Search Florida Keys Cottage Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Jun 12 - Jun 14
In two months
Jul 24 - Jul 26
In three months
Aug 21 - Aug 23
In four months
Sep 18 - Sep 20

Our top choices for Florida Keys cottages

Exterior

Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (342 reviews)
"Very nice, clean and cozy, with the deers walking around."
United States
Sofia
The price is ￥21,358
￥46,427 total
includes taxes & fees
Jun 8 - Jun 9
Old Wooden Bridge Resort and Marina
Exterior

Tropical Cottages

Tropical Cottages
3.0 star property
Marathon
8.6 out of 10, Excellent, (977 reviews)
"It was a very enjoyable stay, highly recommend."
United States
Andrea
The price is ￥20,546
￥23,115 total
includes taxes & fees
Jun 4 - Jun 5
Tropical Cottages
House (2 Bedrooms) | Interior

The Grinnell Cottage by Avantstay Shared Pool + Backyard Lounge Charming Cottage Steps to Waterfront Dining

The Grinnell Cottage by Avantstay Shared Pool + Backyard Lounge Charming Cottage Steps to Waterfront Dining
3.0 star property
Old Town Key West
The price is ￥24,209
￥88,274 total
includes taxes & fees
Jun 8 - Jun 9
The Grinnell Cottage by Avantstay Shared Pool + Backyard Lounge Charming Cottage Steps to Waterfront Dining
Exterior

Cottage with Pool and Dockage, just minutes to Key West

Cottage with Pool and Dockage, just minutes to Key West
Cudjoe Key
9.2 out of 10, Wonderful, (170 reviews)
"Great place "
United States
David
The price is ￥28,669
￥56,541 total
includes taxes & fees
Jun 3 - Jun 4
Cottage with Pool and Dockage, just minutes to Key West
Property grounds

Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!

Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!
Cudjoe Key
9.6 out of 10, Exceptional, (14 reviews)
"All was excellent "
United States
Bryan M.
The price is ￥28,669
￥66,297 total
includes taxes & fees
Jun 2 - Jun 3
Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!
Outdoor dining

Waterfront Home

Waterfront Home
Cudjoe Key
8.8 out of 10, Excellent, (186 reviews)
"Clean, great view, wonderful porch, comfortable bed"
United States
Karen H.
The price is ￥31,854
￥65,919 total
includes taxes & fees
Jun 23 - Jun 24
Waterfront Home
Outdoor dining

Canal front, dockage, 2 bedroom, 2 bath

Canal front, dockage, 2 bedroom, 2 bath
Cudjoe Key
8.8 out of 10, Excellent, (99 reviews)
"We stayed one night, everything was as described"
United States
Anonymous traveler
The price is ￥32,252
￥67,959 total
includes taxes & fees
Jun 4 - Jun 5
Canal front, dockage, 2 bedroom, 2 bath
Terrace/patio

OSPREY STUDIO @ The Colony-Sleeps up to 4

OSPREY STUDIO @ The Colony-Sleeps up to 4
Old Town Key West
9.4 out of 10, Exceptional, (61 reviews)
"As ex Key west’s, we were very specific in the location that we wanted to bi in. This property was perfect for us. The compound was calm and quiet as well as extremely well kept. The communication with the management company was seamless."
United States
Donald
OSPREY STUDIO @ The Colony-Sleeps up to 4
Property grounds

2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWS

2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWS
Cudjoe Key
9.8 out of 10, Exceptional, (30 reviews)
"Everything about this home is perfect!"
United States
Shari H.
The price is ￥50,027
￥103,247 total
includes taxes & fees
Jun 7 - Jun 8
2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWS
Exterior

NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location

NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location
Old Town Key West
10.0 out of 10, Exceptional, (26 reviews)
"Great location, freshly renovated "
United States
Jackie M.
The price is ￥59,408
￥105,020 total
includes taxes & fees
Jun 14 - Jun 15
NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location
Outdoor dining

HIDDEN OASIS 3 blocks from Duval

HIDDEN OASIS 3 blocks from Duval
Old Town Key West
9.6 out of 10, Exceptional, (100 reviews)
"All around amazing place! Location was perfect! "
United States
Daniel M.
HIDDEN OASIS 3 blocks from Duval
Exterior

Find your zen at HIDDEN TREASURE

Find your zen at HIDDEN TREASURE
Old Town Key West
9.2 out of 10, Wonderful, (21 reviews)
"Location was great. "
United States
Karen B.
The price is ￥73,955
￥150,871 total
includes taxes & fees
Jun 22 - Jun 23
Find your zen at HIDDEN TREASURE
Exterior

Private Studio in Shenandoah

Private Studio in Shenandoah
Coral Way
9.0 out of 10, Wonderful, (7 reviews)
"Excellent"
United States
David R.
The price is ￥5,605
￥23,016 total
includes taxes & fees
Jun 3 - Jun 4
Private Studio in Shenandoah
Exterior

