Uptown - Upper Duval Vacations from $721

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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.
The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4 out of 5
Save 100% on your flight
Price was $1,265, price is now $721 per person
$721
per person
Feb 2 - Feb 6
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (1,151 reviews)
Great Hotel will, clean, great staff, wonderful view in the am. The shuttle service to downtown Key West is the a game changer. Will repeat again.

Reviewed on Nov 26, 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 $2,845, price is now $1,426 per person
$1,426
per person
Jan 2 - Jan 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (390 reviews)
Everything was great. Staff were all super helpful. Location fantastic. Breakfast served outside the room on the verander we loved (the health shots were a lovely touch). We had a great stay. Would definitely recommend.

Reviewed on Nov 22, 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 $2,324, price is now $1,184 per person
$1,184
per person
Jan 10 - Jan 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (1,736 reviews)
Nice resort. Good food. Nice pool. Friendly staff.

Reviewed on Nov 27, 2025

The Key West Hotel

The Key West Hotel

2.5 out of 5
Key West Historic District
Price was $4,556, price is now $2,437 per person
$2,437
per person
Jan 10 - Jan 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (505 reviews)
Beautiful private oasis

Reviewed on Nov 25, 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 $2,302, price is now $1,310 per person
$1,310
per person
Jan 10 - Jan 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.6/10 Exceptional! (1,002 reviews)
Pool was great. Flat volleyballs. No cleaning service for 5d/4nights seemed strange when you pay an extra $220 for a resort fee.

Reviewed on Nov 28, 2025

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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

4 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 refundableReserve now, pay when you stay
$227 nightly
The price is $255 total per night from Dec 2 to Dec 3
$255 total
Dec 2 - Dec 3
Total with taxes and fees
8.6/10 Excellent! (2,881 reviews)
A1

Reviewed on Nov 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
$264 nightly
The price is $297 total per night from Dec 17 to Dec 18
$297 total
Dec 17 - Dec 18
Total with taxes and fees
8.4/10 Very Good! (1,015 reviews)
The beach view was wonderful

Reviewed on Nov 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
$149 nightly
The price is $168 total per night from Nov 30 to Dec 1
$168 total
Nov 30 - Dec 1
Total with taxes and fees
8.2/10 Very Good! (1,195 reviews)
Exceeded expectations

Reviewed on Nov 22, 2025

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
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Kid Friendly Vacations
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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

Miami to Key West Day Trip with Activity Options

Miami to Key West Day Trip with Activity Options

$39
per adult
84% of travellers recommend
Miami to Key West Day Trip with Activity Options
Entertainer in character at the Shipwreck Treasure Museum in Key West

Shipwreck Treasure Museum Tickets

$19
per adult
76% of travellers recommend
Shipwreck Treasure Museum Tickets
Sunset Sail in Key West with Beverages Included

Sunset Sail in Key West with Beverages Included

$79
per adult
98% of travellers recommend
Sunset Sail in Key West with Beverages Included
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.