Search Cottages in Florida Keys

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Check prices for these dates

In two weeks
16 Jan - 18 Jan
In two months
27 Feb - 1 Mar
In three months
27 Mar - 29 Mar
In four months
24 Apr - 26 Apr

Our top choices for Florida Keys cottages

Standard Cottage, Ensuite (Cottage 10) | Exterior
Tropical Cottages

Tropical Cottages

Tropical Cottages
3.0 star property
Marathon
8.6 out of 10, Excellent, (915)
"Decent stay, easy check in and contactless checkout. Very quiet and nice place! "
United States
Swastik
The price is €129
includes taxes & fees
8 Jan - 9 Jan 2026
Tropical Cottages
Exterior
Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (283)
"Enjoyed the duplex, instead of a standard hotel room. Full kitchen, nice bathroom, and bedroom. "
United States
Alejandra
Old Wooden Bridge Resort and Marina
Exterior
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

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Cudjoe Key
8.2 out of 10, Very good, (54)
"Great area. Quiet and comfortable "
United States
nancy c.
The price is €369
includes taxes & fees
11 Jan - 12 Jan 2026
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Exterior
Cottage with Pool and Boat Dockage just minutes to Key West!

Cottage with Pool and Boat Dockage just minutes to Key West!

Cottage with Pool and Boat Dockage just minutes to Key West!
Cudjoe Key
8.6 out of 10, Excellent, (154)
"This cottage served our purpose well, very close to our family’s home and was very clean and comfortable for a short stay."
United States
Richard S.
The price is €268
includes taxes & fees
7 Jan - 8 Jan 2026
Cottage with Pool and Boat Dockage just minutes to Key West!
Exterior
Private Oceanfront Cottage with dockage, pool just minutes to Key West!

Private Oceanfront Cottage with dockage, pool just minutes to Key West!

Private Oceanfront Cottage with dockage, pool just minutes to Key West!
Cudjoe Key
8.6 out of 10, Excellent, (164)
"Beautiful serene, location, located close enough to Key West and also nice restaurants in the area and close to Bahia Honda State Park, which was beautiful and the key deer areas."
United States
Andrea S.
The price is €330
includes taxes & fees
19 Jan - 20 Jan 2026
Private Oceanfront Cottage with dockage, pool just minutes to Key West!
Exterior
Quaint cottage, pool, dockage just minutes to Key West!

Quaint cottage, pool, dockage just minutes to Key West!

Quaint cottage, pool, dockage just minutes to Key West!
Cudjoe Key
9.0 out of 10, Wonderful, (147)
"great location, we are return visitors & will be back!"
United States
Shannon W.
The price is €385
includes taxes & fees
2 Jan - 3 Jan 2026
Quaint cottage, pool, dockage just minutes to Key West!
Outdoor dining
Waterfront Home

Waterfront Home

Waterfront Home
Cudjoe Key
8.6 out of 10, Excellent, (175)
"Great location if you bring a boat. Secure location. Venture Out is a nice community. "
United States
Georgiana V.
The price is €412
includes taxes & fees
11 Jan - 12 Jan 2026
Waterfront Home
Marina
Living Life Dockside

Living Life Dockside

Living Life Dockside
Stock Island
The price is €545
includes taxes & fees
30 Jan - 31 Jan 2026
Living Life Dockside
Exterior
Canal front, dockage, 2 bedroom, 2 bath

Canal front, dockage, 2 bedroom, 2 bath

Canal front, dockage, 2 bedroom, 2 bath
Cudjoe Key
9.0 out of 10, Wonderful, (89)
"The facility is very nice with lots of amenities. It was clean and located close to everything we wanted to do."
United States
Jennifer D.
The price is €390
includes taxes & fees
5 Jan - 6 Jan 2026
Canal front, dockage, 2 bedroom, 2 bath
Terrace/patio
Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!

Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!

Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!
Old Town Key West
9.6 out of 10, Exceptional, (34)
"Good place to stay loved it"
United States
Charles I.
The price is €526
includes taxes & fees
9 Jan - 10 Jan 2026
Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!
Exterior
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

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Cudjoe Key
8.6 out of 10, Excellent, (52)
"We were very happy with our stay. Everything was as expected or above. Old Keys vibe was exactly what we wanted. "
United States
Lauren R.
The price is €369
includes taxes & fees
11 Jan - 12 Jan 2026
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Exterior
Charming cottages, dockage, pool, just minutes to Key West

Charming cottages, dockage, pool, just minutes to Key West

Charming cottages, dockage, pool, just minutes to Key West
Cudjoe Key
8.6 out of 10, Excellent, (121)
"Jennifer was very nice and accommodating."
United States
Randy G.
The price is €325
includes taxes & fees
11 Jan - 12 Jan 2026
Charming cottages, dockage, pool, just minutes to Key West
Exterior
Cottage with Pool and Dockage, just minutes to Key West

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, (161)
"Very nice and quiet! "
United States
Lura H.
The price is €385
includes taxes & fees
2 Jan - 3 Jan 2026
Cottage with Pool and Dockage, just minutes to Key West
Exterior
HIDDEN OASIS 3 blocks from Duval

HIDDEN OASIS 3 blocks from Duval

HIDDEN OASIS 3 blocks from Duval
2.5 star property
Old Town Key West
9.6 out of 10, Exceptional, (96)
"Loved the location of the cottage "
United States
Betty B.
The price is €908
includes taxes & fees
17 Jan - 18 Jan 2026
HIDDEN OASIS 3 blocks from Duval
Terrace/patio
Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!

Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!

Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!
Old Town Key West
10.0 out of 10, Exceptional, (29)
"It was very cozy to be in after running around in all the chaos of the streets all day"
United States
Sabrina L.
The price is €615
includes taxes & fees
25 Jan - 26 Jan 2026
Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!
Terrace/patio
Ibis Suite | Bright Hideaway, Hot Tubs, Steps from Duval!

Ibis Suite | Bright Hideaway, Hot Tubs, Steps from Duval!

Ibis Suite | Bright Hideaway, Hot Tubs, Steps from Duval!
Old Town Key West
9.8 out of 10, Exceptional, (26)
"Bar across street wonderful they didn’t clean room staff talked to great with anything you needed court yard could have been better maintained overall would go back and stay there "
United States
Richele
The price is €525
includes taxes & fees
9 Jan - 10 Jan 2026
Ibis Suite | Bright Hideaway, Hot Tubs, Steps from Duval!
Exterior
Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!

Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!

Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!
Old Town Key West
10.0 out of 10, Exceptional, (25)
"Wonderful clean place. It was an enjoyable experiance. "
United States
Chels J.
The price is €526
includes taxes & fees
9 Jan - 10 Jan 2026
Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!
Terrace/patio
Seagull Suite | Inviting Studio, Just Steps From Duval, Hot Tubs!

Seagull Suite | Inviting Studio, Just Steps From Duval, Hot Tubs!

Seagull Suite | Inviting Studio, Just Steps From Duval, Hot Tubs!
Old Town Key West
9.8 out of 10, Exceptional, (23)
"Great little place, perfect for southernmost area."
United States
Lee G.
The price is €522
includes taxes & fees
4 Jan - 5 Jan 2026
Seagull Suite | Inviting Studio, Just Steps From Duval, Hot Tubs!
Terrace/patio
Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!

Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!

Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!
Old Town Key West
9.8 out of 10, Exceptional, (27)
"Great location! Fun place to stay! Responses to our questions/needs very promptly! "
United States
Teressa S.
The price is €523
includes taxes & fees
4 Jan - 5 Jan 2026
Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!
Iron/ironing board, free WiFi, bed sheets
Privacy and Comfort close to all - 7G

Privacy and Comfort close to all - 7G

Privacy and Comfort close to all - 7G
Little Havana
8.0 out of 10, Very good, (5)
"Great location "
United States
Jeffrey
The price is €111
includes taxes & fees
5 Jan - 6 Jan 2026
Privacy and Comfort close to all - 7G
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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Top Florida Keys Hotel Reviews

Hawks Cay Resort

Hawks Cay Resort

10/10 Excellent
"Room was very clean and refreshed every day. The whole resort was clean and well maintained. Everything you need for a relaxing vacation was right there on the resort "
Amy 6-night trip
Posted 2 days ago
Hawks Cay Resort

Find out more about Florida Keys

Florida Keys Cottages information

Number of reviews
2,524
Accommodation
64 Cottages
Lowest Price
€111
Highest Price
€908

Frequently asked questions

How much do cottages in Florida Keys cost?
Prepare to pay between €111 and €908 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 64 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 holiday 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 favourite 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 holiday in Key Largo? Jimmy Johnson's Big Chill, Baker's Cay Resort Beach and Bluefin Rock Harbour Marina are among the best sights in this city.