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.
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 $2,364, price is now CA $1,578 per person
CA $1,578
per person
Nov 17 - Nov 21
found 18 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9.2/10 Wonderful! (1,006 reviews)
Continental breakfast was poor. Not many choices. Property was quaint and very clean. Staff very friendly and accommodating. I would definitely stay here again. Easy walk to Duval only 1 1/2 blocks.

Reviewed on Sep. 3, 2025

Ella's Cottages - Key West Historic Inns

Ella's Cottages - Key West Historic Inns

3.5 out of 5
Old Town Key West
Price was CA $3,993, price is now CA $2,241 per person
CA $2,241
per person
Oct 26 - Nov 2
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9.4/10 Exceptional! (367 reviews)
This property is absolutely adorable! Room was clean and spacious. Front desk person was very nice and personable. The breakfast baskets that are delivered to your room are top notch! Will definitely be staying here again!

Reviewed on Aug. 31, 2025

Ridley House - Key West Historic Inns

Ridley House - Key West Historic Inns

3.5 out of 5
Key West Historic District
Price was CA $3,847, price is now CA $2,182 per person
CA $2,182
per person
Oct 26 - Nov 2
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9.2/10 Wonderful! (812 reviews)
The staff were wonderful and we loved the breakfast and sangria hour and how walkable the area was! We walked everywhere during our stay. The only downsides were it is very noisy, since you can hear everything outside from in the room, and the AC in our room took about 2 days to cool down enough to be comfortable after the previous guests apparently had left the AC off and the windows open during their stay.

Reviewed on Sep. 3, 2025

Lighthouse Hotel - Key West Historic Inns

Lighthouse Hotel - Key West Historic Inns

3.5 out of 5
Old Town Key West
Price was CA $3,455, price is now CA $2,025 per person
CA $2,025
per person
Oct 26 - Nov 2
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9/10 Wonderful! (779 reviews)
it’s a great location but quiet. Love the free breakfast, pool and rooms! staff was great too!

Reviewed on Aug. 23, 2025

Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

3.5 out of 5
Price was CA $2,723, price is now CA $1,816 per person
CA $1,816
per person
Oct 26 - Nov 2
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9.6/10 Exceptional! (1,011 reviews)
Everything and everyone was wonderful. My family loves Key West and this property.

Reviewed on Sep. 4, 2025

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
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Old Town Key West

3 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 refundable
The price is CA $234 per night from Sep 18 to Sep 19
CA $234
CA $356 total
Sep 18 - Sep 19
includes taxes & fees
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 $323 per night from Oct 1 to Oct 2
CA $323
CA $446 total
Oct 1 - Oct 2
includes taxes & fees
The Reach Key West, Curio Collection by Hilton
The Southernmost Inn - Adults Only

The Southernmost Inn - Adults Only

3 out of 5
525 United Street, Key West, FL
Fully refundableReserve now, pay when you stay
The price is CA $148 per night from Sep 11 to Sep 12
CA $148
CA $228 total
Sep 11 - Sep 12
includes taxes & fees
The Southernmost Inn - Adults Only
See all 2,788 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
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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 $1,578. 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

Florida: Key West Overseas Highway Self-Driving Tour

Florida: Key West Overseas Highway App-Based Driving Audio Tour

CA $23
per traveller
80% of travellers recommend
Florida: Key West Overseas Highway App-Based Driving Audio Tour
Key West’s Old Town Treasures: A Self-Guided Audio Tour

Key West’s Old Town Treasures: A Self-Guided Audio Tour

CA $21
per adult
Key West’s Old Town Treasures: A Self-Guided Audio Tour
Florida Key West Self-Guided Walking Audio Tour

Florida Key West Self-Guided Walking Audio Tour Via App

CA $14
per traveller
Florida Key West Self-Guided Walking Audio Tour Via App
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.