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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 ...
"I was truly amazed by how friendly the staff was. Reasonably priced, and 3 blocks from Duval Street. Highly recommend. 5 🌟 🌟 🌟 🌟 🌟!!"

Reviewed on Jun 7, 2026

Opens in a new windowBishop Hotel Key West
Douglas House - Adults Only

Douglas House - Adults Only

3 out of 5
419 Amelia St Key West FL
$157 nightly
The price is $177 total per night from Jun 9 to Jun 10
$177 total
Jun 9 - Jun 10
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 ...
"We booked for convenience of location as a first time visit to Key West and it did not disappoint. This location puts you within walking distance of a multitude of shops, restaraunts and noted landmarks. Staff was very kind and attentive, and small but safe and clean pool area was excellent for ..."

Reviewed on Jun 7, 2026

Opens in a new windowDouglas House - 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
$294 nightly
The price is $331 total per night from Jun 11 to Jun 12
$331 total
Jun 11 - Jun 12
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 ...
"⭐⭐⭐⭐⭐ This is, without a doubt, my favorite hotel. I stay here every time I visit because the service is always outstanding. The staff is friendly and welcoming, the rooms are spotless, the facilities are well maintained, and the location is perfect. They consistently make me feel at home, which ..."

Reviewed on Jun 7, 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
$215 nightly
The price is $242 total per night from Jun 10 to Jun 11
$242 total
Jun 10 - Jun 11
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 didn’t pay a lot so I guess we can’t complain a lot about a shower door that opens both ways. Open out ten inches and hits a toilet,opens in about two feet and hits a steel cloth holder and the shower head I told Gary the night super of the danger he told me that then you better be careful. I ..."

Reviewed on Jun 8, 2026

Opens in a new windowWinslow's Bungalows - Key West Historic Inns
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
$261 nightly
The price is $294 total per night from Jun 29 to Jun 30
$294 total
Jun 29 - Jun 30
Total with taxes and fees
This hotel features a full-service spa, 3 outdoor pools, and a restaurant. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Traveling ...
"The room was clean and the staff was helpful."

Reviewed on Jun 8, 2026

Opens in a new windowSouthernmost Beach Resort and Guesthouses
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
$285 nightly
The price is $321 total per night from Jun 24 to Jun 25
$321 total
Jun 24 - Jun 25
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 ...
"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

Opens in a new windowCasa Marina Key West, Curio Collection by Hilton
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
$248 nightly
The price is $279 total per night from Jun 17 to Jun 18
$279 total
Jun 17 - Jun 18
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, ...
"Wonderful stay! Highly recommend."

Reviewed on Jun 7, 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
$164 nightly
The price is $185 total per night from Jun 9 to Jun 10
$185 total
Jun 9 - Jun 10
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 ...
"A beautiful Key West Motel! Will definitely stay there again!"

Reviewed on Jun 7, 2026

Opens in a new windowSouthwinds Motel
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
$162 nightly
The price is $182 total per night from Jun 15 to Jun 16
$182 total
Jun 15 - Jun 16
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 ...
"Good vibe. Rooms feel cheap and it’s a little too far to walk from a lot of downtown. That’s why I didn’t give it higher rating but it was a good experience. Parking sucked and was expensive. But it was a good size room with a couch. My dad and I both had a good time. A/c sucked as well. Staff barely ..."

Reviewed on Jun 7, 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

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