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Top hotels in Uptown - Upper Duval

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
An outdoor pool is featured at this guesthouse, along with free WiFi in public areas and a terrace. A garden, a picnic area, and luggage storage are also on ...
"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

Opens in a new windowDouglas House - Adults Only
H2O Suites - Adults Only

H2O Suites - Adults Only

3.5 out of 5
1212 Simonton Street Key West FL
$417 nightly
The price is $469 total per night from Dec 14 to Dec 15
$469 total
Dec 14 - Dec 15
Total with taxes and fees
This hotel features a bar/lounge, a poolside bar, and an outdoor pool. Business travelers can take advantage of the laundry service. There's a gym on site, and ...
"A beautiful property, wonderful room, great amenities (muffins…yumm). Latoya who checked us in was top notch. Hotel location is also good for navigating to the main Key West attractions. Hits every button."

Reviewed on Nov 11, 2026

Opens in a new windowH2O Suites - Adults Only
Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only

3.5 out of 5
1004 Duval St Key West FL
$228 nightly
The price is $257 total per night from Nov 29 to Nov 30
$257 total
Nov 29 - Nov 30
Total with taxes and fees
This hotel features a bar/lounge, a poolside bar, and an outdoor pool. Enjoy the hot tub and free continental breakfast each morning. Self parking, a garden, ...
"Always enjoy our stay here. The drink selection at the bar are fantastic and the drinks themselves are delicious. Very clean property. A lot of attention to detail here"

Reviewed on Nov 12, 2026

Opens in a new windowOrchid Key Inn - Adults Only
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
This smoke-free resort features 2 outdoor pools, a gym, and a restaurant. Relax with a drink at the bar/lounge and enjoy perks like free WiFi. There's a poolside ...
"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

Opens in a new windowSanta Maria Suites
Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

4 out of 5
1400 Duval Street Key West FL
$352 nightly
The price is $396 total per night from Nov 29 to Nov 30
$396 total
Nov 29 - Nov 30
Total with taxes and fees
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Guests will appreciate free perks like continental breakfast and WiFi in public areas. Self ...
"Stunning, I dont have to say anymore"

Reviewed on Nov 10, 2026

Opens in a new windowSouthernmost House - Adult Exclusive
Southwinds Motel

Southwinds Motel

2 out of 5
1321 Simonton Street Key West FL
$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
This hotel features 2 outdoor pools and a bar/lounge. Enjoy the free continental breakfast each morning. Self parking, a picnic area, and luggage storage are ...
"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

Opens in a new windowSouthwinds Motel
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
A full-service spa, 3 outdoor pools, and a restaurant are all featured at this hotel. Traveling on business? Take advantage of the 2 conference rooms, free WiFi ...
Opens in a new windowSouthernmost 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
This hotel's 2 outdoor pools and hot tub are among the featured amenities. Enjoy the free continental breakfast each morning. Self parking, a coffee shop, and ...
Opens in a new windowThe 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 13 to Dec 14
$325 total
Dec 13 - Dec 14
Total with taxes and fees
This resort features a private beach, a full-service spa, and a restaurant. Traveling on business? Take advantage of the express check-out, laundry service, ...
Opens in a new windowThe Reach Key West, Curio Collection by Hilton
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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.

Uptown - Upper Duval Hotel Guide

Don’t keep your travel plans on repeat year after year. The same city with the same hotel every season will bore you and give you an itch to go looking for something new. Expand your geographical horizons to more than just those five blocks around your usual haunt.

Nowhere else can you find better deals on Uptown - Upper Duval area hotels. You’ll find the best prices on the quirky, the haunted, the old, the new, and the legendary. If you’re wondering what side of the pricing scale some of these hotels fall on, you need not to worry. Compare cheap hotels near Uptown - Upper Duval to find the perfect one to will fit your budget.

Leave the ordinary routine you’re set on behind and go. Go anywhere you want. Anywhere that makes you think, “I wonder what that’s like?” Part of Travelocity’s mission is to get you off-the-beaten path and the hotels near Uptown - Upper Duval are perfect for that. Find your new favorite watering hole on a quiet street. Discover a place to escape for the weekend with tasty local fare and unique sights. We want you to consider the places outside your normal comfort zone. Browse our selection and find the ideal hotel, in a place you’d like to explore.

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