Search Vacation Homes in Raccoon Key

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Compare 722 Vacation Homes in Raccoon Key with updated reviews, rates, and availability.

INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub!

9.6 out of 10, Exceptional, (30)
"This was a very smooth, perfect 5 night visit. The property offered us everything that we could need. It was a short drive to Duval St and all of the activities in Key West yet the property was very peaceful with a wonderful waterfront patio that we sat out on and enjoyed. The hot tub was a nice treat as well. I have to mention the incredible responsiveness of the property manager. Every question that I had they responded to within minutes which was very much appreciated. "
INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub!

ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!

9.0 out of 10, Wonderful, (32)
"Peaceful and paradise!"
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!

OFF CALL ~ Rustic, Nautical Decor With King Primary Suite & Heated Pool!

9.8 out of 10, Exceptional, (76)
"This was our first time staying in an air b&b. We absolutely loved our stay! We wish we would have booked for longer. We highly recommend this place as it was super clean, spacious, and relaxing! We will be back! "
OFF CALL ~ Rustic, Nautical Decor With King Primary Suite & Heated Pool!

CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!

9.6 out of 10, Exceptional, (174)
"Captains Quarters is a beautiful house, great location, walking distance to Duval, clean, heated pool and plenty of amenities to make your stay enjoyable. Would def stay there again. "
CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!

Poolside Cottage #411

10.0 out of 10, Exceptional, (33)
"Really nice place to stay. We had a pleasant stay and the property was great "
The price is ¥53,188
¥82,399 total
includes taxes & fees
Jan 8 - Jan 9
Poolside Cottage #411

Banana Breeze: Oceanview 4-bedroom home with private pool & lush landscaping!

9.8 out of 10, Exceptional, (99)
"Great place to stay very kid friendly and a short golfcart ride to everything "
Banana Breeze: Oceanview 4-bedroom home with private pool & lush landscaping!

SUNKISSED ~ Come Enjoy this Charming 3 Bedroom Home When Location Is Key!

9.8 out of 10, Exceptional, (171)
"Accommodations were great. Loft bedroom was a little noisy if people got up early. Noise came straight upstairs. Otherwise accommodations were great. Kitchen well stocked and washer and dryer!! "
SUNKISSED ~ Come Enjoy this Charming 3 Bedroom Home When Location Is Key!

DUVAL SQUARE, KEY WEST Lovely 2 Bedroom 2.5 Bath Condo in a GREAT Location!

9.2 out of 10, Wonderful, (178)
"Nice place to stay. Very comfortable, spacious, lots of extras we didn’t have to provide. Would stay here again. 😎"
DUVAL SQUARE, KEY WEST Lovely 2 Bedroom 2.5 Bath Condo in a GREAT Location!

CONCH HEAVEN ~ Stylish 2B/2Ba, Sleeps 6 in Old Town w/ Heated Cocktail Pool!

9.8 out of 10, Exceptional, (204)
"The property looks like the pictures . It is very cozy . It is located in a very quiet neighborhood , about 20 min walking from the center. It does not have a designated parking spot but parking around the house is not a problem. Check in and communication with the property manager is very easy . I read I’m another review that the pool was not warm enough but in our case since we arrived the pool was perfectly warm"
CONCH HEAVEN ~ Stylish 2B/2Ba, Sleeps 6 in Old Town w/ Heated Cocktail Pool!

Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes

9.8 out of 10, Exceptional, (219)
"Perfect location with sunset views and kayaking "
The price is ¥47,208
¥117,666 total
includes taxes & fees
Jan 8 - Jan 9
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes

Historic Mansion in Old Town Key West with Private Pool - Sleeps 16!

9.8 out of 10, Exceptional, (212)
"This house is in a great location - very convenient to walk to shops and restaurants/ bars in downtown Key West. The house is clean and well stocked. We stayed with a large group and would definitely book again!"
The price is ¥110,253
¥239,730 total
includes taxes & fees
Jan 26 - Jan 27
Historic Mansion in Old Town Key West with Private Pool - Sleeps 16!

