxurious amenities that make a long stay worthwhile. It features a heated pool, a Tiki-hut dock, and a private sandy beach. The pool dock showcases a breathtaking view of the ocean. Inside, guests will find a 32-inch flat-screen HDTV, Bluetooth stereo system, and air conditioning. There are also two kayaks and two bicycles available for use. Additionally, guests can avail of a private boat at an additional cost.

Finally, the house is only 2.1 mi (3.3 km) from Upper Sugarloaf Sound, 5.3 mi (8.5 km) from Sugarloaf Beach, and 8.9 mi (14.3 km) from the National Key Deer Refuge Visitor Center.

Private home in the keys -POOL-Bikes-Kayaks Special pricing SAVE!
59 reviews  Wifi Available
House 6 Guests 2 Bedrooms 3 Bathrooms

Accommodates: 6
Minimum Nights: 5
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
Amenities & Room:
the house has a tank-type water heater that worked perfectly
Cleanliness:
the unit was clean and had everything needed for our stay
very clean well maintained property responsive professional property manager very good location
Host:
comfortable nicely furnished homey quiet friendly people nice pool and dock
Location:
great location and a short drive to key west
cool place great location away from crowded key west
close to a few very good restaurants and fish markets
great location just 25-30 minutes from key west nice clean & updated
Read more reviews

7. Fully furnished condo with stunning ocean views (from USD 280)

This two-bedroom unit can offer guests stunning ocean views, which you can enjoy on the balcony. Cooking will not be a problem as the kitchen is well-stocked with a microwave, coffee maker, and refrigerator. Bathroom essentials are provided in this rental for convenience. The unit has laundry facilities, so you need not worry about your dirty clothes. Guests can have access to the property’s pool and the beach. WiFi, cable TV, air conditioning, and heating are also available. The host can allow long-term bookings.

Beachfront Condo w/ Ocean Views in Marathon
73 reviews Superhost  Wifi Available
Entire rental unit 3 Beds 4 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 4

Top guest reviews
Amenities & Room:
the air conditioning was wonderful without question
wi-fi was reliable and the views of the atlantic were outstanding
we all enjoyed the screened in porch with 4 comfortable wicker chairs overlooking the ocean
the condo itself is modern spacious and has the most amazing views from the living room
mike’s place was right on the beach with fast wifi - perfect for what we needed
Cleanliness:
the condo is clean and comfortable
the condo was meticulously clean and comfortable
the place was very clean and comfortable
like the condo the pool is always spotless clear and clean
the property is clean up to date and decorated for ocean front living
Host:
mike was a great host
and the owner was very responsive to our questions and inquiries
mike is a very proactive and responsive host
mike was so helpful and easy to talk to
mike is an awesome person to work with this is why he is a "super host"
Location:
the location was outstanding
the location was perfect
even extra sunscreen the location was wonderful
we would be delighted to book this place again
very quiet and peaceful but close to anything you might need
Read more reviews
Monthly discount: 20% off

8. Comfortable cottage with amazing sunset views (from USD 126)

The property has a nice front porch where guests can sit and enjoy the ocean breeze. It has a spacious living area with a couch and a TV, a dining area, and a mini kitchen packed with the appliances needed to prepare delicious meals. The air-conditioned bedroom has a cozy queen bed that can ensure guests a good night’s rest. You can enjoy access to the beach, where you can witness fantastic sunset views. Pets are welcome to stay here for a fee. If you are planning to stay here longer, the host can allow long-term rentals.

