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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
$345 nightly
The price is $389 total per night from Jan 26 to Jan 27
$389 total
Jan 26 - Jan 27, 2026
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 ...
Nice small and cozy hotel inside Annex, parking is included, water and coffee is complimentary, breakfast is very simple. At walking distance to the main street in KW. WIFI disappointed as i had to stay in the bathroom to have wifi. This is very simple to solve but they seemed to know the issue ...

Reviewed on Dec 21, 2025

Opens in a new windowWeatherstation Inn
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
$292 nightly
The price is $328 total per night from Jan 26 to Jan 27
$328 total
Jan 26 - Jan 27, 2026
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. ...
So many activities and amazing staff and service. The shuttle was very convenient. I would stay here again! Perfect for families. I felt safe. Very laid back environment.

Reviewed on Dec 26, 2025

Opens in a new windowOceans Edge Key West Resort, Hotel & Marina
Havana Cabana at Key West

Havana Cabana at Key West

4 out of 5
3420 N. Roosevelt Blvd Key West FL
$331 nightly
The price is $372 total per night from Jan 4 to Jan 5
$372 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Business travelers can take advantage of the free WiFi in public areas. Enjoy the hot tub ...
This is the first time I’ve stayed at the Havana cabana and definitely will be back! Staff was very friendly and knowledgeable of the area. The room that we stayed in was perfectly clean, easy access to the pool area, which was made up for Christmas, which was overly exciting for all of us. Bartenders ...

Reviewed on Dec 22, 2025

Opens in a new windowHavana Cabana at Key West
Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
3841 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$289 nightly
The price is $325 total per night from Jan 4 to Jan 5
$325 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
This smoke-free hotel features a private beach, a marina, and 2 restaurants. Enjoy a day at the beach kayaking, or relax with sun loungers. Unwind with a drink ...
Pool and hot tub were very nice,chicken walk was excellent! Great staff!!!!

Reviewed on Dec 26, 2025

Opens in a new windowBeachside Resort & Residences
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
Fully refundable
$360 nightly
The price is $405 total per night from Jan 13 to Jan 14
$405 total
Jan 13 - Jan 14, 2026
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 ...
Amazing 👌

Reviewed on Dec 22, 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
Fully refundableReserve now, pay when you stay
$377 nightly
The price is $424 total per night from Jan 14 to Jan 15
$424 total
Jan 14 - Jan 15, 2026
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 ...
Nice spot and great staff

Reviewed on Dec 24, 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
$349 nightly
The price is $393 total per night from Jan 8 to Jan 9
$393 total
Jan 8 - Jan 9, 2026
Total with taxes and fees
An outdoor pool, self parking, and concierge services are featured at this hotel. WiFi in public areas is free.
Great location and staff was friendly. The pool area was perfect.

Reviewed on Dec 20, 2025

Opens in a new windowHyatt Vacation Club at Sunset Harbor, Key West
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
$283 nightly
The price is $318 total per night from Jan 8 to Jan 9
$318 total
Jan 8 - Jan 9, 2026
Total with taxes and fees
This hotel features 2 restaurants, 2 outdoor pools, and a 24-hour gym. There's fun for all ages with mini golf and an arcade/game room, and families will appreciate ...
Very clean

Reviewed on Dec 26, 2025

Opens in a new windowBlue Flamingo Resort Key West
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
$261 nightly
The price is $294 total per night from Jan 4 to Jan 5
$294 total
Jan 4 - Jan 5, 2026
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 ...
Dinner menu ok, food below average, eat in town! Tram services ok, frequently over loaded requiring a wait for second vehicle. Hotel had no hot water for showering or our last day. Complimentary coffee had coffee grounds and staff didn’t seem to care when notified. Place was clean, well kept.

Reviewed on Dec 25, 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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