Top 9 Cottages For Rent In Florida Keys, Florida - Updated 2024

Charisse
Charisse 
Updated
| 5 min read

The Florida Keys, an archipelago of 800 islands, is the ultimate summer destination. Diving in John Pennekamp Coral Reef State Park to see its amazing marine life is a must. A snorkeling trip to Bahia Honda State Park or a boat tour of Dry Tortugas National Park are also crowd favorites. If you’re visiting with kids, the city of Marathon is the perfect place for you. It has a Turtle Hospital and Dolphin Research Center with hands-on activities for children of all ages. For couples, a romantic sunset cruise in Key West is a great way to spend their evening. Meanwhile, solo travelers will love strolling through the galleries, museums, and cafes on Duval Street. Read on for the top cottages for rent in Florida Keys, Florida.

We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on March 12, 2024.

1. Cozy cottage with a private dock, Islamorada (from USD 225)

Featuring a private boat dock and ramp, four bicycles, and four kayaks, this waterfront cottage is a perfect summer holiday home. It also has a barbecue grill and a picnic table, perfect for an outdoor get-together with friends and family.

The cottage comes with one bedroom and one bathroom and can sleep up to four guests. The interiors are newly renovated and feature a kitchen with stainless steel appliances and a living room with a flat-screen TV. Wi-Fi and air conditioning are also provided.

Stayed at this property?
Islamorada, Florida, United States
70.37 km (43.8 mi) from Bahia Honda State Park
cottage 1 Bedroom 1 Bathroom

Top guest reviews
Amenities & Room:
Downstairs is one bedroom upstairs
pretty much anything you need
Having a large truck also made it difficult to back boat to slip due to one palm tree which is in line with boat slip
There is a full size kitchen and a washer/dryer
but is was our own private paradise
Cleanliness:
Everything was clean and well maintained
The property was very clean spacious and provided everything we needed for our relaxing vacation
Loved our stay so clean and well kept
Was newly renovated clean and smelled amazing
The view and location was awesome and secure The property provide a large boat dock and slip which we were excited about
Host:
Carmen was awesome to work with Always very quick to respond to any questions
They answered all our questions very quick
They are the absolute best genuine people we have met :)
We spoke with Carmen and the neighbors both very nice and welcoming
's since she also has a boat ramp
Location:
it has everything you need and in a great location
Islamorada is a beautiful area with delicious restaurants and lots of shops
The owners Carmen and Pablo are very nice people
We're in the keys 3 to 4 times a year and this place has become our first pick
The location is perfect Easy access to the marinas for fishing charters and other attractions Carmen and Pablo
Read more reviews
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2. Homely cottage with a balcony and back porch, Marathon (from USD 525)

Guests will love the views of the sunset from the spacious balcony and back porch of this waterfront cottage. Guests don’t have to bring any gear with them to fully enjoy the place as the rental comes with free use of kayaks, a ComPac sailboat, and bicycles. Inside, you’ll find comfy furnishings, quirky motifs and art, giving the space a homely vibe.

Ideal for up to eight guests, the cottage offers four bedrooms and two bathrooms. Guests can prepare delectable meals in the fully equipped kitchen and spend quality time together in the living room with a flat-screen TV. Wi-Fi and air conditioning are also provided.

Stayed at this property?
Marathon, Florida, United States
39.61 km (24.7 mi) from Bahia Honda State Park
24 reviews   Superhost Wifi Available
Entire cottage 4 Beds 8 Guests 4 Bedrooms 2 Bathrooms

Accommodates: 8

Top guest reviews
Amenities & Room:
terrific location beds were comfy and the small island vibe is terrific
Host:
love this place adorable comfortable friendly hosts
barry jim and pam are the most thoughtful and kind hosts i have ever encountered
Location:
awesome weekend very convenient location
sailboats if you like come with the place
Read more reviews

3. Paggit House, Key West (from USD 935)

If you’re looking for a home away from home experience, then this three-bedroom, two-bathroom house with a white picket fence is perfect for you. The house is located smack dab in the middle of Old Town, so a stay here will put you within easy reach of local attractions, including Duval Street, South Beach, and Mallory Square.

