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Compare 725 Vacation Homes in Raccoon Key with updated reviews, rates, and availability.

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

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

9.6 out of 10, Exceptional, (29)
"Beautiful property, amazing outdoor space on the water, clean and comfortable Given the cleaning fees are 50% of the cost I was little annoyed at how much check out chores are required of the guests. "
INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub!
BAHAMA DREAMING ~ Incredibly Located 3 Bedroom, 2 Bath w/ Private Pool!
A heated pool

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

9.8 out of 10, Exceptional, (59)
"Excellent location, clean, roomy, wonderful!"
BAHAMA DREAMING ~ Incredibly Located 3 Bedroom, 2 Bath w/ Private Pool!
OFF CALL ~ Rustic, Nautical Decor With King Primary Suite & Heated Pool!
A heated pool

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

9.6 out of 10, Exceptional, (74)
"My brother and I hadn’t seen each other for quite a while. This place offered us so much comfort and convenience. GREAT place to stay. We will be back. Thank you. "
OFF CALL ~ Rustic, Nautical Decor With King Primary Suite & Heated Pool!
ISLAND DAZE ~ Perfectly Located 2 Bedroom, 2 Bathroom Cottage!
Interior

ISLAND DAZE ~ Perfectly Located 2 Bedroom, 2 Bathroom Cottage!

9.8 out of 10, Exceptional, (114)
"The cottage was perfect for two couples. Both bedrooms had attached bathrooms. Just a few houses down from Duval Street and a few blocks from the beach."
ISLAND DAZE ~ Perfectly Located 2 Bedroom, 2 Bathroom Cottage!
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
Beach nearby

Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

9.0 out of 10, Wonderful, (67)
"House needs many minor repairs but is very functional. Good location."
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
Terrace/patio

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

9.0 out of 10, Wonderful, (30)
"Peaceful and paradise!"
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
PAGITT HOUSE - 3/ 2 - OLD TOWN KEY WEST WITH POOL
Fridge, microwave, oven, stovetop

PAGITT HOUSE - 3/ 2 - OLD TOWN KEY WEST WITH POOL

9.8 out of 10, Exceptional, (10)
"Property was clean with everything we needed, including linens and beach towels. Kitchen was fully equipped. The upstairs was a little too warm at night, but it was in the 90's every day during our stay, so we could understand this. One of the twin beds has a mattress that was very uncomfortable, and needs replaced. We have a vacation rental of our own and we were well pleased with this property. We would recommend! Thank you for the little longer checkout time, as the hurricane changed...
The price is ￥92,868
￥224,606 total
includes taxes & fees
Dec 2 - Dec 3
PAGITT HOUSE - 3/ 2 - OLD TOWN KEY WEST WITH POOL
Spacious Key West Conch Cottage with WiFi & Private Hot Tub - Dogs OK
Fridge, microwave, oven, stovetop

Spacious Key West Conch Cottage with WiFi & Private Hot Tub - Dogs OK

9.0 out of 10, Wonderful, (183)
"Had a great time. Great location. Doesn’t provide more than one trash bag which was an issue we ran into. "
The price is ￥102,155
￥182,675 total
includes taxes & fees
Dec 8 - Dec 9
Spacious Key West Conch Cottage with WiFi & Private Hot Tub - Dogs OK
Poolside Cottage #411
Outdoor dining

Poolside Cottage #411

10.0 out of 10, Exceptional, (30)
"Nice location very close to everything and close enough to Duval St. Unit itself was in good condition and the kitchen stocked pretty good but was missing dish cloths, dish towels and dishwasher detergent. None of the grills on the property were functional. Host was very responsive the entire process. Would stay there again"
The price is ￥34,826
￥58,894 total
includes taxes & fees
Dec 2 - Dec 3
Poolside Cottage #411
Poolside Cottage #412
Outdoor dining

Poolside Cottage #412

10.0 out of 10, Exceptional, (13)
"Nice place right by the pool."
The price is ￥34,826
￥58,430 total
includes taxes & fees
Dec 1 - Dec 2
Poolside Cottage #412
HAVANA DAYDREAMING ~ Waterfront 1 BR/1 Ba w/ Dockage & Hot Tub!
Terrace/patio

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

9.8 out of 10, Exceptional, (21)
"Clean, cozy and cute "
HAVANA DAYDREAMING ~ Waterfront 1 BR/1 Ba w/ Dockage & Hot Tub!
CONCH HEAVEN ~ Stylish 2B/2Ba, Sleeps 6 in Old Town w/ Heated Cocktail Pool!
A heated pool