Conchs Cove in Key Largo
Key Largo, Florida, United States
51 reviews Superhost
Entire rental unit 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
the couches and brand new tv made for a conveniently comfortable space
the space is both cute and comfortable and reminds me of staying at someone's cottage only better decorated
super comfortable - nice beds really hot water for the shower nice outdoor patio
the queen bed is nice on the softer side
Cleanliness:
cottage was very clean upon our arrival
great place very clean and cozy
when we arrived the place was spotless and smelled really good
meticulously clean friendly neighborhood
house is clean convenient and centrally located
Host:
she is an awesome host very quick to communicate and reply with any info or concerns
host is very responsive and helpful
she's helpful and professional--definitely a superhost
her friendly welcoming personality helped us make this decision for our trip down to the keys
our stay in key largo was great and kristen was a perfect host
Location:
location was perfect close to many restaurants activities and store
it was comfortable quiet and close to restaurants and attractions
the location was perfect and the house had just what we needed
it had everything you could possibly need and in such a good location
we had a great time in key largo this place was extremely convenient to everything we wanted to do
Read more reviews
Monthly discount: 25% off

9. Attractive condo with airy interiors (from USD 256)

This newly furnished condo unit can easily accommodate up to two guests, perfect for a romantic getaway. The kitchen is fully equipped to make cooking more convenient. Essentials such as beddings and towels are provided. WiFi, a Smart TV, and a sound system are in place for the guests’ entertainment needs. The condominium also has a heated pool, lounge areas, tiki huts, barbecue facilities, and a private beach. You can inform the host if you are planning to stay longer.

Keys Time Condo Oceanfront Complex Heated Pool
Key Colony Beach, Florida, United States
102 reviews Superhost  Wifi Available
Entire condo 1 Bed 2 Guests 0 Bedrooms 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
bed was very comfy and the ac worked like a dream
nice beach side area to view the water and pool to lounge in
the condo was perfect for us (a couple) and we enjoyed the private pool and beach area
the bed was very comfortable and both the kitchen and bathroom were well stocked
Cleanliness:
very clean quick with communication
very clean and spacious for two
the condo was very clean and comfortable
kimm’s place was extremely clean and welcoming
condo was very clean
Host:
kim is an awesome host
the private beach is awesome and kimm was very responsive and accurate with the details
the condo and kim were both exceptional great place to stay with wonderful host
host kimm was very responsive and thorough explaining everything regarding the location amenities check-in procedures and rules
Location:
the location is perfect to just relax or drive to key west
other benefits of the location include being nearby to marathon where we joined fishing and snorkeling tours
it was a great central location in the keys
outstanding spot that has ideal location combined with well-appointed unit
her knowledge of the area was spot on and the location was fantastic
Read more reviews
Monthly discount: 10% off

10. Two-bedroom apartment for four (from USD 232)

This home’s spacious living room is equipped with a sofa, ceiling fan, and TV with a DVD player for entertainment. The bedrooms are homey and cozy, ensuring guests a good night’s rest. The bathroom is stocked with complimentary essentials and features a double rain shower. There is a yard with additional seating and lounge areas. Other amenities include WiFi, laundry facilities, heating, air conditioning, and barbecue facilities. If you want to stay longer, you can always let the host know.

Salty Nest ~ 2 Bed/1 Bath ~ Salty Air Retreat
Marathon, Florida, United States
49 reviews Superhost  Wifi Available
Entire home 2 Beds 4 Guests 2 Bedrooms 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
super comfortable for a tech fan like myself
beautiful modern space with great amenities comfy beds and a sweet outdoor space
Cleanliness:
it was immaculately clean
it was very clean and a beautiful design
amy's place was really neat and clean and well decorated
very clean and spacious with all the appliances you need
everything is new and kept very clean
Host:
the owner was very responsive and helpful
she is a very good host as she responds back very quickly amd sort out things for you
Location:
amy’s place is located pretty central in marathon with a short drive to key west
awesome place in a great location
the house in marathon is a good central location if you want to see all the keys
this was also the perfect location as it sits in the middle of all the keys
the neighborhood was quiet and friendly
Read more reviews
Monthly discount: 44% off

11. Beautiful beach house with WiFi (from USD 148)

The interior of this home is bright, and it can accommodate up to six guests. The kitchen has a breakfast counter and is fully equipped. You can gather up in the living room to bond while watching TV. The bathroom has plenty of towels and is stocked with bathroom essentials. You can also have al fresco barbecue dinners on the spacious balcony. The newly installed pool can allow guests to have a relaxing swim after a long and tiring day. The host accepts long-term rentals.

