Find a Hotel in Old Town Key West

Seize Your Someday with our amazing deals for the whole family!

Save an extra 10% or more on select hotels with Member Discounts

Access exclusive hotel deals, only with the Travelocity app

Filter by

Guest rating
Guest rating
Star rating
Payment type
Payment type
Property type
Property type
Neighborhood
Neighborhood
Traveler experience
Traveler experience
Popular locations
Popular locations
Meal plans available
Meal plans available
Property amenities
Property amenities
Accessibility
Accessibility

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 ...
"This property was amazing. The entire staff took great pride in this place. Every area was clean and inviting. We were there 4 days and the pools were cleaned twice! Every staff member was kind and helpful. We will be staying here again!"

Reviewed on Jun 12, 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 15 to Jun 16
$177 total
Jun 15 - Jun 16
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 ...
"The Douglas house is lovely! Our 2nd time here in 4 months! The staff is very kind and the accommodations are lovely and comfortable! The pool area is the cherry on the sundae too!! Terrific location as well!! We highly recommend!!"

Reviewed on Jun 10, 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 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 ...
"The Opal Key Resort was close to the heart of Key West. The grounds were well kept and everything was clean and in order. The staff was friendly and very accommodating. Our room was immaculate. We ate at Lolita’s restaurant and the food and prices were good. The only issues I had were minor maintenance ..."

Reviewed on Jun 12, 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
$221 nightly
The price is $249 total per night from Jun 30 to Jul 1
$249 total
Jun 30 - Jul 1
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 ...
"Staff/Service was great...... facilities are beautiful..... perfect location...... would definitely stay again."

Reviewed on Jun 9, 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
$269 nightly
The price is $302 total per night from Jun 22 to Jun 23
$302 total
Jun 22 - Jun 23
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 property is dated. The rooms were small and old. The so-called balconies were not in the rooms, they were common for all. The pool bar closed at 7, the main bar closed at 9. Sometimes there were no towels at the pool and the number of chairs were limited."

Reviewed on Jun 12, 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
$283 nightly
The price is $319 total per night from Jun 23 to Jun 24
$319 total
Jun 23 - Jun 24
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 ...
"Very beautiful....feels like old money clasic vibes. Feels like you stepped back in time to an area when"

Reviewed on Jun 12, 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
$243 nightly
The price is $274 total per night from Jun 28 to Jun 29
$274 total
Jun 28 - Jun 29
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, ...
"Stayed the first week of June. Rooms were nice but property felt very dated. Not a lot of beaches in Key West so was excited to find a property with a man made one. Unfortunately there was a ton of seaweed and it was essentially not usable. The pool was small and underwhelming. Food and drink on ..."

Reviewed on Jun 11, 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
$158 nightly
The price is $178 total per night from Jun 23 to Jun 24
$178 total
Jun 23 - Jun 24
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 ...
"Plan on spending more for amenities! We were hit with an additional charge at checkin! Nowhere in our reservation were we told about the additional charge"

Reviewed on Jun 12, 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
$155 nightly
The price is $175 total per night from Jun 15 to Jun 16
$175 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 ...
"Lovely hotel very comfortable room. Great pool facilities. Helpful staff. Would recommend this hotel."

Reviewed on Jun 11, 2026

Opens in a new windowThe Southernmost Inn - Adults Only
Don't see what you're looking for?
See all available properties in Old Town Key West
View all properties
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

Explore More Ways to Travel with Travelocity