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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 6 to Jul 7
$201 total
Jul 6 - Jul 7
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 ...
"Beautiful location. Room was immaculate and large. Great for a one night stay but plan on coming back and staying longer."

Reviewed on Jul 5, 2026

Opens in a new windowWeatherstation Inn
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
$328 nightly
The price is $369 total per night from Jul 14 to Jul 15
$369 total
Jul 14 - Jul 15
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 location. Beautiful beach area"

Reviewed on Jul 5, 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
$232 nightly
The price is $261 total per night from Jul 14 to Jul 15
$261 total
Jul 14 - Jul 15
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 ...
"The room was basic and not worth the price."

Reviewed on Jul 5, 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
$254 nightly
The price is $286 total per night from Jul 19 to Jul 20
$286 total
Jul 19 - Jul 20
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 enjoyed our stay."

Reviewed on Jul 5, 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
$277 nightly
The price is $312 total per night from Jul 28 to Jul 29
$312 total
Jul 28 - Jul 29
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
$195 nightly
The price is $219 total per night from Jul 6 to Jul 7
$219 total
Jul 6 - Jul 7
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 ...
"Our rooms appliances were very worn. Washer and dryer were very loud when using. No phones to call front desk. Master bathroom door locks were broken and my daughter got locked in. Our main door didn't lock so we had to move a table in Front of it, so we knew if someone was coming in. No pool towels ..."

Reviewed on Jul 4, 2026

Opens in a new windowBeachside Resort & Residences
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
$256 nightly
The price is $288 total per night from Jul 13 to Jul 14
$288 total
Jul 13 - Jul 14
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 ...
"Rooms & amenities were great, but definitely not a beach place to stay."

Reviewed on Jul 5, 2026

Opens in a new windowCasa Marina Key West, Curio Collection by Hilton
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 Jul 6 to Jul 7
$197 total
Jul 6 - Jul 7
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 ...
"Everything was exceptional and staff were friendly and assisted me with whatever I needed. Pools were clean and nice, lots of activities for kids! Food at rum row was Great! Starbucks is a plus to have connected to resort hotel. Shuttle service to old town was Great! Definitely a family friendly ..."

Reviewed on Jul 5, 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
$135 nightly
The price is $152 total per night from Jul 12 to Jul 13
$152 total
Jul 12 - Jul 13
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 ...
"Very good, As I am first time visitor to Key West, staff have guided us where to visit. Also they have shuttle service for downtown."

Reviewed on Jul 5, 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 1 hour ago
Travelocity Verified Review
"I loved that Southernmost Resort had direct access to the beach, 3 pools, a spa. A concierge that could connect you to any tour or restaurant recommendation to anything on the Island. You never had to leave their space if you did not want. you could opt for a quiet stay to recharge and disconnect from the world or be involved in all the fun goings on each day at the resort or steps away from shops, museums, tours. It was a perfect week away for a solo traveler looking to find a bit of respite from the world while trying some new and exciting things like snorkeling the reef, and kayaking the mangroves. Seeing dolphins, tropical fish, manatees, turtles all within an arms reach........GLORIOUS!!"
A verified traveler stayed at Southernmost Beach Resort and Guesthouses
Southernmost Beach Resort and Guesthouses

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