Charming 1 bed Apartment in lovely Miami with AC, TROPICAL FOOD FOREST GARDEN

Charming 1 bed Apartment in lovely Miami with AC, TROPICAL FOOD FOREST GARDEN
Coral Way
10.0 out of 10, Exceptional, (6 reviews)
"Great location and easy check in and checkout. "
United States
Raymond Y.
The price is ￥11,324
￥24,981 total
includes taxes & fees
Jun 2 - Jun 3
Charming 1 bed Apartment in lovely Miami with AC, TROPICAL FOOD FOREST GARDEN
Shower, hair dryer, towels, soap

Walk to Restaurants and Shops

Walk to Restaurants and Shops
Coral Way
7.6 out of 10, Good, (4 reviews)
"Everything was absolutely perfect. Exactly what you would want with a VRBO. So quaint, clean just everything, not to mention the location. What is special is is in the residential side of little Havana."
United States
Loren G.
The price is ￥5,605
￥23,016 total
includes taxes & fees
Jun 2 - Jun 3
Walk to Restaurants and Shops
Shower, hair dryer, towels, soap

New York Loft in the Heart of Miami

New York Loft in the Heart of Miami
Coral Way
10.0 out of 10, Exceptional, (3 reviews)
"I loved everything about this place!"
United States
Rebecca L.
The price is ￥5,605
￥23,016 total
includes taxes & fees
Jun 2 - Jun 3
New York Loft in the Heart of Miami
Exterior

Charming 1-bedroom cottage in lovely Miami with AC, TROPICAL FOOD FOREST GARDEN

Charming 1-bedroom cottage in lovely Miami with AC, TROPICAL FOOD FOREST GARDEN
Coral Way
9.4 out of 10, Exceptional, (21 reviews)
"Lovely and cute place to stay!"
United States
Christopher P.
The price is ￥9,174
￥22,553 total
includes taxes & fees
Jun 3 - Jun 4
Charming 1-bedroom cottage in lovely Miami with AC, TROPICAL FOOD FOREST GARDEN
Desk, iron/ironing board, free WiFi, bed sheets

Studio close to Everything

Studio close to Everything
Coral Way
9.0 out of 10, Wonderful, (8 reviews)
"The place is unique and comfy "
United States
Samuel
The price is ￥5,769
￥23,201 total
includes taxes & fees
Jun 2 - Jun 3
Studio close to Everything
Property grounds

Villa Capri Cozy 2 Bedroom Cottage in the heart of Miami

Villa Capri Cozy 2 Bedroom Cottage in the heart of Miami
Little Havana
10.0 out of 10, Exceptional, (1 review)
"Lovely cottage, very clean with all the amenities. Nice little patio in the rear. Super markets, restaurants close by. 10 minutes from a Casino. The owner, Alberto, is a Gentleman. I'd book this again!"
United States
John S.
The price is ￥48,063
￥100,501 total
includes taxes & fees
Jun 2 - Jun 3
Villa Capri Cozy 2 Bedroom Cottage in the heart of Miami
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Florida Keys Hotel Reviews

Waterside Suites & Marina

Waterside Suites & Marina

10/10 Excellent
"Very nice space, great view of the marina and passing boats, plenty of room for two guests, all the amenities you should need, clean, working thermostat, nice staff. Overall, an excellent stay that gives you all you need and more!"
Memphis 3-night trip
Posted 2 hours ago
Waterside Suites & Marina

Find out more about Florida Keys

Florida Keys Cottages information

Number of reviews
1,319
Accommodation
60 Cottages
Lowest Price
￥23,115
Highest Price
￥88,274

Frequently asked questions

How much do cottages in Florida Keys cost?
Prepare to pay between ￥23,115 and ￥88,274 per night for cottages in Florida Keys. No matter your budget, an awesome stay is only a click or two away on Expedia. 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.
How many cottages are there in Florida Keys?
Florida Keys has 60 cottages to choose from. Click on your travel dates, enter your destination and get a head start on planning your dream getaway today.
Are there any family-friendly cottages in Florida Keys?
There are family-friendly cottages in locations around Florida Keys, including Key West. Casa Manana Key West Monthly: 2 Br is one option that'll meet your needs in this vibrant city. It has a 3-star rating and amenities such as an oven and a barbecue grill. Also consider Simonton Court Cottages. With housekeeping services and WiFi, this 3-star cottage in Key West will make you and your travel buddies feel nice and relaxed. Key West has tons of family-friendly attractions when you're ready to see the sights. Smathers Beach and South Beach promise fun for the entire crew.
Why book your cottage in Florida Keys with Expedia?
We think that a vacation should be stress-free, so if you're searching for cottages in Florida Keys at an affordable price, Expedia has got you covered. Keep the budget in check and stay in a cheap option far away from the city rush, or splurge on an upmarket cottage to really pamper your favorite people.
How can I find cheap cottages in Florida Keys?
With Expedia's useful filter tool, getting your hands on cheap cottages in Florida Keys has never been easier. To find stays that'll make your hip pocket happy, refine your search results by star rating, budget and amenities.
What is there to do in Florida Keys near my cottage?
You'll discover countless things to keep you on the go in Florida Keys. If you're visiting Key West, swing by Duval Street, Clarence S. Higgs Memorial Beach Park and Nancy Forrester's Secret Garden. Spending your vacay in Key Largo? Jimmy Johnson's Big Chill, Baker's Cay Resort Beach and Bluefin Rock Harbor Marina are among the best sights in this city.