Search Cottages in Florida Keys

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Check prices for these dates

In two weeks
9 Jan - 11 Jan
In two months
20 Feb - 22 Feb
In three months
20 Mar - 22 Mar
In four months
17 Apr - 19 Apr

Our top choices for Florida Keys cottages

Exterior
Tropical Cottages

Cottage in Marathon

Tropical Cottages
3.0 star property
8.6 out of 10, Excellent, (911)
"Decent stay, easy check in and contactless checkout. Very quiet and nice place! "
United States
Swastik
The price is HK$1,049
HK$1,180 total
includes taxes & fees
8 Jan - 9 Jan 2026
Tropical Cottages
Exterior
Old Wooden Bridge Resort and Marina

Cottage in Punta Brisa

Old Wooden Bridge Resort and Marina
2.5 star property
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
Cottage with Pool and Boat Dockage just minutes to Key West!

Cottage in Cudjoe Key

Cottage with Pool and Boat Dockage just minutes to Key West!
8.6 out of 10, Excellent, (153)
"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 HK$1,360
HK$2,419 total
includes taxes & fees
9 Jan - 10 Jan 2026
Cottage with Pool and Boat Dockage just minutes to Key West!
Exterior
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Cottage in Cudjoe Key

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
8.2 out of 10, Very good, (53)
"Great area. Quiet and comfortable "
United States
nancy c.
The price is HK$1,923
HK$3,558 total
includes taxes & fees
2 Jan - 3 Jan 2026
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Exterior
Private Oceanfront Cottage with dockage, pool just minutes to Key West!

Cottage in Cudjoe Key

Private Oceanfront Cottage with dockage, pool just minutes to Key West!
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 HK$1,749
HK$2,941 total
includes taxes & fees
19 Jan - 20 Jan 2026
Private Oceanfront Cottage with dockage, pool just minutes to Key West!
Exterior
Charming cottages, dockage, pool, just minutes to Key West

Cottage in Cudjoe Key

Charming cottages, dockage, pool, just minutes to Key West
8.6 out of 10, Excellent, (121)
"Jennifer was very nice and accommodating."
United States
Randy G.
The price is HK$1,943
HK$3,433 total
includes taxes & fees
2 Jan - 3 Jan 2026
Charming cottages, dockage, pool, just minutes to Key West
Outdoor dining
Waterfront Home

Cottage in Cudjoe Key

Waterfront Home
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 HK$1,943
HK$3,700 total
includes taxes & fees
10 Jan - 11 Jan 2026
Waterfront Home
Marina
Living Life Dockside

Cottage in Stock Island

Living Life Dockside
The price is HK$2,938
HK$4,435 total
includes taxes & fees
4 Jan - 5 Jan 2026
Living Life Dockside
Terrace/patio
Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!

Cottage in Old Town Key West

Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!
9.8 out of 10, Exceptional, (33)
"Good place to stay loved it"
United States
Charles I.
The price is HK$2,223
HK$4,624 total
includes taxes & fees
9 Jan - 10 Jan 2026
Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!
Exterior
NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location

Cottage in Old Town Key West

NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location
9.6 out of 10, Exceptional, (10)
"I nice place cool place to go back to after touring Key West."
United States
Karen V.
The price is HK$3,070
HK$5,355 total
includes taxes & fees
9 Jan - 10 Jan 2026
NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location
Exterior
HIDDEN OASIS 3 blocks from Duval

Cottage in Old Town Key West

HIDDEN OASIS 3 blocks from Duval
2.5 star property
9.6 out of 10, Exceptional, (96)
"We absolutely loved this place! It was quaint and quiet location. It was beautifully landscaped and I loved the Hidden Oasis unit and would stay there again!"
United States
Kathryn W.
The price is HK$4,540
HK$8,265 total
includes taxes & fees
17 Jan - 18 Jan 2026
HIDDEN OASIS 3 blocks from Duval
Exterior
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Cottage in Cudjoe Key

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
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 HK$1,749
HK$3,307 total
includes taxes & fees
9 Jan - 10 Jan 2026
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Exterior
Cottage with Pool and Dockage, just minutes to Key West

Cottage in Cudjoe Key

Cottage with Pool and Dockage, just minutes to Key West
9.2 out of 10, Wonderful, (161)
"Very nice and quiet! "
United States
Lura H.
The price is HK$2,137
HK$3,675 total
includes taxes & fees
2 Jan - 3 Jan 2026
Cottage with Pool and Dockage, just minutes to Key West
Exterior
Quaint cottage, pool, dockage just minutes to Key West!

Cottage in Cudjoe Key

Quaint cottage, pool, dockage just minutes to Key West!
9.0 out of 10, Wonderful, (147)
"great location, we are return visitors & will be back!"
United States
Shannon W.
The price is HK$2,137
HK$3,675 total
includes taxes & fees
2 Jan - 3 Jan 2026
Quaint cottage, pool, dockage just minutes to Key West!
Terrace/patio
Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!

Cottage in Old Town Key West

Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!
10.0 out of 10, Exceptional, (29)
"Clean room, amazing location, the host was very communicative and helpful. They had a car service ready to pick us up at the airport which was phenomenal. "
United States
Lauren S.
The price is HK$2,223
HK$4,624 total
includes taxes & fees
9 Jan - 10 Jan 2026
Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!
Terrace/patio
Ibis Suite | Bright Hideaway, Hot Tubs, Steps from Duval!

Cottage in Old Town Key West

Ibis Suite | Bright Hideaway, Hot Tubs, Steps from Duval!
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 HK$2,223
HK$4,624 total
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!

Cottage in Old Town Key West

Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!
10.0 out of 10, Exceptional, (25)
"Wonderful clean place. It was an enjoyable experiance. "
United States
Chels J.
The price is HK$2,223
HK$4,624 total
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!

Cottage in Old Town Key West

Seagull Suite | Inviting Studio, Just Steps From Duval, Hot Tubs!
9.8 out of 10, Exceptional, (23)
"Great little place, perfect for southernmost area."
United States
Lee G.
The price is HK$2,238
HK$4,619 total
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!

Cottage in Old Town Key West

Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!
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 HK$2,238
HK$4,619 total
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

Cottage in Little Havana

Privacy and Comfort close to all - 7G
8.0 out of 10, Very good, (5)
"Great location "
United States
Jeffrey
The price is HK$316
HK$996 total
includes taxes & fees
14 Jan - 15 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

Lime Tree Bay Resort

Lime Tree Bay Resort

10/10 Excellent
"Very niche property offering beautiful and relaxing scenery and lots of entertainment options such as kayak, pedal board and tennis. "
Dongbing 2-night trip
Posted 17 hours ago
Lime Tree Bay Resort

Find out more about Florida Keys

Florida Keys Cottages information

Number of reviews
2,445
Accommodation
64 Cottages
Lowest Price
HK$996
Highest Price
HK$8,265

Frequently asked questions

How much do cottages in Florida Keys cost?
Prepare to pay between HK$996 and HK$8,265 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.

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