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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
$109 nightly
The price is $123 total per night from Aug 25 to Aug 26
$123 total
Aug 25 - Aug 26
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 room was large and clean. We liked the additional coffee station by the pool. The room could of uses a few more towels."

Reviewed on Aug 11, 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
$294 nightly
The price is $331 total per night from Aug 13 to Aug 14
$331 total
Aug 13 - Aug 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 ...
"I was pleasantly surprised by this hotel. The rooms are ample and well cared for. The Mexican restaurant embedded in the hotel was also an unexpected highlight. Everything was great with this stay. I would book again for sure."

Reviewed on Aug 12, 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
$149 nightly
The price is $167 total per night from Aug 16 to Aug 17
$167 total
Aug 16 - Aug 17
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 ...
"Staff was warm and helpful. The place had that tropical vibe but is the soft gentle vacation mode. Extremeley relaxing. I actually did not want to write to good of a review as I would like to keep this place a secret but hardly fair for the staff and owners. This is our new go-to BnB!!"

Reviewed on Aug 11, 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
$203 nightly
The price is $228 total per night from Sep 1 to Sep 2
$228 total
Sep 1 - Sep 2
Total with taxes and fees
A full-service spa, 3 outdoor pools, and a restaurant are all featured at this hotel. Traveling on business? Take advantage of the 2 conference rooms, along ...
"We checked into the hotel on Wed and they didn’t clean our room until Friday afternoon after we asked them if they planned on cleaning our room. We were late to a fishing trip I planned for my family after the front desk never called a cab after asking them to the night before. Then after the cab ..."

Reviewed on Aug 12, 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
$286 nightly
The price is $322 total per night from Aug 24 to Aug 25
$322 total
Aug 24 - Aug 25
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 ...
"Incredible property. We loved the rich history of this hotel. The recent updates only made the property even more wonderful."

Reviewed on Aug 12, 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
$216 nightly
The price is $243 total per night from Sep 3 to Sep 4
$243 total
Sep 3 - Sep 4
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, ...
"Our room was nice. Very clean and the staff was pleasant. We wish we knew we couldn’t use the beach because of the seaweed."

Reviewed on Aug 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
$155 nightly
The price is $175 total per night from Aug 26 to Aug 27
$175 total
Aug 26 - Aug 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 ...
"Old and worn out! Many physical and administrative issues. Also, extreme fees that were unknown until we arrived. We did not save money (as we thought) by using Expedia! Lots of detailed problems I won’t get into now, just don’t book a room at Southwinds in Key West."

Reviewed on Aug 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
$143 nightly
The price is $161 total per night from Aug 19 to Aug 20
$161 total
Aug 19 - Aug 20
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 ...
"Didn't use the hot tub in the middle of August. Room was clean, bed and pillows were comfortable, towels were clean and well maintained, air conditioning blew nice and cold! Staff were pleasant, we didn't need much from them. We didn't bother to go to the breakfast because we are gluten free and ..."

Reviewed on Aug 12, 2026

Opens in a new windowThe Southernmost Inn - Adults Only
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
$225 nightly
The price is $253 total per night from Aug 26 to Aug 27
$253 total
Aug 26 - Aug 27
Total with taxes and fees
This smoke-free hotel features 3 outdoor pools, a bar/lounge, and a poolside bar. WiFi in public areas is free. Self parking, a garden, and luggage storage are ...
Opens in a new windowWinslow's Bungalows - Key West Historic Inns
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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

Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West

5 out of 5
Posted 2 hours ago
Travelocity Verified Review
"I was pleasantly surprised by this hotel. The rooms are ample and well cared for. The Mexican restaurant embedded in the hotel was also an unexpected highlight. Everything was great with this stay. I would book again for sure."
A verified traveler stayed at Opal Key Resort & Marina, Key West
Opal Key Resort & Marina, Key West

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