Raccoon Key Vacations from $1,536
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The Latest Raccoon Key Vacation Packages
Price found within the past 48 hours. Click for updated prices.
- The Key West Hotel
Jan 20 - Jan 23The Key West Hotel + Flight
Key West Historic District3 nights3.0 star property9.2/10 - Wonderful (565 reviews)"Clean, clean, clean. Hidden! Elite Backyard Oasis. Top Tier bar and fantastic nightly entertainment. If your traveling with anyone under 25, choose different. Will be back, no doubt!"Reviewed October 29, 2026Roundtrip • Boston (BOS) - Key West (EYW)BOS - EYW • Nonstop EYW - BOS • Nonstop - The Gardens Hotel
Jan 20 - Jan 23The Gardens Hotel + Flight
Old Town Key West3 nights4.0 star property9.8/10 - Exceptional (1,001 reviews)"Wonderful location, great room, cozy property. Check in and out was very easy. Would definitely stay here again the next time Im in Key West"Reviewed November 8, 2026Roundtrip • Boston (BOS) - Key West (EYW)BOS - EYW • Nonstop EYW - BOS • Nonstop - Beachfront 2bdr Condo, Pool & Hot Tub w/ Ocean Views Papaya Place by Avantstay
Jan 11 - Jan 16Beachfront 2bdr Condo, Pool & Hot Tub w/ Ocean Views Papaya Place by Avantstay + Flight
Beachside5 nights3.0 star propertyRoundtrip • New York (NYC) - Key West (EYW)LGA - EYW • Nonstop EYW - EWR • 1 stop - Duval Breeze by Avantstay Great Location Close to Beach & Nightlife Shared Pool! Week Long Stays
Jan 28 - Feb 1Duval Breeze by Avantstay Great Location Close to Beach & Nightlife Shared Pool! Week Long Stays + Flight
Old Town Key West4 nights3.0 star property10/10 - Exceptional (1 review)"Location, comfort and great customer service! A great place for a family to stay and share in some fun together!!"Reviewed July 26, 2026Roundtrip • Boston (BOS) - Key West (EYW)BOS - FLL • Nonstop MIA - BOS • Nonstop$2,378$1,790found 1 day agoper traveler - Amelia Home by Avantstay In Historic Old Town w/ Pool
Jan 9 - Jan 13Amelia Home by Avantstay In Historic Old Town w/ Pool + Flight
Old Town Key West4 nights3.0 star property10/10 - Exceptional (3 reviews)"Loved it"Reviewed March 20, 2026Roundtrip • Minneapolis (MSP) - Key West (EYW)MSP - EYW • 1 stop EYW - MSP • 1 stop$3,454$2,615found 1 day agoper traveler
Where to stay in Raccoon Key
Find the best Raccoon Key areas and neighborhoods for the activities you enjoy most. Learn more about Raccoon Key
Learn more about Raccoon Key
Old Town Key West
Old Town, the historic heart of Key West, boasts a central business district and numerous tourist attractions. Explore the Key West Aquarium, Ernest Hemingway House, Mallory Square, and more in this vibrant area.
Downtown Key West
If you're spending some time in Downtown Key West, Duval Street and Ernest Hemingway Home and Museum are top sights worth seeing.
Key West Historic District
Old Town Key West boasts a rich history with 2485 historic buildings, and is home to popular attractions like Ernest Hemingway House and Mallory Square. Enjoy the lively atmosphere in the central business district.
Photo by Ronaldo Esteves
Open Photo by Ronaldo Esteves
New Town
Though New Town might not have many top sights, you can venture to the surrounding area to see attractions like Smathers Beach and Fort East Martello Museum and Gallery.
What to do in Raccoon Key
Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar
$79
per adult
94% of travelers recommend
Champagne and Sunsets: A Key West Catamaran Adventure
$59
per adult
94% of travelers recommend
Sunset Sail in Key West with Beverages Included
$79
per adult
98% of travelers recommend
Raccoon Key Hotel Deals
Parking Pool Dock - Shellstone House
Parking Pool Dock - Shellstone House2.0 star property
0.7 mi from Raccoon Key
$2,177 nightly
The price is $2,449
$2,449 total
Nov 26 - Nov 27
Total with taxes and fees
The Fairhaven House at Solaire Lunara Bay
The Fairhaven House at Solaire Lunara Bay2.0 star property
0.7 mi from Raccoon Key
$2,206 nightly
The price is $2,482
$2,482 total
Nov 10 - Nov 11
Total with taxes and fees
Springtide House by Brightwild Waterfront Pool
Springtide House by Brightwild Waterfront Pool2.0 star property
0.6 mi from Raccoon Key
$1,489 nightly
The price is $1,675
$1,675 total
Nov 10 - Nov 11
Total with taxes and fees
$2,004 nightly
The price is $2,255
$2,255 total
Nov 10 - Nov 11
Total with taxes and fees
Suncoast House by Brightwild Pool Boat Dock
Suncoast House by Brightwild Pool Boat Dock2.0 star property
0.6 mi from Raccoon Key
$1,640 nightly
The price is $1,845
$1,845 total
Nov 10 - Nov 11
Total with taxes and fees
Aquaria House by Brightwild Pool Boat Dock
Aquaria House by Brightwild Pool Boat Dock2.0 star property
0.6 mi from Raccoon Key
$1,489 nightly
The price is $1,675
$1,675 total
Nov 10 - Nov 11
Total with taxes and fees
$1,773 nightly
The price is $1,994
$1,994 total
Nov 10 - Nov 11
Total with taxes and fees
Brand New Catchlight House With Private Pool
Brand New Catchlight House With Private Pool3.0 star property
0.6 mi from Raccoon Key
$1,865 nightly
The price is $2,098
$2,098 total
Nov 10 - Nov 11
Total with taxes and fees
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.
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.