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Compare 69 Cottages in Raccoon Key with updated reviews, rates, and availability.

Conch Republic Consul General's Cottage.-Historic District
Conch Republic Style Swimming Pool.

Conch Republic Consul General's Cottage.-Historic District

9.4 out of 10, Exceptional, (149)
"Very clean and well equipped kitchen although we didn’t cook! Quiet neighborhood but not far from everything! Pool was very nice and relaxing!"
Conch Republic Consul General's Cottage.-Historic District
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Exterior detail

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

8.8 out of 10, Excellent, (55)
"Close to Key West, one of its madness or expensive hotel costs! Two bedrooms. Shared - Boat dock and tiny swimming beach on property, we swam every day in the ocean. Also a swimming pool that seemed to be cleaned regularly. Kitchen is partly stocked - reading instructions helps a lot! "
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
Exterior

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

9.0 out of 10, Wonderful, (39)
"The cottage was clean and well appointed. Loved the little porch to sit in late in the evening or drink coffee in early in the morning. Beds were comfy, shower was not as strong as I like (but I'm spoiled by my home one, so . . . ) Only problem we noted was sometimes the toilet would not refill after flushing - simple fix, but kind of annoying. Pool was much smaller than it looked in the picture, though. Really enjoyed our stay and would not hesitate to stay again!"
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
ISLE BE BACK To The Sunny Keys

ISLE BE BACK To The Sunny Keys

9.6 out of 10, Exceptional, (24)
"Rxcellent"
ISLE BE BACK To The Sunny Keys
Waterfront Home
View from the porch

Waterfront Home

8.8 out of 10, Excellent, (150)
"Has a nice seawall that can accomodate about a 30 foot boat. Cleaning station for fish was nice also. Actual house unit was older, but nice. We really just used it for cooking our fish and sleeping. The main perks of this place is that it has a seawall on a protected canal to keep a boat, has good channel access to both the oceanside and gulf, and is clean. Marina with boat fuel and boat ramp is in Venture Out neighborhood just a few hundred feet away from this actual unit. Overall a good...
Waterfront Home
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

9.2 out of 10, Wonderful, (64)
"The cottage worked great for our sister trip. It was a good halfway point to many of the Key's attractions and was in a nice quieter community. The cottage was cozy and clean, but don't expect a fancy accommodation. The property was right on some water which was really nice."
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Riley's Retreat - Venture Out 107

Riley's Retreat - Venture Out 107

9.2 out of 10, Wonderful, (5)
"Quiet neighborhood close enough yet far enough from Key West madness "
Riley's Retreat - Venture Out 107
Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK

Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK

9.4 out of 10, Exceptional, (214)
"Very clean. Could use some updating such as fresh paint. "
The price is AED 1,120
AED 2,336 total
includes taxes & fees
24 Dec - 25 Dec
Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK
The Dancing Rooster: 2 Blocks from Duval in Old Town.
Main Entrance off Street - Peaceful and Quiet!

The Dancing Rooster: 2 Blocks from Duval in Old Town.

10.0 out of 10, Exceptional, (108)
"Our 3 bedroom, 2 bathroom bungalow accommodated the 5 of us perfectly. Kitchen had all that we needed, space to sit outside, and so close to the action on Duval St. "
The price is AED 1,836
AED 3,002 total
includes taxes & fees
16 Jan - 17 January 2025
The Dancing Rooster: 2 Blocks from Duval in Old Town.
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Exterior detail

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

8.0 out of 10, Very Good, (31)
"Just as advertised. "
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Duval Sea Turtle by Avantstay Great Location Close to Shops Shared Pool!
Pool

Duval Sea Turtle by Avantstay Great Location Close to Shops Shared Pool!

3.5 star property
8.0 out of 10, Very Good, (2)
"The living room furniture and mattresses are not the most comfortable. Worn. Mattresses in small bedroom need replacement. Air conditioner does not reach small bedroom. "
Duval Sea Turtle by Avantstay Great Location Close to Shops Shared Pool!
Sea Breeze Cottage with 2 Large Decks in Beautiful Truman Annex
Front of Cottage

Sea Breeze Cottage with 2 Large Decks in Beautiful Truman Annex

10.0 out of 10, Exceptional, (182)
"The property was exactly what we wanted and was clean, comfortable, and extended an unexpected level of privacy. The accommodation was perfect for our trip and the location was excellent. "
Sea Breeze Cottage with 2 Large Decks in Beautiful Truman Annex
**TIDEWATER VIEWS @ VENTURE OUT** 2BR/2BA Cottage + 35’ Private Slip | 80’ Pool
Welcome to Tidewater Views...

**TIDEWATER VIEWS @ VENTURE OUT** 2BR/2BA Cottage + 35’ Private Slip | 80’ Pool

10.0 out of 10, Exceptional, (203)
"Excellent stay at Tidewater View in Cudjoe Key. Lovely home and amenities. We will be back "
**TIDEWATER VIEWS @ VENTURE OUT** 2BR/2BA Cottage + 35’ Private Slip | 80’ Pool
Key West Found by Avantstay Close to Shops w/ Patio & Shared Pool! Week Long Stays Only
Living area

Key West Found by Avantstay Close to Shops w/ Patio & Shared Pool! Week Long Stays Only

3.0 star property
10.0 out of 10, Exceptional, (1)
"There are 3 things I would say could and should be better. 1) extra toilet paper. There was only one partial roll in each bathroom and one extra partial roll. 2) no shampoo/conditioner. 3) no directions to the pool. I had to call and find out where it was. For the amount you pay, you’d think those items would be available as there are everywhere else I’ve stayed. "
Key West Found by Avantstay Close to Shops w/ Patio & Shared Pool! Week Long Stays Only
FL Keys Cottage with Ocean Views - Venture Out Unit 395

