Hotels with smoking rooms in Key West Historic District from $145

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Top Key West Historic District Hotels with smoking rooms

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
$268 total
Dec 10 - Dec 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, ...
Andrews Inn & Garden Cottages

Andrews Inn & Garden Cottages

3.5 out of 5
223 Eanes Lane Key West FL
$241 nightly
The price is $271 total per night
$271 total
Dec 8 - Dec 9
Total with taxes and fees
An outdoor pool, self parking, and concierge services are featured at this bed & breakfast. Guests will appreciate free perks like self-serve breakfast and WiFi ...
Artist House Key West

Artist House Key West

3.5 out of 5
534 Eaton Street Key West FL
$377 nightly
The price is $424 total per night
$424 total
Dec 25 - Dec 26
Total with taxes and fees
This bed & breakfast doesn't skimp on freebies - guests receive free buffet breakfast and free WiFi. If you want to take your pet along, this pet-friendly property ...
Island City House Hotel

Island City House Hotel

3 out of 5
411 William Street Key West FL
$207 nightly
The price is $233 total per night
$233 total
Dec 15 - Dec 16
Total with taxes and fees
This hotel features an outdoor pool and a rooftop terrace. WiFi in public areas is free. A terrace, a garden, and a library are also on offer.
The Inn on Fleming

The Inn on Fleming

3.5 out of 5
1016 Fleming St. Key West FL
Get rates
This guesthouse features an outdoor pool and a hot tub. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A terrace, a garden, ...
The Key West Hotel

The Key West Hotel

2.5 out of 5
325 Duval St. Key West FL
$245 nightly
The price is $275 total per night
$275 total
Dec 8 - Dec 9
Total with taxes and fees
An outdoor pool is featured at this guesthouse, along with free WiFi in public areas and a garden. Luggage storage and concierge services are also provided.
Authors of Key West Guest House

Authors of Key West Guest House

3 out of 5
725 White St. & Petronia Key West FL
$129 nightly
The price is $145 total per night
$145 total
Dec 9 - Dec 10
Total with taxes and fees
An outdoor pool is featured at this bed & breakfast, along with free WiFi in public areas and a terrace. Enjoy the free continental breakfast each morning. A ...
La Concha Key West, Autograph Collection

La Concha Key West, Autograph Collection

4 out of 5
430 Duval St Key West FL
Free Cancellation
Reserve now, pay when you stay
$259 nightly
The price is $291 total per night
$291 total
Dec 14 - Dec 15
Total with taxes and fees
This smoke-free hotel includes 3 restaurants, an outdoor pool, and a 24-hour gym. Traveling on business? Take advantage of the free WiFi in public areas, express ...
Duval Inn

Duval Inn

3 out of 5
511 Angela Street Key West FL
$257 nightly
The price is $290 total per night
$290 total
Dec 18 - Dec 19
Total with taxes and fees
An outdoor pool is featured at this guesthouse, along with free WiFi in public areas and a terrace. Enjoy the free continental breakfast each morning. A garden, ...
New Orleans House - Gay Men Adult Resort

New Orleans House - Gay Men Adult Resort

2.5 out of 5
724 Duval Street Key West FL
$231 nightly
The price is $259 total per night
$259 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
A nightclub, a 24-hour gym, and a restaurant are all featured at this guesthouse. Unwind with a drink at one of the 3 bars/lounges and enjoy free perks like ...
Wicker Guesthouse

Wicker Guesthouse

3.5 out of 5
913 Duval Street Key West FL
$319 nightly
The price is $359 total per night
$359 total
Dec 8 - Dec 9
Total with taxes and fees
This guesthouse features an outdoor pool and a bar/lounge. Guests will appreciate free perks like free self parking and WiFi in public areas. A terrace, a garden, ...
NYAH Key West - Adults Only

NYAH Key West - Adults Only

3 out of 5
420 Margaret Street Key West FL
Free Cancellation
Reserve now, pay when you stay
$147 nightly
The price is $165 total per night
$165 total
Dec 16 - Dec 17
Total with taxes and fees
This guesthouse's 3 outdoor pools and a rooftop terrace are among the featured amenities. Enjoy the hot tub and free continental breakfast each morning. There's ...
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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.

Key West Historic District hotels essential information

Accommodation
1,770 hotels
Lowest Price
$145
Highest Price
$424
Popular hotels
Andrews Inn & Garden Cottages, Artist House Key West, The Inn on Fleming, Authors of Key West Guest House, The Key West Hotel, Duval Inn, Island City House Hotel, Wicker Guesthouse, La Concha Key West, Autograph Collection, New Orleans House - Gay Men Adult Resort, NYAH Key West - Adults Only, Orchid Key Inn - Adults Only

Recent Key West Historic District hotel reviews by fellow wanderers

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

5 out of 5
Posted 2 days ago
Travelocity Verified Review
"Resort was fantastic and grounds were kept beautiful and clean. Staff was friendly and helpful. We ate at onsite restaurant and food was delicious. "
A verified traveler stayed at Southernmost Beach Resort and Guesthouses
Southernmost Beach Resort and Guesthouses

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