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Featured Cottages in Florida Keys and around

Tropical Cottages
Superior Bungalow, Ensuite (Cottage 04) | Exterior
Tropical Cottages
3.0 star property
8.4 out of 10, Very good, (745)
"Great place. Clean rooms and great staff. Thanks for the hospitality. Highly recommended "
The price is €101
includes taxes & fees
2 Dec - 3 Dec
Tropical Cottages
Old Wooden Bridge Resort and Marina
2 Bedroom Aqua Lodge # 13 Barracuda | Living area
Old Wooden Bridge Resort and Marina
2.5 star property
8.4 out of 10, Very good, (161)
"Loved this stay!!! May not be for everyone but we loved the rustic feel and being away from the crowds!!! The staff was very friendly and our cabin on the water was comfy and cozy! Would definitely stay again. "
The price is €231
includes taxes & fees
8 Dec - 9 Dec
Old Wooden Bridge Resort and Marina
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Beach nearby
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
8.0 out of 10, Very good, (29)
"Just as advertised. "
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
waterfront cottage near key west, sleeps 6
Property grounds
waterfront cottage near key west, sleeps 6
9.4 out of 10, Exceptional, (16)
"We had a great stay! Other than the weather, everything was perfect! We had plans to dock our boat up at the house but it was too windy to take the boat out. We still enjoyed the patio and grilled out one night! We took showers across the street at the camp restrooms bc there were four of us and we would’ve ran out of hot water but that was no problem. We enjoyed our stay!"
waterfront cottage near key west, sleeps 6
Beautiful Modern House in Key Largo
Marina
Beautiful Modern House in Key Largo
10.0 out of 10, Exceptional, (33)
"Very clean and very comfortable had every thing you would need to make your stay great and easy access to main highway. I would book it again if I ever go back to the Keys"
The price is €654
includes taxes & fees
22 Nov - 23 Nov
Beautiful Modern House in Key Largo
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Fridge, microwave, oven, stovetop
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
9.2 out of 10, Wonderful, (62)
"We are old Florida Keys visitors and past residents. We were delighted with the accommodations, pool and view.We are planning our next stay...same time, same place minus the two days of Helene.Will have to make arraignments for a recliner to be delivered for my wifes sleeping and sitting comfort.Our first night was Sept 20 not the 19th as indicated in error. We stayed 9 nights.Thanks again for the great stay!"
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Blue Mind - Venture Out Unit 225
Outdoor dining
Blue Mind - Venture Out Unit 225
9.4 out of 10, Exceptional, (66)
"nice place 3rd time there"
Blue Mind - Venture Out Unit 225
Waterfront Cozy Cottage with Boat Ramp & Dock!
Property grounds
Waterfront Cozy Cottage with Boat Ramp & Dock!
10.0 out of 10, Exceptional, (51)
"I really enjoyed it there we / my 12 year old and I . Took out charters everyday that we were there . They will pick you up from your dock ! We will be back .. Great experience!"
Waterfront Cozy Cottage with Boat Ramp & Dock!
SEA SHELL COTTAGE UNIT #2
Beach
SEA SHELL COTTAGE UNIT #2
9.2 out of 10, Wonderful, (11)
"We thoroughly enjoyed our stay here, the room we rented was perfect for us it definitely has an old school vibe. The pool was nice on the hot summer days but they were going through a bit of a crab invasion while we were there. But that was no big deal for us. Hope was super nice and have a bunch of suggestions for things to do and places to eat while down there. Ask in all we had a great time and will try to return in the future."
SEA SHELL COTTAGE UNIT #2
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Beach nearby
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
8.8 out of 10, Excellent, (53)
"The grounds are good. The pools were clean and plenty of deck and dock space. The cottage itself needs help. It needed general maintenance on it. It needs caulking in the bathroom. It needs weather strips around door as it is not tight. There was not enough hand towels and there are no oven mitts in the kitchen. The exhaust fan has been taken out. The ceiling fan in one room only works on high. The ac vents and exhaust fan in the bathroom needs cleaning. We were happy about the porch except the...
