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Hotels near Old Town Key West

Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West

4 out of 5
245 Front Street Key West FL
The price is CA $358 per night from Jun 11 to Jun 12
CA $358
CA $458 total
Jun 11 - Jun 12
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. ...
"We booked this hotel because it is situated in the heart of the tourist area in Key West. It is within walking distance to everything. The hotel was great and we had an excellent stay."

Reviewed on Jun 2, 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
The price is CA $225 per night from Jun 10 to Jun 11
CA $225
CA $323 total
Jun 10 - Jun 11
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 ...
"Great location and facilities. The breakfast was excellent."

Reviewed on May 30, 2026

Opens in a new windowWinslow's Bungalows - Key West Historic Inns
Heron House - Adult Only

Heron House - Adult Only

3.5 out of 5
512 Simonton St Key West FL
The price is CA $169 per night from Jun 4 to Jun 5
CA $169
CA $237 total
Jun 4 - Jun 5
includes taxes & fees
Stay at this B&B in Key West. Enjoy free breakfast, free WiFi, and a rooftop terrace. Our guests praise the breakfast and the pool in our reviews. Popular attractions ...
"We enjoyed our stay, location was great!"

Reviewed on Jun 2, 2026

Opens in a new windowHeron House - Adult Only
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
The price is CA $272 per night from Jun 29 to Jun 30
CA $272
CA $407 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 ...
"Are room was ok. There was an unusable beach. The smell was terrible. The restaurants were not kid friendly and made no effort to accommodate a 10 year old. Had 3 different menus and wouldn't cook anything that was on the bar menu that used the same kitchen. All kinds of additional fees at checkout. ..."

Reviewed on Jun 1, 2026

Opens in a new windowSouthernmost Beach Resort and Guesthouses
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
The price is CA $267 per night from Jul 2 to Jul 3
CA $267
CA $393 total
Jul 2 - Jul 3
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 ...
"These guys went above and beyond, especially Connor, who really helped me when I realized we booked the wrong days. He worked diligently with Expedia to make sure that our dates were changed. Even upgrading our room for the troubles we had with the being able to rebook through Expedia. The hotel ..."

Reviewed on Jun 2, 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
The price is CA $186 per night from Jun 7 to Jun 8
CA $186
CA $256 total
Jun 7 - Jun 8
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. ...
"The rooms are nice. We like the continental breakfast before we head to the close by beach. You can get passes for a beach chair and towels. We like the convenience of the location. The only thing we didn't like is that the pool closest to our room was locked before the actual time, but we were able ..."

Reviewed on Jun 3, 2026

Opens in a new windowSouthwinds Motel
Wicker Guesthouse

Wicker Guesthouse

3.5 out of 5
913 Duval Street Key West FL
The price is CA $260 per night from Jun 11 to Jun 12
CA $260
CA $293 total
Jun 11 - Jun 12
includes taxes & fees
Stay at this guesthouse in Key West. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular ...
"Location was the best part but they need to find a way to get rid of some of those roosters keeping people up at night. The bed had coils sticking up"

Reviewed on Jun 2, 2026

Opens in a new windowWicker Guesthouse
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
The price is CA $383 per night from Jun 30 to Jul 1
CA $383
CA $525 total
Jun 30 - Jul 1
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 ...
"We were really disappointed by the beach. It’s rocky and was covered in seaweed (during our visit). The pools are beautiful, staff was lovely. The room was enormous and well maintained. I just wish we had more transparency regarding the condition of the beach."

Reviewed on May 30, 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
The price is CA $168 per night from Jun 10 to Jun 11
CA $168
CA $251 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. ...
"Pool was wonderful"

Reviewed on May 28, 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.

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Recent Old Town Key West hotel reviews by fellow wanderers

Southwinds Motel

Southwinds Motel

4 out of 5
Posted less than an hour ago
Travelocity Verified Review
"The rooms are nice. We like the continental breakfast before we head to the close by beach. You can get passes for a beach chair and towels. We like the convenience of the location. The only thing we didn't like is that the pool closest to our room was locked before the actual time, but we were able to go to the other pool. There was also an very early morning truck that emptied a dumpster. The staff was nice and we were able to leave our luggage after check out, because we had a late ferry trip."
A verified traveller stayed at Southwinds Motel
Southwinds Motel

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