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Top hotels in Old Town Key West

Douglas House - Adults Only

Douglas House - Adults Only

3 out of 5
419 Amelia St Key West FL
$148 nightly
The price is $166 total per night from Jul 20 to Jul 21
$166 total
Jul 20 - Jul 21
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 ...
"Hamza and Jen at the front desk were very knowledgeable, efficient and so friendly! The room was clean and there was a system as most hotels have for room service to clean. Temperature was good with AC and ceiling fans to cool the room. We were able to rent a golf cart directly through the hotel, ..."

Reviewed on Jul 10, 2026

Opens in a new windowDouglas House - Adults Only
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
$150 nightly
The price is $169 total per night from Aug 2 to Aug 3
$169 total
Aug 2 - Aug 3
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 ...
"The hotel has an excellent location very close from the center. The breakfast surprises us because it says a continental, but it was more than that totally free . The pool water transparent. The only inconvenience was the parking lot. The Hotel does not have to many lots. Overall Good 👍"

Reviewed on Jul 10, 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 Jul 13 to Jul 14
$331 total
Jul 13 - Jul 14
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 ...
"Rooms are very outdated. Hallways have old carpet that is dirty. Great location but needs renovation"

Reviewed on Jul 11, 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
$179 nightly
The price is $202 total per night from Jul 27 to Jul 28
$202 total
Jul 27 - Jul 28
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 stayed here for two nights in June and had an amazing experience! The weather was very hot, but having three different pools to choose from made it easy to cool off and relax. The breakfast was delicious—we especially loved the Belgian waffles and the fresh fruit. The entire resort had a peaceful, ..."

Reviewed on Jul 11, 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
$218 nightly
The price is $245 total per night from Aug 11 to Aug 12
$245 total
Aug 11 - Aug 12
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 ...
"Staffs don’t speak English. I call from room to ask for safety box and microwave. The operator seems not to happy. She said hotel doesn’t have. Before checking out room, I found safety box was in drawer. Room is not clean. Big problem is seaweed smell is typically strongest directly on top of the ..."

Reviewed on Jul 11, 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
$259 nightly
The price is $291 total per night from Jul 12 to Jul 13
$291 total
Jul 12 - Jul 13
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 ...
"This is a very nice place to stay. The staff is very friendly and the property is top notch."

Reviewed on Jul 11, 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
$223 nightly
The price is $251 total per night from Aug 11 to Aug 12
$251 total
Aug 11 - Aug 12
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, ...
"Everything was wonderful except for thee seaweed smell, which Iater on found out, they have the option to clean up. It was a consent smell like an outhouse and yes, it did reach past the hotel beach, swimming pool, court yard, and up to my room that I could smell it whenever I opened my balcony door. ..."

Reviewed on Jul 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 Aug 6 to Aug 7
$178 total
Aug 6 - Aug 7
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 ...
"We spent a long weekend at this hotel for my birthday. The room was nice and cold and the location was great. We especially liked the bar next-door and the Cuban restaurant across the street."

Reviewed on Jul 11, 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 Jul 16 to Jul 17
$182 total
Jul 16 - Jul 17
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 ...
"Our overall stay was amazing! Peaceful and friendly staff! Highly recommended’"

Reviewed on Jul 10, 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

Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

5 out of 5
Posted 2 hours ago
Travelocity Verified Review
"This is a very nice place to stay. The staff is very friendly and the property is top notch."
A verified traveler stayed at Casa Marina Key West, Curio Collection by Hilton
Casa Marina Key West, Curio Collection by Hilton

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