
Raccoon Key Vacations from $1,158
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The Latest Raccoon Key vacation packages
Price found within the past 48 hours. Click for updated prices.

Oceans Edge Key West Resort, Hotel & Marina
Save 100% on your flight
Price was $1,957, price is now $1,158 per person
$1,158
per person
Nov 2 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (1,722 reviews)
This property was wonderful! Absolutely gorgeous!
Reviewed on Aug 23, 2025

Lighthouse Hotel - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was $2,221, price is now $1,361 per person
$1,361
per person
Nov 2 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (775 reviews)
it’s a great location but quiet. Love the free breakfast, pool and rooms! staff was great too!
Reviewed on Aug 23, 2025

Winslow's Bungalows - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was $2,279, price is now $1,446 per person
$1,446
per person
Nov 2 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (1,006 reviews)
Beautiful property with several private pools. The front desk was very helpful in helping us get bikes delivered. They were always helping people and answering questions.The breakfast is perfect to get your day started. We will definitely return.
Reviewed on Aug 22, 2025

The Perry Hotel & Marina Key West
Save 100% on your flight
Price was $2,805, price is now $1,786 per person
$1,786
per person
Nov 2 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (1,068 reviews)
This property was beautiful and everyone was very friendly it’s an amazing option !!!
Reviewed on Aug 23, 2025

Ibis Bay Beach Resort
Northside Resort
Save 100% on your flight
Price was $2,364, price is now $1,545 per person
$1,545
per person
Nov 2 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
8.2/10 Very Good! (2,007 reviews)
It is 10 minutes drive from downtown center. The swimming pool is cool and well as the music.
Reviewed on Aug 19, 2025
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Beachside Resort & Residences
3841 N Roosevelt Blvd, Key West, FL
Fully refundableReserve now, pay when you stay
$184 nightly
The price is $207 total per night from Aug 25 to Aug 26
$207 total
Aug 25 - Aug 26
Total with taxes and fees
8.4/10 Very Good! (1,479 reviews)
"The property was excellent, located in the heart of everything!! 😍"
Reviewed on Aug 23, 2025

Oceans Edge Key West Resort, Hotel & Marina
5950 Peninsular Avenue, Key West, FL
Fully refundableReserve now, pay when you stay
$219 nightly
The price is $247 total per night from Sep 2 to Sep 3
$247 total
Sep 2 - Sep 3
Total with taxes and fees
8.8/10 Excellent! (1,685 reviews)
"Nice rooms. Pool water needs attention due to some algae growth on bottom."
Reviewed on Aug 21, 2025

Hilton Garden Inn Key West / The Keys Collection
3850 N Roosevelt Blvd, Key West, FL
Fully refundableReserve now, pay when you stay
$126 nightly
The price is $142 total per night from Sep 1 to Sep 2
$142 total
Sep 1 - Sep 2
Total with taxes and fees
7.8/10 Good! (1,070 reviews)
"Most excellent facility with very accommodating staff."
Reviewed on Aug 18, 2025
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.