Search Deals onRaccoon Key Vacation Packages
Raccoon Key Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Ibis Bay Beach Resort
Save 100% on your flight
Price was $835, price is now $546 per person
$546
per person
Sep 20 - Sep 24
found 1 day ago
Roundtrip non-stop flight included
Columbus (CMH) to Key West (EYW)
Book a stay at this beach hotel in Key West. Enjoy free breakfast, free WiFi, and a private beach. Our guests praise the breakfast and the pool in our reviews. Popular attractions Duval Street and Smathers Beach are located nearby.
Clean, peaceful and friendly staff.
Reviewed on Aug 14, 2026
Winslow's Bungalows - Key West Historic Inns
Save 100% on your flight
Price was $1,496, price is now $896 per person
$896
per person
Oct 30 - Nov 4
found 1 day ago
Roundtrip non-stop flight included
Columbus (CMH) to Key West (EYW)
Stay at this hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and breakfast (surcharge). Our guests praise the breakfast and the pool in our reviews. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
The staff was fantastic and we loved the hotel!!! Great location!
Reviewed on Aug 13, 2026
The Key West Hotel
Save 100% on your flight
Price was $3,259, price is now $1,998 per person
$1,998
per person
Oct 30 - Nov 4
found 1 day ago
Roundtrip non-stop flight included
Columbus (CMH) to Key West (EYW)
Stay at this guesthouse in Key West. Enjoy free WiFi, room service, and daily housekeeping. Popular attractions Duval Street and Mallory Square are located nearby.
This is the best place to stay in Key West! It is a hotel but it has the quaint B&B vibes. The tiki bar by the pool is amazing and they are adding food soon which makes it literally perfect. Close to everything you’d want to do- walk or scooter. 10/10 recommend!
Reviewed on Jul 27, 2026
Lighthouse Hotel - Key West Historic Inns
Save 100% on your flight
Price was $1,496, price is now $920 per person
$920
per person
Oct 30 - Nov 4
found 1 day ago
Roundtrip non-stop flight included
Columbus (CMH) to Key West (EYW)
Stay at this hotel in Key West. Enjoy free breakfast, free WiFi, and daily housekeeping. Our guests praise the helpful staff in our reviews. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
Not being able to check in past midnight and having to pay for a room somewhere else for August 9. And not receiving a refund for the lighthouse it expedia. This was caused for weather delay. The Lighthouse was nice but probably wouldn't stay again.
Reviewed on Aug 14, 2026
Ella's Cottages - Key West Historic Inns
Save 100% on your flight
Price was $1,496, price is now $942 per person
$942
per person
Oct 30 - Nov 4
found 1 day ago
Roundtrip non-stop flight included
Columbus (CMH) to Key West (EYW)
Book a stay at this business-friendly hotel in Key West. Enjoy free breakfast, free WiFi, and parking (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
We had a wonderful stay at Ella’s cottages. The staff were so wonderful. Happy hour at the pool was really fun. The only complaint I have is there was construction right behind our room, but that’s not the hotels fault.
Reviewed on Aug 11, 2026
Curry House
Price was $1,235, price is now $788 per person
$788
per person
Oct 5 - Oct 9
found 22 hours ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Key West (EYW)
Stay at this guesthouse in Key West. Enjoy free WiFi, cable TV channels, and premium bedding. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
Duval Sea Turtle by Avantstay Great Location Close to Shops Shared Pool!
Price was $2,463, price is now $1,636 per person
$1,636
per person
Oct 26 - Oct 30
found 3 hours ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Key West (EYW)
Stay at this cottage in Key West. Enjoy free parking, a beach locale, and concierge services. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
The location to the things we wanted to do was perfect
Reviewed on May 1, 2026
Tropical Dreaming by Avantstay 4 Blks to Beach! Private Pool!
Save 100% on your flight
Price was $3,035, price is now $2,030 per person
$2,030
per person
Oct 26 - Oct 30
found 3 hours ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Key West (EYW)
Stay at this cottage in Key West. Enjoy a beach locale, patios, and an in-room coffeemaker. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
Loved the closeness to Duval st and the privacy
Reviewed on Oct 17, 2025
Raccoon Key Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Raccoon Key Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Sun, Aug 23 - Tue, Aug 25
TPA
Tampa Intl.
EYW
Key West Intl.
$93 Roundtrip, just found
$93
Roundtrip
just found
Sun, Oct 18 - Wed, Oct 28
PIE
St. Petersburg-Clearwater Intl.
EYW
Key West Intl.
$122 Roundtrip, found 2 hours ago
$122
Roundtrip
found 2 hours ago
Sun, Sep 20 - Thu, Oct 1
ATL
Hartsfield-Jackson Atlanta Intl.
EYW
Key West Intl.
$263 Roundtrip, found 2 hours ago
$263
Roundtrip
found 2 hours ago
Tue, Nov 10 - Thu, Nov 26
EWR
Newark Liberty Intl. Airport
EYW
Key West Intl.
$299 Roundtrip, found 2 hours ago
$299
Roundtrip
found 2 hours ago
Discover Other Travel Deals
- Duval Street Vacations
- Mallory Square Vacations
- Southernmost Point Vacations
- Smathers Beach Vacations
- Fort Zachary Taylor Historic State Park Vacations
- Ernest Hemingway Home and Museum Vacations
- South Beach Vacations
- Clarence S. Higgs Memorial Beach Park Vacations
- Florida Keys National Marine Sanctuary Vacations
- Stock Island Yacht Club & Marina Vacations
- Key West Golf Club Vacations
- Las Vegas Vacations
- Cancun Vacations
- Miami Vacations
- Corona Vacations
- Cabo San Lucas Vacations
- Disneyland Park Vacations
- New York Vacations
- Honolulu Vacations
- Los Angeles Vacations
- Maui Vacations
- Orlando Vacations
- New Orleans Vacations
- Canada Vacations
- Tulum Vacations
- Bali Vacations
- Maldives Vacations
- Clearwater Beach Vacations
- Denver Vacations
- South Beach Vacations
- Key West Vacations
