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Hotels near Old Town Key West
Bishop Hotel Key West
822 Fleming St Key West FL
Stay at this guesthouse in Key West. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Popular attractions Duval Street and Southernmost Point are located ...
"21 or older limit turned out to be plus. Although I like kids, the peace was great Room well cleaned and stocked. Free breakfast was perfect to tide you over to a great lunch or diner. Room was always comfortable, never heard any street noise."
Reviewed on Jun 2, 2026
Douglas House - Adults Only
419 Amelia St Key West FL
The price is CA $152 per night from Jun 9 to Jun 10
CA $152
CA $188 total
Jun 9 - Jun 10
includes taxes & fees
Stay at this guesthouse in Key West. Enjoy free WiFi, daily housekeeping, and a garden. Popular attractions Duval Street and Ernest Hemingway Home and Museum ...
"It’s clean and nice but no parking I’ve paid $98 for 2 nights parking"
Reviewed on Jun 5, 2026
Opal Key Resort & Marina, Key West
245 Front Street Key West FL
Fully refundableReserve now, pay when you stay
The price is CA $361 per night from Jun 23 to Jun 24
CA $361
CA $461 total
Jun 23 - Jun 24
includes taxes & fees
Stay at this hotel in Key West. Enjoy a marina, 3 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. ...
"Cleanness and helpfulness of staff members alongside with the location makes it a very pleasurable and worry free stay in Key West."
Reviewed on Jun 5, 2026
Winslow's Bungalows - Key West Historic Inns
725 Truman Avenue Key West FL
Fully refundableReserve now, pay when you stay
The price is CA $258 per night from Jun 22 to Jun 23
CA $258
CA $360 total
Jun 22 - Jun 23
includes taxes & fees
Stay at this hotel in Key West. Enjoy free breakfast, free WiFi, and 3 outdoor pools. Our guests praise the breakfast and the pool in our reviews. Popular attractions ...
"We totally enjoyed our stay at Winslow Bungalows. The property was well maintained and in a great location. The breakfast was filling and a great way to start our day. We can't wait to go back to Key West and stay there again."
Reviewed on Jun 6, 2026
Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Fully refundableReserve now, pay when you stay
The price is CA $274 per night from Jun 29 to Jun 30
CA $274
CA $410 total
Jun 29 - Jun 30
includes taxes & fees
Book a stay at this beach hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
"Property was beautiful! Booked 2 queen partial ocean view. Room was clean, some things needed a little updating but understandable being right on the water. Staff were pleasant, text notifications about activities of the day. I stayed with a friend in the Atlantic building, in the 6300s (3rd floor), ..."
Reviewed on Jun 6, 2026
The Reach Key West, Curio Collection by Hilton
1435 Simonton Street Key West FL
Fully refundableReserve now, pay when you stay
The price is CA $235 per night from Jun 15 to Jun 16
CA $235
CA $359 total
Jun 15 - Jun 16
includes taxes & fees
Book a stay at this beach resort in Key West. Enjoy a full-service spa, a private beach, and breakfast (surcharge). Our guests praise the helpful staff and the ...
"The property was excellent our room very large and had the ocean view. Everything was amazing and in walking distance to everything in old town."
Reviewed on Jun 6, 2026
Southwinds Motel
1321 Simonton Street Key West FL
The price is CA $187 per night from Jun 8 to Jun 9
CA $187
CA $257 total
Jun 8 - Jun 9
includes taxes & fees
Stay at this hotel in Key West. Enjoy free breakfast, 2 outdoor pools, and parking (surcharge). Our guests praise the breakfast and the pool in our reviews. ...
"Older but remodeled inside hotel. Very clean and fresh. A bit noisy AC. Decent breakfast. Sweet spot. Extremely close to everything. Will book again"
Reviewed on Jun 6, 2026
Casa Marina Key West, Curio Collection by Hilton
1500 Reynolds Street Key West FL
Fully refundableReserve now, pay when you stay
The price is CA $357 per night from Jun 24 to Jun 25
CA $357
CA $496 total
Jun 24 - Jun 25
includes taxes & fees
Book a stay at this beach resort in Key West. Enjoy 2 outdoor pools, a full-service spa, and a private beach. Popular attractions Duval Street and South Beach ...
"Historic hotel away from the noise and crowds on Duval St. Two private beaches, Beach dining, and friendly staff. The breakfast buffet is to die for! You get what you pay for and well worth the little extra cost. In my opinion by far the best hotel / resort on the island. Will stay at the Casa Marina ..."
Reviewed on Jun 6, 2026
The Southernmost Inn - Adults Only
525 United Street Key West FL
Fully refundableReserve now, pay when you stay
The price is CA $169 per night from Jun 10 to Jun 11
CA $169
CA $253 total
Jun 10 - Jun 11
includes taxes & fees
Stay at this hotel in Key West. Enjoy free breakfast, 2 outdoor pools, and parking (surcharge). Our guests praise the breakfast and the pool in our reviews. ...
"Nice quiet Inn, it is very deceiving from the outside. It looks very smalls but it is very open and large once you walk thru front. Nice, clean room; couldn’t ask for anything better."
Reviewed on Jun 5, 2026
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Recent Old Town Key West hotel reviews by fellow wanderers
Winslow's Bungalows - Key West Historic Inns
5 out of 5
Posted less than an hour ago
Travelocity Verified Review
"We totally enjoyed our stay at Winslow Bungalows. The property was well maintained and in a great location. The breakfast was filling and a great way to start our day. We can't wait to go back to Key West and stay there again."
A verified traveller stayed at Winslow's Bungalows - Key West Historic Inns
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