Find 2 Star Hotels in Key West Historic District, FL from $153

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

  • Upfront pricing

    Our total price for your stay includes taxes and fees

  • Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check availability on Key West Historic District 2 Star Hotels

Our top choices for Key West Historic District 2-star hotels

Exterior
Southwinds Motel

Southwinds Motel

Southwinds Motel
2.0 star property
Old Town Key West
8.8 out of 10, Excellent, (1238)
"Everyone was so nice, great location. "
United States
Holly
$172 nightly
The price is $194
Dec 14 - Dec 15
Total with taxes and fees
Southwinds Motel
Sundeck
Pegasus International Hotel

Pegasus International Hotel

Pegasus International Hotel
2.5 star property
Old Town Key West
8.2 out of 10, Very Good, (1001)
"Wonderful place to stay right in the heart of Key West. The pool and deck area are nice and cozy for a relaxing time. "
United States
Daniel
$182 nightly
The price is $205
Dec 15 - Dec 16
Total with taxes and fees
Pegasus International Hotel
Premium bedding, iron/ironing board, free WiFi, bed sheets
Weatherstation Inn

Weatherstation Inn

Weatherstation Inn
2.5 star property
Old Town Key West
9.4 out of 10, Exceptional, (992)
"Wonderful property safe neighborhood convenient to all activities would stay here again."
United States
William
$219 nightly
The price is $246
Dec 16 - Dec 17
Total with taxes and fees
Weatherstation Inn
King Room D | Balcony
Simonton Court Historic Inn & Cottages

Simonton Court Historic Inn & Cottages

Simonton Court Historic Inn & Cottages
2.5 star property
Key West Historic District
9.8 out of 10, Exceptional, (877)
"The staff was really nice"
United States
doug
$155 nightly
The price is $175
Dec 15 - Dec 16
Total with taxes and fees
Simonton Court Historic Inn & Cottages
Queen Suite #6, Full Kitchen, Ground Floor, Pool View, Private Bathroom | Room amenity
Alexander Palms Court

Alexander Palms Court

Alexander Palms Court
2.5 star property
Old Town Key West
9.2 out of 10, Wonderful, (1000)
"Great spot to spend a couple days. Tropical Oasis!"
United States
Zach
$319 nightly
The price is $359
Dec 14 - Dec 15
Total with taxes and fees
Alexander Palms Court
Front of property
L'Habitation Guest House

L'Habitation Guest House

L'Habitation Guest House
2.5 star property
Key West Historic District
9.4 out of 10, Exceptional, (920)
"Great place close to all. Manager was very helpful in recommending how to get around the island, what to do and where to eat."
United States
Robert
$136 nightly
The price is $153
Dec 15 - Dec 16
Total with taxes and fees
L'Habitation Guest House
Exterior
The Grand Guesthouse

The Grand Guesthouse

The Grand Guesthouse
2.5 star property
Old Town Key West
9.6 out of 10, Exceptional, (1002)
"Great stay"
United States
Ginger
$172 nightly
The price is $193
Dec 15 - Dec 16
Total with taxes and fees
The Grand Guesthouse
Superior Villa, 2 Bedrooms, Private Pool (Room 409) | Outdoor pool
New Orleans House - Gay Men Adult Resort

New Orleans House - Gay Men Adult Resort

New Orleans House - Gay Men Adult Resort
2.5 star property
Old Town Key West
8.6 out of 10, Excellent, (340)
"Overall good place to stay. "
United States
David
$231 nightly
The price is $259
Jan 4 - Jan 5, 2026
Total with taxes and fees
New Orleans House - Gay Men Adult Resort
Outdoor pool, a heated pool
Treehouse Condo 2nd Floor Balcony sleeps 6 free parking

Treehouse Condo 2nd Floor Balcony sleeps 6 free parking

Treehouse Condo 2nd Floor Balcony sleeps 6 free parking
2.0 star property
Old Town Key West
Treehouse Condo 2nd Floor Balcony sleeps 6 free parking
Outdoor pool
The Key West Hotel

The Key West Hotel

The Key West Hotel
2.5 star property
Key West Historic District
9.2 out of 10, Wonderful, (513)
"location was great nice bar party vibe"
United States
Robert Howard
$253 nightly
The price is $278
Dec 15 - Dec 16
Total with taxes and fees
The Key West Hotel
Beach nearby
LA TE DA Hotel - Adults Only

LA TE DA Hotel - Adults Only

LA TE DA Hotel - Adults Only
2.5 star property
Old Town Key West
9.8 out of 10, Exceptional, (70)
"Great hotel with great staff! Can’t beat the food, drinks, music and live entertainment. Great location to walk up and down Duval to shop and dine. "
United States
Dani
LA TE DA Hotel - Adults Only
Standard Suite | Resort view
Coconut Beach Resort

Coconut Beach Resort

Coconut Beach Resort
2.5 star property
Old Town Key West
9.0 out of 10, Wonderful, (146)
"Delightful beachfront property. Time share units, well maintained. "
United States
Darlene
$584 nightly
The price is $658
Dec 14 - Dec 15
Total with taxes and fees
Coconut Beach Resort
Interior
Grand Maloney Hotel

Grand Maloney Hotel

Grand Maloney Hotel
2.0 star property
Key West Historic District
7.6 out of 10, Good, (11)
"It was clean quiet and was within walking distance to every thing. Going to stay there again in the future "
United States
Jodee
$333 nightly
The price is $366
Dec 14 - Dec 15
Total with taxes and fees
Grand Maloney Hotel
Classic Room, 1 Queen Bed, Balcony, Pool View (1) | Balcony view
Curry House