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
PALM COTTAGE
Sun-loungers, beach towels
PALM COTTAGE
10.0 out of 10, Exceptional, (28)
"First time we had stayed in Summerland Key. Great place to stay. Close to everything we wanted to do. Due to Hurricane Milton we decided to cut our visit short. Trina and Hope were very accommodating with our needs!! We will be back "
PALM COTTAGE
OCEAN BREEZE COTTAGE AT HIDDEN HAMMOCK
Beach
OCEAN BREEZE COTTAGE AT HIDDEN HAMMOCK
9.4 out of 10, Exceptional, (15)
"We loved the area Hope wad great and wr had a great time!"
OCEAN BREEZE COTTAGE AT HIDDEN HAMMOCK
Beachfront Retreat w Pool, Boat Ramp & Dock Rental
Property grounds
Beachfront Retreat w Pool, Boat Ramp & Dock Rental
9.0 out of 10, Wonderful, (23)
"Evacuating from Milton. Booking was easy and the place was a safe harbor."
The price is €289
includes taxes & fees
11 Dec - 12 Dec
Beachfront Retreat w Pool, Boat Ramp & Dock Rental
THE NEW HIDDEN HAMMOCK RESORT - Pink Cottage Unit #3 Sleeps 4
Sun-loungers, beach towels
THE NEW HIDDEN HAMMOCK RESORT - Pink Cottage Unit #3 Sleeps 4
9.6 out of 10, Exceptional, (40)
"The property was just as it was listed as, very clean and very inviting. We loved that it was so quiet! We will definitely go back again!"
THE NEW HIDDEN HAMMOCK RESORT - Pink Cottage Unit #3 Sleeps 4
FL Keys Cottage with Ocean Views - Venture Out Unit 395
Fridge, microwave, oven, stovetop
FL Keys Cottage with Ocean Views - Venture Out Unit 395
8.8 out of 10, Excellent, (3)
"Very clean, comfortable beds. Close to everything we wanted to do!"
FL Keys Cottage with Ocean Views - Venture Out Unit 395
Luxury cottage in the heart of paradise
Outdoor pool, a heated pool
Luxury cottage in the heart of paradise
9.6 out of 10, Exceptional, (25)
"From check in, to check out all smooth. Beautifully decorated unit with attention to detail, highly recommended. Use of golf cart to get to hammocks and pool was wonderful. Thank you!"
Luxury cottage in the heart of paradise
Escape to the Keys! Pet-Friendly Sugarloaf Key Bungalow - Great Amenities (84)
Exterior
Escape to the Keys! Pet-Friendly Sugarloaf Key Bungalow - Great Amenities (84)
9.8 out of 10, Exceptional, (8)
"Our stay was amazing. The property was immaculate. The amenities were great. We will be back next year. The location was perfect. Close to Key West and alot to do in the area. Thank you for making our stay wonderful. See you next year!"
Escape to the Keys! Pet-Friendly Sugarloaf Key Bungalow - Great Amenities (84)
Waterfront Home
Terrace/patio
Waterfront Home
8.8 out of 10, Excellent, (150)
"Has a nice seawall that can accomodate about a 30 foot boat. Cleaning station for fish was nice also. Actual house unit was older, but nice. We really just used it for cooking our fish and sleeping. The main perks of this place is that it has a seawall on a protected canal to keep a boat, has good channel access to both the oceanside and gulf, and is clean. Marina with boat fuel and boat ramp is in Venture Out neighborhood just a few hundred feet away from this actual unit. Overall a good...
Waterfront Home
3BR/3BA Sunset Cottage located at The Villages of Hawks Cay
Terrace/patio
3BR/3BA Sunset Cottage located at The Villages of Hawks Cay
10.0 out of 10, Exceptional, (193)
"The property description failed to mention that the cabana club is 10 miles away."