Ocean Islamorada BeachHouse POOL!70' DOCK boatrent
Islamorada, Florida, United States
16 reviews Superhost  Wifi Available
Entire townhouse 3 Beds 6 Guests 2 Bedrooms 1 Bathroom

Accommodates: 6

Top guest reviews
Amenities & Room:
the condo is very well stocked with towels and the kitchen is a full array of supplies
Cleanliness:
fantastic location large apartment with all we needed clean modern i recommend it
Host:
and it was all possible with the help of walter our host
he was so helpful and his place is great
Location:
wonderful place in a great location
we had an amazing vacation at walter's place
Read more reviews
Monthly discount: 21% off

12. Charming apartment with a full kitchen (from USD 275)

Couples and solo travelers can enjoy a long-term stay in the charming apartment. The living room is equipped with a modern couch, allowing guests to relax. The kitchen features modern equipment such as an oven, coffee maker, stove, refrigerator, and microwave. Pots, pans, and other cooking basics are also available. The bedroom has a king-sized bed and a flat-screen TV. Other amenities include WiFi, heating, air conditioning, and free parking.

STUDIO / APARTMENT
Key West, Florida, United States
286 reviews Superhost  Wifi Available
Entire guest suite 1 Bed 3 Guests 1 Bedroom 1 Bathroom

Accommodates: 3

Top guest reviews
Amenities & Room:
comfortable apartment with all the amenities of home
two comfortable beach chairs are provided the sofa bed is large and comfortable for up to 2 (bigger) children
the bed was very comfortable the second bed is a sofa bed that did the job
very spacious floor plan with a beautiful full kitchen
bed was extremely comfortable bathroom was quite nice
Cleanliness:
very clean and had plenty of towels and pillows
very clean and quiet
very clean and modern exactly how advertised
very clean and nice place to stay
very clean and beautiful private room
Host:
beautiful place and owner was very attentive
incredible host gorgeous setting thank you
eli is definitely a great host his place is very quiet and beautiful
convenient parking right outside the door and a great host with elli
elli was so nice and helpful and was quick to respond when we had questions during our stay
Location:
very nice place conveniently located
a great place to stay close to keywest attractions
great location quiet nice in every way
great location to access the golf course
the place is also close to keywest main attractions
Read more reviews
Monthly discount: 18% off

13. Lovely apartment in the heart of Key Largo (from USD 246)

This lovely apartment for six is located in the heart of Key Largo and is perfect if you are planning to stay for a month. The living room has a large TV where you can enjoy your favorite TV shows. The kitchen is fully equipped with a microwave, refrigerator, and coffee maker. Each room has tasteful decorations that can make you feel at home. Beddings and toiletries are available for convenience. Guests can have access to the pool and other recreational areas. Restaurants, bars, and other nightlife establishments are within walking distance.

Key Largo, Florida - Gem by the Sea
37 reviews Superhost  Wifi Available
Entire rental unit 2 Beds 5 Guests 2 Bedrooms 1 Bathrooms

Accommodates: 5

Top guest reviews
Amenities & Room:
we particularly loved the balcony and the views the kitchen is very well stocked and organized
location is very good with gorgeous views beautiful property and pool
Cleanliness:
apartment was clean and comfortable
the condo was impeccably clean and inviting
the apartment super clean and nicely decorated
very clean and it smelled good everytime we walked in very safe place to stay
the condo was spacious clean and we were not wanting for anything
Host:
wonderful space with a thoughtful host
diana was very communicative and provided very detailed instructions to help make our stay enjoyable
diana was very nice and responsive the entire trip
communication with the host was quick and easy
hosts were very responsive with codes etc
Location:
great location in key largo
very close to a very nice winn dixie
location was really great with close proximity to all attractions in key largo and easy access to miami
lovely condo in a good location in key largo situated on a nice property
walking distance to some great ocean-side restaurants
Read more reviews
Monthly discount: 35% off

