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Top hotels in Old Town Key West

Bishop Hotel Key West

Bishop Hotel Key West

4 out of 5
822 Fleming St Key West FL
This guesthouse's 2 outdoor pools and hot tub are among the featured amenities. Unwind with a drink at the poolside bar and enjoy perks like free continental ...
Only complaint was the A/C didn’t work well at all. Literally everything else was fantastic. Loved the heated pools. Everything was in walking distance. Very clean and well maintained.

Reviewed on Mar 21, 2026

Opens in a new windowBishop Hotel Key West
Duval House

Duval House

3 out of 5
815 Duval St Key West FL
$311 nightly
The price is $347 total per night from Mar 22 to Mar 23
$347 total
Mar 22 - Mar 23
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.
Staff was wonderful very helpful. The gardens were beautiful. Very quiet and peaceful. Great location, easy access to all restaurants and shops and attractions.

Reviewed on Mar 19, 2026

Opens in a new windowDuval House
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 $500 total per night from Apr 19 to Apr 20
$500 total
Apr 19 - Apr 20
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 ...
The room was musty with an old window AC unit. It rained one night and we had a large puddle in the room in front of the door Over priced and had to keep asking for service. The only advantage was being two blocks from Duval street and having available parking for an additional $30/night. Management ...

Reviewed on Mar 20, 2026

Opens in a new windowWinslow's Bungalows - Key West Historic Inns
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
$439 nightly
The price is $494 total per night from Mar 25 to Mar 26
$494 total
Mar 25 - Mar 26
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 ...
Yes

Reviewed on Mar 21, 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
$468 nightly
The price is $527 total per night from Apr 5 to Apr 6
$527 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, ...
Great food at restaurants, great beach, I would stay there again

Reviewed on Mar 17, 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
$544 nightly
The price is $612 total per night from Apr 5 to Apr 6
$612 total
Apr 5 - Apr 6
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 ...
Outside building was great. Could improve with room maintenace. Our room was ocean view, but toilet fil valve was broken, and takes 30 minutes wait to flush. Window frame paint was peeling. Otherwise its a great place.

Reviewed on Mar 20, 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
$339 nightly
The price is $381 total per night from Mar 22 to Mar 23
$381 total
Mar 22 - Mar 23
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 ...
The staff was helpful and friendly, we were able to park on site and the pool and hot tub were the most clean of any B&B in The Keys. Our room was spacious with an extra room with couch, table/chairs which is rare for a B&B. The room was very clean but old use some updating. The reason I did not ...

Reviewed on Mar 20, 2026

Opens in a new windowThe Southernmost Inn - Adults Only
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
$449 nightly
The price is $505 total per night from Apr 19 to Apr 20
$505 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 ...
Opens in a new windowOpal Key Resort & Marina, Key West
Southwinds Motel

Southwinds Motel

2 out of 5
1321 Simonton Street Key West FL
$339 nightly
The price is $382 total per night from Apr 5 to Apr 6
$382 total
Apr 5 - Apr 6
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 ...
Opens in a new windowSouthwinds Motel
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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

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