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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
$227 nightly
The price is $255 total per night from Apr 28 to Apr 29
$255 total
Apr 28 - Apr 29
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 ...
We loved staying at this super cute little resort within walking distance of everything. The pool was warm and the gardens pretty. Just note there’s only a few free parking spaces out front.

Reviewed on Apr 26, 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
$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 ...
Perfect place to walk to old town, delightful setting and beautiful rooms. Staff is so helpful and caring. Great hotel!

Reviewed on Apr 26, 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
$166 nightly
The price is $187 total per night from May 3 to May 4
$187 total
May 3 - May 4
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 ...
Everything was good, except for the horrible Pillows, and no conditioner in the shower. Everything else was good. Pricey, but you are paying for an excellent location. Had to park the car a quarter mile away, but managed to find a free spot which was good for our 3 days there. Staff was very helpful ...

Reviewed on Apr 27, 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 ...
I don't know if my expectations were too high but I had always wanted to stay at this resort. I've been to Key West numerous times and have always wanted to stay here. My husband and i stayed for 4 nights late April and it really did not meet expectations. First off, we did not book the most basic ...

Reviewed on Apr 27, 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 good

Reviewed on Apr 26, 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
$295 nightly
The price is $332 total per night from May 25 to May 26
$332 total
May 25 - May 26
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, ...
Friendly staff, room cleaning could have been better. Last two days of our stay there was no room cleaning performed. Did not know about the parking fees at the resort until we arrived. I may have overlooked that while reviewing the property while booking.

Reviewed on Apr 25, 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
$233 nightly
The price is $262 total per night from May 26 to May 27
$262 total
May 26 - May 27
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 ...
Everything was great. Breakfast was good too.However there was no place to sit for breakfast.

Reviewed on Apr 27, 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
$371 nightly
The price is $417 total per night from May 6 to May 7
$417 total
May 6 - May 7
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 ...
Was good location but did not know about $100 per day is resort fee and valet parking

Reviewed on Apr 27, 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 place was nice and the coffee/happy hour were great. Only negative was there were a bunch of nails sticking up from the floor in my room and I ripped two separate socks.

Reviewed on Apr 25, 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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