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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 9 to Jul 10
$166 total
Jul 9 - Jul 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 ...
"This was our first stay at the Douglas House. We stayed for 6 nights. We had a great stay and were very happy with everything especially the free amenities offered at the pool. They offer free sunscreen, water, and coffee. The property was very clean and easily accessible. We did not rent a car and ..."

Reviewed on Jul 3, 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
$179 nightly
The price is $201 total per night from Jul 6 to Jul 7
$201 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 ...
"Very clean and enjoyable hotel .. pool is nice staff is great ,parking close to everything but quiet … best part free omelet station every morning saves u 30 bucks every day"

Reviewed on Jul 3, 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 6 to Jul 7
$331 total
Jul 6 - Jul 7
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 ...
"Damir and Andre were fabulous"

Reviewed on Jul 3, 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
$191 nightly
The price is $215 total per night from Jul 6 to Jul 7
$215 total
Jul 6 - Jul 7
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 room was very clean and the staff was good. I would definitely recommend!"

Reviewed on Jul 2, 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
$232 nightly
The price is $261 total per night from Jul 14 to Jul 15
$261 total
Jul 14 - Jul 15
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 rooms. Do not come for the beach as there is none. Come for the Key West atmosphere."

Reviewed on Jul 5, 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
$252 nightly
The price is $283 total per night from Jul 12 to Jul 13
$283 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 ...
"Rooms & amenities were great, but definitely not a beach place to stay."

Reviewed on Jul 5, 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
$228 nightly
The price is $257 total per night from Jul 16 to Jul 17
$257 total
Jul 16 - Jul 17
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, ...
"We checked into a room that the a/c did not work. They tried to tell us that it was when it wouldn’t cool below 79 when it was sat on 68 with the curtains closed for 4 hours. Asked us to go check out another room that was in the same situation. Finally found a room that would hold at 70. This rooms ..."

Reviewed on Jul 2, 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
$151 nightly
The price is $170 total per night from Aug 3 to Aug 4
$170 total
Aug 3 - Aug 4
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 ...
"It was a great trip! Close to many things."

Reviewed on Jul 4, 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
$146 nightly
The price is $164 total per night from Jul 6 to Jul 7
$164 total
Jul 6 - Jul 7
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 ...
"Nice location clean room"

Reviewed on Jul 4, 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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