The rental sleeps up to six guests and comes with a full kitchen for home cooking, a cozy living room with a flat-screen TV, and a spacious dining room. You will be charmed by the outdoor space as it offers a swimming pool that is ideal for a relaxing dip and a patio with a barbecue grill, which is a perfect spot for alfresco dining.

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56.21 km (35.0 mi) from Bahia Honda State Park
121 reviews   Wifi Available
cottage 6 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 6
Minimum Nights: 1
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
Amenities & Room:
the a/c worked very well
plenty of room with good internet
also for the price of our stay we expected more comfortable mattresses
the rooms are all large and fit my family and the pack n play we brought
Cleanliness:
very clean and was as described in advertisements
reviewer comments: incredible home and very clean
home is older but everything was clean and in working condition
Host:
rating details: the property manager was very helpful
rating details: the property manager was very helpful
rating details: the property manager was very helpful
rating details: the property manager was very helpful
rating details: the property manager was very helpful
Location:
this is a great property close to everything
location location location perfect house for 3 couples
reviewer comments: perfect property for 6 adults and within walking distance to many great locations
what a great trip and a perfect place to stay
the house was definitely walking distance to most attractions (including duval st
Read more reviews
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4. Waterfront cottage with a large deck, Marathon (from USD 170)

Ideal for a small group, this one-bedroom cottage can sleep four guests. It comes with a fully equipped kitchen, a living room with a flat-screen TV and Netflix, brand-new furniture, a washer and dryer, and Wi-Fi, making it perfect for long-term stays.

Guests staying here will love hanging out on the spacious deck overlooking the channel. They can also bring their boat as the rental has its own dock. For recreation, Sombrero Beach is only 4 miles (6.4 kilometers) away. It’s a great spot for snorkeling, fishing, and lounging on the sandy shores.

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21.73 km (13.5 mi) from Bahia Honda State Park
53 reviews   Wifi Available
cottage 4 Guests 1 Bedroom 1 Bathroom

Accommodates: 4
Minimum Nights: 7
Refund Policy : 100% refund if you cancel at least 30 days before check-in.

Top guest reviews
Amenities & Room:
we enjoyed the comfortable seashore themed ambience
we enjoyed the screened in porch with the couch and dining table
also the back patio is very spacious and comfortable
Cleanliness:
very clean and updated
very clean and neat
perfect clean comfortable couldn’t of been better
the property was very clean and we'll stocked
it was clean comfortable and well stocked
Host:
the owners have done an excellent job in a recent remodel
very responsive with any questions about our stay
we really enjoyed the kayaks and stand up paddle board the owner was very nice to work with
i would highly recommend staying at this house the owners were great and the location was perfect
the owners were always available we had more than we needed we wish we could’ve stayed longer
Location:
great location that's close to everything
great location in the middle of marathon
perfect location and great accommodations
great central location and nice quiet street
stores close by and plenty of very nice dinning places
Read more reviews
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5. Well-furnished cottage for couples, Key Largo

This cozy cottage is a good choice for couples who want to spend a romantic time together. It offers a great vantage point for beautiful sunsets and is also located close to “the diving capital of the world,” John Pennekamp Coral Reef State Park. Guests also have access to the community amenities, such as a heated pool, a tennis court, and a basketball court.

For date nights, couples will be happy to know that there are fantastic local restaurants nearby. The cottage offers one bedroom and one bathroom. A full kitchen, a flat-screen TV, air conditioning, a washer and dryer, and Wi-Fi are provided as well.

