Sunset Key Holidays
- Plan, book, travel with confidence
- Better togetherSave up to €900 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Price found within the past 48 hours. Click for updated prices.
The Key West Hotel
Key West Historic District
€1,251
per person
24 Sept - 28 Sept
found 5 hours ago
Return direct flight included
Chicago (ORD) to Key West (EYW)
9.2/10 Wonderful! (561 reviews)
This is the best place to stay in Key West! It is a hotel but it has the quaint B&B vibes. The tiki bar by the pool is amazing and they are adding food soon which makes it literally perfect. Close to everything you’d want to do- walk or scooter. 10/10 recommend!
Reviewed on 27 Jul 2026
Pier House Resort & Spa
Key West Historic District
€1,131
per person
24 Sept - 28 Sept
found 5 hours ago
Return direct flight included
Chicago (ORD) to Key West (EYW)
9/10 Wonderful! (1,258 reviews)
Room was ok only, AC had issues and location was difficult. There were upgraded rooms available but the charges didn’t make any sense, $50 a night for a room the same size but a slightly better location. Beach area was nice, location is great, Beach attendant couldn’t be bothered to help guests, Food servers never picked up after serving which left the birds to clean off the plates. You get the idea, great location not so great service.
Reviewed on 18 Aug 2026
The Marker Key West Harbor Resort
Key West Historic District
€988
per person
24 Sept - 28 Sept
found 5 hours ago
Return direct flight included
Chicago (ORD) to Key West (EYW)
9.2/10 Wonderful! (1,002 reviews)
The fact they have an EV charger in their garage was a HUGE PLUS! The property is really nice and the staff was awesome!
Reviewed on 18 Aug 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
4 out of top 10 points of interest in this area
While visiting Old Town Key West, you might make a stop by sights like Duval Street and Florida Keys Beaches.
Downtown Key West
While visiting Downtown Key West, you might make a stop by sights like Duval Street and Ernest Hemingway Home and Museum.
Key West Historic District
2 out of top 10 points of interest in this area
Travellers to Key West Historic District praise its fantastic nightlife. If you've got some more time to explore, be sure to stop by Duval Street and Florida Keys Beaches.
New Town
While there might not be top attractions in New Town, you can explore the larger area and discover places like Smathers Beach and Key West Tropical Forest and Botanical Garden.
Uptown - Upper Duval
If you're spending some time in Uptown - Upper Duval, Duval Street and Florida Keys Beaches are top sights worth seeing.
Top hotels in Sunset Key
Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Fully refundableReserve now, pay when you stay
€197
1 Sept - 2 Sept
includes taxes & fees
Ibis Bay Beach Resort
3101 N. Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
€132
20 Aug - 21 Aug
includes taxes & fees
8.2/10 Very good! (2,348 reviews)
"Room too small and breakfast not so good"
Reviewed on 19 Aug 2026
Havana Cabana at Key West
3420 N. Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
€195
17 Sept - 18 Sept
includes taxes & fees
9/10 Wonderful! (1,858 reviews)
"Very good 😊"
Reviewed on 19 Aug 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 holiday package cost?
Create unforgettable memories with our Sunset Key holiday packages, which start from only €716. 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 holiday packages offer plenty of savings for the savvy traveller. 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 holiday 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 holiday?
It can be tricky to know exactly when is the ideal time to book your Sunset Key holiday. 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 holiday package lets you plan your escape your way. Plus, you'll get access to great discounts just for combining your accommodation with your rental car and flights. The more you bundle, the bigger the savings!
Can I choose my airline with a Sunset Key Expedia holiday 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 organising your Sunset Key escape.
If I'm not able to travel, can I cancel my Sunset Key holiday 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
€39
per adult
94% of travellers recommend
Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar
€68
per adult
94% of travellers recommend
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
€48
per adult
88% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.