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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 ...
Very clean room, pools were always clean and warm but cool enough to keep you cool on warm days. Very relaxing atmosphere. Staff was spectacular, helpful and very nice. And location was perfect close enough to everything but far enough to be quiet and relaxing.

Reviewed on Mar 18, 2026

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Opens in a new windowBishop Hotel Key West
Duval House

Duval House

3 out of 5
815 Duval St Key West FL
$321 nightly
The price is $358 total per night from Mar 24 to Mar 25
$358 total
Mar 24 - Mar 25
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.
no kitchen ....shops nearby good, morning breakfast spotty except for waffle. Attendant was too attentive, sort of in the way.

Reviewed on Mar 17, 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
$534 nightly
The price is $601 total per night from Apr 5 to Apr 6
$601 total
Apr 5 - Apr 6
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 ...
Stunning view and sunset the rooms were huge and amazing, and the staff were super friendly. One minor surprise was the huge cruise ship outside our window on the Sunday morning. It wasn't really a negative, but definitely a surprise.

Reviewed on Mar 18, 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
$464 nightly
The price is $522 total per night from Apr 13 to Apr 14
$522 total
Apr 13 - Apr 14
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 ...
Our King Room was very small but clean. No room for luggage and no desk or table to set a computer or cocktails on. They have no in in room coffee makers, room safes or iron. When I called for a extra pillow, they said they would need to look around because they think they do t have any?

Reviewed on Mar 18, 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
$321 nightly
The price is $362 total per night from Apr 6 to Apr 7
$362 total
Apr 6 - Apr 7
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 ...
We absolutely loved our stay! Our room was so quaint and very clean. The pools were lovely and it was nice to have one heated. Location is excellent. We parked our car and walked everywhere.

Reviewed on Mar 17, 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
$375 nightly
The price is $422 total per night from Mar 22 to Mar 23
$422 total
Mar 22 - Mar 23
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 ...
Pool great

Reviewed on Mar 17, 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
$549 nightly
The price is $617 total per night from Apr 5 to Apr 6
$617 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
$535 nightly
The price is $602 total per night from Apr 5 to Apr 6
$602 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 ...
It was great

Reviewed on Mar 18, 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
$439 nightly
The price is $494 total per night from Mar 22 to Mar 23
$494 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 ...
Very nice quiet clean place with very nice staff

Reviewed on Mar 17, 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

4 out of 5
Posted 2 hours ago
Travelocity Verified Review
"Our King Room was very small but clean. No room for luggage and no desk or table to set a computer or cocktails on. They have no in in room coffee makers, room safes or iron. When I called for a extra pillow, they said they would need to look around because they think they do t have any? "
A verified traveler stayed at Winslow's Bungalows - Key West Historic Inns
Winslow's Bungalows - Key West Historic Inns

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