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

9.8 out of 10, Exceptional, (201)
"The house was clean and conveniently located. We walked to everything!"
CONCH HEAVEN ~ Stylish 2B/2Ba, Sleeps 6 in Old Town w/ Heated Cocktail Pool!
Dog-friendly Key West Cottage with Private Hot Tub & Unbeatable Location
Fridge, microwave, coffee/tea maker, toaster

Dog-friendly Key West Cottage with Private Hot Tub & Unbeatable Location

9.0 out of 10, Wonderful, (169)
"My sister and I rented the place for ourselves and our 4 young adult kids (ranging from 18-21), and we had a very nice time. The AC is not really "central", has free-standing units in 2 of the bedrooms that vent outside, but they are well installed and do the trick, if a bit tricky to regulate the temperature correctly initially. The place is a typical Key West bungalow that feels like some shoeboxes were nailed together, and the back yard is even smaller than expected. Location is great, we did...
The price is ￥56,804
￥118,461 total
includes taxes & fees
Nov 29 - Nov 30
Dog-friendly Key West Cottage with Private Hot Tub & Unbeatable Location
Kelly's Kabin - Adorable Private Summerland Key Cottage
Fridge, microwave, oven, stovetop

Kelly's Kabin - Adorable Private Summerland Key Cottage

9.8 out of 10, Exceptional, (104)
"Check in was super easy.Over all was a very comfortable place.Air condition was nice and cold..Everything worked properly.Located just South of Boondocks Bar&Grille which os one of our favorite spots.Easy to get back and forth to Key West.Would definately stay here again."
The price is ￥42,565
￥93,642 total
includes taxes & fees
Dec 1 - Dec 2
Kelly's Kabin - Adorable Private Summerland Key Cottage
20 MINUTES TO KEY WEST , BOATERS PARADISE
Exterior

20 MINUTES TO KEY WEST , BOATERS PARADISE

9.6 out of 10, Exceptional, (44)
"The property is perfect for a couple maybe 3. Its on the smaller side but we loved our time there. Property owner was very attentive even went and bought fishing poles when we asked if there were some available! We will be back!"
20 MINUTES TO KEY WEST , BOATERS PARADISE
Year Rd. w.7 night stay get 10% Off!. Full kitchen & outside area 1/2 mile beach
Terrace/patio

Year Rd. w.7 night stay get 10% Off!. Full kitchen & outside area 1/2 mile beach

9.0 out of 10, Wonderful, (152)
"A lovely, typical property located in Old Town area of Key West. Very comfortable stay, quiet ensuring good sleep. Great location and I did everything either by walking or on the bicycle I hired. Excellent communication with host who replied within a couple of hours if not sooner!!"
Year Rd. w.7 night stay get 10% Off!. Full kitchen & outside area 1/2 mile beach
SUNKISSED ~ Come Enjoy this Charming 3 Bedroom Home When Location Is Key!
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (168)
"We enjoyed our stay. The house was very clean and in a convenient location. We would stay again."
SUNKISSED ~ Come Enjoy this Charming 3 Bedroom Home When Location Is Key!
WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS
Outdoor dining

WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS

9.6 out of 10, Exceptional, (79)
"The stay was good. It was close enough to wedding venue. Few things wrong when we got there. My husband fixed the closet door because it would not open n shut also a door knob was about to fall off so he tightened it."
The price is ￥30,801
￥77,274 total
includes taxes & fees
Nov 26 - Nov 27
WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS
COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!
Outdoor dining

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

9.4 out of 10, Exceptional, (26)
"Super nice place Comfortable Couch Comfortable Bed"
COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!
12% Off Wk.stay Feb,March & April 1/2 mile 2 beach, full kitchen & front porch
Exterior detail

12% Off Wk.stay Feb,March & April 1/2 mile 2 beach, full kitchen & front porch

9.6 out of 10, Exceptional, (200)
"Very walkable. Cozy comfortable place. Cute and safe neighborhood. Setup well for cooking. AC pumps some good cold air. "
12% Off Wk.stay Feb,March & April 1/2 mile 2 beach, full kitchen & front porch
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
Aerial view

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 ￥309,405
￥585,262 total
includes taxes & fees
Dec 2 - Dec 3
Real World MTV House-18 to 22 guests, Not Just a House Your Own Private Resort
Aqua Lodges at Hurricane Hole Marina
Restaurant

Aqua Lodges at Hurricane Hole Marina

2.0 star property
8.8 out of 10, Excellent, (104)
"Nice for affordable price "
The price is ￥18,805
￥42,921 total
includes taxes & fees
Nov 26 - Nov 27
Aqua Lodges at Hurricane Hole Marina
Steps from Duval, Pool on Site & Bikes Included!
Beach towels

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 ￥15,323
￥36,935 total
includes taxes & fees
Dec 2 - Dec 3
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.