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Oct 17 - Oct 19
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Discover 2,790 Truman Annex hotels and places to stay, with room rates, reviews, and availability. Most hotels are fully refundable.

Premium bedding, iron/ironing board, free WiFi, bed sheets
Weatherstation Inn
Weatherstation Inn
2.5 star property
9.4 out of 10, Exceptional, (973)
"Excellent place to stay, walking distance to historic downtown area. Quaint Room at this historical building was very clean and our check-in was very efficient and friendly. Nice property with parking safely gated for protection. Would definetly stay here again. "
The price is ￥31,252
￥35,159 total
includes taxes & fees
Oct 16 - Oct 17
Weatherstation Inn
Exterior
Hyatt Vacation Club at Sunset Harbor, Key West
Hyatt Vacation Club at Sunset Harbor, Key West
3.5 star property
8.4 out of 10, Very Good, (314)
"Great hotel with excellent location "
The price is ￥36,671
￥46,398 total
includes taxes & fees
Oct 30 - Oct 31
Hyatt Vacation Club at Sunset Harbor, Key West
Waterfront King Guest Room | Exterior
Parrot Key Hotel & Villas
Parrot Key Hotel & Villas
4.0 star property
9.0 out of 10, Wonderful, (1126)
"Nice spacious rooms; shuttle service was great; loved the garden pool area; very convenient location and staff was so helpful! Would definitely stay there again. "
The price is ￥24,168
￥35,900 total
includes taxes & fees
Oct 26 - Oct 27
Parrot Key Hotel & Villas
2 outdoor pools, open 8:00 AM to 10:00 PM, sun loungers
The Perry Hotel & Marina Key West
The Perry Hotel & Marina Key West
4.0 star property
9.4 out of 10, Exceptional, (1120)
"Nice stay. "
The price is ￥26,597
￥38,461 total
includes taxes & fees
Nov 3 - Nov 4
The Perry Hotel & Marina Key West
Outdoor pool, open 7:00 AM to 11:00 PM, cabanas (surcharge)
DoubleTree Resort by Hilton Grand Key - Key West
DoubleTree Resort by Hilton Grand Key - Key West
4.0 star property
8.0 out of 10, Very Good, (1020)
"Great stay. Helpful and attentive staff, transportation provided to the old town and to the beach. "
The price is ￥20,525
￥28,214 total
includes taxes & fees
Oct 27 - Oct 28
DoubleTree Resort by Hilton Grand Key - Key West
Front of property - evening/night
Opal Key Resort & Marina, Key West
Opal Key Resort & Marina, Key West
4.0 star property
9.2 out of 10, Wonderful, (1008)
"Staff was tremendous and location is perfect!! "
The price is ￥37,801
￥48,505 total
includes taxes & fees
Oct 16 - Oct 17
Opal Key Resort & Marina, Key West
Outdoor pool, sun loungers
Havana Cabana at Key West
Havana Cabana at Key West
4.0 star property
8.8 out of 10, Excellent, (1749)
"Great place to stay!"
The price is ￥22,657
￥35,137 total
includes taxes & fees
Oct 29 - Oct 30
Havana Cabana at Key West
Outdoor pool, open 6:00 AM to 10:00 PM, cabanas (surcharge)
Hilton Garden Inn Key West / The Keys Collection
Hilton Garden Inn Key West / The Keys Collection
3.5 star property
7.8 out of 10, Good, (1107)
"Very nice hotel."
The price is ￥14,065
￥20,093 total
includes taxes & fees
Oct 26 - Oct 27
Hilton Garden Inn Key West / The Keys Collection
Garden
Douglas House
Douglas House
3.0 star property
9.6 out of 10, Exceptional, (186)
"Absolute awesome place to stay"
The price is ￥22,312
￥25,979 total
includes taxes & fees
Oct 26 - Oct 27
Douglas House
Boating
Ibis Bay Beach Resort
Ibis Bay Beach Resort
2.5 star property
8.2 out of 10, Very Good, (2002)
