Uptown - Upper Duval, FL

Key West

A street with a pharmacy, a theater, and a yellow building.
A colorful monument with text indicating it is the Southernmost Point of the Continental U.S.A. in Key West, Florida.
A vintage red bus with 'Old Town Trolley Tours' written on it, parked on a paved area with people around.
A large sculpture with text indicating it is the Southernmost Point of the Continental U.S.A. and 90 miles to Cuba.
A colorful marker labeled 'Southernmost Point' in Key West, FL, with a view of the ocean in the background.

Get to know Uptown - Upper Duval with its lively streets, historical landmarks, and family-friendly beaches waiting to be explored.

Uptown - Upper Duval is an ideal destination for city and family travelers. You can explore attractions such as the nearby Duval Street, a vibrant thoroughfare known for its lively atmosphere. For landmarks, visit the Southernmost Point, a symbolic site that marks the southern tip of the continental United States. If you enjoy open spaces, Mallory Square offers a modern square where you can relax and take in the surroundings, while nearby venues like Papa's Pilar Rum Distillery provide opportunities to learn about local spirits, and theaters like the Waterfront Playhouse and Red Barn Theater showcase performances.

Make sure to explore the distinct neighborhoods surrounding Uptown - Upper Duval. Truman Annex is known for its family-friendly experiences, featuring the Florida Keys National Marine Sanctuary and Truman Beach. Old Town Key West also offers family experiences, with attractions like Clarence S. Higgs Memorial Beach Park and the Mel Fisher Maritime Museum. Additionally, the Key West Historic District is rich in history, home to the Key West Shipwreck Museum and the Audubon House and Tropical Gardens, providing a glimpse into the area's past.

The best time to visit Uptown - Upper Duval aligns with the warm months from June to September, when temperatures range from 83 to 84°F and the weather is mostly dry and sunny. Demand for accommodations remains steady throughout the year, but it tends to be a little quieter in August and between October to November. This timing allows you to enjoy the area with fewer crowds while still experiencing pleasant weather.


Stay near popular Uptown - Upper Duval attractions

Things to do


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
$279 nightly
The price is $314 total per night from Nov 30 to Dec 1
$314 total
Nov 30 - Dec 1
Total with taxes and fees
Book a stay at this spa hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
Southernmost Beach Resort and Guesthouses
The Southernmost Inn - Adults Only

The Southernmost Inn - Adults Only

3 out of 5
525 United Street Key West FL
$219 nightly
The price is $246 total per night from Nov 30 to Dec 1
$246 total
Nov 30 - Dec 1
Total with taxes and fees
Stay at this hotel in Key West. Enjoy free breakfast, 2 outdoor pools, and parking (surcharge). Our guests praise the breakfast and the pool in our reviews. ...
The Southernmost Inn - Adults Only
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
$289 nightly
The price is $325 total per night from Dec 14 to Dec 15
$325 total
Dec 14 - Dec 15
Total with taxes and fees
Book a stay at this beach resort in Key West. Enjoy a full-service spa, a private beach, and breakfast (surcharge). Our guests praise the helpful staff and the ...
The Reach Key West, Curio Collection by Hilton
Douglas House - Adults Only

Douglas House - Adults Only

3 out of 5
419 Amelia St Key West FL
$277 nightly
The price is $312 total per night from Nov 17 to Nov 18
$312 total
Nov 17 - Nov 18
Total with taxes and fees
Stay at this guesthouse in Key West. Enjoy free WiFi, daily housekeeping, and a garden. Popular attractions Duval Street and Mallory Square are located ...
9.8/10 Exceptional! (594 reviews)
"This place is so cute. It's location is perfect. The staff was amazing. We can not wait to come back"

Reviewed on Nov 14, 2026

Douglas House - Adults Only
Southwinds Motel

Southwinds Motel

2 out of 5
1321 Simonton Street Key West FL
Fully refundable
$184 nightly
The price is $207 total per night from Dec 1 to Dec 2
$207 total
Dec 1 - Dec 2
Total with taxes and fees
Stay at this hotel in Key West. Enjoy free breakfast, 2 outdoor pools, and parking (surcharge). Our guests praise the breakfast and the pool in our reviews. ...
8.6/10 Excellent! (1,398 reviews)
"Great location walking distance to everything. Quiet, clean property. Continental breakfast was a great start to day. Has a bar on site with music daily great way to unwind and not go far. Very nice clean pools"

Reviewed on Nov 13, 2026

Southwinds Motel
Santa Maria Suites

Santa Maria Suites

4 out of 5
1401 Simonton St Key West FL
$412 nightly
The price is $464 total per night from Nov 29 to Nov 30
$464 total
Nov 29 - Nov 30
Total with taxes and fees
Stay at this resort in Key West. Enjoy free WiFi, 2 outdoor pools, and a fitness center. Our guests praise the pool and the helpful staff in our reviews. Popular ...
9.6/10 Exceptional! (1,000 reviews)
"Check in was easy. Staff is extremely friendly and accommodating. The rooms and surrounding pools and grounds were very clean. Easy parking. On site restaurant (Italian) is beautiful...clean, modern, friendly and fantastic food. Great location....coffee shop/deli, scooter rental, bar, ice cream and ..."

Reviewed on Nov 11, 2026

Santa Maria Suites
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.

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
Learn more about Uptown - Upper Duval

Old Town Key West

If you're spending some time in Old Town Key West, Duval Street and Florida Keys Beaches are top sights worth seeing.

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.

Key West Historic District

Travelers to Key West Historic District praise its fantastic nightlife. If you've got some more time to explore, be sure to make a stop by Duval Street and Florida Keys Beaches.

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 Fort East Martello Museum and Gallery.



Uptown - Upper Duval, FL

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