
Raccoon Key Vacations from $828
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The Latest Raccoon Key vacation packages
Price found within the past 48 hours. Click for updated prices.

Winslow's Bungalows - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was $1,405, price is now $828 per person
$828
per person
Jan 30 - Feb 2
found 2 days ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
18.4/10 Exceptional! (1,044 reviews)
Pleasant stay, nice property but room a little run down for the money
Reviewed on Nov 17, 2025

Ella's Cottages - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was $1,696, price is now $887 per person
$887
per person
Jan 30 - Feb 2
found 2 days ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
18.8/10 Exceptional! (390 reviews)
I absolutely loved my stay at Ella’s Cottage. The location was perfect, the rooms and outdoor areas were stunning. Really great service with breakfast baskets and super friendly staff. The only downside was that my room was located very close to the maintenance staff office/storage so unfortunately in the morning I was woken up and could hear everything going on.
Side note beware that the roosters will wake you up at sunrise!
Reviewed on Nov 16, 2025

The Key West Hotel
Key West Historic District
Price was $3,736, price is now $2,001 per person
$2,001
per person
Feb 8 - Feb 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
18.4/10 Exceptional! (505 reviews)
Great place, will definitely stay there again!!!
Reviewed on Nov 12, 2025

Hyatt Vacation Club at Beach House, Key West
Save 100% on your flight
Price was $1,879, price is now $1,067 per person
$1,067
per person
Jan 9 - Jan 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
18.8/10 Exceptional! (1,002 reviews)
The room was amazing, spotless. The resort was clean and the pool was nice. I could not give this a five star because of the following reasons…
Don’t go there for any type of beach (there is none) the tiki bar is old, it needs a face lift.
If you arrive early and you want to go to the pool, you can but you have to change in the bathroom on a wet floors outside the resort. They will hold onto your luggage.
Most hotels that I stay at offer one free bottle of water in your room, this one does not.
The last thing I would say is, I found that one of the girls working at the front desk was not the friendliest.
She was a little bit snooty, and short with me.
I think it is important to have someone at the front desk that makes you feel welcome.
Again, I must say our room with spectacular and very clean.
Reviewed on Nov 12, 2025

Hyatt Vacation Club at Windward Pointe, Key West
Save 100% on your flight
Price was $1,808, price is now $1,030 per person
$1,030
per person
Jan 9 - Jan 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
19.2/10 Exceptional! (1,002 reviews)
The staff was wonderful and the room was very nice.
Reviewed on Nov 17, 2025
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Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$187 nightly
The price is $210 total per night from Nov 18 to Nov 19
$210 total
Nov 18 - Nov 19
Total with taxes and fees
8.6/10 Excellent! (1,680 reviews)
Staff was horrible on directions to room. We had to give directions to 4 different sets of new guests as well as getting lost ourselves. Place was great. Nice location.
Reviewed on Nov 13, 2025

Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
$157 nightly
The price is $177 total per night from Nov 18 to Nov 19
$177 total
Nov 18 - Nov 19
Total with taxes and fees
7.8/10 Good! (1,693 reviews)
What a fun little resort. The amenities are fabulous! They have live music. We heard Ike Kanakanaui. He was REALLY good!
Reviewed on Nov 14, 2025

Oceans Edge Key West Resort, Hotel & Marina
5950 Peninsular Avenue Key West FL
Fully refundableReserve now, pay when you stay
$195 nightly
The price is $220 total per night from Dec 8 to Dec 9
$220 total
Dec 8 - Dec 9
Total with taxes and fees
8.8/10 Excellent! (1,736 reviews)
If you book Oceans Edge through hotels.com or Expedia expect a resort fee & parking fee before booking. These extra costs are not included with your online booking which is misleading to hotel guests. The staff at Oceans Edge worked through this misleading situation which caused a lengthy check in ...
Reviewed on Nov 15, 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.
Find the Best Raccoon Key Vacation Packages
Raccoon Key Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Key West Intl. Airport (EYW) |
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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.



















