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Top hotels in Truman Annex

Weatherstation Inn

Weatherstation Inn

2.5 out of 5
57 Front St, Key West, FL
Fully refundableReserve now, pay when you stay
$162 nightly
The price is $183 total per night from Sep 30 to Oct 1
$183 total
Sep 30 - Oct 1
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 ...
Beautiful Key West location
"Amazing stay at Weatherstation Inn. Perfect location in beautiful Truman Annex neighborhood. Short walk to historic Key West Duvall st, Mallory Square, and harbor."

Reviewed on Sep 22, 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
Fully refundableReserve now, pay when you stay
$166 nightly
The price is $187 total per night from Oct 1 to Oct 2
$187 total
Oct 1 - Oct 2
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 ...
"We were pleasantly surprised to find that we had two large balconies overlooking the pool and one overlooking the lagoon. The four pools were a nice touch as well."

Reviewed on Sep 20, 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
$215 nightly
The price is $242 total per night from Oct 4 to Oct 5
$242 total
Oct 4 - Oct 5
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. ...
"my stay at this resort was good at first they gave me a room that I didn’t like I booked a suite with ocean view, they gave me a room seeing the mangrove was upset about that so they didn’t get to switch me out until the next day which they gave me a room which wasn’t a suite and then on the last ..."

Reviewed on Sep 17, 2025

Opens in a new windowOceans Edge Key West Resort, Hotel & Marina
Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Boulevard, Key West, FL
Fully refundableReserve now, pay when you stay
$235 nightly
The price is $264 total per night from Oct 13 to Oct 14
$264 total
Oct 13 - Oct 14
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 ...
"Transportation is great to and from downtown and the bus drivers are full of personality."

Reviewed on Sep 18, 2025

Opens in a new windowMargaritaville Beach House Key West
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street, Key West, FL
Fully refundable
$237 nightly
The price is $266 total per night from Oct 13 to Oct 14
$266 total
Oct 13 - Oct 14
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 love that everything is at arms reach. The pool, beach, restaurants, stores. Everything is a hop skip & a jump."

Reviewed on Sep 21, 2025

Opens in a new windowSouthernmost Beach Resort and Guesthouses
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
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
Fully refundableReserve now, pay when you stay
$233 nightly
The price is $262 total per night from Oct 14 to Oct 15
$262 total
Oct 14 - Oct 15
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 ...
"Elevator was broken but other than that enjoyed our stay"

Reviewed on Sep 18, 2025

Opens in a new windowCasa Marina Key West, Curio Collection by Hilton
Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection

3.5 out of 5
3850 N Roosevelt Blvd, Key West, FL
Fully refundableReserve now, pay when you stay
$135 nightly
The price is $151 total per night from Oct 1 to Oct 2
$151 total
Oct 1 - Oct 2
Total with taxes and fees
This smoke-free hotel includes 2 restaurants, an outdoor pool, and a gym. Traveling on business? Take advantage of the business center and free WiFi in public ...
"Very nice hotel."

Reviewed on Sep 17, 2025

Opens in a new windowHilton Garden Inn Key West / The Keys Collection
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
Fully refundableReserve now, pay when you stay
$137 nightly
The price is $154 total per night from Oct 1 to Oct 2
$154 total
Oct 1 - Oct 2
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 ...
"Clean"

Reviewed on Sep 19, 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.

Recent Truman Annex hotel reviews by fellow wanderers