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Top hotels in Truman Annex

Weatherstation Inn

Weatherstation Inn

2.5 out of 5
57 Front St, Key West, FL
$219 nightly
The price is $246 total per night from Oct 16 to Oct 17
$246 total
Oct 16 - Oct 17
Total with taxes and fees
An outdoor pool, free self parking, and concierge services are featured at this bed & breakfast. Guests will appreciate free perks like continental breakfast ...
"Excellent place to stay, walking distance to historic downtown area. Quaint Room at this historical building was very clean and our check-in was very efficient and friendly. Nice property with parking safely gated for protection. Would definetly stay here again."

Reviewed on Oct 10, 2025

Opens in a new windowWeatherstation Inn
Parrot Key Hotel & Villas

Parrot Key Hotel & Villas

4 out of 5
2801 N Roosevelt Blvd, Key West, FL
$210 nightly
The price is $236 total per night from Oct 26 to Oct 27
$236 total
Oct 26 - Oct 27
Total with taxes and fees
This eco-certified hotel features 4 outdoor pools, a gym, and a restaurant. Traveling on business? Take advantage of the business center, free WiFi in public ...
"Impeccable service"

Reviewed on Oct 7, 2025

Opens in a new windowParrot Key Hotel & Villas
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
5950 Peninsular Avenue, Key West, FL
Fully refundableReserve now, pay when you stay
$189 nightly
The price is $212 total per night from Oct 28 to Oct 29
$212 total
Oct 28 - Oct 29
Total with taxes and fees
A marina, 6 outdoor pools, and a 24-hour gym are all featured at this smoke-free hotel. Business travelers can take advantage of the free WiFi in public areas. ...
"Phenomenal"

Reviewed on Oct 13, 2025

Opens in a new windowOceans Edge Key West Resort, Hotel & Marina
Hyatt Centric Key West Resort and Spa

Hyatt Centric Key West Resort and Spa

4 out of 5
601 Front St, Key West, FL
Fully refundableReserve now, pay when you stay
$242 nightly
The price is $272 total per night from Oct 26 to Oct 27
$272 total
Oct 26 - Oct 27
Total with taxes and fees
This smoke-free resort features a full-service spa, a marina, and a restaurant. Enjoy the outdoor pool and perks like free WiFi. Enjoy the 24-hour gym and unwind ...
"Beautiful hotel rooms are awesome"

Reviewed on Oct 3, 2025

Opens in a new windowHyatt Centric Key West Resort and Spa
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street, Key West, FL
Fully refundable
$234 nightly
The price is $264 total per night from Oct 29 to Oct 30
$264 total
Oct 29 - Oct 30
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 hotel. It was amazing."

Reviewed on Oct 11, 2025

Opens in a new windowSouthernmost Beach Resort and Guesthouses
Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Boulevard, Key West, FL
$235 nightly
The price is $264 total per night from Oct 28 to Oct 29
$264 total
Oct 28 - Oct 29
Total with taxes and fees
This hotel features a restaurant, an outdoor pool, and a bar/lounge. If you want to take your pet along, this pet-friendly property offers everything you'll ...
"Property was fun, inviting and a great place to relax after a day in Old Town Key West. Shuttle to Old Town was great, food at Margaritaville was very good, staff very friendly. Jimmy Buffett tunes playing all the time was perfect!"

Reviewed on Oct 8, 2025

Opens in a new windowMargaritaville Beach House Key West
Hyatt Vacation Club at Sunset Harbor, Key West

Hyatt Vacation Club at Sunset Harbor, Key West

3.5 out of 5
200 Sunset Lane, Key West, FL
$276 nightly
The price is $310 total per night from Oct 30 to Oct 31
$310 total
Oct 30 - Oct 31
Total with taxes and fees
An outdoor pool, self parking, and concierge services are featured at this apartment. WiFi in public areas is free.
"Good location"

Reviewed on Sep 9, 2025

Opens in a new windowHyatt Vacation Club at Sunset Harbor, Key West
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
$278 nightly
The price is $312 total per night from Oct 22 to Oct 23
$312 total
Oct 22 - Oct 23
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 ...
"Truly beautiful custom century hotel, sitting on one of the few beaches in Key West"

Reviewed on Oct 12, 2025

Opens in a new windowCasa Marina Key West, Curio Collection by Hilton
DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West

4 out of 5
3990 S Roosevelt Blvd, Key West, FL
$165 nightly
The price is $186 total per night from Oct 27 to Oct 28
$186 total
Oct 27 - Oct 28
Total with taxes and fees
This resort features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public ...
"We really enjoyed staying at this property. It was gorgeous and very clean. The staff was very kind and helpful. Highly recommend the Doubletree Key West!"

Reviewed on Oct 14, 2025

Opens in a new windowDoubleTree Resort by Hilton Grand Key - Key West
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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.

Truman Annex 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 Truman Annex 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 Truman Annex 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 Truman Annex 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.

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