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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
$169 nightly
The price is $190 total per night from Sep 15 to Sep 16
$190 total
Sep 15 - Sep 16
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 ...
"Awesome spot"

Reviewed on Sep 7, 2026

Opens in a new windowWeatherstation Inn
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
$166 nightly
The price is $187 total per night from Sep 28 to Sep 29
$187 total
Sep 28 - Sep 29
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 ...
"Excellent"

Reviewed on Sep 14, 2026

Opens in a new windowHavana Cabana at Key West
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
$306 nightly
The price is $344 total per night from Sep 27 to Sep 28
$344 total
Sep 27 - Sep 28
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. ...
"Having driven over 4 hours to reach the hotel we were given a room overlooking the car (not what I had hoped and not like the photos on website). I asked if we could move but no other room available for 2 nights. I had made my booking quite a few months ago, I was disappointed as I had really been ..."

Reviewed on Sep 13, 2026

Opens in a new windowPier House Resort & Spa
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
$234 nightly
The price is $263 total per night from Sep 28 to Sep 29
$263 total
Sep 28 - Sep 29
Total with taxes and fees
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the 24-hour gym and perks like a free airport shuttle. You'll appreciate the hot tub, ...
"The only beach on island is across the road and I love that about this location. Very small beach and not much to it, coming from Tampa we have better beaches. The location of hotel is 20-30 minutes away from the bars and restaurants. Good thing is they have a free shuttle running daily with helps ..."

Reviewed on Sep 13, 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 refundableReserve now, pay when you stay
$224 nightly
The price is $252 total per night from Sep 29 to Sep 30
$252 total
Sep 29 - Sep 30
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. Near everything. Walking distance to Duval. Quiet area near the water. Lots of activities around - rooms were spacious and pool area was nice. Staff was friendly. Kathy at the front was very nice and helpful."

Reviewed on Sep 13, 2026

Opens in a new windowHyatt Vacation Club at Sunset Harbor, Key West
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
$239 nightly
The price is $269 total per night from Sep 27 to Sep 28
$269 total
Sep 27 - Sep 28
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 ...
"Pools were well maintained but crowded. Property was beautiful. Staff was helpful. Breakfast was very good."

Reviewed on Sep 13, 2026

Opens in a new windowSouthernmost Beach Resort and Guesthouses
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
$160 nightly
The price is $180 total per night from Sep 15 to Sep 16
$180 total
Sep 15 - Sep 16
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 ...
"I really liked the hotel, polite staff. But they are confusing. We went through a lot of stress. At all times at the reception. We found the unprepared team. We were in a group of friends 18 people. Another thing the reservation was made for payment at the hotel. There were several attempts on my ..."

Reviewed on Sep 13, 2026

Opens in a new windowBlue Flamingo Resort 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
$185 nightly
The price is $208 total per night from Sep 15 to Sep 16
$208 total
Sep 15 - Sep 16
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 ...
"Pictures do NOT do this property justice. I have beeen ti all 50 states, 6 provinces in Canada and 14 countries and this was the best surprise ever"

Reviewed on Sep 14, 2026

Opens in a new windowBeachside Resort & Residences
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
$130 nightly
The price is $146 total per night from Sep 15 to Sep 16
$146 total
Sep 15 - Sep 16
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
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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

Havana Cabana at Key West

Havana Cabana at Key West

5 out of 5
Posted 5 hours ago
Travelocity Verified Review
"Excellent"
A verified traveler stayed at Havana Cabana at Key West
Havana Cabana at Key West

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