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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
$179 nightly
The price is $201 total per night from Jul 12 to Jul 13
$201 total
Jul 12 - Jul 13
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 ...
"This is the third time to stay at the Weather Station. We like the rooms, the location and the ability to park our car without additional fees. The history of the building and the area is important to us. Check in was terrible - they gave our reservation to a person with the same last name that didn’t ..."

Reviewed on Jul 9, 2026

Opens in a new windowWeatherstation Inn
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
$261 nightly
The price is $294 total per night from Aug 11 to Aug 12
$294 total
Aug 11 - Aug 12
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 ...
"Room was very clean and bright…. Turtles we adorable and so fun to feed everyday! Staff was on the pool service!"

Reviewed on Jul 8, 2026

Opens in a new windowHyatt Centric Key West Resort and Spa
Pier House Resort & Spa

Pier House Resort & Spa

4 out of 5
1 Duval St Key West FL
Fully refundableReserve now, pay when you stay
$384 nightly
The price is $432 total per night from Aug 9 to Aug 10
$432 total
Aug 9 - Aug 10
Total with taxes and fees
This smoke-free resort features a private beach, a full-service spa, and a restaurant. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. ...
"Great hotel and stay. Highly recommend in Key West. Close to everything. Wished the bar and pool stay open longer."

Reviewed on Jul 11, 2026

Opens in a new windowPier House Resort & Spa
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
$218 nightly
The price is $245 total per night from Aug 11 to Aug 12
$245 total
Aug 11 - Aug 12
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 ...
"Enter being happy to be on vacation with my husband to arrive a front desk only to be pressured into upgrading our room, we declined and was charged anyway. We then was put in a room right outside the parking lot! I wish we had known before hand getting a room on Expedia like this. Ants all over ..."

Reviewed on Jul 11, 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
Fully refundableReserve now, pay when you stay
$238 nightly
The price is $268 total per night from Aug 11 to Aug 12
$268 total
Aug 11 - Aug 12
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 ...
"Overall great stay"

Reviewed on Jul 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
$293 nightly
The price is $330 total per night from Jul 27 to Jul 28
$330 total
Jul 27 - Jul 28
Total with taxes and fees
An outdoor pool, self parking, and concierge services are featured at this hotel. WiFi in public areas is free.
"Pool area is nice. Location is great, close to Duval street and Mallory Square."

Reviewed on Jul 4, 2026

Opens in a new windowHyatt Vacation Club at Sunset Harbor, 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
$212 nightly
The price is $239 total per night from Jul 12 to Jul 13
$239 total
Jul 12 - Jul 13
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 ...
"Elevator was down. All of them. My dad is handicap and their only solution was to give him “waived parking fee”. Not really a solution… in the meantime, I’m Hauling everything up 4 flights of stairs. They should’ve waived the parking fee for everyone. We’ve stayed here before. And came back an again. ..."

Reviewed on Jul 10, 2026

Opens in a new windowBeachside Resort & Residences
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard Key West FL
$171 nightly
The price is $192 total per night from Aug 10 to Aug 11
$192 total
Aug 10 - Aug 11
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 a playground, and families will appreciate ...
"Great stay, great value"

Reviewed on Jul 11, 2026

Opens in a new windowBlue Flamingo Resort 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
$164 nightly
The price is $184 total per night from Aug 10 to Aug 11
$184 total
Aug 10 - Aug 11
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 ...
"I saw first time the people staff was very argent. The bathrooms were not cleaned also there is no doors closing facility in the bathroom doors. Cleaning staff was not well educated to understand and help if i need from them. Please don't suggest me when I am looking for hotel at Expedia."

Reviewed on Jul 11, 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.

Recent Truman Annex hotel reviews by fellow wanderers

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
Posted less than an hour ago
Travelocity Verified Review
"Enter being happy to be on vacation with my husband to arrive a front desk only to be pressured into upgrading our room, we declined and was charged anyway. We then was put in a room right outside the parking lot! I wish we had known before hand getting a room on Expedia like this. Ants all over the bed!!! They came in changed bedding but did not offer a room change or did counted rate. They did however take the upgrade charge that we did not take charge back no balcony to these parking lot rooms no beach views and as stated had an ant problem."
A verified traveler stayed at Southernmost Beach Resort and Guesthouses
Southernmost Beach Resort and Guesthouses

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