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
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-jettyMarathon, FL, US
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 CottageAccommodates: 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 appointedif you are looking for a great breakfast i highly recommend the galley grillCleanliness:
clean & comfortable place to vacationthe place was clean quiet and comfortablereally a nice clean and comfortable placethe house was very clean stocked well even for a family of 5we spent 8 days at the spotlessly clean comfortable adorable kabinHost:
very communicative and helpful hoststhe owners communicated with us prior to arrival so we could easily access the househost is also great with communicationlori and tom were responsive and helpfulbahia-honda park was very nice too owners were prompt and very easy to work withRead more reviewsLocation:
loved the location and the cabinfor us the location was perfectgreat location away from crowds but close to restaurants and fishingit was in a nice quiet locationadorable little place within in perfect driving distance to key west for our 1/2 marathon this past january
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!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 bedroomHost:
everyone was friendly neighbors and staffhad a few questions and the owner was quick and responsive with our needsthank you to such wonderful owners who rent out the really family friendly home to stayi'm sure the owner felt this review comingthe community the property is on is very quiet and everyone was friendlyRead more reviewsLocation:
a great location on cudjoe key close to stores and restaurantslocation is excellent not too far away from key west or marathonthe location of the property is great
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 1Accommodates: 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 vacationCleanliness:
very clean and relaxingthe kitchen was well stocked king size bed was great all was clean and comfortablehouse had everything you could possibly need and was spotlessly cleanHost:
the owner made sure you had everything you needed to have the perfect vacationoverall great property with a great owner (rhonda was great too )Read more reviewsLocation:
it's a great location being midway to visit all of the keys and the attractionsthis location is private and the views are amazing a plus was watching the iguanasandy was very easy to work with rhonda had great ideas for things to do and places to gowe stayed overnight so we could enjoy duval street in full but the whole place is great
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!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 perfectlyCleanliness:
the unit was clean and had everything needed for our stayvery clean well maintained property responsive professional property manager very good locationHost:
comfortable nicely furnished homey quiet friendly people nice pool and dockRead more reviewsLocation:
great location and a short drive to key westcool place great location away from crowded key westclose to a few very good restaurants and fish marketsgreat location just 25-30 minutes from key west nice clean & updated
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 MarathonSuperhost
Accommodates: 4
Top guest reviews
Amenities & Room:
the air conditioning was wonderful without questionwi-fi was reliable and the views of the atlantic were outstandingwe all enjoyed the screened in porch with 4 comfortable wicker chairs overlooking the oceanthe condo itself is modern spacious and has the most amazing views from the living roommike’s place was right on the beach with fast wifi - perfect for what we neededCleanliness:
the condo is clean and comfortablethe condo was meticulously clean and comfortablethe place was very clean and comfortablelike the condo the pool is always spotless clear and cleanthe property is clean up to date and decorated for ocean front livingHost:
mike was a great hostand the owner was very responsive to our questions and inquiriesmike is a very proactive and responsive hostmike was so helpful and easy to talk tomike is an awesome person to work with this is why he is a "super host"Read more reviewsLocation:
the location was outstandingthe location was perfecteven extra sunscreen the location was wonderfulwe would be delighted to book this place againvery quiet and peaceful but close to anything you might needMonthly 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 LargoKey Largo, Florida, United StatesAccommodates: 2
Top guest reviews
Amenities & Room:
the couches and brand new tv made for a conveniently comfortable spacethe space is both cute and comfortable and reminds me of staying at someone's cottage only better decoratedsuper comfortable - nice beds really hot water for the shower nice outdoor patiothe queen bed is nice on the softer sideCleanliness:
cottage was very clean upon our arrivalgreat place very clean and cozywhen we arrived the place was spotless and smelled really goodmeticulously clean friendly neighborhoodhouse is clean convenient and centrally locatedHost:
she is an awesome host very quick to communicate and reply with any info or concernshost is very responsive and helpfulshe's helpful and professional--definitely a superhosther friendly welcoming personality helped us make this decision for our trip down to the keysour stay in key largo was great and kristen was a perfect hostRead more reviewsLocation:
location was perfect close to many restaurants activities and storeit was comfortable quiet and close to restaurants and attractionsthe location was perfect and the house had just what we neededit had everything you could possibly need and in such a good locationwe had a great time in key largo this place was extremely convenient to everything we wanted to doMonthly 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 PoolKey Colony Beach, Florida, United StatesAccommodates: 2
Top guest reviews
Amenities & Room:
bed was very comfy and the ac worked like a dreamnice beach side area to view the water and pool to lounge inthe condo was perfect for us (a couple) and we enjoyed the private pool and beach areathe bed was very comfortable and both the kitchen and bathroom were well stockedCleanliness:
very clean quick with communicationvery clean and spacious for twothe condo was very clean and comfortablekimm’s place was extremely clean and welcomingcondo was very cleanHost:
