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.
Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

3.5 out of 5
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Key West (EYW)
9.6/10 Exceptional! (1,002 reviews)
Clean, beautful and very comfortable

Reviewed on Jul. 24, 2025

Almond Tree Inn Hotel - Adults Only

Almond Tree Inn Hotel - Adults Only

3.5 out of 5
Old Town Key West
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Key West (EYW)
10/10 Exceptional! (1,002 reviews)
Excellent property! We very much enjoyed the location (right off of Duval but not loud at all), pool, Happy Hour and Breakfast. Our room was very nicely appointed and although the elevator was not working, that did not hinder us at all. The property is well taken care of and the staff was top notch, we particularly appreciated Cary and Catherine (I hope I got her name right, she was awesome) as the front desk and HH and Breakfast attendants. Would certainly stay here again and highly recommend.

Reviewed on Jul. 26, 2025

Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only

3.5 out of 5
Old Town Key West
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Key West (EYW)
9.8/10 Exceptional! (1,005 reviews)
Had a great time place was awesome. Can’t wait to return

Reviewed on Jul. 26, 2025

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
Old Town Key West
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Key West (EYW)
8.6/10 Excellent! (2,611 reviews)
Beautiful hotel..we stayed at Duval gardens guesthouse on duval street about 5 mins walk from the lobby..bellmen are available for transport..breakfast was nice and pool area was well kept..staff is attentive and made sure we had everything we need

Reviewed on Jul. 26, 2025

The Gardens Hotel

The Gardens Hotel

4 out of 5
Old Town Key West
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Key West (EYW)
9.8/10 Exceptional! (1,003 reviews)
Magical! The staff was amazing, friendly, and very accommodating. Breakfast was delicious. Loved the wine bar. The pool was clean. The room was clean. No complaints! Would definitely return.

Reviewed on Jul. 24, 2025

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
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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

Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
3841 N Roosevelt Blvd, Key West, FL
Fully refundableReserve now, pay when you stay
The price is CA $184 per night from Aug 18 to Aug 19
CA $184
CA $276 total
Aug 18 - Aug 19
includes taxes & fees
8.4/10 Very Good! (1,375 reviews)
"There wasn’t anything we didn’t like, we had a suite overlooking the ocean and it was quiet and peaceful. The concierge’s were always friendly and helpful with things to do. I will definitely stay here again."

Reviewed on Jul. 23, 2025

Beachside Resort & Residences
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street, Key West, FL
Fully refundable
The price is CA $252 per night from Aug 25 to Aug 26
CA $252
CA $377 total
Aug 25 - Aug 26
includes taxes & fees
8.6/10 Excellent! (2,641 reviews)
"Very nice resort and great staff!!! Julie at concierge was the best ever!!!!"

Reviewed on Jul. 24, 2025

Southernmost Beach Resort and Guesthouses
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 $167 per night from Aug 24 to Aug 25
CA $167
CA $265 total
Aug 24 - Aug 25
includes taxes & fees
7.6/10 Good! (1,488 reviews)
Wonderful
"Had a wonderful experience at this hotel. Staff was friendly and facilities were clean. Soma at the front desk was helpful and ready to assist us with navigating the shuttle service. Sasha and davit were absolute gems when it came to operating the breakfast service all by themselves. Overall had ..."

Reviewed on Jul. 23, 2025

Blue Flamingo Resort Key West
See all 2,769 properties in Sunset 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.
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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 $1,372. 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.