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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
$360 nightly
The price is $404 total per night from May 10 to May 11
$404 total
May 10 - May 11
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 is our favorite, and only place we stay, while in Key West! It’s always perfect and the staff is so accommodating. Room is always as expected, breakfast is lovely, especially sitting by the pool, and then, of course, the rest is Key West! It’s always so much fun, until the drive home!

Reviewed on Apr 13, 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
$473 nightly
The price is $532 total per night from May 12 to May 13
$532 total
May 12 - May 13
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 private pool is not private. It is near the walkways so everyone walking by can see into the pool/your room. The bar on the roof deck is small and the seats are not comfortable. The staff was awful, unfriendly, rude, and acted as we were bothering them. From the moment we arrived it was really ...

Reviewed on Apr 5, 2026

Opens in a new windowH2O Suites - Adults Only
Douglas House - Adults Only

Douglas House - Adults Only

3 out of 5
419 Amelia St Key West FL
$227 nightly
The price is $255 total per night from Apr 19 to Apr 20
$255 total
Apr 19 - Apr 20
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 ...
great place, great staff and well equiped

Reviewed on Apr 16, 2026

Opens in a new windowDouglas House - Adults Only
Santa Maria Suites

Santa Maria Suites

4 out of 5
1401 Simonton St Key West FL
$499 nightly
The price is $561 total per night from May 11 to May 12
$561 total
May 11 - May 12
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 ...
Nice suites , staff very friendly. Conveniently located. Check your room bills carefully.

Reviewed on Apr 14, 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
$412 nightly
The price is $463 total per night from Apr 19 to Apr 20
$463 total
Apr 19 - Apr 20
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 ...
Fresh continental breakfast, clean room, close to everything.

Reviewed on Apr 12, 2026

Opens in a new windowSouthernmost House - Adult Exclusive
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
$365 nightly
The price is $411 total per night from May 10 to May 11
$411 total
May 10 - May 11
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 ...
Everything was wonderful! The hotel, beach, restaurants and hotel staff was very accommodating! Will be staying here again

Reviewed on Apr 16, 2026

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
$333 nightly
The price is $375 total per night from May 3 to May 4
$375 total
May 3 - May 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, ...
Our room was over looking the resort. The staff was extremely nice and accommodating. The only negative I have to say is that the walls are so thin you could hear your next-door neighbor talking. I could hear someone drop something above us and sounded like normal conversations from our neighbors ...

Reviewed on Apr 16, 2026

Opens in a new windowThe Reach Key West, Curio Collection by Hilton
Southwinds Motel

Southwinds Motel

2 out of 5
1321 Simonton Street Key West FL
$242 nightly
The price is $272 total per night from Apr 20 to Apr 21
$272 total
Apr 20 - Apr 21
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 place to stay, within 30 minute walk to all fun places in old Key West. Very weak water supply during our stay.

Reviewed on Apr 14, 2026

Opens in a new windowSouthwinds Motel
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
$264 nightly
The price is $297 total per night from May 10 to May 11
$297 total
May 10 - May 11
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 ...
Clean, great location, quite even In front room on street level! Please consider putting two luggage racks in king rooms.

Reviewed on Apr 16, 2026

Opens in a new windowThe Southernmost Inn - Adults Only
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Uptown - Upper Duval Hotel Guide

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