Hotels with smoking rooms in Key West Historic District from $111

Start date: Check-in selected.
To Date
End date: Check-out

Seize Your Someday with our amazing deals for the whole family!

Save an extra 10% or more on select hotels with Member Discounts

Access exclusive hotel deals, only with the Travelocity app

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
$158 nightly
The price is $177 total per night
$177 total
Oct 28 - Oct 29
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
$317 nightly
The price is $357 total per night
$357 total
Oct 26 - Oct 27
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
$121 nightly
The price is $136 total per night
$136 total
Oct 28 - Oct 29
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
Oct 27 - Oct 28
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, ...
Authors of Key West Guest House

Authors of Key West Guest House

3 out of 5
725 White St. & Petronia, Key West, FL
$99 nightly
The price is $111 total per night
$111 total
Oct 26 - Oct 27
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 ...
The Key West Hotel

The Key West Hotel

2.5 out of 5
325 Duval St., Key West, FL
Free Cancellation
Reserve now, pay when you stay
$206 nightly
The price is $232 total per night
$232 total
Oct 27 - Oct 28
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.
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
$229 nightly
The price is $258 total per night
$258 total
Oct 26 - Oct 27
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
$169 nightly
The price is $191 total per night
$191 total
Oct 28 - Oct 29
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, luggage storage, and concierge services are also ...
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
$221 nightly
The price is $247 total per night
$247 total
Oct 27 - Oct 28
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
$260 nightly
The price is $293 total per night
$293 total
Oct 27 - Oct 28
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
$124 nightly
The price is $140 total per night
$140 total
Oct 29 - Oct 30
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 ...
Don't see what you're looking for?
See all available properties in Key West Historic District
View all properties
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
1,734 hotels
Lowest Price
$111
Highest Price
$357
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

Southwinds Motel

Southwinds Motel

5 out of 5
Posted 2 days ago
Travelocity Verified Review
"We loved the island vibe of this older establishment. Everyone on the staff was pleasant, helpful, and great! On the Duval bus loop, but the entire area is an easy walk away. We had the pool to ourselves over half the time. Thank you!"
A verified traveler stayed at Southwinds Motel
Southwinds Motel

Explore More Ways to Travel with Travelocity