Sunset Key Vacation Packages

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Top Holiday Package Deals in Sunset Key

Price found within the past 48 hours. Click for updated prices.
The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4 out of 5
Price was CA $2,579, price is now CA $1,748 per person
CA $1,748
per person
May 10 - May 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Key West (EYW)
9.4/10 Exceptional! (1,234 reviews)
Did not eat any meals on the property. Overall it's a nice place to stay. Rooms and furniture are dated in some areas. Very nice staff including Jamey and Mitchell.

Reviewed on Apr 2, 2026

Hyatt Vacation Club at Beach House, Key West

Hyatt Vacation Club at Beach House, Key West

3.5 out of 5
Price was CA $3,458, price is now CA $2,105 per person
CA $2,105
per person
May 10 - May 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Key West (EYW)
9.4/10 Exceptional! (1,004 reviews)
These are recently renovated “condos” with 2 beds/2 baths, full kitchen, dining, and living area. Master bath is very nicely done with a giant shower for two. Very large deck/porch off each unit. The A/C went out but the friendly front desk and maintenance crew repaired it quickly. Resort has a large pool and large sand beach area with plenty of chairs and cabanas. New gas grills are near the pool area. There is a tiki bar on site with food. No complaints about this property whatsoever. There is a kayak tour guide right next door and I highly recommend their night kayak tour. The property is at the opposite end of the island to Old town/Duvall street. It’s about a 20 min bike ride to Duvall, and a 9 minute bike ride to Publix.

Reviewed on Apr 1, 2026

Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

3.5 out of 5
Price was CA $3,263, price is now CA $1,996 per person
CA $1,996
per person
May 10 - May 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Key West (EYW)
9.4/10 Exceptional! (1,020 reviews)
Beautiful property!

Reviewed on Apr 3, 2026

Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

4 out of 5
Old Town Key West
Price was CA $3,022, price is now CA $1,873 per person
CA $1,873
per person
May 10 - May 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Key West (EYW)
9.2/10 Wonderful! (1,194 reviews)
Second time we have stayed here.Staff is excellent, accommodating. The property is very well maintained and a great location.

Reviewed on Apr 1, 2026

The Key West Hotel

The Key West Hotel

2.5 out of 5
Key West Historic District
Price was CA $3,784, price is now CA $2,483 per person
CA $2,483
per person
May 18 - May 23
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9.2/10 Wonderful! (536 reviews)
The tag line of the hotel is "Come Hide" which was appropriate as it is hidden from plain view of the hustle and bustle of Duval St. The entrance is mysterious as it is set back and the pathway leading to the reception office is filled with green ferns/palms. Loved it! The center of the property is highlighted the bar and the permanent stage for the daily entertainment. Great place to stay and close to everything!

Reviewed on Mar 30, 2026

Where to stay in Sunset Key

Find the best Sunset Key areas and neighborhoods for the activities you enjoy most. Learn more about Sunset Key
Old Town Key West

Old Town Key West

4 out of top 10 points of interest in this area
3.5/5(8 area reviews)

Old Town, the historic heart of Key West, boasts a central business district and numerous tourist attractions. Explore the Key West Aquarium, Ernest Hemingway House, Mallory Square, and more in this vibrant area.

Find hotels in Old Town Key West

Sunset Key Hotel Deals

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 $350 per night from Apr 19 to Apr 20
CA $350
CA $472 total
Apr 19 - Apr 20
includes taxes & fees
8.2/10 Very Good! (2,029 reviews)
The concierge was very helpful. The beds and rooms were comfortable. The location was good and the pools fun.

Reviewed on Apr 3, 2026

Blue Flamingo Resort Key West
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
Fully refundableReserve now, pay when you stay
The price is CA $667 per night from May 4 to May 5
CA $667
CA $852 total
May 4 - May 5
includes taxes & fees
8.8/10 Excellent! (3,177 reviews)
We stayed in the Adults ONLY Duval Gardens. We enjoyed the privacy and location on Duval Street. It was nice to have the option of the amenities at the resort for the different pools and beach access. Free breakfast too! We would stay here again. The room was clean, staff is friendly no beach view ...

Reviewed on Apr 2, 2026

Southernmost Beach Resort and Guesthouses
Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
The price is CA $416 per night from Apr 15 to Apr 16
CA $416
CA $557 total
Apr 15 - Apr 16
includes taxes & fees
8.8/10 Excellent! (1,798 reviews)
Ideal for families with smaller children, and the pool was smaller than was indicated in the pictures overall good experience

Reviewed on Apr 2, 2026

Margaritaville Beach House Key West
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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.
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Frequently asked questions

How much does a Sunset Key vacation package cost?
Create unforgettable memories with our Sunset Key vacation packages, which start from only CA $1,748. Handpick the flights and hotels that fit your travel plans. Then, add on a couple of sightseeing tours for a memorable escape.
How do I get a cheap travel package to Sunset Key?
Our Sunset Key vacation packages offer plenty of savings for the savvy traveler. For the best deals, simply bundle your hotel, flights and tours into one neat package. But low prices are just the beginning of your next epic adventure. When you book with Expedia, and you'll have over 550 air carriers and 1,000,000 hotel options globally to select from. Whatever your style or budget, there's a vacation package here just for you.
Where should I stay in Sunset Key?
Most visitors who travel to Sunset Key put both Ernest Hemingway Home and Museum and Audubon House and Tropical Gardens on their itineraries. Why not book a hotel near these top attractions?
How far in advance should I book my Sunset Key vacation?
It can be tricky to know exactly when is the ideal time to book your Sunset Key vacation. But typically the earlier you book, the better the prices. In some cases, you can reserve your flights and hotels nearly 12 months before departure. If you're thinking of a last-minute getaway, no need to fret! There are fabulous bargains popping up on Expedia all the time.
What does an Expedia Sunset Key travel package include?
Flights, rental cars and hotels — you'll discover them all here. With Expedia, you can shape your Sunset Key travel package the way you want. All you have to do is determine just what you need. Once you've made your booking, you can add on extras like experiences and activities. The more you bundle, the bigger the savings!
What should I know before booking a Sunset Key travel package?
Whether it's relaxation or adventure you're chasing, a Sunset Key vacation package lets you plan your escape your way. Plus, you'll get access to great discounts just for combining your accommodations with your rental car and flights. The more you bundle, the bigger the savings!
Can I choose my airline with a Sunset Key Expedia vacation package?
Yes — that's the beauty of an Expedia package. You're in control. We have access to more than 550 partner airlines all over the world, so you have lots of choice when organizing your Sunset Key escape.
If I'm not able to travel, can I cancel my Sunset Key vacation package?
If your travel plans in Sunset Key have been upended, it's a relief to know that it's possible to cancel or amend your booking. If your booking was made in the last 24 hours, you may be able to get a refund. If your booking was made more than 24 hours ago, your airline, hotel or car rental company may impose a cancellation fee. To find out more, check our Customer Service Portal.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.