3BR/3BA Sunset Cottage located at The Villages of Hawks Cay
Canal front, dockage, 2 bedroom, 2 bath
Outdoor pool, a heated pool
Canal front, dockage, 2 bedroom, 2 bath
9.0 out of 10, Wonderful, (73)
"Property was just as advertised and looked as nice in person as in ads"
Canal front, dockage, 2 bedroom, 2 bath
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Florida Keys

Breezy Palms Resort
Exterior
Breezy Palms Resort
2.5 star property
8.6 out of 10, Excellent, (371)
"Beautiful views "
The price is €164
includes taxes & fees
24 Nov - 25 Nov
Breezy Palms Resort
Aqua Lodge Rentals At Coconut Cay
Front of property
Aqua Lodge Rentals At Coconut Cay
3.5 star property
9.6 out of 10, Exceptional, (124)
"Clean, quiet. Balcony to the sea was a big plus. Everything was excellent."
The price is €317
includes taxes & fees
2 Dec - 3 Dec
Aqua Lodge Rentals At Coconut Cay
Skipjack Resort & Marina
Outdoor pool, pool loungers
Skipjack Resort & Marina
3.0 star property
8.6 out of 10, Excellent, (1133)
"Large rooms, clean, quiet."
The price is €187
includes taxes & fees
24 Nov - 25 Nov
Skipjack Resort & Marina
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much do cottages in Florida Keys cost?
Cottages in Florida Keys range between €101 and €654 per night. These properties offer a chance to reconnect with nature — at a price you can afford. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What are the best cottages in Florida Keys?
There are multiple cottages in Florida Keys with a total average guest review rating of 9.1, so you’re sure to snag a place that suits your style. Basing yourself in Key West? Simonton Court Cottages is one property loved by guests. This 3.5-star cottage includes amenities such as a garden and a nearby beach. Simonton Court Cottages is another highly rated getaway where you can unwind close to nature. WiFi and concierge services are just a couple of the conveniences you can expect at this 3.5-star pick in Key West.
How many cottages are there in Florida Keys?
Take a peek at our 34 cottages in Florida Keys and then reserve your favourite. Whether you’re embarking on a holiday with the fam or a break with friends, your perfect stay is just a few clicks away with Expedia.
Are there any family-friendly cottages in Florida Keys?
There are family-friendly cottages in locations around Florida Keys, including Key West. Simonton Court Cottages is one property that’ll check your boxes in this renowned city. It has a 3.5-star rating and handy amenities like WiFi and housekeeping services. Also take a look at Casa Manana Key West Monthly: 2 Br. With a king bed and an oven, this 3-star cottage in Key West will make you and your travel buddies feel relaxed and welcome. Key West has tons of family-friendly attractions when you’re ready to sightsee. Smathers Beach and South Beach has something for all ages.
Why book your cottage in Florida Keys with Expedia?
Reserving a cottage in Florida Keys is as simple as clicking on your travel dates and picking an ideal place for outdoor relaxation and recreation. From upscale retreats to inexpensive properties and cottages that have conveniences like a kitchen, Expedia has something for all styles and tastes. As for the best offers around? We’ve got them too!
How can I find cheap cottages in Florida Keys?
With Expedia’s convenient filter tool, getting your hands on cheap cottages in Florida Keys is easy. To find accommodation that’ll make your wallet happy, refine your search by budget, amenities and star rating.
What is there to do in Florida Keys near my cottage?
Whether you love shopping, dining, history or culture, Florida Keys offers it all, and then some! The terrific city of Key West has loads of things to see and do, including Smathers Beach, Fort Zachary Taylor Historic State Park and South Beach. If you’re on your way to Key Largo, Jimmy Johnson’s Big Chill, Bluefin Rock Harbour Marina and Jacob’s Aquatic Centre should be on your to-do list.