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.
Ella's Cottages - Key West Historic Inns
Old Town Key West
CA $4,014
per person
Dec 25 - Jan 1
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Key West (EYW)
9.4/10 Exceptional! (503 reviews)
We have stayed at this property before and we love the location. The continental breakfast was great, and the staff was amazing. Special thanks to Dwight for making us feel so welcome and at home. All of the little extra touches here and there make the property special.
Reviewed on Oct 10, 2026
The Key West Hotel
Key West Historic District
CA $5,809
per person
Dec 25 - Jan 1
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Key West (EYW)
9.2/10 Wonderful! (563 reviews)
Property was everything as described, clean, in the heart of the excitement that is Key West
Pool was refreshing and close to tiki bar and local entertainment.
The room was spacious, clean and comfy beds. There were issues and there was really no staff to address. Most impactive was the fire alarm. First started going off rang for a min or two, then reset. Happened a dozen times, each causing us to avoid sleep, leave room to make sure nothing was wrong. It wasn't. Then around 10 PM it went off and would not stop. Tried to call office, but nobody there after 6pm. Freaking insane, no emergency contact, maintenance number, nothing. We sent email in hopes it w
May have been monitored... nope. Been 2 days and heard nothing back at all. Found the bartender at on site tici bar and though he abd is barback wete busy they found a ladder, called someone who told them to remove the devise. Eureka after almost 3 hours problem solved. Safety device removed and left peace and quite, perhaps fo fire warning, buy fine
Also internet and this TV / entertainment no work. No maintenance, no visible router to reboot, be gave up and ended the insanity
Maintenance guy was at the door early morning to properly troubleshoot or replace fire annunciator
We only were booked for a night so when we checked out in morning front desk girl simply apologized and was actually sort of blowing us off as she was leaving the desk empty the service a near $600 o/n should offer
Reviewed on Oct 6, 2026
Southernmost Beach Resort and Guesthouses
Old Town Key West
CA $4,662
per person
Dec 25 - Jan 1
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Key West (EYW)
8.6/10 Excellent! (3,636 reviews)
We went with 2 other couples 2nd year in a row at Southern Most, that should tell you how much we enjoyed it! Great location, food rooms were always cleaned.
Reviewed on Oct 12, 2026
Southernmost House - Adult Exclusive
Old Town Key West
CA $4,532
per person
Dec 25 - Jan 1
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Key West (EYW)
9.4/10 Exceptional! (1,001 reviews)
Great stay. Older locations like this face many challenges so there is certainly more work to be done but everything worked like new and the staff was super helpful even offering an upgrade at no charge due to availability.
Reviewed on Oct 11, 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
5 out of top 10 points of interest in this area
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.
Downtown Key West
If you're spending some time in Downtown Key West, Duval Street and Ernest Hemingway Home and Museum are top sights worth seeing.
Key West Historic District
2 out of top 10 points of interest in this area
Old Town Key West boasts a rich history with 2485 historic buildings, and is home to popular attractions like Ernest Hemingway House and Mallory Square. Enjoy the lively atmosphere in the central business district.
New Town
Though New Town might not have many top sights, you can venture to the surrounding area to see attractions like Smathers Beach and Fort East Martello Museum and Gallery.
Uptown - Upper Duval
If you're spending some time in Uptown - Upper Duval, Duval Street and Florida Keys Beaches are top sights worth seeing.
Sunset Key Hotel Deals
Margaritaville Beach House Key West
2001 South Roosevelt Blvd Key West FL
CA $298
CA $425 total
Oct 13 - Oct 14
includes taxes & fees
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
CA $178
CA $281 total
Oct 13 - Oct 14
includes taxes & fees
Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
CA $152
CA $308 total
Oct 13 - Oct 14
includes taxes & fees
8.6/10 Excellent! (2,607 reviews)
"Tried to check into my room at 3:45 (4pm check-in). They ran my credit card for incidentals and then informed me that my room was not clean yet. The young woman at the check-in desk took my cell number and said I would receive a text when I could check in. No room number was given, nor was I given ..."
Reviewed on Oct 11, 2026
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 does a Sunset Key vacation package cost?
Create unforgettable memories with our Sunset Key vacation packages, which start from only CA $4,014. 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.
Things to do
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
CA $59
per adult
94% of travellers recommend
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
CA $78
per adult
88% of travellers recommend
Champagne and Sunsets: A Key West Catamaran Adventure
CA $82
per adult
94% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.