kim is an awesome hostthe private beach is awesome and kimm was very responsive and accurate with the detailsthe condo and kim were both exceptional great place to stay with wonderful hosthost kimm was very responsive and thorough explaining everything regarding the location amenities check-in procedures and rulesRead more reviewsLocation:
the location is perfect to just relax or drive to key westother benefits of the location include being nearby to marathon where we joined fishing and snorkeling toursit was a great central location in the keysoutstanding spot that has ideal location combined with well-appointed unither knowledge of the area was spot on and the location was fantasticMonthly 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 RetreatMarathon, Florida, United StatesAccommodates: 4
Top guest reviews
Amenities & Room:
super comfortable for a tech fan like myselfbeautiful modern space with great amenities comfy beds and a sweet outdoor spaceCleanliness:
it was immaculately cleanit was very clean and a beautiful designamy's place was really neat and clean and well decoratedvery clean and spacious with all the appliances you needeverything is new and kept very cleanHost:
the owner was very responsive and helpfulshe is a very good host as she responds back very quickly amd sort out things for youRead more reviewsLocation:
amy’s place is located pretty central in marathon with a short drive to key westawesome place in a great locationthe house in marathon is a good central location if you want to see all the keysthis was also the perfect location as it sits in the middle of all the keysthe neighborhood was quiet and friendlyMonthly 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 boatrentIslamorada, Florida, United StatesAccommodates: 6
Top guest reviews
Amenities & Room:
the condo is very well stocked with towels and the kitchen is a full array of suppliesCleanliness:
fantastic location large apartment with all we needed clean modern i recommend itRead more reviewsHost:
and it was all possible with the help of walter our hosthe was so helpful and his place is greatMonthly 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 / APARTMENTKey West, Florida, United StatesAccommodates: 3
Top guest reviews
Amenities & Room:
comfortable apartment with all the amenities of hometwo comfortable beach chairs are provided the sofa bed is large and comfortable for up to 2 (bigger) childrenthe bed was very comfortable the second bed is a sofa bed that did the jobvery spacious floor plan with a beautiful full kitchenbed was extremely comfortable bathroom was quite niceCleanliness:
very clean and had plenty of towels and pillowsvery clean and quietvery clean and modern exactly how advertisedvery clean and nice place to stayvery clean and beautiful private roomHost:
beautiful place and owner was very attentiveincredible host gorgeous setting thank youeli is definitely a great host his place is very quiet and beautifulconvenient parking right outside the door and a great host with ellielli was so nice and helpful and was quick to respond when we had questions during our stayRead more reviewsLocation:
very nice place conveniently locateda great place to stay close to keywest attractionsgreat location quiet nice in every waygreat location to access the golf coursethe place is also close to keywest main attractionsMonthly 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 SeaAccommodates: 5
Top guest reviews
Amenities & Room:
we particularly loved the balcony and the views the kitchen is very well stocked and organizedlocation is very good with gorgeous views beautiful property and poolCleanliness:
apartment was clean and comfortablethe condo was impeccably clean and invitingthe apartment super clean and nicely decoratedvery clean and it smelled good everytime we walked in very safe place to staythe condo was spacious clean and we were not wanting for anythingHost:
wonderful space with a thoughtful hostdiana was very communicative and provided very detailed instructions to help make our stay enjoyablediana was very nice and responsive the entire tripcommunication with the host was quick and easyhosts were very responsive with codes etcRead more reviewsLocation:
great location in key largovery close to a very nice winn dixielocation was really great with close proximity to all attractions in key largo and easy access to miamilovely condo in a good location in key largo situated on a nice propertywalking distance to some great ocean-side restaurantsMonthly 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 settingIslamorada, Florida, United StatesTop guest reviews
Amenities & Room:
the apartment was lovely with a small but private beachCleanliness:
very clean and so quietbeautiful calm clean and invitinggreat quiet stylish cleanthe apartment was super clean and surprisingly largethe place was great super comfortable clean and beautiful touches throughout the placeHost:
nice host who accommodated our checkin changes graciouslyshe was a thoughtful host and i highly recommend a stay in her rentalhosts are incredibly friendly and accommodating but give you your spaceour interactions were limited but the host is very nicethe owners are wonderful and we’ll never forget those fruit tarts they made for usRead more reviewsLocation:
this is a great place for many reasonsgreat location and super value for a visit to all the keysgreat value and a wonderful quiet isolated spotlovely spot in islamorada beautiful place and close to all the local amenitiesvery nice location and the owners are awesome
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 ParadiseLong key, Florida, United StatesTop guest reviews
Amenities & Room:
nice little gated community also with pool basketball courts small playground mini-marketCleanliness:
a very nice clean quiet cozy place on the waterHost:
jorge was a great host and was easy to get into contact witheven the neighbors were warm and friendly we will definitely be backRead more reviewsLocation:
the location of this property is magical the property itself is stylish and well equipped
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 LookoutBig Pine Key, Florida, United StatesAccommodates: 4
Top guest reviews
Cleanliness:
the room is excellent the ac is cool shower has great pressure and everything is clean and tidyRead more reviewsHost:
fantastic hosts made us feel like old friends
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.
Get Trip101 in your inbox
Unsubscribe in one click. See our privacy policy for more information on how we use your data
Create an account to bookmark our articles, like local expert tips, receive great stories in your inbox, and follow writers and topics that you love.
Log in with Facebook Log in with Twitter Log in with Google ×