Uptown - Upper Duval Vacation Packages

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Top Holiday Package Deals in Uptown - Upper Duval

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
Price was CA $2,840, price is now CA $2,019 per person
CA $2,019
per person
May 24 - May 29
found 24 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
9.4/10 Exceptional! (1,011 reviews)
Everting was excellent!

Reviewed on Apr 18, 2026

The Key West Hotel

The Key West Hotel

2.5 out of 5
Key West Historic District
Price was CA $3,787, price is now CA $2,445 per person
CA $2,445
per person
May 24 - May 29
found 24 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
9.2/10 Wonderful! (542 reviews)
Great location! We were very impressed with Chris! He told us where to park and was very welcoming when we arrived. The loft room setup was perfect for us and the Bali Bar did not disappoint! We will be back!!

Reviewed on Apr 5, 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 $2,820, price is now CA $2,023 per person
CA $2,023
per person
May 24 - May 29
found 24 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
9.4/10 Exceptional! (1,017 reviews)
Wry clean and updated property. The screened in porch was a plus. Clean grounds with small beach access. Nice location to key west if you have a car.

Reviewed on Apr 17, 2026

The Marker Key West Harbor Resort

The Marker Key West Harbor Resort

4 out of 5
Key West Historic District
Price was CA $3,827, price is now CA $2,819 per person
CA $2,819
per person
May 20 - May 27
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9.2/10 Wonderful! (1,003 reviews)
Great place to stay. Friendly staff well kept property. Great food as well

Reviewed on Apr 18, 2026

Paradise Place by Avantstay Key West Old Town Condo w/ Shared Pool

Paradise Place by Avantstay Key West Old Town Condo w/ Shared Pool

3 out of 5
Key West Historic District
Price was CA $4,506, price is now CA $3,361 per person
CA $3,361
per person
May 20 - May 27
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
No reviews

Where to stay in Uptown - Upper Duval

Find the best Uptown - Upper Duval areas and neighborhoods for the activities you enjoy most. Learn more about Uptown - Upper Duval
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

Uptown - Upper Duval Hotel Deals

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 $363 per night from May 19 to May 20
CA $363
CA $509 total
May 19 - May 20
includes taxes & fees
8.8/10 Excellent! (3,215 reviews)
I loved everything but the bed, hard as a rock!

Reviewed on Apr 18, 2026

Southernmost Beach Resort and Guesthouses
The Reach Key West, Curio Collection by Hilton

The Reach Key West, Curio Collection by Hilton

4 out of 5
1435 Simonton Street Key West FL
Fully refundableReserve now, pay when you stay
The price is CA $440 per night from May 10 to May 11
CA $440
CA $587 total
May 10 - May 11
includes taxes & fees
8.6/10 Excellent! (1,005 reviews)
The rooms and property were clean and comfortable. The staff were respectful, kind, and accommodating. The beach and pool were close and made it convenient for kids to jump from pool to beach. We loved our stay

Reviewed on Apr 16, 2026

The Reach Key West, Curio Collection by Hilton
Southwinds Motel

Southwinds Motel

2 out of 5
1321 Simonton Street Key West FL
The price is CA $304 per night from May 12 to May 13
CA $304
CA $388 total
May 12 - May 13
includes taxes & fees
8.6/10 Excellent! (1,302 reviews)
This is not a 5 star hotel but the beds were clean and comfortable. We had a large room with 2 queen beds and a kitchenette with a coffee maker, microwave and full sized refrigerator. The staff was friendly and efficient. Breakfast was nothing special but typical grab & go options. I heard they are ...

Reviewed on Apr 17, 2026

Southwinds Motel
See all 2,737 properties in Uptown - Upper Duval
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 an Uptown - Upper Duval vacation package cost?
Explore the best of Uptown - Upper Duval from just CA $2,019. Choose from a great selection of flights, hotels and rental cars to suit your budget. Land even more discounts when you add a few tours or activities to your vacation package.
How do I get a cheap travel package to Uptown - Upper Duval?
Bundling your flight and hotel with Expedia won't just save precious time — it'll save you a nice amount too. An Uptown - Upper Duval vacation package makes it easy to organize the perfect trip. With more than 550 airlines worldwide to pick from, finding convenient flights that fit your schedule will be no sweat. In addition to that, we've got over 1,000,000 hotel options globally to pick from. Now that's what we call choice. No matter who you are, Expedia can show you the world.
Where should I stay in Uptown - Upper Duval?
A trip to Uptown - Upper Duval isn't complete without stopping by Ernest Hemingway Home and Museum and Audubon House and Tropical Gardens. Reserve a room close by so you can easily access these fantastic sights.
What are the top hotels in Uptown - Upper Duval?
Sea Breeze - Walking Distance And Off and Casa Key West - Rooftop Pool Access And Free Parking are two of the most popular properties in Uptown - Upper Duval. Why not look up the rates and facilities at each and then decide?
How far in advance should I book my Uptown - Upper Duval vacation?
While prices change from time to time, we generally suggest booking your spot as early as possible. Most international fares can be compared on Expedia up to 12 months in advance. If circumstances have left you booking late, you may still get lucky. Cheaper tickets to Uptown - Upper Duval sometimes emerge only weeks before departure.
What does an Expedia Uptown - Upper Duval travel package include?
It depends on what kind of trip you have in the works. Uptown - Upper Duval travel deals can include car rentals, hotels and flights. You can mix and match to create the bundle that fits your needs. You can also add on experiences and activities after you've booked to land even bigger discounts.
What should I know before booking an Uptown - Upper Duval travel package?
When you book your flights, hotels and car rentals together, you'll nab awesome discounts. Whether you're planning a beach escape in a villa or prefer to stay in a cozy apartment in the city, Expedia can help make it happen.
Can I choose my airline with an Uptown - Upper Duval Expedia vacation package?
Definitely. Expedia has over 550 airline partners to choose from all over the world. With such a huge range of choice, finding the ideal carrier to whisk you away to Uptown - Upper Duval won't be difficult.
If I'm not able to travel, can I cancel my Uptown - Upper Duval vacation package?
Don't stress if you're rethinking your Uptown - Upper Duval vacation package — it's possible to change or amend your booking. And if you've booked it within the last 24 hours, you may be able to do it at no cost. However, bookings made more than 24 hours ago may incur a fee from your hotel, airline or car rental company. We understand life can throw the occasional spanner in the works, so head to our Customer Service Portal if that happens. When you're ready to make changes, we'll be here to help.

Discover the most popular places to visit in Uptown - Upper Duval

Southernmost Point

Southernmost Point

Snap a memorable photograph from the edge of North America at this monumental landmark.

Southernmost Point
South Beach

South Beach

The southernmost beach in the continental United States is a convenient sandy enclave, just minutes from the center of town.

South Beach

Things to do

Aerial view of people snorkeling in Key West

Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast

CA $58
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
Combo image of activity in Key West

Key West Rum & Reggae: Snorkel & Sunset Sail Combo

CA $75
per adult
88% of travellers recommend
Key West Rum & Reggae: Snorkel & Sunset Sail Combo
See all activities in Key West
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.