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Our top choices for Florida Keys cottages

Exterior
Tropical Cottages

Tropical Cottages

Tropical Cottages
3.0 star property
Marathon
8.6 out of 10, Excellent, (910)
"Decent stay, easy check in and contactless checkout. Very quiet and nice place! "
United States
Swastik
$135 nightly
The price is $152
Jan 8 - Jan 9, 2026
Total with taxes and fees
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, (280)
"Enjoyed the duplex, instead of a standard hotel room. Full kitchen, nice bathroom, and bedroom. "
United States
Alejandra
$241 nightly
The price is $271
Jan 7 - Jan 8, 2026
Total with taxes and fees
Old Wooden Bridge Resort and Marina
Exterior
Cottage with swimming pool and dockage, just minutes to Key West!

Cottage with swimming pool and dockage, just minutes to Key West!

Cottage with swimming pool and dockage, just minutes to Key West!
Cudjoe Key
9.0 out of 10, Wonderful, (160)
"Everything was there that I needed. Very nice area for my dog."
United States
Terry
$315 nightly
The price is $349
Dec 27 - Dec 28
Total with taxes and fees
Cottage with swimming pool and dockage, just minutes to Key West!
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
8.8 out of 10, Excellent, (90)
"Nice place to vacation "
United States
Kevin D.
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!

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.
$257 nightly
The price is $285
Dec 23 - Dec 24
Total with taxes and fees
Private Oceanfront Cottage with dockage, pool 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!

Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!
Cudjoe Key
9.6 out of 10, Exceptional, (12)
"The owners were fantastic to deal with and the house was great. "
United States
Anonymous traveler
$348 nightly
The price is $387
Dec 23 - Dec 24
Total with taxes and fees
Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!
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.
$541 nightly
The price is $595
Jan 9 - Jan 10, 2026
Total with taxes and fees
Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!
Marina
Living Life Dockside

Living Life Dockside

Living Life Dockside
Stock Island
$513 nightly
The price is $570
Jan 4 - Jan 5, 2026
Total with taxes and fees
Living Life Dockside
1 bedroom, iron/ironing board, free WiFi, bed sheets
OSPREY STUDIO @ The Colony-Sleeps up to 4

OSPREY STUDIO @ The Colony-Sleeps up to 4

OSPREY STUDIO @ The Colony-Sleeps up to 4
2.0 star property
Old Town Key West
9.6 out of 10, Exceptional, (54)
"We loved our stay here. It was calm and quiet--such a nice place to lounge and enjoy a morning coffee when you're not hanging out on Duval or exploring the island! We loved it!"
United States
Dean H.
$627 nightly
The price is $686
Dec 24 - Dec 25
Total with taxes and fees
OSPREY STUDIO @ The Colony-Sleeps up to 4
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

NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location
Old Town Key West
9.6 out of 10, Exceptional, (10)
"I nice place cool place to go back to after touring Key West."
United States
Karen V.
$678 nightly
The price is $752
Jan 9 - Jan 10, 2026
Total with taxes and fees
NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location
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, (51)
"Great area. Quiet and comfortable "
United States
nancy c.
$312 nightly
The price is $346
Dec 23 - Dec 24
Total with taxes and fees
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, (120)
"Jennifer was very nice and accommodating."
United States
Randy G.
$297 nightly
The price is $330
Dec 23 - Dec 24
Total with taxes and fees
Charming cottages, dockage, pool, just minutes to Key West
Beach nearby
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, (75)
"Place was everything we needed, would definitely stay again "
United States
James h.
$312 nightly
The price is $346
Dec 23 - Dec 24
Total with taxes and fees
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
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
9.8 out of 10, Exceptional, (33)
"Good place to stay loved it"
United States
Charles I.
$541 nightly
The price is $595
Jan 9 - Jan 10, 2026
Total with taxes and fees
Egret Suite | Bright Retreat, Hot Tubs, Steps 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)
"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.
$541 nightly
The price is $595
Jan 9 - Jan 10, 2026
Total with taxes and fees
Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!
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, (26)
"Great location! Fun place to stay! Responses to our questions/needs very promptly! "
United States
Teressa S.
$539 nightly
The price is $593
Jan 4 - Jan 5, 2026
Total with taxes and fees
Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!
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
$541 nightly
The price is $595
Jan 9 - Jan 10, 2026
Total with taxes and fees
Ibis Suite | Bright Hideaway, Hot Tubs, Steps from 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.
$539 nightly
The price is $593
Jan 4 - Jan 5, 2026
Total with taxes and fees
Seagull Suite | Inviting Studio, Just Steps From Duval, Hot Tubs!
Exterior
Find your zen at HIDDEN TREASURE

Find your zen at HIDDEN TREASURE

Find your zen at HIDDEN TREASURE
3.0 star property
Old Town Key West
8.8 out of 10, Excellent, (10)
"Great place to stay! "
United States
sarah R.
$888 nightly
The price is $976
Dec 24 - Dec 25
Total with taxes and fees
Find your zen at HIDDEN TREASURE
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)
"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.
$966 nightly
The price is $1,064
Jan 17 - Jan 18, 2026
Total with taxes and fees
HIDDEN OASIS 3 blocks from Duval
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

Waterside Suites & Marina

Waterside Suites & Marina

10/10 Excellent
"Always a great experience every time we go to key largo we stay there "
AMYRSA 1-night trip
Posted 1 day ago
Waterside Suites & Marina

Find out more about Florida Keys

Florida Keys Cottages information

Number of reviews
2,142
Accommodation
64 Cottages
Lowest Price
$152
Highest Price
$1,064

Frequently asked questions

How much do cottages in Florida Keys cost?
Prepare to pay between $152 and $1,064 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 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.