Uptown - Upper Duval Vacations from $665

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Your Uptown - Upper Duval Vacation

Take the hassle out of planning your next escape by booking an Uptown - Upper Duval vacation package. Immerse yourself in the sights and sounds of this unique neighborhood and enjoy what it has to offer. Some leading nearby attractions to check out during your trip to Uptown - Upper Duval include Ernest Hemingway Home and Museum, Audubon House and Tropical Gardens and Mallory Square. No matter your travel plans or the size of your budget, booking the ultimate Uptown - Upper Duval vacation is simple with Expedia.

The Latest Uptown - Upper Duval Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hyatt Vacation Club at Beach House, Key West

Hyatt Vacation Club at Beach House, Key West

3.5 out of 5
Save 100% on your flight
Price was $1,035, price is now $665 per person
$665
per person
Oct 18 - Oct 21
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Key West (EYW)
9.4/10 Exceptional! (1,008 reviews)
This vacation was a real treat for us, long overdue. The staff certainly was helpful and pleasant. The screened in porches were very nice. There was always something each day at the resort to do along with other excursions to choose from. We most definitely will be back!

Reviewed on Aug 27, 2025

Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

3.5 out of 5
Save 100% on your flight
Price was $1,516, price is now $912 per person
$912
per person
Oct 18 - Oct 23
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.6/10 Exceptional! (1,008 reviews)
clean room everything is perfect

Reviewed on Aug 28, 2025

Lighthouse Hotel - Key West Historic Inns

Lighthouse Hotel - Key West Historic Inns

3.5 out of 5
Old Town Key West
Save 100% on your flight
Price was $1,155, price is now $778 per person
$778
per person
Oct 30 - Nov 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (775 reviews)
it’s a great location but quiet. Love the free breakfast, pool and rooms! staff was great too!

Reviewed on Aug 23, 2025

The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4 out of 5
Save 100% on your flight
Price was $1,050, price is now $708 per person
$708
per person
Oct 30 - Nov 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (1,068 reviews)
I had a great stay at the Perry. The concierge Jeremy set me up on some great excursions. Food and staff were good. I would go back next time. I’m in Key West.

Reviewed on Aug 27, 2025

Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

4 out of 5
Old Town Key West
Save 100% on your flight
Price was $1,152, price is now $803 per person
$803
per person
Oct 30 - Nov 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (1,006 reviews)
This is a very nice property, it’s unique you kinda feel like you’re in the jungle with all the trees and plants around you which is the part I liked the most. It’s also very close and walkable to nearby bars and stores. Property is clean and the staff is very friendly as well.

Reviewed on Aug 27, 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
Key West Historic District

Old Town Key West

3 out of top 10 points of interest in this area
4.5/5(226 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
$229 nightly
The price is $258 total per night from Sep 11 to Sep 12
$258 total
Sep 11 - Sep 12
Total with taxes and fees
8.6/10 Excellent! (2,701 reviews)
"Out dated."

Reviewed on Aug 24, 2025

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
$295 nightly
The price is $332 total per night from Sep 7 to Sep 8
$332 total
Sep 7 - Sep 8
Total with taxes and fees
8.4/10 Very Good! (1,011 reviews)
"The Reach Hilton Resort was excellent. The staff was professional and took care of our every need. The location was accessible to everywhere we wanted to go whether it was by walking or a quick uber ride. Even with only one working elevator at times we hardly had to wait. We would definitely stay ..."

Reviewed on Aug 24, 2025

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
$147 nightly
The price is $165 total per night from Sep 11 to Sep 12
$165 total
Sep 11 - Sep 12
Total with taxes and fees
The Southernmost Inn - Adults Only
See all 2,767 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
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

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

Southernmost Point featuring signage as well as a large group of people

Southernmost Point

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

Southernmost Point
South Beach featuring a sandy beach and general coastal views as well as a small group of people

South Beach

Head to the southernmost beach of the continental United States to relax and swim in the waters where famous writer Tennessee Williams once took his daily swim.

South Beach
Key West Butterfly and Nature Conservatory showing animals, zoo animals and food

Key West Butterfly and Nature Conservatory

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.

Key West Butterfly and Nature Conservatory

Things to do

Florida: Key West Overseas Highway Self-Driving Tour

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

$17
per traveler
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

$15
per adult
Key West’s Old Town Treasures: A Self-Guided Audio Tour
Bahama Village Walking Tour

Bahama Village Walking Tour

$30
per adult
Bahama Village Walking Tour
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.