Truman Annex hotels in Key West

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21 Dec - 22 Dec
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22 Dec - 23 Dec
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26 Dec - 28 Dec
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2 Jan - 4 Jan

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Our top choices for Truman Annex hotels

Premium bedding, iron/ironing board, free WiFi, bed sheets
Weatherstation Inn

Weatherstation Inn

Weatherstation Inn
2.5 star property
Truman Annex
9.4 out of 10, Exceptional, (995)
"Wonderful property safe neighborhood convenient to all activities would stay here again."
United States
William
The price is HK$2,164
HK$2,435 total
includes taxes & fees
22 Dec - 23 Dec
Weatherstation Inn
Exterior
Hyatt Vacation Club at Sunset Harbor, Key West

Hyatt Vacation Club at Sunset Harbor, Key West

Hyatt Vacation Club at Sunset Harbor, Key West
3.5 star property
Truman Annex
8.6 out of 10, Excellent, (323)
"Great location and staff was friendly. The pool area was perfect. "
United States
Deborah
The price is HK$2,581
HK$3,167 total
includes taxes & fees
23 Dec - 24 Dec
Hyatt Vacation Club at Sunset Harbor, Key West
Indoor pool, outdoor pool, open 7:00 AM to 10:00 PM, pool umbrellas
The Laureate Key West

The Laureate Key West

The Laureate Key West
3.5 star property
New Town, 5.2 km from Truman Annex
9.0 out of 10, Wonderful, (1005)
"Nice place to stay!"
Canada
Baohua
The price is HK$1,937
HK$2,399 total
includes taxes & fees
6 Jan - 7 Jan 2026
The Laureate Key West
Outdoor pool
Fairfield by Marriott Inn & Suites Key West at The Keys Collection

Fairfield by Marriott Inn & Suites Key West at The Keys Collection

Fairfield by Marriott Inn & Suites Key West at The Keys Collection
3.5 star property
New Town, 5.8 km from Truman Annex
8.6 out of 10, Excellent, (1009)
"Staff is friendly and knowledgeable in local attractions."
United States
Sheng
The price is HK$1,813
HK$2,258 total
includes taxes & fees
4 Jan - 5 Jan 2026
Fairfield by Marriott Inn & Suites Key West at The Keys Collection
Outdoor pool, pool umbrellas, pool loungers
Hampton Inn Key West FL

Hampton Inn Key West FL

Hampton Inn Key West FL
2.5 star property
5.8 km from Truman Annex
9.0 out of 10, Wonderful, (1292)
"Wonderful stay"
United States
Lindsey
The price is HK$2,164
HK$2,434 total
includes taxes & fees
4 Jan - 5 Jan 2026
Hampton Inn Key West FL
Outdoor pool, open 7:00 AM to 11:00 PM, pool cabanas (surcharge)
DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West
4.0 star property
5.8 km from Truman Annex
8.2 out of 10, Very good, (1003)
"Nice property, comfortable stay - cookies and staff are great!"
United States
David
The price is HK$1,861
HK$2,357 total
includes taxes & fees
4 Jan - 5 Jan 2026
DoubleTree Resort by Hilton Grand Key - Key West
View from property
Courtyard by Marriott Key West Waterfront

Courtyard by Marriott Key West Waterfront

Courtyard by Marriott Key West Waterfront
3.0 star property
Northside Resort, 4.1 km from Truman Annex
9.0 out of 10, Wonderful, (1002)
"Room clean, nice pool area"
United States
Tami
The price is HK$2,132
HK$2,399 total
includes taxes & fees
4 Jan - 5 Jan 2026
Courtyard by Marriott Key West Waterfront
Individually decorated, individually furnished, iron/ironing board
Authors of Key West Guest House

Authors of Key West Guest House

Authors of Key West Guest House
3.0 star property
The Meadows, 1.6 km from Truman Annex
9.0 out of 10, Wonderful, (1002)
"The hotel was beautiful and perfectly located! We loved our stay and would love to come back one day!"
United States
Lenin
Authors of Key West Guest House
Outdoor pool, open 6:00 AM to 10:00 PM, pool cabanas (surcharge)
Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection
3.5 star property
New Town, 5.8 km from Truman Annex
8.0 out of 10, Very good, (1164)
"Great location, clean rooms, and great pools!"
United States
Robin
The price is HK$2,429
HK$2,951 total
includes taxes & fees
14 Jan - 15 Jan 2026
Hilton Garden Inn Key West / The Keys Collection
Restaurant
Sugar Loaf Lodge

