Raccoon Key Vacation Rentals

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Check prices for these dates

Next weekend
Apr 25 - Apr 27
In two weeks
May 2 - May 4
In one month
May 16 - May 18
In two months
Jun 13 - Jun 15

Browse Select Raccoon Key Vacation Homes

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)
"Really enjoyed our stay at this condo. It is very well appointed and had everything we needed. Large space to spread out with a nice patio. Location was great, enjoyed the heated pool and was very quiet. Would stay here again and highly recommend."
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, (95)
"Great stay. Great location "
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, (161)
"Excellent location very clean. Excellent communication with the owner of the accommodations were wonderful. We enjoyed our New Year’s."
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, (214)
"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, (44)
"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, (126)
"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, (78)
"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, (179)
"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!
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, (18)
"Big, clean condo on the quiet side of Duval. Perfect for families. "
The price is CA $484
CA $1,192 total
includes taxes & fees
Apr 20 - Apr 21
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, (216)
"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, (182)
"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, (14)
"Place was perfect and property management was great. Will definitely try to stay here again."
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, (145)
"Good location "
The price is CA $416
CA $868 total
includes taxes & fees
Apr 25 - Apr 26
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, (81)
"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, (168)
"Great place. Great location and everything was perfect "
The price is CA $2,079
CA $3,584 total
includes taxes & fees
Apr 26 - Apr 27
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, (137)
"Great location and house was clean. "
The price is CA $381
CA $835 total
includes taxes & fees
Apr 20 - Apr 21
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!

10.0 out of 10, Exceptional, (82)
"This was a perfect stay for our family getaway from the cold weather. The house was perfect and there was enough space for everyone to have some privacy. The pool was a perfect size for our teenagers and adults."
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, (146)
"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, (86)
"Perfect location and the unit was just the right size for our family of 5. The property is well landscaped with a game room and restrooms near the docks. Victor was very helpful from pre-check in to post check out. Will definitely consider staying here again on our next KW trip."
**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, (128)
"Would definitely stay here again! "
The price is CA $160
CA $413 total
includes taxes & fees
Apr 20 - Apr 21
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, (292)
"This was an amazing property. Wish we had stayed for more than a night and we're already planning a trip to Key West again just to stay here another time. Very friendly and helpful reception staff. Parking deck is directly across the street. Beautiful pool. Near the water (cruise port), a 5 minute walk to Duval Street, and the Truman Little White House was basically next door. Genuinely cannot say enough good things about this hotel."
The price is CA $453
CA $549 total
includes taxes & fees
Apr 24 - Apr 25
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.