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Top hotels in Uptown - Upper Duval

Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only

3.5 out of 5
1004 Duval St Key West FL
$526 nightly
The price is $592 total per night from Mar 9 to Mar 10
$592 total
Mar 9 - Mar 10
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, ...
Loved this little hotel. It’s right in the heart of Duval Street, with so much going on, yet we never heard a peep in our room. It was surprisingly quiet and peaceful. We originally booked just one night but ended up adding another. We did have to switch rooms, but the staff had our second room ready ...

Reviewed on Feb 22, 2026

Opens in a new windowOrchid Key Inn - Adults Only
H2O Suites - Adults Only

H2O Suites - Adults Only

3.5 out of 5
1212 Simonton Street Key West FL
$789 nightly
The price is $888 total per night from Mar 22 to Mar 23
$888 total
Mar 22 - Mar 23
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 ...
. The tropical Landscaping, pool area, and overall vibe were special. The morning, bloody Mary’s, muffins and the afternoon happy hour were all signs that somebody knows what they’re doing. It was our first time visit, but we will not come back to Key West without staying here.

Reviewed on Feb 16, 2026

Opens in a new windowH2O Suites - Adults Only
Douglas House

Douglas House

3 out of 5
419 Amelia St Key West FL
$395 nightly
The price is $444 total per night from Mar 3 to Mar 4
$444 total
Mar 3 - Mar 4
Total with taxes and fees
An outdoor pool, self parking, and concierge services are featured at this guesthouse. WiFi in public areas is free. A terrace, a garden, and a picnic area are ...
A quieter area off Duval street. Was truly very peaceful and relaxing. Able to walk anywhere on the island within 20 minutes or less. There’s a great coffee place right down the street, but also coffee/tea/water by the pool at all times if you prefer. Check-in process was easy and the staff are all ...

Reviewed on Mar 2, 2026

Opens in a new windowDouglas House
Santa Maria Suites

Santa Maria Suites

4 out of 5
1401 Simonton St Key West FL
$765 nightly
The price is $861 total per night from Mar 4 to Mar 5
$861 total
Mar 4 - Mar 5
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 ...
Yes

Reviewed on Feb 22, 2026

Opens in a new windowSanta Maria Suites
Southernmost House

Southernmost House

4 out of 5
1400 Duval Street Key West FL
$682 nightly
The price is $767 total per night from Mar 5 to Mar 6
$767 total
Mar 5 - Mar 6
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 ...
The experience was splendid, and the entire staff of The Southernmost House are professional and courteous. The breakfast was delicious and abundant. The location is wonderful, on the quiet end of Dubal. The pool was heavenly.

Reviewed on Feb 27, 2026

Opens in a new windowSouthernmost House
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
Fully refundable
$530 nightly
The price is $596 total per night from Mar 12 to Mar 13
$596 total
Mar 12 - Mar 13
Total with taxes and fees
This hotel features a full-service spa, 3 outdoor pools, and a restaurant. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Traveling ...
Clean room, great location

Reviewed on Mar 2, 2026

Opens in a new windowSouthernmost Beach Resort and Guesthouses
Southwinds Motel

Southwinds Motel

2 out of 5
1321 Simonton Street Key West FL
$346 nightly
The price is $390 total per night from Mar 29 to Mar 30
$390 total
Mar 29 - Mar 30
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 ...
Room was nice staff was nice

Reviewed on Mar 2, 2026

Opens in a new windowSouthwinds Motel
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
$619 nightly
The price is $696 total per night from Mar 3 to Mar 4
$696 total
Mar 3 - Mar 4
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, ...
The front desk seemed just OK. The room had several problems: 1) The caulk was worn in the shower and water would flood the bathroom and adjacent closet. Noatter how carefully you showered. 2) The TV volume would not go down beyond level 10. It was never fixed, although they tries several times. ...

Reviewed on Mar 1, 2026

Opens in a new windowThe 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
$439 nightly
The price is $494 total per night from Mar 3 to Mar 4
$494 total
Mar 3 - Mar 4
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 ...
Everything was lovely, and the breakfast was quite good. My only quibble was that I did not know that I would need to pay $30 per night to park at the Inn.

Reviewed on Mar 1, 2026

Opens in a new windowThe Southernmost Inn - Adults Only
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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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