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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
$169 nightly
The price is $190 total per night from Oct 5 to Oct 6
$190 total
Oct 5 - Oct 6
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 ...
"I stayed in the Christmas Palm room and really enjoyed the large balcony overlooking the garden. Unfortunately, the property directly beside us were doing construction and the noise in tge morning kept me from having coffee outside. Thankfully, the Cuban Coffee Queen is only 2 minutes down on Duval ..."

Reviewed on Oct 1, 2026

Opens in a new windowDouglas House - Adults Only
Southwinds Motel

Southwinds Motel

2 out of 5
1321 Simonton Street Key West FL
$169 nightly
The price is $190 total per night from Oct 5 to Oct 6
$190 total
Oct 5 - Oct 6
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 ...
"Clean room, nice pool, nice staff. Good little Cuban restaurant and grocery store across the street. Loved it."

Reviewed on Oct 1, 2026

Opens in a new windowSouthwinds Motel
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
$276 nightly
The price is $310 total per night from Oct 14 to Oct 15
$310 total
Oct 14 - Oct 15
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, ...
"Constant construction all day long, thin walls so you hear everything in the hotel on top of it all and only 1 working elevator. Room was nice but when we got there the ceiling fan didn't work, the ac couldn't keep up and our balcony door was seized shut. Maintenance was able to get the fan working ..."

Reviewed on Oct 1, 2026

Opens in a new windowThe Reach Key West, Curio Collection by Hilton
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
$309 nightly
The price is $348 total per night from Oct 4 to Oct 5
$348 total
Oct 4 - Oct 5
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 ...
"The property was immaculate, the staff friendly and the location was perfect. We love that the resort allows you access to The Reach, which is basically next door. You are able to use all of their amenities as well and charge them to Your room. We had a beach front room with a balcony. It was ..."

Reviewed on Oct 1, 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
$141 nightly
The price is $159 total per night from Oct 5 to Oct 6
$159 total
Oct 5 - Oct 6
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 ...
"Very close to all the action"

Reviewed on Oct 2, 2026

Opens in a new windowThe Southernmost Inn - Adults 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
$225 nightly
The price is $253 total per night from Oct 11 to Oct 12
$253 total
Oct 11 - Oct 12
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, free WiFi ...
Opens in a new windowSouthernmost Beach Resort and Guesthouses
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
$275 nightly
The price is $309 total per night from Oct 4 to Oct 5
$309 total
Oct 4 - Oct 5
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
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 Oct 4 to Oct 5
$331 total
Oct 4 - Oct 5
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 ...
Opens in a new windowOpal Key Resort & Marina, Key West
Duval House

Duval House

3 out of 5
815 Duval St Key West FL
$119 nightly
The price is $131 total per night from Oct 5 to Oct 6
$131 total
Oct 5 - Oct 6
Total with taxes and fees
This bed & breakfast features a terrace, concierge services, and self parking. A garden, a picnic area, and express check-in are also on offer.
Opens in a new windowDuval House
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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

The Southernmost Inn - Adults Only

The Southernmost Inn - Adults Only

4 out of 5
Posted 12 hours ago
Travelocity Verified Review
"Very close to all the action"
A verified traveler stayed at The Southernmost Inn - Adults Only
The Southernmost Inn - Adults Only

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