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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 nice staff, Continental breakfast, rooms were clean, facility was clean. We were on the second floor which I would recommend vs the 1st floor. We were in room 46. Four blocks to Duval. Great location, safe. Would stay again."

Reviewed on Jun 23, 2026

Opens in a new windowBishop Hotel Key West
Silver Palms Inn & Historic Homes

Silver Palms Inn & Historic Homes

3.5 out of 5
830 Truman Ave Key West FL
Fully refundableReserve now, pay when you stay
$158 nightly
The price is $178 total per night from Jul 6 to Jul 7
$178 total
Jul 6 - Jul 7
Total with taxes and fees
An outdoor pool is featured at this hotel, along with free WiFi in public areas and luggage storage. Enjoy the free continental breakfast each morning. There's ...
"Clean room with very comfortable beds. Balcony to dry clothes. Fresh omelettes in the morning and other food, such as yogurt, bagels, fruit, and cereal. Coffee in the room or in the lobby. Great pool. We enjoyed our stay!"

Reviewed on Jun 23, 2026

Opens in a new windowSilver Palms Inn & Historic Homes
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 28 to Jun 29
$331 total
Jun 28 - Jun 29
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 ...
"Great place to stay with a great view. The Mexican restaurant and bar is amazing. Beautiful pool area as well."

Reviewed on Jun 23, 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
$184 nightly
The price is $207 total per night from Jun 24 to Jun 25
$207 total
Jun 24 - Jun 25
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 Winslow was perfect! The location was excellent, staff was very kind and helpful, rooms were great, and the property is incredible. We’ll definitely stay there again when we visit Key West."

Reviewed on Jun 23, 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
$254 nightly
The price is $286 total per night from Jul 7 to Jul 8
$286 total
Jul 7 - Jul 8
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 ...
"Clean room Pools Staff very friendly"

Reviewed on Jun 23, 2026

Opens in a new windowSouthernmost Beach Resort and Guesthouses
Southwinds Motel

Southwinds Motel

2 out of 5
1321 Simonton Street Key West FL
$175 nightly
The price is $196 total per night from Jun 24 to Jun 25
$196 total
Jun 24 - Jun 25
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 ...
"Close to duval and southernmost point"

Reviewed on Jun 23, 2026

Opens in a new windowSouthwinds Motel
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
$227 nightly
The price is $256 total per night from Jul 7 to Jul 8
$256 total
Jul 7 - Jul 8
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, ...
"Staff and hotel were great."

Reviewed on Jun 21, 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
$267 nightly
The price is $301 total per night from Jul 5 to Jul 6
$301 total
Jul 5 - Jul 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 ...
"The resort itself was beautiful, and our room was spacious and comfortable. The property has a lot to offer, and we were looking forward to a relaxing vacation. Unfortunately, the first three nights of our stay were anything but relaxing due to a business event being held at the resort. Our room ..."

Reviewed on Jun 21, 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
$159 nightly
The price is $179 total per night from Jun 24 to Jun 25
$179 total
Jun 24 - Jun 25
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 ...
"Wonderful place, super clean, friendly staff, parking + pool amenities. Totally recommanded"

Reviewed on Jun 23, 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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