Sugar Loaf Lodge

Sugar Loaf Lodge
2.5 star property
26.5 km from Truman Annex
8.2 out of 10, Very good, (1005)
"Great place to stary. Staff was very nice."
United States
norka
The price is HK$1,082
HK$1,217 total
includes taxes & fees
22 Dec - 23 Dec
Sugar Loaf Lodge
Terrace/patio
Alexanders Guesthouse - Adult Exclusive, LGBTQ Friendly

Alexanders Guesthouse - Adult Exclusive, LGBTQ Friendly

Alexanders Guesthouse - Adult Exclusive, LGBTQ Friendly
3.5 star property
Old Town Key West, 1.4 km from Truman Annex
9.8 out of 10, Exceptional, (134)
"We absolutely loved finding this gem to stay on our first visit to Key West. Great location, wonderful staff, and excellent room. "
United States
Sammy
Alexanders Guesthouse - Adult Exclusive, LGBTQ Friendly
Outdoor pool, pool loungers
The Saint Hotel Key West, Autograph Collection, Adult Only

The Saint Hotel Key West, Autograph Collection, Adult Only

The Saint Hotel Key West, Autograph Collection, Adult Only
3.5 star property
Historic Seaport, 0.4 km from Truman Annex
9.0 out of 10, Wonderful, (344)
"Great spot!"
United States
Elizabeth
The price is HK$2,404
HK$2,705 total
includes taxes & fees
23 Dec - 24 Dec
The Saint Hotel Key West, Autograph Collection, Adult Only
Beach nearby, white sand
Margaritaville Beach House Key West

Margaritaville Beach House Key West

Margaritaville Beach House Key West
4.0 star property
3.6 km from Truman Annex
8.8 out of 10, Excellent, (1773)
" Great location "
United States
Kristen
The price is HK$2,630
HK$3,461 total
includes taxes & fees
14 Jan - 15 Jan 2026
Margaritaville Beach House Key West
Outdoor pool, open 7:00 AM to 10:00 PM, free pool cabanas, pool loungers
Fairfield Inn and Suites by Marriott Key West

Fairfield Inn and Suites by Marriott Key West

Fairfield Inn and Suites by Marriott Key West
3.0 star property
New Town, 3.3 km from Truman Annex
7.8 out of 10, Good, (1182)
"Overall good stay! The breakfast was good and always clean. Hotel seemed a little older but was well kept. Pool was relaxing to sit by and enjoy!"
United States
Michelle
The price is HK$1,712
HK$2,145 total
includes taxes & fees
19 Jan - 20 Jan 2026
Fairfield Inn and Suites by Marriott Key West
1 bedroom
Island View 1BR Residence With Balcony

Island View 1BR Residence With Balcony

Island View 1BR Residence With Balcony
2.0 star property
5.9 km from Truman Annex
10.0 out of 10, Exceptional, (2)
"Great place it is a full apartment with everything you could need and very clean "
United States
Luis
The price is HK$3,785
HK$4,919 total
includes taxes & fees
5 Jan - 6 Jan 2026
Island View 1BR Residence With Balcony
Outdoor pool
Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West
3.5 star property
5.7 km from Truman Annex
9.6 out of 10, Exceptional, (1004)
"Great staff, hotel and pool."
United States
Lilly
The price is HK$3,102
HK$3,840 total
includes taxes & fees
7 Jan - 8 Jan 2026
Hyatt Vacation Club at Windward Pointe, Key West
Exterior
La Concha Key West, Autograph Collection

La Concha Key West, Autograph Collection

La Concha Key West, Autograph Collection
4.0 star property
Historic Seaport, 0.5 km from Truman Annex
9.0 out of 10, Wonderful, (295)
"Very nice staff! Clean hotel! "
United States
Tabitha Hall
The price is HK$2,327
HK$2,880 total
includes taxes & fees
22 Dec - 23 Dec
La Concha Key West, Autograph Collection
Outdoor pool
Hyatt Vacation Club at Beach House, Key West

