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
$238 nightly
The price is $268 total per night from Dec 2 to Dec 3
$268 total
Dec 2 - Dec 3
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, ...
This was our second time there and it didn't dissapoint! Great staff, room, bar, and all around atmosphere. It's always easy to relax at The Orchid Key!

Reviewed on Nov 28, 2025

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
$354 nightly
The price is $399 total per night from Dec 2 to Dec 3
$399 total
Dec 2 - Dec 3
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 ...
Wilfredo was phenomenal and the resort takes such good care of you!!

Reviewed on Nov 27, 2025

Opens in a new windowSanta Maria Suites
Douglas House

Douglas House

3 out of 5
419 Amelia St Key West FL
$143 nightly
The price is $161 total per night from Dec 2 to Dec 3
$161 total
Dec 2 - Dec 3
Total with taxes and fees
An outdoor pool, free self parking, and concierge services are featured at this guesthouse. A terrace, a garden, and a picnic area are also on offer.
The room was just perfect for our few day stay. He staff was lovely and so helpful. The room was equipped with a coffee maker, mini fridge, microwave, small table, and two comfy chairs. Black out curtains would have been the only thing to make this the perfect stay!

Reviewed on Nov 23, 2025

Opens in a new windowDouglas House
Southernmost House

Southernmost House

4 out of 5
1400 Duval Street Key West FL
$322 nightly
The price is $362 total per night from Dec 16 to Dec 17
$362 total
Dec 16 - Dec 17
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 ...
Great location. Loved the history of this Southernmost House. I did a lot of investigating for an historical accommodation in Key West, this matched my checklist perfectly! History, architecture, superior accommodations, great oceanfront view and delightful heated pool. Breakfast was top notch and ...

Reviewed on Nov 25, 2025

Opens in a new windowSouthernmost House
Southwinds Motel

Southwinds Motel

2 out of 5
1321 Simonton Street Key West FL
$167 nightly
The price is $188 total per night from Dec 2 to Dec 3
$188 total
Dec 2 - Dec 3
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 ...
Nice breakfast and room was nice. Only problem was parking was tight on the side of the hotel we was on. Hotel was in a very nice area and the staff was very good.

Reviewed on Nov 25, 2025

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
Fully refundableReserve now, pay when you stay
$227 nightly
The price is $255 total per night from Dec 2 to Dec 3
$255 total
Dec 2 - Dec 3
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 ...
Another great stay at the Southernmost. Staff is great. Entertainment at pools are enjoyable. This is our 5 th stay there and have found a few minor glitches this time. None of them are serious enough to complain or change my mind about a return. There was no longer a staff member on South Beach ...

Reviewed on Nov 29, 2025

Opens in a new windowSouthernmost Beach Resort and Guesthouses
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
$256 nightly
The price is $288 total per night from Dec 15 to Dec 16
$288 total
Dec 15 - Dec 16
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 beach view was wonderful

Reviewed on Nov 24, 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
$152 nightly
The price is $171 total per night from Dec 2 to Dec 3
$171 total
Dec 2 - Dec 3
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 location! The staff was helpful and they had off-street parking less than a block away after we dropped off our bags. However, there was no an elevator.

Reviewed on Nov 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
$153 nightly
The price is $172 total per night from Dec 4 to Dec 5
$172 total
Dec 4 - Dec 5
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 ...
It’s so nice

Reviewed on Nov 19, 2025

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

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