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Compare 712 Vacation Homes in Raccoon Key with updated reviews, rates, and availability.

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

9.0 out of 10, Wonderful, (34)
"Great place in a very convenient location! Pull out couch isn’t the most comfortable thing in the world, but it sleeps. Super clean, super easy check in (was even able to get in early) and a great price! "
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!

Spec.Feb.24-Mar 1 @265 lodg + w. 3 night stay close beach

9.0 out of 10, Wonderful, (157)
"The good: convenient location, quiet, bed was comfortable, the little patio in the back is nice. The bad: there is no “on site’ parking but we always found parking on the street about a block away, The communication with property manager was a bit strange, she accused us of still being inside the unit a full day after we had check out on time, despite texting her to tell her we had left (an hour before check out)"
Spec.Feb.24-Mar 1 @265 lodg + w. 3 night stay close beach

Poolside Cottage #411

9.8 out of 10, Exceptional, (38)
"Quiet area close to everything we were looking for. "
The price is ¥51,589
¥79,616 total
includes taxes & fees
Feb 12 - Feb 13
Poolside Cottage #411

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

9.6 out of 10, Exceptional, (32)
"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!

Feb 2-5 spec 279.lodg. + extras Close to beach w full kitchen. & patio

9.6 out of 10, Exceptional, (208)
"The location, size and layout were excellent. For the cost, however, it was lacking in cleanliness, and shabby, bleach-stained bath towels, and as others have mentioned, the lack of shampoo, soap, a dish towel and dish drainer, are unacceptable. "
Feb 2-5 spec 279.lodg. + extras Close to beach w full kitchen. & patio

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

9.6 out of 10, Exceptional, (175)
"My family enjoyed our stay at Captain’s Quarters. The children especially enjoyed the heated pool and there was adequate room for the seven of us. The bedding was comfortable and it was handy that all of the bedrooms had TVs. There is normally places to park out front if one happens to have a golf cart. There are some issues that need to be addressed and we had many electrical plugs that were very old and wouldn’t work so charging phones became an issue. … It could use a freshen up as window...
CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!

Villa Déjà vu Key West - Steps Off Duval w Private Pool

9.4 out of 10, Exceptional, (54)
"Amazing time and experience! "
Villa Déjà vu Key West - Steps Off Duval w Private Pool

Coastal Comfort; Waterfront Luxury Home with private pool!

9.4 out of 10, Exceptional, (63)
"This property was awsome! The area is quiet and close to grocery stores. And a.short drive to down townlpve it, love it, love it. Definitely coming back!!"
Coastal Comfort; Waterfront Luxury Home with private pool!

Casa Bonita | Stylish Condo with Pool, Gardens & Prime Old Town Location

10.0 out of 10, Exceptional, (3)
"Had a wonderful short trip to the keys - this place was in the perfect location to walk all of Key West from shopping Duval street shopping and sight seeing ate lighthouse and even the coast guard station - would highly recommend. "
The price is ¥53,298
¥131,216 total
includes taxes & fees
Feb 11 - Feb 12
Casa Bonita | Stylish Condo with Pool, Gardens & Prime Old Town Location

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

9.8 out of 10, Exceptional, (90)
"Beautiful property. Great communication. Very clean. Literally right next to duval street. Highly recommend "
EL CORAZON~ Renovated Home w/ Direct Access to Duval St. w/ Pool & Parking!

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

9.6 out of 10, Exceptional, (25)
"Great property! Easy to get back and forth to Key West! Loved the water view!"
HAVANA DAYDREAMING ~ Waterfront 1 BR/1 Ba w/ Dockage & Hot Tub!

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!

Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security

9.8 out of 10, Exceptional, (234)
"Clean, easy access, friendly complex/neighborhood. "
Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security

The Flower Power House - Boho Beautiful

2.5 star property
8.8 out of 10, Excellent, (25)
"We truly enjoyed our stay at the Flower Power House! The house was awesome, in a great neighborhood and had everything we needed! The property manager was very pleasant, responsive and accommodating! We will definitely return the next time we are in Key West! Thank you! "
The Flower Power House - Boho Beautiful

Conch Cove - 3br/3ba with private heated pool and private parking

10.0 out of 10, Exceptional, (4)
"Rick and team were awesome and exceptional throughout the whole stay! Nice house!! "
The price is ¥135,719
¥264,357 total
includes taxes & fees
Feb 13 - Feb 14
Conch Cove - 3br/3ba with private heated pool and private parking

Luxurious 3-Bedroom Key West Home with WiFi, EV charging, AC & Tropical Vibes!

2.0 star property
6.0 out of 10, (2)
"Plenty of room indoors and outdoors to live in. Comfortable beds. Clean and tidy"
Luxurious 3-Bedroom Key West Home with WiFi, EV charging, AC & Tropical Vibes!

COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!

9.4 out of 10, Exceptional, (29)
"Excellent views, very quiet, pool was outstanding "
COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!

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

9.6 out of 10, Exceptional, (200)
"Delighted with the location & size. Quiet but close to activities. Enjoyed the outdoor space- well appointed."
MANGO MARGARITA~ 2 bedroom/2.5 bath, heated private pool, and close to Duval!

BAHAMA DREAMING ~ Incredibly Located 3 Bedroom, 2 Bath w/ Private Pool!

9.6 out of 10, Exceptional, (65)
"Overall the best things about the home was location to Duval St and historic sites. The pool was relaxing and the large covered porch with big table was an ideal place to eat and hang outdoors."
BAHAMA DREAMING ~ Incredibly Located 3 Bedroom, 2 Bath w/ Private Pool!

Beautiful Family-Friendly, Dock, Marina, Heated Pool, near Key West, MM21.5

10.0 out of 10, Exceptional, (214)
"Fantastic experience, beautiful place & location! Exactly as advertised! Hosts were attentive and accommodating! Highly recommend! "
Beautiful Family-Friendly, Dock, Marina, Heated Pool, near Key West, MM21.5
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, (114)
"Great getaway, yet very close to Key West. It is about a 5-10 minute drive from property to Duval Street."
The price is ¥17,757
¥41,441 total
includes taxes & fees
Feb 9 - Feb 10
Aqua Lodges at Hurricane Hole Marina

Hyatt Vacation Club at Sunset Harbor, Key West

3.5 star property
8.4 out of 10, Very Good, (289)
"I had a great experience with my family!"
The price is ¥82,329
¥96,913 total
includes taxes & fees
Feb 17 - Feb 18
Hyatt Vacation Club at Sunset Harbor, Key West
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.