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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 6 to May 7
$244 total
May 6 - May 7
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 ...
Lovely property with good amenity. Convenient but peaceful location away from night noise.

Reviewed on Apr 25, 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
$284 nightly
The price is $320 total per night from May 7 to May 8
$320 total
May 7 - May 8
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 ...
Beautiful views and such a classy relaxed tropical vibe. Second time staying and we will be back!

Reviewed on Apr 23, 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 27 to Apr 28
$196 total
Apr 27 - Apr 28
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 ...
The breakfast menu was fresh but rather limited. Room was clean, fresh towels daily, bed linens change every 3 days. (which was ok)

Reviewed on Apr 24, 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 ...
Easy access to the small beach. Plenty of beach chairs available. Free breakfast was convenient, included omelet station, potatoes, bagels, breakfast pesto pizza, pastries, parfait, fruit, juice, coffee, etc. Lots of activities by the pools. Convenient location. Many room choices, our room was very ...

Reviewed on Apr 25, 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
$199 nightly
The price is $224 total per night from May 4 to May 5
$224 total
May 4 - May 5
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, ...
Wonderful beach view. Comfortable, clean room, excellent restaurants and service.

Reviewed on Apr 24, 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 ...
We are SO glad we chosed the Southwinds Motel. If you want the REAL Key West experience go there. We wanted something authentic, not the standard marble and glass hotels that are the same everywhere. Great friendly staff, Great pool, great bar with live music, a full liqour store and ice cream / ...

Reviewed on Apr 25, 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
$374 nightly
The price is $421 total per night from May 3 to May 4
$421 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 ...
Everything from start to finish was spectacular here! Friendly clean… views!!! Made a dream of ours come true

Reviewed on Apr 24, 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
$245 nightly
The price is $276 total per night from May 26 to May 27
$276 total
May 26 - May 27
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 breakfast was less than expected, nothing cooked fresh, mixed fruit in a bowl that all tasted like cantelope and pre pkgd boiled eggs. Coffee machine worked well. Hot tub and heated pool was awesome. Stairs leading up to our room were straight up and very narrow. Coming down was treacherous, ...

Reviewed on Apr 24, 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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