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Top hotels in Truman Annex

Weatherstation Inn

Weatherstation Inn

2.5 out of 5
57 Front St Key West FL
$179 nightly
The price is $201 total per night from Oct 27 to Oct 28
$201 total
Oct 27 - Oct 28
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 ...
"So don't arrive after 4:00 pm if you actually want to check in at this hotel. No one will be there. You'll have to make your way to another hotel and check in there and then go back to get yourself in. You'll have to use 3 different keys to get into the place. Even when they say they are open, no ..."

Reviewed on Oct 22, 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
$236 nightly
The price is $265 total per night from Oct 30 to Oct 31
$265 total
Oct 30 - Oct 31
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 ...
"We had a great time. The staff was amazing. The main Pool Guy worked so hard at making everybody happy best we’ve ever seen. Kids had a great time. This property goes out and over and beyond to make everyone feel welcome."

Reviewed on Oct 23, 2026

Opens in a new windowHavana Cabana at 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
$278 nightly
The price is $313 total per night from Nov 18 to Nov 19
$313 total
Nov 18 - Nov 19
Total with taxes and fees
An outdoor pool, self parking, and concierge services are featured at this hotel. WiFi in public areas is free.
"The room was ok. They charged us a $30 a day ($210) resort fee but never told us what if anything it included. We had to beg to get beach towels. They have a continental breakfast one day a week from 8 to 9. By 8:20 they were out of food and never replenished it. There weren’t any dining/drink options ..."

Reviewed on Oct 17, 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
$166 nightly
The price is $187 total per night from Oct 25 to Oct 26
$187 total
Oct 25 - Oct 26
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 ...
"First staff member gave us (4) people together rooms all the way in the back which we had told her we needed a handicap and wheel chair excess-able room. So we had told come back and do again. There were no microwaves in rooms."

Reviewed on Oct 23, 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
$202 nightly
The price is $227 total per night from Oct 25 to Oct 26
$227 total
Oct 25 - Oct 26
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 ...
"Loved the place. Will definitely be back in the future with the family."

Reviewed on Oct 23, 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
$193 nightly
The price is $218 total per night from Oct 25 to Oct 26
$218 total
Oct 25 - Oct 26
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 ...
"Beautiful decor, but noisy Aircon and no drapes in room!"

Reviewed on Oct 23, 2026

Opens in a new windowIbis Bay Beach Resort
Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Blvd Key West FL
$255 nightly
The price is $287 total per night from Oct 25 to Oct 26
$287 total
Oct 25 - Oct 26
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, ...
Opens in a new windowMargaritaville Beach House Key West
Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

4 out of 5
1500 Reynolds Street Key West FL
Fully refundableReserve now, pay when you stay
$306 nightly
The price is $344 total per night from Nov 1 to Nov 2
$344 total
Nov 1 - Nov 2
Total with taxes and fees
A private beach, a full-service spa, and 2 outdoor pools are all featured at this smoke-free resort. Relax with sun loungers and beach umbrellas, and cool off ...
Opens in a new windowCasa Marina Key West, Curio Collection by Hilton
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
$149 nightly
The price is $167 total per night from Oct 29 to Oct 30
$167 total
Oct 29 - Oct 30
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 ...
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.

Recent Truman Annex hotel reviews by fellow wanderers

Beachside Resort & Residences

Beachside Resort & Residences

5 out of 5
Posted less than an hour ago
Travelocity Verified Review
"Loved the place. Will definitely be back in the future with the family."
A verified traveler stayed at Beachside Resort & Residences
Beachside Resort & Residences

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