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Compare 70 Cottages in Raccoon Key with updated reviews, rates, and availability.

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 SAR 604
SAR 1,639 total
includes taxes & fees
26 Nov - 27 Nov
Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK
Southernmost Retreat: 2 Blocks from Duval in Old Town.
Main Entrance off Street - Peaceful and Quiet!
Southernmost Retreat: 2 Blocks from Duval in Old Town.
10.0 out of 10, Exceptional, (106)
"Key West after fantasy week we had a great time manager always got right back to us"
The price is SAR 1,877
SAR 3,094 total
includes taxes & fees
24 Nov - 25 Nov
Southernmost Retreat: 2 Blocks from Duval in Old Town.
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
8.0 out of 10, Very Good, (29)
"Just as advertised. "
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
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, (179)
"The property is great location. Nice and clean. We really enjoyed stay. Pillows would be the only negative feedback. Need some softer ones."
Sea Breeze Cottage with 2 Large Decks in Beautiful Truman Annex
Conch Republic Consul General's Cottage.-Pool-Historic District-Assigned Parking
Lots of sitting including lounge chairs and table and chair sets
Conch Republic Consul General's Cottage.-Pool-Historic District-Assigned Parking
9.2 out of 10, Wonderful, (69)
"This quaint little bungalow has everything you need. We walked about 21 miles overall during our 8 day stay but we were able to see so many amazing things. We went fishing, went on a sunset cruise, walked to several of the museums. We were Awed by the rich history. I think we actually ate our way through Key West and still had a few meals in the bungalow. Oh did I mention the almost private pool. We loved that, after a long day walking we would come back and soak in the pool for a while. We...
Conch Republic Consul General's Cottage.-Pool-Historic District-Assigned Parking
waterfront cottage near key west, sleeps 6
pools, a spa and the ocean, what more do you need?
waterfront cottage near key west, sleeps 6
9.4 out of 10, Exceptional, (16)
"We had a great stay! Other than the weather, everything was perfect! We had plans to dock our boat up at the house but it was too windy to take the boat out. We still enjoyed the patio and grilled out one night! We took showers across the street at the camp restrooms bc there were four of us and we would’ve ran out of hot water but that was no problem. We enjoyed our stay!"
waterfront cottage near key west, sleeps 6
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, (62)
"We are old Florida Keys visitors and past residents. We were delighted with the accommodations, pool and view.We are planning our next stay...same time, same place minus the two days of Helene.Will have to make arraignments for a recliner to be delivered for my wifes sleeping and sitting comfort.Our first night was Sept 20 not the 19th as indicated in error. We stayed 9 nights.Thanks again for the great stay!"
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Blue Mind - Venture Out Unit 225
Blue Mind - Venture Out Unit 225
9.4 out of 10, Exceptional, (66)
"nice place 3rd time there"
Blue Mind - Venture Out Unit 225
**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, (200)
"Great little place on the water especially if you are bringing a boat. The house was perfect! It was my birthday and our host Charity even got me a birthday cake and card. We will definitely be back!! "
**TIDEWATER VIEWS @ VENTURE OUT** 2BR/2BA Cottage + 35’ Private Slip | 80’ Pool
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, (53)
"The grounds are good. The pools were clean and plenty of deck and dock space. The cottage itself needs help. It needed general maintenance on it. It needs caulking in the bathroom. It needs weather strips around door as it is not tight. There was not enough hand towels and there are no oven mitts in the kitchen. The exhaust fan has been taken out. The ceiling fan in one room only works on high. The ac vents and exhaust fan in the bathroom needs cleaning. We were happy about the porch except the...
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
~ Chick-A-Pea Cottage ~ Enjoy Key West’s charisma, with a pool, and parking!
Chick-a-Pea Cottage has an amazing pool with waterfall!
~ Chick-A-Pea Cottage ~ Enjoy Key West’s charisma, with a pool, and parking!
10.0 out of 10, Exceptional, (206)
"The house was perfect in every way for us….. 2 married couples. The communication with property manager was beyond superb. Although a few steps from Duval, was a very quiet location. Highly recommend. "
~ Chick-A-Pea Cottage ~ Enjoy Key West’s charisma, with a pool, and parking!
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!
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)
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
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
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, (81)
"Very well run property/operation. The house has tons of things to do and was ideal four our bachelor party. Definitely recommend"
The price is SAR 7,505
SAR 14,196 total
includes taxes & fees
10 Dec - 11 Dec
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, (104)
"Nice for affordable price "
The price is SAR 503
SAR 1,083 total
includes taxes & fees
3 Dec - 4 Dec
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, (356)
"We walked most everywhere and loved the Southernmost Beach Bar! Eating at Moon Dog Cafe was so spectacular that we ate there 3 times in 2 days! This place is all it says it is. Simply perfect. "
The price is SAR 484
SAR 1,034 total
includes taxes & fees
22 Dec - 23 Dec
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 SAR 604 and SAR 1,877 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 9.2. 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 70 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.