Search Vacation Homes in Raccoon Key

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Check prices for these dates

Next weekend
9 May - 11 May
In two weeks
16 May - 18 May
In one month
30 May - 1 Jun
In two months
27 Jun - 29 Jun

Compare 795 Vacation Homes in Raccoon Key with updated reviews, rates, and availability.

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

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

9.2 out of 10, Wonderful, (192)
"This property was very clean and perfect location. We relaxed by the pool area one afternoon and looked over the roof and peple watcged. "
DUVAL SQUARE, KEY WEST Lovely 2 Bedroom 2.5 Bath Condo in a GREAT Location!
EL CORAZON~ Renovated Home w/ Direct Access to Duval St. w/ Pool & Parking!
A heated pool

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

9.8 out of 10, Exceptional, (98)
"Clean, roomy, comfortable. Adequate seating and dishes for 6 adults. Great mattresses and pillows. "
EL CORAZON~ Renovated Home w/ Direct Access to Duval St. w/ Pool & Parking!
NEWLY Redecorated as of 4-15-25. The current pics. do not reflect the changes
Terrace/patio

NEWLY Redecorated as of 4-15-25. The current pics. do not reflect the changes

9.0 out of 10, Wonderful, (162)
"This unit was perfect! Nice updates and a comfortable space close to everything"
NEWLY Redecorated as of 4-15-25. The current pics. do not reflect the changes
Spec. 4-29 &4-30 169.00 lodg. + extras Close to beach plus kitchen
Exterior detail

Spec. 4-29 &4-30 169.00 lodg. + extras Close to beach plus kitchen

9.6 out of 10, Exceptional, (215)
"Great location. The room met our needs. It was clean and comfortable. The owner did a great job of communicating everything we needed to know. Everything was walkable, which we appreciated. "
Spec. 4-29 &4-30 169.00 lodg. + extras Close to beach plus kitchen
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
Terrace/patio

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

8.8 out of 10, Excellent, (46)
"It was just the right place for my family. We really enjoyed the view and close proximity to Key West. "
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
Captain's Daughter: Oversized home for the whole family w/private pool & dock
A heated pool

Captain's Daughter: Oversized home for the whole family w/private pool & dock

9.8 out of 10, Exceptional, (127)
"Very large, modern, and quiet home, perfect for a large family vacation! It made our 7 days on Key West the best!"
Captain's Daughter: Oversized home for the whole family w/private pool & dock
BAHAMA DREAMING ~ Incredibly Located 3 Bed, 2 Bath w/ Private Heated Pool!
A heated pool

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

9.6 out of 10, Exceptional, (76)
"Excellent location, clean, roomy, wonderful!"
BAHAMA DREAMING ~ Incredibly Located 3 Bed, 2 Bath w/ Private Heated Pool!
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, (180)
"Great time very nice place"
SUNKISSED ~ Come Enjoy this Charming 3 Bedroom Home When Location Is Key!
Casa Bonita | Stylish Condo with Pool, Gardens & Prime Old Town Location
A heated pool

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

10.0 out of 10, Exceptional, (20)
"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 AED 1,544
AED 3,505 total
includes taxes & fees
4 May - 5 May
Casa Bonita | Stylish Condo with Pool, Gardens & Prime Old Town Location
LADY ADMIRAL ~ Sweet cottage & guest house with private pool off Duval!
A heated pool

LADY ADMIRAL ~ Sweet cottage & guest house with private pool off Duval!

9.8 out of 10, Exceptional, (217)
"We had so much fun! Location was perfect!"
LADY ADMIRAL ~ Sweet cottage & guest house with private pool off Duval!
SOUTHERNMOST BELLE~ Heated Pool, Gourmet Kitchen & Elegant Large Bedrooms!
A heated pool

SOUTHERNMOST BELLE~ Heated Pool, Gourmet Kitchen & Elegant Large Bedrooms!

