Raccoon Key Holiday Rentals

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Check prices for these dates

Tonight
30 Dec - 31 Dec
Tomorrow
31 Dec - 1 Jan
This weekend
2 Jan - 4 Jan
Next weekend
9 Jan - 11 Jan

Our top choices for Raccoon Key holiday rentals

Fridge, microwave, oven, stovetop
Crestwood House at Lunara Bay

Crestwood House at Lunara Bay

Crestwood House at Lunara Bay
Raccoon Key
10.0 out of 10, Exceptional, (1)
"The house and property was perfect for 4 adults and 4 kids. Gourmet kitchen for great breakfasts to start the day. Grill for cookouts and swimming in the early evenings. Good proximity to downtown key west, but far enough away for quiet time. Would stay again."
United States
Vicki L.
The price is HK$6,989
HK$15,938 total
includes taxes & fees
12 Jan - 13 Jan 2026
Crestwood House at Lunara Bay
Pool
The Shellstone House at Solaire Lunara Bay

The Shellstone House at Solaire Lunara Bay

The Shellstone House at Solaire Lunara Bay
Raccoon Key
The price is HK$10,098
HK$20,682 total
includes taxes & fees
4 Jan - 5 Jan 2026
The Shellstone House at Solaire Lunara Bay
8 bedrooms, Internet
Waterfront Luxury Home - Tidelands House

Waterfront Luxury Home - Tidelands House

Waterfront Luxury Home - Tidelands House
2.0 star property
Raccoon Key
The price is HK$16,322
HK$25,916 total
includes taxes & fees
20 Jan - 21 Jan 2026
Waterfront Luxury Home - Tidelands House
Pool
Capmar House at Lunara Bay

Capmar House at Lunara Bay

Capmar House at Lunara Bay
Raccoon Key
9.8 out of 10, Exceptional, (29)
"The property had all the comforts of home. Plus, being able to enjoy the heated pool even through the overcast and windy conditions! The tropical landscaping and the dock on the bay was awesome!Would definitely recommend!!!"
United States
Anonymous traveller
The price is HK$5,434
HK$12,020 total
includes taxes & fees
5 Jan - 6 Jan 2026
Capmar House at Lunara Bay
Terrace/patio
The Seagate Estate at Lunara Bay

The Seagate Estate at Lunara Bay

The Seagate Estate at Lunara Bay
Raccoon Key
10.0 out of 10, Exceptional, (18)
"The perfect House , everything was good "
United States
CARLOS G.
The price is HK$5,432
HK$11,891 total
includes taxes & fees
4 Jan - 5 Jan 2026
The Seagate Estate at Lunara Bay
Fridge, microwave, oven, stovetop
Springtide House at Lunara Bay

Springtide House at Lunara Bay

Springtide House at Lunara Bay
Raccoon Key
9.8 out of 10, Exceptional, (43)
"It was great. House was amazing"
United States
Ernest H.
The price is HK$5,434
HK$11,825 total
includes taxes & fees
4 Jan - 5 Jan 2026
Springtide House at Lunara Bay
Outdoor dining
Larkshine House at Lunara Bay

Larkshine House at Lunara Bay

Larkshine House at Lunara Bay
2.0 star property
Raccoon Key
10.0 out of 10, Exceptional, (7)
"well maintained, clean, easy to access"
United States
Raj P.
The price is HK$9,321
HK$19,199 total
includes taxes & fees
4 Jan - 5 Jan 2026
Larkshine House at Lunara Bay
Fridge, microwave, oven, stovetop
The Sunray Home at Lunara Bay

The Sunray Home at Lunara Bay

The Sunray Home at Lunara Bay
Raccoon Key
10.0 out of 10, Exceptional, (2)
"Amazing"
United States
Byron D.
The price is HK$9,321
HK$19,691 total
includes taxes & fees
4 Jan - 5 Jan 2026
The Sunray Home at Lunara Bay
TV, stereo, offices
Tidelands House at Lunara Bay

Tidelands House at Lunara Bay

Tidelands House at Lunara Bay
Raccoon Key
The price is HK$9,321
HK$19,691 total
includes taxes & fees
4 Jan - 5 Jan 2026
Tidelands House at Lunara Bay
Pool
The Dreamside House at Lunara Bay

The Dreamside House at Lunara Bay

The Dreamside House at Lunara Bay
Raccoon Key
10.0 out of 10, Exceptional, (1)
"This was a beautiful property and was everything I expected. Staff took great care making sure it was ready for us."
United States
Tony H.
The price is HK$9,318
HK$19,684 total
includes taxes & fees
5 Jan - 6 Jan 2026
The Dreamside House at Lunara Bay
Terrace/patio
Catchlight House at Lunara Bay

Catchlight House at Lunara Bay

Catchlight House at Lunara Bay
2.0 star property
Raccoon Key
9.8 out of 10, Exceptional, (6)
"Awesome place definitely recommend if going to key west "
United States
Brandon M.
The price is HK$6,989
HK$16,249 total
includes taxes & fees
4 Jan - 5 Jan 2026
Catchlight House at Lunara Bay
Pool
Floralee House at Lunara Bay

