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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
$399 nightly
The price is $449 total per night from Jan 25 to Jan 26
$449 total
Jan 25 - Jan 26
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 ...
Staff were wonderful! Room was clean and well supplied. Location was perfect!

Reviewed on Jan 7, 2026

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
$339 nightly
The price is $381 total per night from Jan 21 to Jan 22
$381 total
Jan 21 - Jan 22
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. ...
Although not a lot of amenities you didn't need to pay for, we enjoyed the option to be away from the craziness of Key West and still be able to enjoy it via the very convenient shuttle. Gorgeous resort - we will be back!

Reviewed on Jan 13, 2026

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
$616 nightly
The price is $693 total per night from Jan 26 to Jan 27
$693 total
Jan 26 - Jan 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 ...
Lovely location and goodnbreakfast

Reviewed on Jan 9, 2026

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
$530 nightly
The price is $596 total per night from Jan 26 to Jan 27
$596 total
Jan 26 - Jan 27
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 ...
The room were clean and well appointed. Support staff was very friendly and ready to assist when asked for help. The views were amazing, pools clean and lots of activities each day. The food at the cafe was excellent. Everything you need all in one location, while being in the heart of Duvall ...

Reviewed on Jan 9, 2026

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
$572 nightly
The price is $644 total per night from Feb 8 to Feb 9
$644 total
Feb 8 - Feb 9
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 ...
Great staff ,Evelyn front desk and the concierge Maria are wonderful . Very nice place great location , very clean considering the ocean is across the street . Love Key West first time here and not the last ! Very DOG friendly !!!

Reviewed on Jan 11, 2026

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
Fully refundable
$476 nightly
The price is $535 total per night from Jan 26 to Jan 27
$535 total
Jan 26 - Jan 27
Total with taxes and fees
An outdoor pool, self parking, and concierge services are featured at this hotel. WiFi in public areas is free.
Can’t beat the location. Ro

Reviewed on Jan 10, 2026

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
$346 nightly
The price is $389 total per night from Jan 19 to Jan 20
$389 total
Jan 19 - Jan 20
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 ...
No free breakfast

Reviewed on Jan 13, 2026

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
$339 nightly
The price is $382 total per night from Jan 19 to Jan 20
$382 total
Jan 19 - Jan 20
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 ...
Beautiful room

Reviewed on Jan 14, 2026

Opens in a new windowDoubleTree Resort by Hilton Grand Key - Key West
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
$344 nightly
The price is $387 total per night from Jan 19 to Jan 20
$387 total
Jan 19 - Jan 20
Total with taxes and fees
This smoke-free hotel includes 2 restaurants, an outdoor pool, and a hot tub. Traveling on business? Take advantage of the business center and free WiFi in public ...
Wonderful stay, clean room, attentive staff

Reviewed on Jan 9, 2026

Opens in a new windowHilton Garden Inn Key West / The Keys Collection
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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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