Deals on vacations and trips to Raccoon Key

Save when you book Raccoon Key package deals

Choose two or more items and save on your trip:

Raccoon Key flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Hyatt Vacation Club at Beach House, Key West

Hyatt Vacation Club at Beach House, Key West

3.5 out of 5
Save 100% on your flight
Price was $1,180, price is now $713 per person
$713
per person
Feb 3 - Feb 6
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
This hotel features an outdoor pool and a hot tub. Relax with a drink at the bar/lounge and enjoy perks like free self parking and free WiFi. A safe deposit box and concierge services are also provided.
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
Save 100% on your flight
Price was $2,709, price is now $1,556 per person
$1,556
per person
Jan 28 - Feb 4
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
A marina, 6 outdoor pools, and a 24-hour gym are all featured at this smoke-free hotel. Business travelers can take advantage of the free WiFi in public areas. The restaurant provides options for dining, while the bar/lounge and poolside bar are great spots to unwind.
Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

3.5 out of 5
Save 100% on your flight
Price was $1,191, price is now $719 per person
$719
per person
Feb 3 - Feb 6
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
This hotel features an outdoor pool, a hot tub, and a restaurant. Guests will appreciate free perks like free self parking and WiFi in public areas. A snack bar/deli, concierge services, and barbecue grills are also on offer.
The Key West Hotel

The Key West Hotel

2.5 out of 5
Key West Historic District
Save 100% on your flight
Price was $2,550, price is now $1,560 per person
$1,560
per person
Mar 18 - Mar 22
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
An outdoor pool is featured at this guesthouse, along with free WiFi in public areas and a garden. Luggage storage and concierge services are also provided.
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
Old Town Key West
Save 100% on your flight
Price was $3,819, price is now $2,366 per person
$2,366
per person
Jan 28 - Feb 4
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
This hotel features a full-service spa, 3 outdoor pools, and a restaurant. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Traveling for business? Take advantage of the 24-hour business center, laundry service, and conference space.

Top Raccoon Key hotels deals

Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
3841 N Roosevelt Blvd Key West FL
Free Cancellation
Reserve now, pay when you stay
$313 nightly
The price is $352 total per night
$352 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
This smoke-free hotel features a private beach, a marina, and 2 restaurants. Enjoy a day at the beach kayaking, or relax with sun loungers. Unwind with a drink at one of the 2 bars/lounges and enjoy freebies like WiFi in public areas and an area shuttle.
On private beach
Pool
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard Key West FL
Free Cancellation
Reserve now, pay when you stay
$274 nightly
The price is $308 total per night
$308 total
Jan 8 - Jan 9, 2026
Total with taxes and fees
This hotel features 2 restaurants, 2 outdoor pools, and a 24-hour gym. There's fun for all ages with mini golf and an arcade/game room, and families will appreciate the picnic area. Unwind with a drink at one of the 2 poolside bars and enjoy freebies like WiFi in public areas and an area shuttle.
Pool
Hot Tub
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
5950 Peninsular Avenue Key West FL
Free Cancellation
Reserve now, pay when you stay
$292 nightly
The price is $328 total per night
$328 total
Jan 26 - Jan 27, 2026
Total with taxes and fees
A marina, 6 outdoor pools, and a 24-hour gym are all featured at this smoke-free hotel. Business travelers can take advantage of the free WiFi in public areas. The restaurant provides options for dining, while the bar/lounge and poolside bar are great spots to unwind.
Pool
Pet friendly
DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West

4 out of 5
3990 S Roosevelt Blvd Key West FL
Free Cancellation
Reserve now, pay when you stay
$277 nightly
The price is $312 total per night
$312 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
This resort features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Enjoy the 24-hour gym and perks like a free beach shuttle.
Pool
Free airport shuttle
Havana Cabana at Key West

Havana Cabana at Key West

4 out of 5
3420 N. Roosevelt Blvd Key West FL
$293 nightly
The price is $329 total per night
$329 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Business travelers can take advantage of the free WiFi in public areas. Enjoy the hot tub and perks like free self parking.
Pool
Hot Tub
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
Free Cancellation
$360 nightly
The price is $405 total per night
$405 total
Jan 13 - Jan 14, 2026
Total with taxes and fees
This hotel features a full-service spa, 3 outdoor pools, and a restaurant. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Traveling for business? Take advantage of the 24-hour business center, laundry service, and conference space.
Pool
Spa
Don't see what you're looking for?
See all available properties in Raccoon Key
View all properties
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.

Frequently asked questions

How much are vacation packages to Raccoon Key?
Starting at just $713, flight and hotel packages are an ideal way to make your travel budget stretch further. Watch out Raccoon Key — here you come!
Where can I get the best vacation package deals for Raccoon Key?
It's difficult to beat Travelocity when it comes to crafting your Raccoon Key package deal. There are as many as 400 air carriers and 1,000,000 worldwide properties to choose from. Book your trip now and get ready to tick another amazing destination off your list.
Why should I purchase my Raccoon Key vacation package via Travelocity?
Savings, support and a stress-free booking are just the beginning. Enjoy a fulfilling travel experience knowing you have access to 24/7 customer support. With the Travelocity Price Match Guarantee, you can rest easy knowing you're getting the best deal available.
Can I save on my Raccoon Key car rental if I book it with hotels and flights?
Combining your flight, hotel and car into a Raccoon Key vacation package is a great way to score an amazing deal. Plus, having your own wheels gives you the freedom to make your way to all those amazing sights you're itching to see. Located 110 mi from Raccoon Key, Zoo Miami is one attraction that should have a place on your itinerary. Fill up the tank and make a day trip of it.
What is the best time of year to go to Raccoon Key?
You'll be able to avoid the tourist crowds and save cold, hard cash in August, September and October, which are the quietest times for tourism. Peak season months of January, February and July are naturally busier (and more expensive), but there's likely to be more going on around Raccoon Key. Lock in a hotel in and get a lot more bang for your buck. Room rates tend to be higher in .
Which airport is best for Raccoon Key?
Heading to Raccoon Key will see you touching down at Key West Intl. Airport (EYW). It's roughly 2 mi southwest of the downtown area.
Where should I stay when visiting Raccoon Key?
Many travelers opt to check in to the Catamaran with kayak. It's a great base for your Raccoon Key escape.

Photos of local treasures

Browse Raccoon Key vacation photos for more inspiration

Explore More Ways to Travel with Travelocity