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Top hotels in Old Town Key West

Douglas House - Adults Only

Douglas House - Adults Only

3 out of 5
419 Amelia St Key West FL
$346 nightly
The price is $389 total per night from Mar 31 to Apr 1
$389 total
Mar 31 - Apr 1
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 ...
The walls are very thin, we could hear every step the people above us made. The showers did not get very hot and the pillows were very flat.

Reviewed on Mar 25, 2026

Opens in a new windowDouglas House - Adults Only
Duval House

Duval House

3 out of 5
815 Duval St Key West FL
$321 nightly
The price is $358 total per night from Apr 26 to Apr 27
$358 total
Apr 26 - Apr 27
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.
Not one complaint about our stay here. Staff and owners where amazing. We will come back again next year for sure. Amazing atmosphere. Beautiful gardens. Owners make you feel at home.

Reviewed on Mar 25, 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
$414 nightly
The price is $466 total per night from Apr 19 to Apr 20
$466 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 ...
The Resort was great and the staff was fantastic. the room has everything you need. This was our fourth time to this resort and Tim one of the managers remembered us and greeted us by name at the door. They really make you feel like family.

Reviewed on Mar 26, 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
$444 nightly
The price is $499 total per night from Apr 5 to Apr 6
$499 total
Apr 5 - Apr 6
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 ...
We had the best time while in Key West. This property has so much charm. The front desk staff were friendly and helpful. The breakfast in the morning was the perfect way to start the day. The whole vibe of the resort reminded me of resorts in Mexico. We can’t wait to come back soon!

Reviewed on Mar 26, 2026

Opens in a new windowWinslow's Bungalows - Key West Historic Inns
Southwinds Motel

Southwinds Motel

2 out of 5
1321 Simonton Street Key West FL
$320 nightly
The price is $360 total per night from Mar 30 to Mar 31
$360 total
Mar 30 - Mar 31
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 ...
Rooms are decent. Clean, could use some shelves in the shower, but big shower. Great area. Pool is warm and clean. Staff.... Not sure what is happening there... Not very friendly, they say good morning when you speak to them first. We gave our # so they could advise when room was ready, but nobody ...

Reviewed on Mar 26, 2026

Opens in a new windowSouthwinds Motel
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
$367 nightly
The price is $413 total per night from Mar 29 to Mar 30
$413 total
Mar 29 - Mar 30
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 ...
clean, staff friendly, pool clean , shops nearby. but the room key did not work. we only use the mast key. after 10pm, no staff can find in the property

Reviewed on Mar 25, 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
$444 nightly
The price is $500 total per night from Apr 5 to Apr 6
$500 total
Apr 5 - Apr 6
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, ...
We had a great stay and experience. Access to sister resort was great. Beach was perfect.

Reviewed on Mar 21, 2026

Opens in a new windowThe Reach Key West, Curio Collection by Hilton
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
$484 nightly
The price is $545 total per night from Mar 30 to Mar 31
$545 total
Mar 30 - Mar 31
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 ...
what a disappointment to stay in a hotel with such great potential but obvious neglect. From the cold, unwelcoming staff to the dirty, dated rooms to the old ugly dining areas with big heavy curtains and dark scratched floors-the hotel is clearly mismanaged. The entire place needs a good scrubbing, ...

Reviewed on Mar 25, 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
$331 nightly
The price is $372 total per night from Mar 30 to Mar 31
$372 total
Mar 30 - Mar 31
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 ...
Lovely place, with lots of different areas. Two pools and hot tub, all very private. Happy hour daily with wine, cheese and nut. Breakfast was a nice variety. Location is walkable to all major tourist sites and eateries. Pretty quiet, except for the roosters and pigeons, which are all over town. ...

Reviewed on Mar 25, 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.

Recent Old Town Key West hotel reviews by fellow wanderers

Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

5 out of 5
Posted 1 hour ago
Travelocity Verified Review
"We had the best time while in Key West. This property has so much charm. The front desk staff were friendly and helpful. The breakfast in the morning was the perfect way to start the day. The whole vibe of the resort reminded me of resorts in Mexico. We can’t wait to come back soon! "
A verified traveler stayed at Winslow's Bungalows - Key West Historic Inns
Winslow's Bungalows - Key West Historic Inns

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