Uptown - Upper Duval Vacations from $897

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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.
Lighthouse Hotel - Key West Historic Inns

Lighthouse Hotel - Key West Historic Inns

3.5 out of 5
Old Town Key West
Price was $1,783, price is now $897 per person
$897
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip flight included
Boston (BOS) 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

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 $2,372, price is now $1,254 per person
$1,254
per person
Nov 10 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (1,006 reviews)
Excellent staff. Conveniently located and breakfast was good.

Reviewed on Sep 1, 2025

Fitch Lodge - Key West Historic Inns

Fitch Lodge - Key West Historic Inns

3.5 out of 5
Key West Historic District
Save 100% on your flight
Price was $1,712, price is now $981 per person
$981
per person
Nov 10 - Nov 16
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
8.8/10 Excellent! (479 reviews)
Property has a very cozy feel Very nice lobby area breakfast was cute and fun. Parking is very limited. Flash flooding made it a tad bit difficult to reach out room.

Reviewed on Aug 24, 2025

Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
Save 100% on your flight
Price was $1,588, price is now $967 per person
$967
per person
Nov 10 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (1,729 reviews)
Great and easy experience

Reviewed on Sep 1, 2025

Ella's Cottages - Key West Historic Inns

Ella's Cottages - Key West Historic Inns

3.5 out of 5
Old Town Key West
Save 100% on your flight
Price was $2,896, price is now $1,796 per person
$1,796
per person
Nov 10 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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

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

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 15 to Sep 16
$258 total
Sep 15 - Sep 16
Total with taxes and 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
$287 nightly
The price is $323 total per night from Oct 1 to Oct 2
$323 total
Oct 1 - Oct 2
Total with taxes and 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
$139 nightly
The price is $157 total per night from Sep 11 to Sep 12
$157 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

4.5/5(3,182 reviews)

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

4/5(980 reviews)

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

4.5/5(760 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.

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
Florida Key West Self-Guided Walking Audio Tour

Florida Key West Self-Guided Walking Audio Tour Via App

$10
per traveler
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.