Find a Hotel in Truman Annex

Seize Your Someday with our amazing deals for the whole family!

Save an extra 10% or more on select hotels with Member Discounts

Access exclusive hotel deals, only with the Travelocity app

Filter by

Guest rating
Guest rating
Star rating
Payment type
Payment type
Property type
Property type
Neighborhood
Neighborhood
Traveler experience
Traveler experience
Popular locations
Popular locations
Meal plans available
Meal plans available
Property amenities
Property amenities
Accessibility
Accessibility

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 Aug 24 to Aug 25
$201 total
Aug 24 - Aug 25
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 self-serve breakfast ...
"Nice place"

Reviewed on Aug 15, 2026

Opens in a new windowWeatherstation Inn
Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$204 nightly
The price is $295 total per night from Sep 8 to Sep 9
$295 total
Sep 8 - Sep 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 ...
"We had a fantastic time at this cozy establishment. The customer service was impeccable; they promptly sent someone to check the faulty TV in our room within three minutes. The cocktails and food were delicious and reasonably priced. However, we did wish they offered more entertainment options for ..."

Reviewed on Aug 23, 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
$277 nightly
The price is $312 total per night from Aug 30 to Aug 31
$312 total
Aug 30 - Aug 31
Total with taxes and fees
An outdoor pool, self parking, and concierge services are featured at this hotel. WiFi in public areas is free.
"Make sure to unload your luggage before parking. The garage is across the street and there is no elevator. Also, I was not aware that they charge you $40 a night to park. I would also recommend calling before your arrival and confirming your stay. My Hotels app had me arriving Friday and checking ..."

Reviewed on Aug 17, 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
$184 nightly
The price is $207 total per night from Aug 30 to Aug 31
$207 total
Aug 30 - Aug 31
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 ...
"We stayed here for 5 nights. The room was clean, the property was also clean and the pool area was well taken care of. However, the elevator to our building was out the entire time of our stay and there seemed to be no attempts or urgency in fixing it. Not a huge deal to walk the stairs for us, but ..."

Reviewed on Aug 23, 2026

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 refundableReserve now, pay when you stay
$203 nightly
The price is $228 total per night from Sep 1 to Sep 2
$228 total
Sep 1 - Sep 2
Total with taxes and fees
A full-service spa, 3 outdoor pools, and a restaurant are all featured at this hotel. Traveling on business? Take advantage of the 2 conference rooms, along ...
Opens in a new windowSouthernmost Beach Resort and Guesthouses
Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
3101 N. Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$136 nightly
The price is $153 total per night from Aug 24 to Aug 25
$153 total
Aug 24 - Aug 25
Total with taxes and fees
This Art Deco hotel features a private beach, a marina, and a restaurant. Enjoy a day at the beach kayaking, or relax with sun loungers. Enjoy the outdoor pool ...
Opens in a new windowIbis Bay Beach Resort
Havana Cabana at Key West

Havana Cabana at Key West

4 out of 5
3420 N. Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$200 nightly
The price is $225 total per night from Sep 7 to Sep 8
$225 total
Sep 7 - Sep 8
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 ...
Opens in a new windowHavana Cabana at 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
$166 nightly
The price is $187 total per night from Aug 24 to Aug 25
$187 total
Aug 24 - Aug 25
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 ...
Opens in a new windowBlue Flamingo Resort Key West
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
$190 nightly
The price is $213 total per night from Aug 30 to Aug 31
$213 total
Aug 30 - Aug 31
Total with taxes and fees
This smoke-free hotel features 4 outdoor pools, a gym, and a restaurant. Traveling on business? Take advantage of the business center, free WiFi in public areas, ...
Opens in a new windowParrot Key Hotel & Villas
Don't see what you're looking for?
See all available properties in Truman Annex
View all properties
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

Pier House Resort & Spa

Pier House Resort & Spa

5 out of 5
Posted 3 hours ago
Travelocity Verified Review
"We loved our stay! Within walking distance to so much, the grounds felt tropical and the private beach was a definite plus. Good food and drink options too."
A verified traveler stayed at Pier House Resort & Spa
Pier House Resort & Spa

Explore More Ways to Travel with Travelocity