Curry House

Curry House
2.0 star property
Old Town Key West
7.2 out of 10, Good, (45)
"This was a great older home with an amazing location to all the action on Duval. Seriously considering heading back next weekend for my Wife's B-Day! "
United States
Steven
$335 nightly
The price is $377
Dec 16 - Dec 17
Total with taxes and fees
Curry House
Fridge, microwave, oven, toaster
La Casa de Luces 2 Bed condo off Duval

La Casa de Luces 2 Bed condo off Duval

La Casa de Luces 2 Bed condo off Duval
2.0 star property
Old Town Key West
9.4 out of 10, Exceptional, (136)
"Perfect property for 4 people. "
United States
Crystal G.
$708 nightly
The price is $787
Jan 4 - Jan 5, 2026
Total with taxes and fees
La Casa de Luces 2 Bed condo off Duval
Exterior
Custom House Inn

Custom House Inn

Custom House Inn
2.0 star property
Key West Historic District
8.6 out of 10, Excellent, (11)
"Great little oasis right in the heart of it all"
United States
Reggie
Custom House Inn
Sweet Caroline - Two Bedroom Spacious Apartment | Private kitchen | Microwave
Banana's Foster Guesthouse

Banana's Foster Guesthouse

Banana's Foster Guesthouse
2.0 star property
Key West Historic District
9.0 out of 10, Wonderful, (7)
"The room was spotless and very comfortable."
United States
KARLA
$314 nightly
The price is $353
Dec 15 - Dec 16
Total with taxes and fees
Banana's Foster Guesthouse
Fridge, microwave, oven, stovetop
LA CASA CUBANA @ Cuban Club Suites

LA CASA CUBANA @ Cuban Club Suites

LA CASA CUBANA @ Cuban Club Suites
2.0 star property
Old Town Key West
9.6 out of 10, Exceptional, (71)
"Place was great and close to everything "
United States
Michelle O.
LA CASA CUBANA @ Cuban Club Suites
Property grounds
Palm Isle: Tropical 2nd-Floor Unit, Shared Heated Pool, Near Duval St, Historic Seaport & Beaches

Palm Isle: Tropical 2nd-Floor Unit, Shared Heated Pool, Near Duval St, Historic Seaport & Beaches

Palm Isle: Tropical 2nd-Floor Unit, Shared Heated Pool, Near Duval St, Historic Seaport & Beaches
2.0 star property
Key West Historic District
9.6 out of 10, Exceptional, (7)
"This condo was perfect for us. The location was in a quiet area which is great for unwinding in the evening. "
United States
Victoria P.
Palm Isle: Tropical 2nd-Floor Unit, Shared Heated Pool, Near Duval St, Historic Seaport & Beaches
Property grounds
THALIA'S RETREAT @ Duval Square 2bd/2ba townhome

THALIA'S RETREAT @ Duval Square 2bd/2ba townhome

THALIA'S RETREAT @ Duval Square 2bd/2ba townhome
2.0 star property
Old Town Key West
9.4 out of 10, Exceptional, (131)
"The place was amazingly clean and in a perfect location!"
United States
LeAnne J.
$860 nightly
The price is $941
Dec 21 - Dec 22
Total with taxes and fees
THALIA'S RETREAT @ Duval Square 2bd/2ba townhome
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Explore similar 3-star hotels

Many 3-star hotels have the same amenities as 2-star hotels. See all 3-star hotels in Key West Historic District.
The Southernmost Inn - Adults Only

The Southernmost Inn - Adults Only

525 United Street Key West FL
$172 nightly
The price is $193 total per night from Dec 18 to Dec 19
$193 total
Dec 18 - Dec 19
Total with taxes and fees
8.2/10 Very Good! (1,204 reviews)
Still don't see what you're looking for?
See all properties in Key West Historic District.
You can also use these popular filters to refine your search.
PoolSpaHot tubBreakfast includedWaterpark
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.

Learn more about Key West Historic District

Museums and tropical gardens complement the fascinating homes and monuments that include the residence and writing desk of Ernest Hemingway.

See all hotels in Key West Historic District
Audubon House and Tropical Gardens featuring a house

Top Key West Historic District Hotel Reviews

Southwinds Motel

Southwinds Motel

10/10 Excellent
"Really sweet little place with fantastic beach access. The beach is a block away but the hotel provides free towels and long chairs with umbrellas. Nice cuban deli across the street. Close to Duval but without its busy-ness. "
joan 4-night trip
Posted 3 days ago
Southwinds Motel

Find out more about Key West Historic District

When you've got to get away to a new or favorite destination without breaking the bank, Key West Historic District awaits with convenient 2 Star hotels and a change of scenery. Stay on your feet visiting top attractions that draw of visitors, or discover a new favorite bookstore or nearby and relax. You're about to find out why both locals and travelers love this place.

The Ideal 2 Star Hotel at the Ideal Price

Thanks to several convenient locations and comfortable amenities, you'll find accommodation that suits your vacation style. Stay here and be one of the first guests to write a review and share your thoughts. So, savor the comfort of a well-kept room and attentive hospitality. With our travel deals, the world is wide open to you one hotel at a time, and the jet-setting starts in Key West Historic District.

Reserve a Stay in a Two-Star Hotel Today

Plan your trip to Key West Historic District now with Expedia's easy online travel booking and start relaxing before you even leave the house. Recently, traveling to this region has become cheaper due to more supply. Take advantage of the 2 Star Hotel availability and easy-going atmosphere.

Explore a world of travel with Expedia