
Raccoon Key Vacations from $1,447
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $1,045 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
The Latest Raccoon Key vacation packages
Price found within the past 48 hours. Click for updated prices.

Oceans Edge Key West Resort, Hotel & Marina
Price was $2,228, price is now $1,447 per person
$1,447
per person
Mar 30 - Apr 6
found 3 hours ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (1,736 reviews)
Reception was courteous but housekeeping was terrible. Waitstaff was overwhelmed.
Reviewed on Jan 2, 2026

The Key West Hotel
Key West Historic District
Price was $3,376, price is now $1,860 per person
$1,860
per person
Mar 30 - Apr 6
found 2 hours ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (505 reviews)
Being right on Duval Street if city noise bothers you you might want to stay a block or two off Duval. But if you want all the action then this place is fantastic. Staff is great and the room was nicely appointed and very comfortable.
Reviewed on Dec 12, 2025

The Gardens Hotel
Old Town Key West
Price was $3,458, price is now $2,182 per person
$2,182
per person
Mar 30 - Apr 6
found 3 hours ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.8/10 Exceptional! (1,000 reviews)
We absolutely loved the hotel! The house was classic Key west, so spotless, the staff was fantastic, the tortises and birds were definately entertaining, the pool was heavenly and being greeted with a glass of Proscuitta definately started the vacation off perfectly. We will definately be back!!
Reviewed on Dec 27, 2025

Southernmost Beach Resort and Guesthouses
Old Town Key West
Price was $2,515, price is now $1,657 per person
$1,657
per person
Mar 30 - Apr 6
found 2 hours ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
8.6/10 Excellent! (2,844 reviews)
The location is perfect—right on the beach with beautiful views and easy access to the sand and sea. The hotel is clean and comfortable, and the staff are friendly and helpful. The amenities added to a relaxing stay. I really enjoyed my time here and would definitely recommend this hotel to anyone looking for a beachfront getaway.
Reviewed on Jan 6, 2026

The Perry Hotel & Marina Key West
Price was $2,181, price is now $1,461 per person
$1,461
per person
Mar 30 - Apr 6
found 3 hours ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (1,151 reviews)
There were some issues with our room in the beginning. Mainly since it was Christmas time and regular staff was out on our checkin day. However, they accommodated all our requests the next day and made up for it.
Reviewed on Dec 30, 2025
Don't see what you're looking for?
See all available trips from Columbus to Raccoon Key
View all tripsRaccoon Key Hotel Deals

Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$295 nightly
The price is $332 total per night from Jan 8 to Jan 9
$332 total
Jan 8 - Jan 9
Total with taxes and fees
8.6/10 Excellent! (1,871 reviews)
Very awesome and accommodating place!
Reviewed on Jan 5, 2026

Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
$292 nightly
The price is $329 total per night from Jan 11 to Jan 12
$329 total
Jan 11 - Jan 12
Total with taxes and fees
8/10 Very Good! (1,831 reviews)
Room was clean. Amenities were great.
Reviewed on Jan 6, 2026

Oceans Edge Key West Resort, Hotel & Marina
5950 Peninsular Avenue Key West FL
Fully refundableReserve now, pay when you stay
$289 nightly
The price is $325 total per night from Jan 11 to Jan 12
$325 total
Jan 11 - Jan 12
Total with taxes and fees
8.8/10 Excellent! (1,743 reviews)
Friendly staff
Reviewed on Jan 2, 2026
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.
Find the Best Raccoon Key Vacation Packages
Raccoon Key Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Key West Intl. Airport (EYW) |
More vacations you might like
Explore a world of travel with Expedia
- Key West Hotels
- All-inclusive Resorts in Key West
- Key Haven Hotels
- Stock Island Hotels
- Hotels near Key West Golf Club
- Houseboats in Stock Island
- Fishing Resorts & in Stock Island
- Pet-friendly Hotels in Stock Island
- Condo Rentals in Stock Island
- Cottages in Stock Island
- Resorts in Stock Island
- Beach Hotels in Stock Island
- Vacation Homes in Stock Island
- 5 Star Hotels in Stock Island
- Boutique Hotels in Stock Island
- 4 Star Hotels in Stock Island
- Apartments in Stock Island
- Oceanfront Hotels in Stock Island
- RV Parks in Stock Island
- Luxury Hotels in Stock Island
- Guest Houses in Stock Island
- Hostels in Stock Island
- B&B in Stock Island
- Golf Hotels in Stock Island
- Condo Resorts in Stock Island
- Aparthotels in Stock Island
- Villas in Stock Island
- Resorts & Hotels with Spas in Stock Island
- Hotels with a Pool in Stock Island
- Hotels with an Outdoor Pool in Stock Island
- Hotels with Air Conditioning in Stock Island
- 3 Star Hotels in Stock Island
- Motels in Stock Island
- Hotels with Laundry Facilities in Stock Island
- Hotel Wedding Venues Hotels in Stock Island
- Hotels on the River in Stock Island
- Hotels & Resorts for Couples in Stock Island
- Family Hotels in Stock Island
- Romantic Hotels in Stock Island
- Hyatt Hotels in Stock Island
- Quiet Resorts & in Stock Island
- Hotels with Hot Tubs in Stock Island
- Hotels with Free Parking in Stock Island
- Hotels near Key West Tropical Forest and Botanical Garden
- Cow Key Hotels
- Hotels near Robbie's
- Houseboats in Cow Key
- Vacation Homes in Cow Key
- Condo Rentals in Cow Key
- Resorts in Cow Key
- B&B in Cow Key
- Apartments in Cow Key
- Villas in Cow Key
- RV Parks in Cow Key
- 5 Star Hotels in Cow Key
- Guest Houses in Cow Key
- 4 Star Hotels in Cow Key
- Cottages in Cow Key
- Condo Resorts in Cow Key
- Hotels near Stock Island Yacht Club & Marina
- Flights to Key West
- Flights to Stock Island
- Flights from Chicago to Stock Island
- Flights from Philadelphia to Stock Island
- Flights from Philadelphia (PHL) to Key West (EYW)
- Flights from Tampa (TPA) to Key West (EYW)
- Flights from Orlando (MCO) to Key West (EYW)
- Flights from Miami (MIA) to Key West (EYW)
- Flights from Boston (BOS) to Key West (EYW)
- Flights from New York (JFK) to Key West (EYW)
- Flights from Fort Lauderdale (FLL) to Key West (EYW)
- Flights from Fort Myers (RSW) to Key West (EYW)
- Flights from Chicago (ORD) to Key West (EYW)
- Flights from Atlanta (ATL) to Key West (EYW)
- Flights from Baltimore (BWI) to Key West (EYW)
- Flights from Charlotte (CLT) to Key West (EYW)
- Flights from Key West Intl.
- Flights from Detroit (DTW) to Key West (EYW)
- Flights from Washington (DCA) to Key West (EYW)
- Car rentals near Key West Golf Club
- Van Car Rentals near Key West Golf Club
- Mini Car Rentals near Key West Golf Club
- Car rentals near Stock Island
- National Car Rental Rental Cars in Stock Island
- Enterprise Rental Cars in Stock Island
- Car rentals near Cow Key
- Car rentals near Stock Island Yacht Club & Marina
- Car rental Key West Airport (EYW)
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.



















