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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
$217 nightly
The price is $244 total per night from May 4 to May 5
$244 total
May 4 - May 5
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 property was located off Duval St. near the southern end. It was located perfectly for our needs, staff was friendly and accommodating. Coffee in the morning, near the pool, perfect for adults.

Reviewed on Apr 21, 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
$304 nightly
The price is $342 total per night from May 3 to May 4
$342 total
May 3 - May 4
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 ...
Was perfect.

Reviewed on Apr 21, 2026

Opens in a new windowOpal Key Resort & Marina, Key West
Heron House - Adult Only

Heron House - Adult Only

3.5 out of 5
512 Simonton St Key West FL
$174 nightly
The price is $196 total per night from Apr 28 to Apr 29
$196 total
Apr 28 - Apr 29
Total with taxes and fees
This bed & breakfast features an outdoor pool and a rooftop terrace. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A ...
Our stay was amazing- first off the staff was excellent. Every person on the staff that we interacted with was so nice and helpful. Our room was great - good size and very clean. They did a happy hour in the evenings.

Reviewed on Apr 21, 2026

Opens in a new windowHeron House - Adult Only
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
$330 nightly
The price is $372 total per night from May 19 to May 20
$372 total
May 19 - May 20
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 ...
Great view and pool bars!

Reviewed on Apr 22, 2026

Opens in a new windowSouthernmost Beach Resort and Guesthouses
The Cabana Inn Key West - Adults Only

The Cabana Inn Key West - Adults Only

3 out of 5
413 Applerouth Lane Key West FL
$203 nightly
The price is $229 total per night from May 10 to May 11
$229 total
May 10 - May 11
Total with taxes and fees
This guesthouse features an outdoor pool and a hot tub. Enjoy the free continental breakfast each morning. Self parking, a terrace, and a garden are also ...
Breakfast was very good, fresh fruit, waffles cereal toast etc. The Starbuck's coffee machine was wonderful to have on the premises. The happy hour was great, wine and snacks every day at 5:00.

Reviewed on Apr 20, 2026

Opens in a new windowThe Cabana Inn Key West - Adults Only
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
$330 nightly
The price is $371 total per night from May 4 to May 5
$371 total
May 4 - May 5
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, ...
Great location. Had to call on several occasions to get our room cleaned. Still was not cleaned real well, dirty floors etc... Pool did not seem clean to me

Reviewed on Apr 20, 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
$223 nightly
The price is $251 total per night from Apr 27 to Apr 28
$251 total
Apr 27 - Apr 28
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 ...
The room was ready but staff would not allow us to check in early because we booked on Expedia. The water pressure was the worst I have ever experienced. The ac unit was rusty and leaked water. The entire room smelled like the sewer. Staff member was leaf blowing right outside our room at 6:00 ...

Reviewed on Apr 22, 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
$377 nightly
The price is $424 total per night from May 3 to May 4
$424 total
May 3 - May 4
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 ...
Yes

Reviewed on Apr 22, 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
$264 nightly
The price is $297 total per night from May 10 to May 11
$297 total
May 10 - May 11
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 ...
El personas muy amables, el área de desayuno limpio y variedad en el desayunó ,cuarto limpio y buen aire acondicionado, cerca de southernmost point

Reviewed on Apr 22, 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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