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.
The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

CA $1,684
per person
Oct 20 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Key West (EYW)
9.4/10 Exceptional! (1,314 reviews)
Beautiful Marina Views

Reviewed on Aug 19, 2026

The Key West Hotel

The Key West Hotel

Key West Historic District
CA $4,724
per person
Oct 24 - Oct 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) 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 Jul 27, 2026

Ella's Cottages - Key West Historic Inns

Ella's Cottages - Key West Historic Inns

Old Town Key West
CA $2,014
per person
Nov 8 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Key West (EYW)
9.4/10 Exceptional! (490 reviews)
Ridley House - Key West Historic Inns

Ridley House - Key West Historic Inns

Key West Historic District
CA $1,941
per person
Nov 8 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Key West (EYW)
9.2/10 Wonderful! (946 reviews)
The Gardens Hotel

The Gardens Hotel

Old Town Key West
CA $3,255
per person
Oct 24 - Oct 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9.8/10 Exceptional! (1,002 reviews)
Beautiful property, relaxing and enjoyable atmosphere, exceptional customer service!

Reviewed on Aug 14, 2026

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
A white building with shutters, palm trees, and a lawn.

Old Town Key West

4 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.

A coastal town with a prominent building featuring a blue awning, a chicken shack, and a store with colorful merchandise.

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.

A two-story house with green shutters and a wooden balcony.

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.

A marina with yachts docked, a prominent red building, and a coastal cityscape in the background.

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 Key West Tropical Forest and Botanical Garden.

A pier with people dining under umbrellas, a sailboat in the distance, and a sunset over the water.

Historic Seaport

While visiting Historic Seaport, you might make a stop by sights like Duval Street and Florida Keys Beaches.

Uptown - Upper Duval Hotel Deals

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

1319 Duval Street Key West FL
Fully refundableReserve now, pay when you stay
CA $192
CA $317 total
Sep 1 - Sep 2
includes taxes & fees
Southernmost Beach Resort and Guesthouses
The Reach Key West, Curio Collection by Hilton

The Reach Key West, Curio Collection by Hilton

1435 Simonton Street Key West FL
Fully refundableReserve now, pay when you stay
CA $217
CA $338 total
Sep 3 - Sep 4
includes taxes & fees
8.6/10 Excellent! (1,013 reviews)
"Toilet was broken. Had to ask for it to be fixed. Plus the resort fees and taxes they add on top of the cost you see when you book will cost you over a hundred dollars a day more at checkout."

Reviewed on Aug 19, 2026

The Reach Key West, Curio Collection by Hilton
Southwinds Motel

Southwinds Motel

1321 Simonton Street Key West FL
CA $154
CA $220 total
Sep 7 - Sep 8
includes taxes & fees
Southwinds Motel
See all 2,685 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.

Frequently asked questions

How much does an Uptown - Upper Duval vacation package cost?
Explore the best of Uptown - Upper Duval from just CA $1,684. 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.

Stay near popular Uptown - Upper Duval attractions

A colorful monument with text indicating it is the Southernmost Point of the Continental U.S.A. in Key West, Florida.

Southernmost Point

8.8/10 (17,214 reviews)
Snap a memorable photograph from the edge of North America at this monumental landmark.
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A beach with people sunbathing, palm trees, and a multi-story building in the background.

South Beach

8.4/10 (5,461 reviews)
The southernmost beach in the continental United States is a convenient sandy enclave, just minutes from the center of town.
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A butterfly on a plant with green leaves and yellow flowers.

Key West Butterfly and Nature Conservatory

9.2/10 (1,711 reviews)
With about 60 species of butterfly, an indoor waterfall and a tropical rainforest, this nature conservatory is one of the most popular attractions in Key West.
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Simonton Beach

Why not spend a carefree afternoon at Simonton Beach during your travels in Key West? While you're in the area, stroll along the seaside.
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City Zoo Gallery

You can spend an afternoon studying the exhibits at City Zoo Gallery during your travels in Key West. Discover the area's beautiful sunsets, or seek out its biking trails.
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Things to do

Aerial view of people snorkeling in Key West

Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast

CA $63
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 $78
per adult
88% of travellers recommend
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
Snorkler waving underwater in Key West

Key West Coral Reef Snorkel with Mimosas, Margaritas or Rum Punch

CA $85
per adult
86% of travellers recommend
Key West Coral Reef Snorkel with Mimosas, Margaritas or Rum Punch
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.