Uptown - Upper Duval, FL

Key West

A sunset over the ocean with scattered clouds.
A rope bridge over turquoise water with a beach and palm trees in the background.
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 hammock tied to a palm tree on a sandy beach with a wooden structure in the background.

Stay near popular Uptown - Upper Duval attractions

A colorful monument with text indicating it is the Southernmost Point of the Continental U.S.A. in Key West, Florida.

Southernmost Point

8.8/10 (17,214 reviews)
Snap a memorable photograph from the edge of North America at this monumental landmark.
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Things to do

Key West Premium Sunset Sail with Champagne, Wine & Tapas

Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar

$79
per adult
94% of travellers recommend
Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar
Key West Champagne Sunset Sail

Champagne and Sunsets: A Key West Catamaran Adventure

$59
per adult
94% of travellers recommend
Champagne and Sunsets: A Key West Catamaran Adventure
Passengers enjoying the shade on the Conch Tour Train in Key West

Key West Conch Tour Train

$41
per adult
88% of travellers recommend
Key West Conch Tour Train
Entertainer in character at the Shipwreck Treasure Museum in Key West

Shipwreck Treasure Museum Tickets

$19
per adult
80% 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
Afternoon Key West Reef Snorkel & Catamaran Sail

Afternoon Reef Snorkel & Catamaran Sail w/ Open Bar in Key West

$68
per adult
90% of travellers recommend
Afternoon Reef Snorkel & Catamaran Sail w/ Open Bar in Key West
See all activities in 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
$186 nightly
The price is $210 total per night from Oct 26 to Oct 27
$210 total
Oct 26 - Oct 27
Total with taxes and fees
Book a stay at this spa hotel in Key West. Enjoy 3 outdoor pools, a full-service spa, and 2 poolside bars. Our guests praise the pool and the helpful staff in ...
8.6/10 Excellent! (3,645 reviews)
"The room was perfectly clean and comfortable. However, our experience with the staff was a bit mixed. While some of the bartenders were incredibly friendly and welcoming, a few others could definitely use some training in hospitality and politeness. Additionally, it would be great if breakfast hours ..."

Reviewed on Oct 25, 2026

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
$151 nightly
The price is $170 total per night from Oct 26 to Oct 27
$170 total
Oct 26 - Oct 27
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. ...
8.4/10 Very Good! (1,453 reviews)
"Wonderfully situated & quiet suite on United. Cleaning could have been better if more attention had been paid. Warm & hot water took forever. Shower could be much better if it had an attached hose for all around water. Water pressure sucked! Maudia (check in person) was excellent. Kitchen staff appeared ..."

Reviewed on Oct 24, 2026

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
$239 nightly
The price is $269 total per night from Oct 26 to Oct 27
$269 total
Oct 26 - Oct 27
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
Southwinds Motel

Southwinds Motel

2 out of 5
1321 Simonton Street Key West FL
$169 nightly
The price is $190 total per night from Oct 26 to Oct 27
$190 total
Oct 26 - Oct 27
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! (1,395 reviews)
"Very clean and the staff was very helpful"

Reviewed on Oct 23, 2026

Southwinds Motel
Douglas House - Adults Only

Douglas House - Adults Only

3 out of 5
419 Amelia St Key West FL
$179 nightly
The price is $201 total per night from Oct 26 to Oct 27
$201 total
Oct 26 - Oct 27
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 Ernest Hemingway Home and Museum ...
9.8/10 Exceptional! (566 reviews)
"The porch was amazing and tranquil. Loved the location and accommodations. 10/10 will be back here next trip"

Reviewed on Oct 22, 2026

Douglas House - Adults Only
Santa Maria Suites

Santa Maria Suites

4 out of 5
1401 Simonton St Key West FL
$359 nightly
The price is $404 total per night from Oct 26 to Oct 27
$404 total
Oct 26 - Oct 27
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! (1,004 reviews)
"We loved staying at Santa Maria! Our bi-level room was spacious and well maintained. Beds were super comfortable and the kitchen was well-adorned. Staff was great; we used the concierge service to rent our golf cart and the outdoor bartenders were great all week. We appreciated the free wine from ..."

Reviewed on Oct 22, 2026

Santa Maria Suites
See all 2,732 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.

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
A large red brick building with arched windows and a prominent entrance.

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.

The Monroe County Courthouse with a clock tower, surrounded by trees and a clear blue sky.

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.

A white lighthouse surrounded by lush greenery and a white picket fence.

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.

A row of pastel-colored houses with white railings and a clear blue sky.

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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