FL Keys Cottage with Ocean Views - Venture Out Unit 395

8.8 out of 10, Excellent, (3)
"Very clean, comfortable beds. Close to everything we wanted to do!"
FL Keys Cottage with Ocean Views - Venture Out Unit 395
Escape to the Keys! Pet-Friendly Sugarloaf Key Bungalow - Great Amenities (84)
Miscellaneous

Escape to the Keys! Pet-Friendly Sugarloaf Key Bungalow - Great Amenities (84)

9.8 out of 10, Exceptional, (8)
"Our stay was amazing. The property was immaculate. The amenities were great. We will be back next year. The location was perfect. Close to Key West and alot to do in the area. Thank you for making our stay wonderful. See you next year!"
Escape to the Keys! Pet-Friendly Sugarloaf Key Bungalow - Great Amenities (84)
Canal front, dockage, 2 bedroom, 2 bath
Exterior

Canal front, dockage, 2 bedroom, 2 bath

9.0 out of 10, Wonderful, (73)
"Property was just as advertised and looked as nice in person as in ads"
Canal front, dockage, 2 bedroom, 2 bath
Pet-Friendly Bungalow in Sugarloaf Key, FL - Fantastic Amenities (83)
Exterior

Pet-Friendly Bungalow in Sugarloaf Key, FL - Fantastic Amenities (83)

9.6 out of 10, Exceptional, (10)
"Our stay was wonderful! The room was perfect for our stay. "
Pet-Friendly Bungalow in Sugarloaf Key, FL - Fantastic Amenities (83)
Tranquility by Avantstay Close to Duval St w/ BBQ & Shared Pool
Exterior

Tranquility by Avantstay Close to Duval St w/ BBQ & Shared Pool

3.0 star property
9.0 out of 10, Wonderful, (4)
"The unit had fun and stylish decor. Bed was comfy and I’m picky. The steeps are a challenge- always forgetting there is one more step. Was concerned about the noise in the back from a restaurant or bar- but when doors closed you can’t hear it. And there is no noise later in the evening. One suggestion- some nightlights for the night for Safety. We will be back. Great experience "
Tranquility by Avantstay Close to Duval St w/ BBQ & Shared Pool
Lakefront Bungalow - Pet-Friendly - Sugarloaf Key - Great Amenities (22)
Aerial view

Lakefront Bungalow - Pet-Friendly - Sugarloaf Key - Great Amenities (22)

10.0 out of 10, Exceptional, (11)
"Super cute bungalow surrounded by a beautiful lake. The location was perfect for us and super convenient to Key West! The staff was very friendly and very helpful. After hours check-in was very smooth. We will stay there again when we are in the area!"
Lakefront Bungalow - Pet-Friendly - Sugarloaf Key - Great Amenities (22)
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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Other property types in Raccoon Key

Real World MTV House-18 to 22 guests, Not Just a House Your Own Private Resort
The House from the Ocean Side--2 Huge Porches

Real World MTV House-18 to 22 guests, Not Just a House Your Own Private Resort

9.6 out of 10, Exceptional, (82)
"Great trip with 16 people for a 50th birthday party. Host was very helpful and informative throughout the trip. Great for large groups."
Real World MTV House-18 to 22 guests, Not Just a House Your Own Private Resort
Aqua Lodges at Hurricane Hole Marina
Exterior

Aqua Lodges at Hurricane Hole Marina

2.0 star property
8.8 out of 10, Excellent, (106)
"Nice for affordable price "
The price is AED 751
AED 1,361 total
includes taxes & fees
8 Jan - 9 January 2025
Aqua Lodges at Hurricane Hole Marina
Steps from Duval, Pool on Site & Bikes Included!
Pool

Steps from Duval, Pool on Site & Bikes Included!

9.6 out of 10, Exceptional, (358)
"very clean, was able to park the car and walk to where we wanted to go. I would stay again."
The price is AED 584
AED 1,161 total
includes taxes & fees
9 Jan - 10 January 2025
Steps from Duval, Pool on Site & Bikes Included!
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.

Frequently asked questions

How much do cottages in Raccoon Key cost?
Cottages in Raccoon Key range between AED 1,120 and AED 1,836 per night. These stays offer a chance to get in tune with nature — at a price you can afford. 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?
Pick from multiple cottages in Raccoon Key with a total average guest review rating of 9.3. Simonton Court Cottages is a wonderful place to put your feet up between adventures. This 3.5-star cottage also comes with WiFi and housekeeping services. Casa Manana Key West Monthly: 2 Br is another top option with travelers in this area. It has a 3-star rating and amenities including a king bed and a barbecue grill.
How many cottages are there in Raccoon Key?
Take your pick of 69 cottages in Raccoon Key. Whether you’re taking a trip with the family or planning a retreat with your closest amigos, Expedia will help you find the perfect place to enjoy nature’s beauty.
Why book your cottage in Raccoon Key with Expedia?
Expedia has some terrific cottages in Raccoon Key, so start packing for a memorable vacay close to nature. If you’re on a budget, select how much you’d like to spend and the preferred star rating of your property. Or, use our handy filters to search for cottages with a pool or a kitchen. We’ll help you find the right fit whatever your style of travel or plans.
How can I find cheap cottages in Raccoon Key?
With Expedia’s user-friendly filter tool, locating cheap cottages in Raccoon Key has never been easier. To find properties that’ll make your bank balance smile, fine-tune your search results by budget, star rating and amenities.