Stayed at this property?
Key Largo, Florida, United States
97.01 km (60.3 mi) from Bahia Honda State Park
69 reviews   Wifi Available
Entire cottage 2 Beds 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
a well stocked kitchen (including coffee and spices) and an awesome air conditioner
the cottage was very updated and modern while being home like and cozy
the pictures are accurate and there are comfortable beds nice sheets and fluffy towels
the tv in the living room is large and easy to use
the place is very well stocked with basic kitchen and bathroom supplies
Cleanliness:
this place was outstanding it was as clean as clean could be
great communication very clean had a wonderful time in key largo
we really appreciated the cleanliness and beauty of the place
the place was spotless and highly comfortable
this place is clean cozy and a great value
Host:
all resort staff were friendly and helpful
the owner did everything he could to help me and he checked in with me frequently
wonderful totally enjoyed our stay and the host was great
thank you so much eric for being such a great host
eric was a very helpful and gracious host
Location:
great restaurants close by too
this place is close to a lot of great restaurants and dive centers
this is a great place for location access to a pool golf-carting around and a friendly cuban neighborhood
a wonderful place to stay with so many extras available
this place is amazing bottle of chilled wine upon arrival with a cute note welcoming you
Read more reviews

6. Spacious cottage with harbor views, Marathon (from USD 429)

This three-bedroom cottage has everything you need for a fulfilling and relaxing vacation in the Florida Keys. Situated in the Village at Hawks Cay on Sunset Drive, it offers stunning views of Tom’s Harbor and Duck Key. The cottage is spacious enough to host up to eight guests.

The living room has glass sliding doors and windows that welcome bags of natural light, giving it a bright and airy feel. You can also enjoy movie nights in the living room that comes with a 52-inch TV and surround sound system. When you get peckish, you can cook delicious meals in the full kitchen and enjoy it outside on the back patio.

Stayed at this property?

36.82 km (22.9 mi) from Bahia Honda State Park
154 reviews   Wifi Available
cottage 8 Guests 3 Bedrooms 3 Bathrooms

Accommodates: 8
Minimum Nights: 3
Refund Policy : 100% refund if you cancel at least 30 days before check-in.

Top guest reviews
Amenities & Room:
beautiful view comfy beds kitchen equipped wonderful place to rent
the only issue was the toilet in the master bedroom upstairs ran pretty much the whole trip
the 3 bed 3 bath was perfect for 3 couples
the bedroom with the one queen size bed is pretty tight but still comfortable
we all were comfortable and had space to have some alone time when needed
Cleanliness:
clean and well appointed condo
very clean and welcoming
everything was really clean & well equipped
very nice house clean modern and well kept
very clean throughout beautiful views
Host:
the owner was very responsive
property owner was easy to work with
very good communication from the owner and very easy to work with
Read more reviews
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7. Charming oceanfront cottage for six, Cudjoe Key (from USD 570)

Featuring ocean-themed décor and aqua tones, this homely and charming cottage is perfect for families. It has two bedrooms and can accommodate up to six people. Complimentary kayaks and bikes are also graciously provided by the hosts. Guests don’t have to go far to access the water as the property is directly located on the dock.

The cottage also has two bathrooms, a full kitchen with modern appliances and a breakfast bar, a cozy living room with beautiful sea views, and a washer and dryer for your laundry needs. HDTVs and Wi-Fi are also available for indoor entertainment.

Stayed at this property?
Cudjoe Key, Florida, United States
21.92 km (13.7 mi) from Bahia Honda State Park
125 reviews   Superhost Wifi Available
Entire cottage 3 Beds 6 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 6

Top guest reviews
Amenities & Room:
fantastic views beautiful kitchen and comfortable beds
beautiful view nice pool and swimming area
community pool was great and looked like it was recently re done
Cleanliness:
on-site pool was clean and local community was friendly
great place to stay very nice and clean
wish they weren't so on top of each other but everything was awesome clean and better than expected
beautiful sunrises lots of amenities great location very clean great communication
atlantis was clean comfortable and beautiful and had just about the most perfect view one could ask for
Host:
manuel is a great host answers any questions promptly
manuel & alan were also excellent hosts
manuel is a great host
great spot and a great host would recommend to anyone in the lower keys area
manuel was a great host and we would definitely recommend
Location:
this is a perfect location
properties are pretty close together
what a wonderful location to watch every sunrise
this is florida keys paradise and this location came as advertised
great location perfect for fishing kayaking paddle boarding
Read more reviews

