Uptown - Upper Duval Vacations from $720

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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 $1,176, price is now $720 per person
$720
per person
Nov 16 - Nov 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (1,025 reviews)
Definitely have to say the staff was so nice makeable helpful. We even decide to extend our stay

Reviewed on Oct 11, 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 $1,301, price is now $803 per person
$803
per person
Nov 28 - Dec 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.6/10 Exceptional! (1,016 reviews)
Very low-key beautiful, stunning property. The great Jacuzzi bathtub was a highlight, after long days of being in the sun walking or excursions. The Jacuzzi bath tub will bring us back to life ! The pool and Jacuzzi and all the other amenities were just as great. The spacious rooms and huge balconies,you & the family could eat dinner watching the sunset.

Reviewed on Oct 14, 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 $4,423, price is now $2,762 per person
$2,762
per person
Dec 26 - Jan 2
found 2 days ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (1,005 reviews)
Clean rooms and property. The grounds were so clean and taken care of. The landscape was so lush and exquisite. I loved everything about this property. Will be back.

Reviewed on Oct 13, 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 $4,435, price is now $2,875 per person
$2,875
per person
Dec 26 - Jan 2
found 2 days ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (1,722 reviews)
Staff was friendly and accommodating. The concierge booked trips for us and made some great recommendations for us.

Reviewed on Oct 8, 2025

The Grand Guesthouse

The Grand Guesthouse

2.5 out of 5
Old Town Key West
Save 100% on your flight
Price was $1,375, price is now $909 per person
$909
per person
Nov 16 - Nov 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.6/10 Exceptional! (1,001 reviews)
Yes it was very safe and convenient.

Reviewed on Oct 10, 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
$234 nightly
The price is $264 total per night from Oct 29 to Oct 30
$264 total
Oct 29 - Oct 30
Total with taxes and fees
8.6/10 Excellent! (2,787 reviews)
"The balcony was not private it was outside our front door located outside. Other then that it was a great stay!"

Reviewed on Oct 13, 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
$241 nightly
The price is $271 total per night from Oct 30 to Oct 31
$271 total
Oct 30 - Oct 31
Total with taxes and fees
8.4/10 Very Good! (1,008 reviews)
"Beach view was spectacular and restaurants were great! The rooms could use more "hooks" on the back of doors to hang things and a few more lighted mirrors. The staff was wonderful!"

Reviewed on Oct 10, 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
$136 nightly
The price is $153 total per night from Oct 15 to Oct 16
$153 total
Oct 15 - Oct 16
Total with taxes and fees
8.2/10 Very Good! (1,166 reviews)
"Great facility. Beautiful rooms. Fantastic pools. Conveniently situated in Key West. Absolute recommendation…."

Reviewed on Oct 8, 2025

The Southernmost Inn - Adults Only
See all 2,802 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

Aerial view of people snorkeling in Key West

Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast

$50
per adult
92% of travellers recommend
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
Commotion on the Ocean Sunset Sail

Key West Sunset Sail with Live Music, Drinks and Appetizers!

$80
per adult
92% of travellers recommend
Key West Sunset Sail with Live Music, Drinks and Appetizers!
12 hours Day at Key West With Boat Tour and Snorkeling

Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar

$27
per adult
80% of travellers recommend
Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar
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.