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Top hotels in Truman Annex

Weatherstation Inn

Weatherstation Inn

2.5 out of 5
57 Front St Key West FL
$219 nightly
The price is $246 total per night from Dec 18 to Dec 19
$246 total
Dec 18 - Dec 19
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 ...
Room was clean and spacious. Good breakfast in the am. Helpful staff. Enjoyed pool at their sister property The Opal.

Reviewed on Dec 14, 2025

Opens in a new windowWeatherstation Inn
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
5950 Peninsular Avenue Key West FL
$236 nightly
The price is $265 total per night from Dec 18 to Dec 19
$265 total
Dec 18 - Dec 19
Total with taxes and fees
A marina, 6 outdoor pools, and a 24-hour gym are all featured at this smoke-free hotel. Business travelers can take advantage of the free WiFi in public areas. ...
Everything was great. Suites were spacious, clean and well designed. Staff was friendly, helpful and courteous in additional knowledgeable. The views were great. Excellent job!

Reviewed on Dec 14, 2025

Opens in a new windowOceans Edge Key West Resort, Hotel & Marina
Hyatt Centric Key West Resort and Spa

Hyatt Centric Key West Resort and Spa

4 out of 5
601 Front St Key West FL
Fully refundableReserve now, pay when you stay
$342 nightly
The price is $385 total per night from Dec 18 to Dec 19
$385 total
Dec 18 - Dec 19
Total with taxes and fees
This smoke-free resort features a full-service spa, a marina, and a restaurant. Enjoy the outdoor pool and perks like free WiFi. Enjoy the 24-hour gym and unwind ...
Nice. Cold weather but still charged $65 for use of pool towels & facilities

Reviewed on Dec 9, 2025

Opens in a new windowHyatt Centric Key West Resort and Spa
Havana Cabana at Key West

Havana Cabana at Key West

4 out of 5
3420 N. Roosevelt Blvd Key West FL
$211 nightly
The price is $237 total per night from Dec 18 to Dec 19
$237 total
Dec 18 - Dec 19
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 ...
Shuttle service was well run and appreciated that they have that service.

Reviewed on Dec 14, 2025

Opens in a new windowHavana Cabana at 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
$219 nightly
The price is $246 total per night from Dec 18 to Dec 19
$246 total
Dec 18 - Dec 19
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 ...
Very comfortable

Reviewed on Dec 15, 2025

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 refundable
$253 nightly
The price is $285 total per night from Dec 18 to Dec 19
$285 total
Dec 18 - Dec 19
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 ...
Room was spotless. Only complaint was the water took awhile to heat up

Reviewed on Dec 10, 2025

Opens in a new windowSouthernmost Beach Resort and Guesthouses
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
$316 nightly
The price is $355 total per night from Dec 18 to Dec 19
$355 total
Dec 18 - Dec 19
Total with taxes and fees
An outdoor pool, self parking, and concierge services are featured at this apartment. WiFi in public areas is free.
staff was friendly room was wonderful

Reviewed on Dec 8, 2025

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
$175 nightly
The price is $197 total per night from Dec 18 to Dec 19
$197 total
Dec 18 - Dec 19
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 an arcade/game room, and families will appreciate ...
Clean, friendly, great pool and game areas, free shuttle was a bonus. Away from the crowded tourist area. Motel has bikes which we rented for two days. Will stay here again.

Reviewed on Dec 14, 2025

Opens in a new windowBlue Flamingo Resort Key West
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
$194 nightly
The price is $218 total per night from Dec 18 to Dec 19
$218 total
Dec 18 - Dec 19
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 ...
Shuttle service was good. Only complaint was we were notified night before mandatory fire alarm testing which was all day the next day. We would have plan our day differently. People in next room were very loud.

Reviewed on Dec 9, 2025

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 1 day ago
Travelocity Verified Review
"Very comfortable "
A verified traveler stayed at Beachside Resort & Residences
Beachside Resort & Residences

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