8. Tidewater Views, Cudjoe Key (from USD 199)

This bright and airy cottage is the perfect place to spend a summer getaway with friends and family. The cottage sleeps 6 guests, with 2 bedrooms, 2 bathrooms, and over 800 square feet (74.3 square meters) of living space. It provides everything you need for a comfortable stay – a boat dock, kayaks, bikes, and access to community amenities such as a heated swimming pool, tennis courts, and basketball courts.

Inside, you can expect newly remodeled interiors with a full kitchen, a living room, HDTVs in all rooms, a washer and dryer, a barbecue grill, and Wi-Fi.

Stayed at this property?
Cudjoe Key, Florida, United States
21.64 km (13.5 mi) from Bahia Honda State Park
29 reviews   Superhost Wifi Available
Entire cottage 3 Beds 6 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 6

Top guest reviews
Amenities & Room:
the lagoon area and swimming pool are lovely with a great view
our concierge had music and fans on when we arrived and a sweet welcome gift
Cleanliness:
the house was beautiful clean updated and spacious for 5 people
this place was great super clean and had everything you needed
the grounds are very clean
the house was clean and very homey with a beautiful view
the house was cute and clean with lovely complimentary snacks when we arrived
Host:
space had everything that was advertised and the property manager was very responsive and welcoming
Location:
close to key west peaceful and quiet
very clean and nice house perfect location last key was very helpful and accommodating we would definitely rent again
beautiful place for a relaxing getaway
Read more reviews

9. Sea Glass Cottage, Tavernier (from USD 350)

Set in a corner lot with a direct bay or ocean access, Sea Glass Cottage is your ideal summer holiday home. This waterfront cottage has two separate docks, so feel free to bring your boats. It is also located in a family-friendly neighborhood and is close to grocery stores and local restaurants.

The cottage features newly remodeled interiors with wood-like floors, ocean-themed décor, comfy furniture, and plenty of natural light. Six people can sleep across its two bedrooms. There’s also a front patio where you can relax and soak up splendid views of sunrises and sunsets.

Stayed at this property?
Tavernier, Florida, United States
82.45 km (51.3 mi) from Bahia Honda State Park
36 reviews   Superhost Wifi Available
Entire cottage 3 Beds 6 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 6

Top guest reviews
Amenities & Room:
sea glass cottage is a beautiful comfortable very accommodating home with a beautiful view
very comfortable mattress in master bed room5
loved all the decor and finishing touches very comfortable beds and couch
sparkling clean great amenities and thoughtfulness in every room
Cleanliness:
very clean and nicely decorated
great property for boaters super clean and cozy
great house very clean perfect location
the house was extremely clean inside and out we were really impressed
very clean and denise is a great host
Host:
friendly and helpful hosts
awesome place to stay and wonderful owners to deal with
denise and frank were great hosts
great house and facilities really friendly and helpful owner
they were responsive to our texts and emails
Location:
great location in a nice neighborhood
great location seriously very good2
the location was easy to find and close to restaurants local dive bars and grocery stores
this place is in the perfect location and it is absolutely beautiful
we loved the location we would stay again without any hesitation
Read more reviews

Sun, sand, and surf await in the Florida Keys

The Florida Keys is a world-famous destination for a reason. With pleasant weather year-round, hundreds of miles of beaches and coral reefs, a vibrant local community and exciting nightlife, visitors here are guaranteed a good time. Bookmark this list of our recommended accommodations so you can easily find your summer home on your next trip.

Stayed at this property?
Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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Charisse is a huge fan of travel documentaries, cooking shows, and storytelling. These interests, combined with her penchant for daydreaming, make travel writing her pastime. She has extensively...Read more

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