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Featured Cottages in Florida Keys and around

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, (170)
"Nice area"
The price is €235
includes taxes & fees
23 Dec - 24 Dec
Old Wooden Bridge Resort and Marina
Tropical Cottages
Superior Bungalow, Ensuite (Cottage 04) | Exterior

Tropical Cottages

3.0 star property
8.4 out of 10, Very good, (755)
"The Cottage made a wonderful stay for a quick getaway. I shared the main cottage with another family and my only complaint is that because the walls are thin, we were awakened by their incessant argument and the constant slamming of their suite and main doors. "
The price is €150
includes taxes & fees
5 Jan - 6 Jan 2025
Tropical Cottages
Beachfront Retreat w Pool, Boat Ramp & Dock Rental
Marina

Beachfront Retreat w Pool, Boat Ramp & Dock Rental

8.8 out of 10, Excellent, (25)
"The RV park is top notch. Many activities to keep kids busy and has laundry facilities, trash pickup - very well cared for. The RV we stayed in was roomy and fairly comfortable. It needs a little TLC and a bit more attention to detail in cleanliness. All in all, it waswonderful stay."
The price is €340
includes taxes & fees
8 Jan - 9 Jan 2025
Beachfront Retreat w Pool, Boat Ramp & Dock Rental
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, (55)
"Close to Key West, one of its madness or expensive hotel costs! Two bedrooms. Shared - Boat dock and tiny swimming beach on property, we swam every day in the ocean. Also a swimming pool that seemed to be cleaned regularly. Kitchen is partly stocked - reading instructions helps a lot! "
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
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

9.0 out of 10, Wonderful, (39)
"The cottage was clean and well appointed. Loved the little porch to sit in late in the evening or drink coffee in early in the morning. Beds were comfy, shower was not as strong as I like (but I'm spoiled by my home one, so . . . ) Only problem we noted was sometimes the toilet would not refill after flushing - simple fix, but kind of annoying. Pool was much smaller than it looked in the picture, though. Really enjoyed our stay and would not hesitate to stay again!"
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
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
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, (64)
"The cottage worked great for our sister trip. It was a good halfway point to many of the Key's attractions and was in a nice quieter community. The cottage was cozy and clean, but don't expect a fancy accommodation. The property was right on some water which was really nice."
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
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, (42)
"This place was a gem. Clean, well kept and charming. The owner was very sweet and helpful."
THE NEW HIDDEN HAMMOCK RESORT - Pink Cottage Unit #3 Sleeps 4
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, (31)
"Just as advertised. "
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
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 €591
includes taxes & fees
23 Dec - 24 Dec
Beautiful Modern House in Key Largo
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, (194)
"Was perfect for our family. Views and convenience were great."
3BR/3BA Sunset Cottage located at The Villages of Hawks Cay
Waterfront Cozy Cottage with Boat Ramp & Dock!
Property grounds

Waterfront Cozy Cottage with Boat Ramp & Dock!

10.0 out of 10, Exceptional, (53)
"Cottage was great pier was great too! "
Waterfront Cozy Cottage with Boat Ramp & Dock!
SEA SHELL COTTAGE UNIT #2
Beach

SEA SHELL COTTAGE UNIT #2

9.4 out of 10, Exceptional, (13)
"Hidden Hammock was a gem for sure. Quiet, clean, located near lots of restaurants, stores, and things to do, Manager Hope was very kind and helpful giving us tips where to go, where to eat etc. Property sits on Summerland Key and close to everything North or South of us. I would recommend this place highly. Cheryl Zelsman "
SEA SHELL COTTAGE UNIT #2
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
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)
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
Pet-Friendly Bungalow in Sugarloaf Key, FL - Fantastic Amenities (83)
Exterior

Pet-Friendly Bungalow in Sugarloaf Key, FL - Fantastic Amenities (83)

9.6 out of 10, Exceptional, (10)
"Our stay was wonderful! The room was perfect for our stay. "
Pet-Friendly Bungalow in Sugarloaf Key, FL - Fantastic Amenities (83)
FLAMINGO COTTAGE UNIT #1
Beach

FLAMINGO COTTAGE UNIT #1

9.8 out of 10, Exceptional, (29)
"Great communication and recommendations on area restaurants. Nice touches including beach chairs, umbrella and beach towels!"
FLAMINGO COTTAGE UNIT #1
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

Skipjack Resort & Marina
Outdoor pool, pool loungers

Skipjack Resort & Marina

3.0 star property
8.6 out of 10, Excellent, (1141)
"We love staying at this property because it’s just like an apartment with all the comforts of home."
The price is €357
includes taxes & fees
23 Dec - 24 Dec
Skipjack Resort & Marina
Breezy Palms Resort
Exterior

Breezy Palms Resort

2.5 star property
8.6 out of 10, Excellent, (379)
"Spacious studio on the water. Highly recommend."
The price is €180
includes taxes & fees
6 Jan - 7 Jan 2025
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, (126)
"Unique floating accommodations were so nice. Highly recommend this stay."
The price is €534
includes taxes & fees
2 Jan - 3 Jan 2025
Aqua Lodge Rentals At Coconut Cay
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 €150 and €591 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 9.2, 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 36 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.