Find a Hotel in Uptown - Upper Duval

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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
$377 nightly
The price is $424 total per night from Jan 8 to Jan 9
$424 total
Jan 8 - Jan 9
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, ...
The orchid key is the perfect place to stay in key west. On Duvall but surprisingly quiet. Can’t wait to come back next year.

Reviewed on Dec 26, 2025

Opens in a new windowOrchid Key Inn - Adults Only
Douglas House

Douglas House

3 out of 5
419 Amelia St Key West FL
$306 nightly
The price is $344 total per night from Jan 13 to Jan 14
$344 total
Jan 13 - Jan 14
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 ...
Great location and the room was clean. The bed was also very comfortable. I would stay there again.

Reviewed on Dec 29, 2025

Opens in a new windowDouglas House
Santa Maria Suites

Santa Maria Suites

4 out of 5
1401 Simonton St Key West FL
$569 nightly
The price is $640 total per night from Jan 7 to Jan 8
$640 total
Jan 7 - Jan 8
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 ...
All great!

Reviewed on Dec 27, 2025

Opens in a new windowSanta Maria Suites
Southernmost House

Southernmost House

4 out of 5
1400 Duval Street Key West FL
$542 nightly
The price is $609 total per night from Jan 14 to Jan 15
$609 total
Jan 14 - Jan 15
Total with taxes and fees
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Unwind with a drink at the poolside bar and enjoy perks like free continental breakfast ...
This property is beautiful and interesting for its rich history. The cottage rooms are right on the water. Staff is amazing and the breakfast is delicious from local bakery.

Reviewed on Dec 27, 2025

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
$419 nightly
The price is $472 total per night from Jan 26 to Jan 27
$472 total
Jan 26 - Jan 27
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 ...
This is the most wonderful place to stay in all of Key West. It has a little bit of everything from multiple pool choices, poolside bars, onsite restaurant, beach access, live music, concierge and full service spa! It’s on the quiet end Duval Street, but still within walking distance of most everything, ...

Reviewed on Dec 29, 2025

Opens in a new windowSouthernmost Beach Resort and Guesthouses
Southwinds Motel

Southwinds Motel

2 out of 5
1321 Simonton Street Key West FL
$252 nightly
The price is $284 total per night from Jan 7 to Jan 8
$284 total
Jan 7 - Jan 8
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 ...
Breakfast is a quick stop and go. Met expectations and was appreciated. Room and property is so clean a quaint. I really enjoyed all of the amenities and location. Ended up in that heated pool everyday. So nice! Will be back.

Reviewed on Jan 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
$381 nightly
The price is $428 total per night from Jan 13 to Jan 14
$428 total
Jan 13 - Jan 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, ...
The resort is beautiful. The private beach was a key feature for us. The room was clean and comfortable. A perfect location. It’s not in the middle of the craziness of Duval Street. But easy walk to it.

Reviewed on Dec 31, 2025

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
$309 nightly
The price is $348 total per night from Jan 6 to Jan 7
$348 total
Jan 6 - Jan 7
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 ...
Great breakfast especially the Starbucks machine for fresh coffee. Great pools and hot tub. Loved the quaint rooms in the original building.

Reviewed on Dec 24, 2025

Opens in a new windowThe Southernmost Inn - Adults Only
Kona Kai Oasis

Kona Kai Oasis

3 out of 5
630 South Street Key West FL
$269 nightly
The price is $303 total per night from Jan 5 to Jan 6
$303 total
Jan 5 - Jan 6
Total with taxes and fees
An outdoor pool, free self parking, and concierge services are featured at this guesthouse. WiFi in public areas is free. A garden, a picnic area, and luggage ...
Love staying at Mona Kai, peaceful, on the quiet end of Duval St

Reviewed on Dec 11, 2025

Opens in a new windowKona Kai Oasis
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Uptown - Upper Duval Hotel Guide

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