9.8 out of 10, Exceptional, (183)
"The house was amazing and Shana took very good care of us during our stay, will definitely plan a return trip! "
SOUTHERNMOST BELLE~ Heated Pool, Gourmet Kitchen & Elegant Large Bedrooms!
NEW listing!! Luxurious Island Pearl, 2 Bed/2 Bath Home near Duval - Pool
Fridge, microwave, oven, stovetop

NEW listing!! Luxurious Island Pearl, 2 Bed/2 Bath Home near Duval - Pool

10.0 out of 10, Exceptional, (15)
"Place was perfect and property management was great. Will definitely try to stay here again."
The price is AED 2,340
AED 4,500 total
includes taxes & fees
26 May - 27 May
NEW listing!! Luxurious Island Pearl, 2 Bed/2 Bath Home near Duval - Pool
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
Fridge, microwave, oven, stovetop

Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

8.8 out of 10, Excellent, (146)
"Good location "
The price is AED 1,102
AED 2,327 total
includes taxes & fees
20 May - 21 May
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
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!

9.8 out of 10, Exceptional, (82)
"We very much enjoyed our stay. Very nice condo and beautiful pool close to Key West and Botanical Gardens which we enjoyed!"
OFF CALL ~ Rustic, Nautical Decor With King Primary Suite & Heated Pool!
Perfect Location, Private Heated Pool & Pristine Luxury Home!
Outdoor pool, a heated pool

Perfect Location, Private Heated Pool & Pristine Luxury Home!

10.0 out of 10, Exceptional, (172)
"Great place. Great location and everything was perfect "
The price is AED 3,673
AED 7,163 total
includes taxes & fees
4 May - 5 May
Perfect Location, Private Heated Pool & Pristine Luxury Home!
Cudjoe Cottages, swimming pool, just 20 miles from Key West
Outdoor dining

Cudjoe Cottages, swimming pool, just 20 miles from Key West

8.8 out of 10, Excellent, (139)
"Great location and house was clean. "
Cudjoe Cottages, swimming pool, just 20 miles from Key West
A KEY ESCAPE ~ 3 Bedroom, 2.5 Bathroom Home in Old Town w/ Private Pool!
A heated pool

A KEY ESCAPE ~ 3 Bedroom, 2.5 Bathroom Home in Old Town w/ Private Pool!

9.8 out of 10, Exceptional, (83)
"Beautiful property. Short walk to Duval"
A KEY ESCAPE ~ 3 Bedroom, 2.5 Bathroom Home in Old Town w/ Private Pool!
Downtown Retreat - A++ Location W/ Private Heated Pool/Hot Tub
Outdoor dining

Downtown Retreat - A++ Location W/ Private Heated Pool/Hot Tub

9.8 out of 10, Exceptional, (147)
"Had a great time in key west. House was close to everything and comfortable "
Downtown Retreat - A++ Location W/ Private Heated Pool/Hot Tub
**DOCKSIDE DAYDREAMS @ COCONUT MALLORY** Marina Villa + LAST KEY SERVICES…
Beach

**DOCKSIDE DAYDREAMS @ COCONUT MALLORY** Marina Villa + LAST KEY SERVICES…

9.8 out of 10, Exceptional, (87)
"Great House, but tight for 5 adults, not sure how 6 adults would fit"
**DOCKSIDE DAYDREAMS @ COCONUT MALLORY** Marina Villa + LAST KEY SERVICES…
Private Secluded Ocean View & Pool Near Key West
Outdoor pool, a heated pool

Private Secluded Ocean View & Pool Near Key West

8.4 out of 10, Very Good, (89)
"Property was as advertised "
Private Secluded Ocean View & Pool Near 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.
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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, (83)
"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
Restaurant

Aqua Lodges at Hurricane Hole Marina

2.0 star property
9.0 out of 10, Wonderful, (136)
"Would definitely stay here again! "
The price is AED 498
AED 1,176 total
includes taxes & fees
5 May - 6 May
Aqua Lodges at Hurricane Hole Marina
Hyatt Vacation Club at Sunset Harbor, Key West
Outdoor pool

Hyatt Vacation Club at Sunset Harbor, Key West

3.5 star property
8.4 out of 10, Very Good, (295)
"We had a nice stay. The property was in a great location."
The price is AED 1,027
AED 1,259 total
includes taxes & fees
5 May - 6 May
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.