Floralee House at Lunara Bay

Floralee House at Lunara Bay
2.0 star property
Raccoon Key
9.8 out of 10, Exceptional, (8)
"Amazing house! Spacious, great pool, & good location "
United States
Paige G.
The price is HK$6,989
HK$16,249 total
includes taxes & fees
4 Jan - 5 Jan 2026
Floralee House at Lunara Bay
4 bedrooms, Internet
Capmar House by Brightwild Huge Home Pool

Capmar House by Brightwild Huge Home Pool

Capmar House by Brightwild Huge Home Pool
2.0 star property
Raccoon Key
10.0 out of 10, Exceptional, (1)
"Wonderful property, 4 large bedroom and en suite bathroom, private pool we really liked our stay"
France
Karen
The price is HK$7,636
HK$13,785 total
includes taxes & fees
5 Jan - 6 Jan 2026
Capmar House by Brightwild Huge Home Pool
TV, offices
Suncoast House at Lunara Bay

Suncoast House at Lunara Bay

Suncoast House at Lunara Bay
Raccoon Key
9.6 out of 10, Exceptional, (41)
"Beautiful House, super clean, perfect location "
United States
carlos s.
The price is HK$7,735
HK$16,318 total
includes taxes & fees
20 Jan - 21 Jan 2026
Suncoast House at Lunara Bay
Pool
Evershore Estate at Lunara Bay | Wellness Home

Evershore Estate at Lunara Bay | Wellness Home

Evershore Estate at Lunara Bay | Wellness Home
Raccoon Key
9.8 out of 10, Exceptional, (27)
"The house is perfect for our family. Access to water, pool and close enough to key west!"
United States
John F.
The price is HK$5,434
HK$12,307 total
includes taxes & fees
5 Jan - 6 Jan 2026
Evershore Estate at Lunara Bay | Wellness Home
Fridge, microwave, oven, stovetop
Spindrift House at Lunara Bay

Spindrift House at Lunara Bay

Spindrift House at Lunara Bay
Raccoon Key
10.0 out of 10, Exceptional, (29)
"The BrightWild team is very professional and responsive. Always a great stay every year!"
United States
Chris S.
The price is HK$5,434
HK$12,307 total
includes taxes & fees
6 Jan - 7 Jan 2026
Spindrift House at Lunara Bay
Outdoor dining
The Starboard House at Solaire Lunara Bay

The Starboard House at Solaire Lunara Bay

The Starboard House at Solaire Lunara Bay
Raccoon Key
10.0 out of 10, Exceptional, (1)
"This was a great house for a holiday getaway. The kitchen was well equipped with plenty of dishes as well as extra accessories that we don't always see like the crock pot, the beverage cooler and the extra kerig upstairs. Lots of pool towels and the ice machines upstairs and down made a huge difference. Although we came as a family, the extra room and the fact that each bedroom had its own bathroom makes this house fantastic for any group. The only thing we could think of to make it better would...
United States
Darlene M.
The price is HK$10,098
HK$20,682 total
includes taxes & fees
4 Jan - 5 Jan 2026
The Starboard House at Solaire Lunara Bay
Exterior
Mastway House at Lunara Bay - Wellness Home

Mastway House at Lunara Bay - Wellness Home

Mastway House at Lunara Bay - Wellness Home
Raccoon Key
9.6 out of 10, Exceptional, (30)
"The stay overall was very positive, we thoroughly enjoyed it. There was ample room for everyone staying, the AC worked well, there were a ton of towels, the sheets were all clean, the pool was a great temperature. A few things we noticed were that there was no baking sheet in the kitchen, there were a few cockroaches outside by the pool area, there were little black ants in the master bedroom/bathroom. Also although check in and check out were easy, it was very frustrating to be told that early...
United States
Megan H.
The price is HK$6,211
HK$13,213 total
includes taxes & fees
21 Jan - 22 Jan 2026
Mastway House at Lunara Bay - Wellness Home
Outdoor dining
The Windrose Estate at Lunara Bay

The Windrose Estate at Lunara Bay

The Windrose Estate at Lunara Bay
Raccoon Key
10.0 out of 10, Exceptional, (5)
"This property offered the perfect amount of space for our group to gather together as well as have our privacy. We really enjoyed our stay here! "
United States
Katie K.
The price is HK$6,986
HK$16,243 total
includes taxes & fees
4 Jan - 5 Jan 2026
The Windrose Estate at Lunara Bay
Pool
Palmgale Estate at Lunara Bay

Palmgale Estate at Lunara Bay

Palmgale Estate at Lunara Bay
2.0 star property
Raccoon Key
10.0 out of 10, Exceptional, (8)
"Very clean and stocked. Pleasant experience!"
United States
Iris H.
The price is HK$6,989
HK$15,650 total
includes taxes & fees
4 Jan - 5 Jan 2026
Palmgale Estate at Lunara Bay
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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Top Raccoon Key Hotel Reviews

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

10/10 Excellent
"Nice clean room, scenic views, accessible area"
Peng 3-night trip
Posted 10 hours ago
Southernmost Beach Resort and Guesthouses

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