14. Bayside apartment in a peaceful setting

The view of the gardens outside can be enjoyed from any room in this apartment. It has a mini kitchen that is equipped with a refrigerator, coffee-making facilities, microwave, stove, and rice cooker. The bedroom can allow guests to enjoy a good night’s rest, with a comfortable queen-sized bed. Bed linens, towels, toiletries, and other essentials are available for the guests’ convenience. The unit has a reading nook with bookshelves full of interesting books and a comfortable seating area. The patio offers cozy seating as well, so you can enjoy your morning coffee while you marvel at the views. The host can allow long-term rentals.

Garden apartment in unique setting
Islamorada, Florida, United States
33 reviews
Entire apartment 2 Beds 1 Bedroom 1 Bathroom
Top guest reviews
Amenities & Room:
the apartment was lovely with a small but private beach
Cleanliness:
very clean and so quiet
beautiful calm clean and inviting
great quiet stylish clean
the apartment was super clean and surprisingly large
the place was great super comfortable clean and beautiful touches throughout the place
Host:
nice host who accommodated our checkin changes graciously
she was a thoughtful host and i highly recommend a stay in her rental
hosts are incredibly friendly and accommodating but give you your space
our interactions were limited but the host is very nice
the owners are wonderful and we’ll never forget those fruit tarts they made for us
Location:
this is a great place for many reasons
great location and super value for a visit to all the keys
great value and a wonderful quiet isolated spot
lovely spot in islamorada beautiful place and close to all the local amenities
very nice location and the owners are awesome
Read more reviews

15. Relaxing oceanfront home with a dock

You can witness breathtaking sunsets every day when you stay in this oceanfront home that is suitable for family outings. With plenty of seating areas inside and outside the home, you and your family can enjoy some fun family bonding. The living room has a wide flat-screen TV and a couch. The kitchen is fully equipped, which makes preparing meals for the whole family easier. The bedrooms are supplied with essential beddings. The bathroom is clean and is well-stocked with toiletries. Snorkeling, fishing, and boating are some of the most enjoyable activities here. You can inform the host if you are planning to stay longer.

Florida Keys Waterfront Paradise
Long key, Florida, United States
15 reviews
Entire house 4 Beds 2 Bedrooms 2 Bathrooms
Top guest reviews
Amenities & Room:
nice little gated community also with pool basketball courts small playground mini-market
Cleanliness:
a very nice clean quiet cozy place on the water
Host:
jorge was a great host and was easy to get into contact with
even the neighbors were warm and friendly we will definitely be back
Location:
the location of this property is magical the property itself is stylish and well equipped
Read more reviews

16. One-bedroom apartment with free parking

This one-bedroom apartment is located on the third floor of a lovely home and can be rented long-term. Homemade meals can easily be prepared in the mini kitchen as it is equipped with a refrigerator, stovetop, microwave, and coffee maker. The roomy living area has a flat-screen cable TV, a sofa bed, comfortable cushioned chairs, and a small table. The bedroom’s queen bed is cozy and perfect for resting after a long day outside. The clean bathroom is stocked with towels, toiletries, and other bathroom essentials.

The Lookout
Big Pine Key, Florida, United States
7 reviews Superhost  Wifi Available
Entire cottage 2 Beds 4 Guests 1 Bedroom 1 Bathroom

Accommodates: 4

Top guest reviews
Cleanliness:
the room is excellent the ac is cool shower has great pressure and everything is clean and tidy
Host:
fantastic hosts made us feel like old friends
Read more reviews

Have a relaxing stay in Florida Keys

With stunning beaches, Florida Keys is a great destination. It offers plenty of outdoor opportunities that tourists will surely want to take advantage of. If you are planning to stay here for a month or more, you can refer to this list of the best long-term rentals in Florida Keys, Florida.

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

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