Raccoon Key Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top Raccoon Key Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

4 out of 5
Old Town Key West
Price was CA $2,425, price is now CA $1,784 per person
CA $1,784
per person
Jan 14 - Jan 17
found 21 hours ago
Roundtrip flight included
Toronto (YTO) to Key West (EYW)
9.4/10 Exceptional! (1,002 reviews)
Stunning, I dont have to say anymore

Reviewed on Nov 10, 2026

The Gardens Hotel

The Gardens Hotel

4 out of 5
Old Town Key West
Price was CA $3,184, price is now CA $2,253 per person
CA $2,253
per person
Jan 14 - Jan 17
found 21 hours ago
Roundtrip flight included
Toronto (YTO) to Key West (EYW)
9.8/10 Exceptional! (1,006 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 on Nov 8, 2026

The Marker Key West Harbor Resort

The Marker Key West Harbor Resort

4 out of 5
Key West Historic District
Price was CA $3,218, price is now CA $2,399 per person
CA $2,399
per person
Jan 14 - Jan 17
found 21 hours ago
Roundtrip flight included
Toronto (YTO) to Key West (EYW)
9.2/10 Wonderful! (1,033 reviews)

Tropical Dreaming by Avantstay 4 Blks to Beach! Private Pool!

Tropical Dreaming by Avantstay 4 Blks to Beach! Private Pool!

3 out of 5
Old Town Key West
Price was CA $5,117, price is now CA $3,913 per person
CA $3,913
per person
Jan 14 - Jan 17
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
10/10 Exceptional! (1 review)
Loved the closeness to Duval st and the privacy

Reviewed on Oct 17, 2025

Seaport Suite by Brightwild 2nd Story Hideaway

Seaport Suite by Brightwild 2nd Story Hideaway

2 out of 5
Key West Historic District
Price was CA $23,172, price is now CA $18,383 per person
CA $18,383
per person
Dec 28 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Key West (EYW)
No reviews

Ready to book your vacation to Raccoon Key?

 

Choose your dates

Raccoon Key Hotel Deals

Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
The price is CA $327 per night from Nov 29 to Nov 30
CA $327
CA $458 total
Nov 29 - Nov 30
includes taxes & fees
Margaritaville Beach House Key West
Havana Cabana at Key West

Havana Cabana at Key West

4 out of 5
3420 N. Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
The price is CA $171 per night from Nov 29 to Nov 30
CA $171
CA $283 total
Nov 29 - Nov 30
includes taxes & fees
Havana Cabana at Key West
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
The price is CA $166 per night from Nov 16 to Nov 17
CA $166
CA $267 total
Nov 16 - Nov 17
includes taxes & fees
Blue Flamingo Resort Key West
See all 3,085 properties in Raccoon Key
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

What to do in Raccoon Key

Aerial view of people snorkeling in Key West

Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast

CA $63
per adult
94% of travellers recommend
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
Aboard the trolley in Key West

Historic Key West Old Town Trolley Hop-On Hop-Off Tour

CA $79
per adult
88% of travellers recommend
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
Key West Champagne Sunset Sail

Champagne and Sunsets: A Key West Catamaran Adventure

CA $83
per adult
94% of travellers recommend
Champagne and Sunsets: A Key West Catamaran Adventure
See all activities in Raccoon Key

Frequently asked questions

How much does a Raccoon Key vacation package cost?
Starting from a low CA $1,784, a vacation package is your portal to low-cost travel. Build your own Raccoon Key escape by choosing from our great range of flights, hotels and rental cars.
How do I get a cheap travel package to Raccoon Key?
Book everything in one place with our Raccoon Key vacation packages. You'll find deals on hotels, flights and more that'll keep your budget happy and your adventurous spirit full. And, with more than 550 air carriers and 1,000,000 properties across the globe to choose from, you'll have endless opportunities to mix and match as you want.
Where should I stay in Raccoon Key?
With popular attractions such as Key West Art and Historical Society and Key West Golf Club in this neighborhood, look for a hotel positioned near either of them. Stock Island Yacht Club & Marina is another sight in Raccoon Key that lures the crowds.
What are the top hotels in Raccoon Key?
Get your trip off to an excellent start by booking a room at Luxurious, Elegant Home. It's one of most sought-after properties in Raccoon Key. Another comfortable option is Modern Keys.
How far in advance should I book my Raccoon Key vacation?
To score cheap prices, book as early as you can. Air carriers generally advertise flights, along with some of the lowest fares, up to a year prior to departure. Hotels, experiences and car rental should also be booked well in advance to avoid disappointment. If you've decided on a last-minute getaway in Raccoon Key, there are always lots of great deals to be had on Expedia. Book something in today!
What does an Expedia Raccoon Key travel package include?
You can select from a combination of flights, rental cars and hotels. Once you've made your booking, you can add experiences and activities. Want to pick your fare class? That's easy to do too. The choice is yours when it comes to organizing your ideal Raccoon Key escape.
What should I know before booking a Raccoon Key travel package?
An Expedia travel package can be customized for your budget and is an easy way to make your budget go further. How much you include is completely up to you. Hotels, rental cars and flights — mix and match whatever combination works with your plans.
Can I choose my airline with a Raccoon Key Expedia vacation package?
You can, and with over 550 airlines to pick from worldwide, you've got lots of choice. Browse the available options and see which airline best suits your needs and budget.
If I'm not able to travel, can I cancel my Raccoon Key vacation package?
Because we know life can throw you a few curveballs, the answer is yes. For more information, visit our Customer Service Portal. But generally speaking, if you've made your booking in the last 24 hours, you may be able to change or cancel it for free. Your airline, hotel or car rental company may charge a fee if your booking is older than that.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.