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Jan 2 - Jan 4
In two weeks
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In one month
Jan 23 - Jan 25
In two months
Feb 20 - Feb 22

Our top choices for Raccoon Key cottages

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.
$341 nightly
The price is $379
Jan 19 - Jan 20, 2026
Total with taxes and fees
Private Oceanfront Cottage with dockage, pool just minutes to Key West!
Marina
Living Life Dockside

Living Life Dockside

Living Life Dockside
Stock Island
$510 nightly
The price is $567
Dec 25 - Dec 26
Total with taxes and fees
Living Life Dockside
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!
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.
$673 nightly
The price is $747
Jan 9 - Jan 10, 2026
Total with taxes and fees
NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location
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.
$952 nightly
The price is $1,050
Jan 17 - Jan 18, 2026
Total with taxes and fees
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)
"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
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
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
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.
$540 nightly
The price is $594
Jan 4 - Jan 5, 2026
Total with taxes and fees
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, (26)
"Great location! Fun place to stay! Responses to our questions/needs very promptly! "
United States
Teressa S.
$513 nightly
The price is $564
Dec 24 - Dec 25
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

Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

10/10 Excellent
"Room was nice and the vibe was good. Pool was excellent and staff are very friendly. Could do better with breakfast. There were limited options and it took 30+ minutes to take our order.overall we enjoyed our stay."
Ashwin 2-night trip
Posted 2 days ago
Blue Flamingo Resort Key West

Find out more about Raccoon Key

Raccoon Key Cottages information

Number of reviews
390
Accommodation
108 Cottages
Lowest Price
$379
Highest Price
$1,050

Frequently asked questions

How much do cottages in Raccoon Key cost?
Rates for cottages in Raccoon Key range between $379 and $1,050 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 9.6.
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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