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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 Jun 28 to Jun 29
$201 total
Jun 28 - Jun 29
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 ...
"Thanks."

Reviewed on Jun 16, 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
$199 nightly
The price is $223 total per night from Jul 14 to Jul 15
$223 total
Jul 14 - Jul 15
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 ...
"my daughter and and I were there for two days. Everything was exceptional. We love the pool the food trucks and the ability to catch the shuttle. Definitely recommend."

Reviewed on Jun 20, 2026

Opens in a new windowHavana Cabana at 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
$266 nightly
The price is $299 total per night from Jun 29 to Jun 30
$299 total
Jun 29 - Jun 30
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 ...
"This was a great stay. The staff were very kind, the property well kept, and the events / amenities were perfect. The location relative to Duval St. was perfect. The cafe, pools, pool bars and beach chairs were mostly available while we were there (mid june)."

Reviewed on Jun 21, 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
$252 nightly
The price is $284 total per night from Jun 29 to Jun 30
$284 total
Jun 29 - Jun 30
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 ...
"The beach shuttle was great. Due to the location of the hotel and the sargassum, it smelled horrible and you couldn’t use the beach. At the pool, there was a bees nest near the pool so the bees were everywhere. They were told by several people, but never handled during our stay. The bed was also ..."

Reviewed on Jun 19, 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
$301 nightly
The price is $339 total per night from Jul 16 to Jul 17
$339 total
Jul 16 - Jul 17
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, wonderful room, great pool, and great views. Lacking services: no shuttle, no restaurant, you pay resort fees per night but no amenities? We feel like they used the bait and switch on us, great reservation price on room but hit you with nightly fees once you get there. That was our ..."

Reviewed on Jun 16, 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 Jun 28 to Jun 29
$239 total
Jun 28 - Jun 29
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 ...
"Staff were nice and helpful. Expedia didn’t put in the notes what I paid for, but this hotel did what was right and gave us the ocean view suite like I paid for."

Reviewed on Jun 20, 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
Fully refundableReserve now, pay when you stay
$175 nightly
The price is $197 total per night from Jun 28 to Jun 29
$197 total
Jun 28 - Jun 29
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"

Reviewed on Jun 21, 2026

Opens in a new windowBlue Flamingo Resort 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
$243 nightly
The price is $274 total per night from Jun 30 to Jul 1
$274 total
Jun 30 - Jul 1
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 ...
"This hotel is overpriced and, in my experience, engages in misleading advertising. As a local who visits the Florida Keys frequently, I have stayed at many hotels throughout the area. This was my first stay at Casa Marina, and I was genuinely excited because I had heard positive things about the ..."

Reviewed on Jun 19, 2026

Opens in a new windowCasa Marina Key West, Curio Collection by Hilton
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
$140 nightly
The price is $158 total per night from Jun 28 to Jun 29
$158 total
Jun 28 - Jun 29
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 have always stayed at Hilton and that Hilton did not have complementary continental breakfast. We had to pay $19 and it was not worth $19 at all, and we were not informed when we checked in. This was the first time that there was a fee for the breakfast at Hilton."

Reviewed on Jun 19, 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

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