Hyatt Vacation Club at Beach House, Key West

Hyatt Vacation Club at Beach House, Key West
3.5 star property
6 km from Truman Annex
9.4 out of 10, Exceptional, (1004)
"The room was clean and property was so nice and relaxing. "
United States
Kristen
The price is HK$3,102
HK$3,840 total
includes taxes & fees
7 Jan - 8 Jan 2026
Hyatt Vacation Club at Beach House, Key West
2 outdoor pools, open 7:00 AM to 11:00 PM, pool cabanas (surcharge)
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

Blue Flamingo Resort Key West
4.0 star property
New Town, 5.6 km from Truman Annex
8.0 out of 10, Very good, (1785)
"Great, friendly staff, nice amenities, easy parking and convenient location "
Canada
Caitlyn
The price is HK$1,884
HK$2,557 total
includes taxes & fees
8 Jan - 9 Jan 2026
Blue Flamingo Resort Key West
Balcony
Simonton Court Historic Inn & Cottages

Simonton Court Historic Inn & Cottages

Simonton Court Historic Inn & Cottages
2.5 star property
Historic Seaport, 0.6 km from Truman Annex
9.8 out of 10, Exceptional, (883)
"The staff was really nice"
United States
doug
The price is HK$2,534
HK$2,851 total
includes taxes & fees
22 Dec - 23 Dec
Simonton Court Historic Inn & Cottages
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.
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Where to stay in Truman Annex

Find the best Truman Annex areas for the activities you enjoy most.

Old Town Key West

While visiting Old Town Key West, you might make a stop by sights like Duval Street and Ernest Hemingway Home and Museum.

Key West Historic District

Travellers to Key West Historic District praise its fantastic nightlife. If you've got some more time to explore, be sure to stop by Duval Street and Key West Cemetery.

Downtown Key West

While visiting Downtown Key West, you might make a stop by sights like Duval Street and Ernest Hemingway Home and Museum.

New Town

While there might not be top attractions in New Town, you can explore the larger area and discover places like Smathers Beach and Key West Tropical Forest and Botanical Garden.

Historic Seaport

If you're spending some time in Historic Seaport, Duval Street and Key West Historic Seaport are top sights worth seeing.

Top Truman Annex Hotel Reviews

Frequently asked questions

What is Truman Annex like?
You'll be sure to have fun exploring Key West's Truman Annex neighbourhood. Make sure that you visit Harry S. Truman Little White House and Jackson Square as part of your Truman Annex travel plans.
Where is the best place to stay in Truman Annex?
Based on our traveller data, Weatherstation Inn is one of the top choices for your stay in Truman Annex. This B&B is a short 5-minute walk from Duval Street, and it offers free breakfast and an outdoor pool. Another good choice for your stay in the area is Hyatt Vacation Club at Sunset Harbor, Key West.
How many hotels will I find in the Truman Annex area?
If you're searching for places to stay in Key West, Expedia has something to meet your needs with 351 Truman Annex hotels and other accommodation options to choose from.
If I need to cancel my hotel reservation in Truman Annex, will I receive a refund?
Yes! You'll find that most hotel reservations are fully refundable provided that you cancel before the hotel's cancellation deadline, which is often 24 or 48 hours before your scheduled arrival. If your reservation is non-refundable, you may still be able to cancel and be given a refund within 24 hours of your booking. Enter your dates, click on "Search", then filter by "fully refundable" to review top deals in Truman Annex.
What is there to do in this Key West neighbourhood?
Harry S. Truman Little White House, Mel Fisher Maritime Museum and USCGC Ingham Maritime Museum feature captivating exhibits to peruse while you're exploring Truman Annex. Jackson Square and Roy John-Karl Gallery are also a couple of places to visit in the neighbourhood. A few places to visit in the area around Truman Annex include Duval Street, Key West Film Society and Florida Keys Eco - Discovery Center. While you're out sightseeing, We Cycle Key West and Heritage House Museum are a couple of additional sights to visit in Key West.

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