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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 ...
"The hotel was absolutely lovely. It was very clean and cozy. The pool was private and peaceful. The staff were very friendly and helpful and our room had everything that we needed. Our room was cleaned everyday and we always had extra towels. The location was perfect, walking distance from everything ..."

Reviewed on Jun 14, 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 23 to Jun 24
$177 total
Jun 23 - Jun 24
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 ...
"Convenient to Duval Steet and restaurants. Staff very helpful . And we loved the salt water pool."

Reviewed on Jun 16, 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
$294 nightly
The price is $331 total per night from Jun 23 to Jun 24
$331 total
Jun 23 - Jun 24
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 ...
"Wonderful all around. Will stay again."

Reviewed on Jun 17, 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
$199 nightly
The price is $224 total per night from Jun 18 to Jun 19
$224 total
Jun 18 - Jun 19
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 ...
"Everything was great, there was one girl at the bar who seemed to be pretty new with not a ton of experience but other then that everything was great would for sure go back"

Reviewed on Jun 15, 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
$266 nightly
The price is $299 total per night from Jun 29 to Jun 30
$299 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 ...
"Easy to get around, excellent pools, clean rooms. Just a very relaxing place to stay."

Reviewed on Jun 17, 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
$243 nightly
The price is $274 total per night from Jun 24 to Jun 25
$274 total
Jun 24 - Jun 25
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, ...
"had an extremely disappointing experience at this hotel. At the end of my stay, I was shocked by excessive fees that were not disclosed in advance. I felt deceived, and I do not recommend anyone stay here without clarifying all costs beforehand.”"

Reviewed on Jun 17, 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
$175 nightly
The price is $196 total per night from Jun 22 to Jun 23
$196 total
Jun 22 - Jun 23
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 ...
"I am the General Manager of a hotel. I am not an easy person to impress in terms of hotels. The staff at this hotel stands apart. I had a wonderful stay, in particular due to the lovely young woman who checked myself and my daughter in. Thank you for everything!"

Reviewed on Jun 16, 2026

Opens in a new windowSouthwinds Motel
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
$269 nightly
The price is $303 total per night from Jun 18 to Jun 19
$303 total
Jun 18 - Jun 19
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 ...
"We liked the resort"

Reviewed on Jun 15, 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
$152 nightly
The price is $171 total per night from Jun 18 to Jun 19
$171 total
Jun 18 - Jun 19
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 ...
"The location, staff, accommodations, and the breakfast/happy hour were wonderful! Unfortunately there is just a lingering foul ofer that is a real put off."

Reviewed on Jun 16, 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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