LOST SHAKER OF SALT ~ 3 Bed, 2 Bath Pet Friendly with 40' Private Heated Pool

10.0 out of 10, Exceptional, (187)
"Another fabulous stay at the Lost Shaker of Salt. Great location on Key West. Accommodations met our needs. The pool is delightful. Can’t wait to stay here again when we come back to Key West. "
LOST SHAKER OF SALT ~ 3 Bed, 2 Bath Pet Friendly with 40' Private Heated Pool

3 night minimum! Spectacular Ocean Views!

8.4 out of 10, Very Good, (18)
"Venture out is a great location for being on the water. This rental was reasonable, spacious and clean! We had an amazing stay with no issues!"
3 night minimum! Spectacular Ocean Views!

NEWLY REMODELED KITCHEN!! PET FRIENDLY! 3 Bedroom 3 bathroom home. Sleeps 8

9.6 out of 10, Exceptional, (197)
"Exactly as advertised with an incredible host. We had a great time in Key West! "
NEWLY REMODELED KITCHEN!! PET FRIENDLY! 3 Bedroom 3 bathroom home. Sleeps 8

EL CORAZON~ Renovated Home w/ Direct Access to Duval St. w/ Pool & Parking!

9.8 out of 10, Exceptional, (88)
"Loved the house it was awesome for our group plenty of space for our large group. The beds were very comfortable and every thing was clean and looked new. "
EL CORAZON~ Renovated Home w/ Direct Access to Duval St. w/ Pool & Parking!

Walk to Beach, Open Water View from porch , dock, bikes, kayaks & snorkel gear

9.8 out of 10, Exceptional, (108)
"This place was beautiful. When staying in a rental, there can always be a little something that is not right or goes wrong. Nothing went wrong with this place. The master bed evidently has an older form top mattress that doesn't dissipate heat, so it you are warm sleeping you will want to sleep in the second bedroom. It's not quite as bad. You may want to bring your own King Sheets and pillowcases. They were very rough!! All in all, I would recommend this place! They seemed to have everything...
Walk to Beach, Open Water View from porch , dock, bikes, kayaks & snorkel gear

MANGO MARGARITA~ 2 bedroom/2.5 bath, heated private pool, and close to Duval!

9.6 out of 10, Exceptional, (199)
"Outstanding property! Cannot recommend highly enough!"
MANGO MARGARITA~ 2 bedroom/2.5 bath, heated private pool, and close to Duval!

HAVANA DAYDREAMING ~ Waterfront 1 BR/1 Ba w/ Dockage & Hot Tub!

9.8 out of 10, Exceptional, (22)
"Clean, cozy and cute "
HAVANA DAYDREAMING ~ Waterfront 1 BR/1 Ba w/ Dockage & Hot Tub!

Multi-home tropical paradise with large, heated pool, & wraparound sundeck

9.8 out of 10, Exceptional, (63)
"The place is FANTASTIC! Great location, beds comfortable and everything we could need. Worked out so well for all of us! The way they do things makes the time there so easy, much appreciated! We want/will come back here. Greatfully, Maria"
Multi-home tropical paradise with large, heated pool, & wraparound sundeck

3/4 Time: Oceanfront, luxury home with private pool & lush landscaping

9.8 out of 10, Exceptional, (70)
"We had an amazing stay, this place was everything shown as well as more!! We at first were worried about the location being so far from Duval, however we could not have been more wrong. EVERYTHING you could want or need you can walk to, we were very happy with our stay and the host. Thank you. Don’t hesitate to book this unit, we will be back!!"
3/4 Time: Oceanfront, luxury home with private pool & lush landscaping
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

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

2.0 star property
8.8 out of 10, Excellent, (108)
"Family had a great time "
The price is ¥29,189
¥54,967 total
includes taxes & fees
Jan 8 - Jan 9
Aqua Lodges at Hurricane Hole Marina

Steps from Duval, Pool on Site & Bikes Included!

9.6 out of 10, Exceptional, (359)
"very clean, was able to park the car and walk to where we wanted to go. I would stay again."
The price is ¥17,193
¥39,729 total
includes taxes & fees
Jan 9 - Jan 10
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.