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Top hotels in Old Town Key West

Duval House

Duval House

3 out of 5
815 Duval St Key West FL
$281 nightly
The price is $313 total per night from May 5 to May 6
$313 total
May 5 - May 6
Total with taxes and fees
This bed & breakfast features a terrace, concierge services, and self parking. A garden, a picnic area, and express check-in are also on offer.
Very accommodating. Very friendly. Excellent facilities, breakfast, pool. Will definitely stay again!!

Reviewed on Apr 1, 2026

Opens in a new windowDuval House
Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West

4 out of 5
245 Front Street Key West FL
Fully refundableReserve now, pay when you stay
$384 nightly
The price is $432 total per night from Apr 19 to Apr 20
$432 total
Apr 19 - Apr 20
Total with taxes and fees
A marina, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Enjoy the outdoor pool and visit the 3 bars/lounges and poolside bar for ...
On site restaurant and food were excellent!

Reviewed on Apr 3, 2026

Opens in a new windowOpal Key Resort & Marina, Key West
Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

4 out of 5
725 Truman Avenue Key West FL
Fully refundableReserve now, pay when you stay
$384 nightly
The price is $432 total per night from May 4 to May 5
$432 total
May 4 - May 5
Total with taxes and fees
This smoke-free hotel features 3 outdoor pools, a bar/lounge, and a poolside bar. Guests will appreciate free perks like continental breakfast and WiFi in public ...
Beautiful property, nice staff, clean rooms, relaxing atmosphere. We definitely recommend.

Reviewed on Apr 3, 2026

Opens in a new windowWinslow's Bungalows - Key West Historic Inns
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
$407 nightly
The price is $458 total per night from May 4 to May 5
$458 total
May 4 - May 5
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 ...
Great beach view, very clean

Reviewed on Apr 3, 2026

Opens in a new windowSouthernmost Beach Resort and Guesthouses
The Cabana Inn Key West - Adults Only

The Cabana Inn Key West - Adults Only

3 out of 5
413 Applerouth Lane Key West FL
Fully refundableReserve now, pay when you stay
$364 nightly
The price is $409 total per night from May 3 to May 4
$409 total
May 3 - May 4
Total with taxes and fees
This guesthouse features an outdoor pool and a hot tub. Enjoy the free continental breakfast each morning. Self parking, a terrace, and a garden are also ...
The breakfast was excellent. Wine and cheese happy hour was fun We enjoyed the pool and hot tub Our room was amazing 621.

Reviewed on Apr 3, 2026

Opens in a new windowThe Cabana Inn Key West - Adults Only
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
$383 nightly
The price is $431 total per night from May 3 to May 4
$431 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, ...
The beach was perfect except when a wedding was going on it was limited and no warnings for this. There was only 1 waitress fir beach and pool orders. Also waitress didnt even knowledge us over 10 when we tried to go for breakfast so we left . The culture is wonderful except wasnt informed roosters ...

Reviewed on Mar 29, 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
$272 nightly
The price is $305 total per night from Apr 12 to Apr 13
$305 total
Apr 12 - Apr 13
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 ...
Yes yes

Reviewed on Apr 3, 2026

Opens in a new windowSouthwinds Motel
Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

4 out of 5
1500 Reynolds Street Key West FL
Fully refundableReserve now, pay when you stay
$406 nightly
The price is $456 total per night from Apr 15 to Apr 16
$456 total
Apr 15 - Apr 16
Total with taxes and fees
A private beach, a full-service spa, and 2 outdoor pools are all featured at this smoke-free resort. Relax with sun loungers and beach umbrellas, and cool off ...
I had an ocean front suite is was wonderful. The room was very clean and well presented. I ate the restaurant a few times during my stay and it was perfect everytime. I also used the fitness center and valet and everything was wonderful.

Reviewed on Apr 3, 2026

Opens in a new windowCasa Marina 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
$279 nightly
The price is $314 total per night from Apr 5 to Apr 6
$314 total
Apr 5 - Apr 6
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 ...
Stay away from this hotel. They sneak in an amenity fee to the total bill and the staff is not very friendly when you inquire about it.

Reviewed on Apr 3, 2026

Opens in a new windowThe Southernmost Inn - Adults Only
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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.

Old Town Key West Hotel Guide

Don’t keep your travel plans on repeat year after year. The same city with the same hotel every season will bore you and give you an itch to go looking for something new. Expand your geographical horizons to more than just those five blocks around your usual haunt.

Nowhere else can you find better deals on Old Town Key West area hotels. You’ll find the best prices on the quirky, the haunted, the old, the new, and the legendary. If you’re wondering what side of the pricing scale some of these hotels fall on, you need not to worry. Compare cheap hotels near Old Town Key West to find the perfect one to will fit your budget.

Leave the ordinary routine you’re set on behind and go. Go anywhere you want. Anywhere that makes you think, “I wonder what that’s like?” Part of Travelocity’s mission is to get you off-the-beaten path and the hotels near Old Town Key West are perfect for that. Find your new favorite watering hole on a quiet street. Discover a place to escape for the weekend with tasty local fare and unique sights. We want you to consider the places outside your normal comfort zone. Browse our selection and find the ideal hotel, in a place you’d like to explore.

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