Search Raccoon Key Cottages

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Check prices for these dates

Next weekend
Dec 26 - Dec 28
In two weeks
Jan 2 - Jan 4
In one month
Jan 16 - Jan 18
In two months
Feb 13 - Feb 15

Our top choices for Raccoon Key cottages

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, (50)
"Great area. Quiet and comfortable "
United States
nancy c.
$312 nightly
The price is $346
Dec 20 - Dec 21
Total with taxes and fees
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from 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, (146)
"great location, we are return visitors & will be back!"
United States
Shannon W.
$286 nightly
The price is $317
Dec 20 - Dec 21
Total with taxes and fees
Quaint cottage, pool, 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)
"Bad need of repair....rust....no boat ramp......shallow water....screened in porch was aweful with holes in the screens and lots of mosquitos and rusted grill."
United States
Debra M.
$257 nightly
The price is $285
Dec 20 - Dec 21
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!
Outdoor dining
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.
$334 nightly
The price is $370
Dec 21 - Dec 22
Total with taxes and fees
Canal front, dockage, 2 bedroom, 2 bath
Property grounds
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.
$351 nightly
The price is $387
Dec 20 - Dec 21
Total with taxes and fees
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.
$312 nightly
The price is $346
Dec 20 - Dec 21
Total with taxes and fees
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from 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.
$312 nightly
The price is $346
Dec 20 - Dec 21
Total with taxes and fees
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Outdoor pool, a heated pool
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)
"It was ok for what we needed. Needs some repairs though."
United States
Craig M.
$312 nightly
The price is $346
Dec 20 - Dec 21
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 20 - Dec 21
Total with taxes and fees
Charming cottages, dockage, pool, just minutes to Key West
Outdoor dining
Living Life Dockside

Living Life Dockside

Living Life Dockside
Stock Island
$560 nightly
The price is $622
Jan 4 - Jan 5, 2026
Total with taxes and fees
Living Life Dockside
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
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)
"Great property,Great location. Will definitely stay there again."
United States
Roy F.
$429 nightly
The price is $476
Dec 21 - Dec 22
Total with taxes and fees
Cottage with Pool and Dockage, just minutes to Key West
Terrace/patio
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.
$657 nightly
The price is $720
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)
"This was the perfect cottage for our stay. Very clean, nicely remodeled, great location to everything. It had everything we needed for or stay."
United States
Michael M.
$690 nightly
The price is $766
Jan 9 - Jan 10, 2026
Total with taxes and fees
NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location
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, (28)
"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.
$341 nightly
The price is $375
Dec 21 - Dec 22
Total with taxes and fees
Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!
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.
$471 nightly
The price is $518
Jan 7 - Jan 8, 2026
Total with taxes and fees
Pelican Suite | Cozy Cottage, 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
$470 nightly
The price is $517
Jan 4 - Jan 5, 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.
$470 nightly
The price is $517
Jan 4 - Jan 5, 2026
Total with taxes and fees
Seagull Suite | Inviting Studio, Just Steps From Duval, Hot Tubs!
Property grounds
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.
$470 nightly
The price is $517
Jan 4 - Jan 5, 2026
Total with taxes and fees
Osprey Suite | Charming Hideaway, Hot Tubs, Close to 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 Raccoon Key Hotel Reviews

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

10/10 Excellent
"The staff is wonderful. Room so clean. Beautiful resort. "
Laurie 3-night trip
Posted 8 hours ago
Southernmost Beach Resort and Guesthouses

Find out more about Raccoon Key

Raccoon Key Cottages information

Number of reviews
4,523
Accommodation
108 Cottages
Lowest Price
$156
Highest Price
$3,341

Frequently asked questions

How much do cottages in Raccoon Key cost?
Rates for cottages in Raccoon Key range between $156 and $3,341 per night. Whatever your budget, you'll find the perfect place to get reacquainted with nature. 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 Raccoon Key?
A guest favorite is Simonton Court Cottages. Cozy up at this 3-star stay which features WiFi and a fridge. Casa Manana Key West Monthly: 2 Br is another popular option to check out. Unpack your suitcase at this 3-star cottage and make the most of conveniences like a swimming pool and a garden. You can pick from multiple cottages in Raccoon Key with a total average guest review rating of 8.9.
How many cottages are there in Raccoon Key?
Lock in your vacation dates and then pick from 108 cottages in Raccoon Key. Dreaming of a place where you can immerse yourself in nature? Expedia will help you find your ideal getaway in a few easy clicks.
Are there any family-friendly cottages in Raccoon Key?
A trip with your group in Raccoon Key is a piece of cake at Simonton Court Cottages. With amenities such as WiFi and housekeeping services, you'll find all the necessary creature comforts at this 3-star cottage. Casa Manana Key West Monthly: 2 Br is another family-friendly option where you and the rest of the squad can escape the relentless pace of the city. This cottage has a 3-star rating and amenities including a barbecue grill and an oven. After checking in and chilling in your comfy digs, it's time to head out and start sightseeing. Smathers Beach and South Beach are top family-friendly attractions in Raccoon Key.
Why book your cottage in Raccoon Key with Expedia?
We think that vacations should be hassle-free, so if you're chasing cottages in Raccoon Key at the perfect price, Expedia delivers. Save money and select an economical option far from the downtown buzz, or splurge on an upscale cottage to spoil your loved ones.
How can I find cheap cottages in Raccoon Key?
With Expedia's user-friendly filter tool, booking cheap cottages in Raccoon Key is a cinch. To discover accommodations that'll make your wallet smile, narrow down your search by budget, amenities and star rating.

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