"Was a pleasant stay and a good location "
The price is ￥16,711
￥22,881 total
includes taxes & fees
Oct 16 - Oct 17
Ibis Bay Beach Resort
Indoor pool, outdoor pool, open 7:00 AM to 10:00 PM, pool umbrellas
The Laureate Key West
The Laureate Key West
3.5 star property
9.0 out of 10, Wonderful, (1003)
"This is our second time staying there. We love the hotel. It close to everything and have a great view "
The price is ￥24,138
￥31,426 total
includes taxes & fees
Oct 19 - Oct 20
The Laureate Key West
View from property
Courtyard by Marriott Key West Waterfront
Courtyard by Marriott Key West Waterfront
3.0 star property
8.8 out of 10, Excellent, (1013)
"Great place! Friendly and helpful staff! "
The price is ￥23,227
￥26,130 total
includes taxes & fees
Oct 16 - Oct 17
Courtyard by Marriott Key West Waterfront
Outdoor spa tub
NYAH Key West - Adults Only
NYAH Key West - Adults Only
3.0 star property
7.8 out of 10, Good, (1005)
"Nice place, perfect location for getting around on foot. "
The price is ￥81,651
￥98,688 total
includes taxes & fees
Oct 24 - Oct 25
NYAH Key West - Adults Only
3 outdoor pools, open 7:00 AM to 10:00 PM, sun loungers
Winslow's Bungalows - Key West Historic Inns
Winslow's Bungalows - Key West Historic Inns
4.0 star property
9.2 out of 10, Wonderful, (1023)
"The room was clean and the facilities lovely. We enjoyed our stay."
The price is ￥28,692
￥39,963 total
includes taxes & fees
Oct 28 - Oct 29
Winslow's Bungalows - Key West Historic Inns
Restaurant
Sugar Loaf Lodge
Sugar Loaf Lodge
2.5 star property
8.2 out of 10, Very Good, (1002)
"Nice family owned spot. "
The price is ￥18,065
￥20,324 total
includes taxes & fees
Oct 16 - Oct 17
Sugar Loaf Lodge
Outdoor pool
Hyatt Vacation Club at Beach House, Key West
Hyatt Vacation Club at Beach House, Key West
3.5 star property
9.4 out of 10, Exceptional, (1010)
"Great stay"
The price is ￥39,873
￥51,688 total
includes taxes & fees
Oct 29 - Oct 30
Hyatt Vacation Club at Beach House, Key West
Outdoor pool, pool umbrellas, sun loungers
Hampton Inn Key West FL
Hampton Inn Key West FL
2.5 star property
9.0 out of 10, Wonderful, (1258)
"Nice hotel with a great free shuttle into town"
The price is ￥25,679
￥28,888 total
includes taxes & fees
Oct 22 - Oct 23
Hampton Inn Key West FL
Beach nearby, white sand
Margaritaville Beach House Key West
Margaritaville Beach House Key West
4.0 star property
8.8 out of 10, Excellent, (1777)
"Great place to stay"
The price is ￥27,174
￥40,098 total
includes taxes & fees
Oct 28 - Oct 29
Margaritaville Beach House Key West
Daily cooked-to-order breakfast for a fee
Oceans Edge Key West Resort, Hotel & Marina
Oceans Edge Key West Resort, Hotel & Marina
4.0 star property
8.8 out of 10, Excellent, (1735)
"Great hotel"
The price is ￥25,459
￥37,468 total
includes taxes & fees
Oct 21 - Oct 22
Oceans Edge Key West Resort, Hotel & Marina
View from property
Duval House
Duval House
3.0 star property
9.4 out of 10, Exceptional, (1018)
"Very friendly, good breakfasts, clean rooms "
The price is ￥17,872
￥23,370 total
includes taxes & fees
Oct 16 - Oct 17
Duval House
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 and neighborhoods for the activities you enjoy most.
Key West Historic District

Old Town Key West

Old Town, the historic heart of Key West, boasts a central business district and numerous tourist attractions. Explore the Key West Aquarium, Ernest Hemingway House, Mallory Square, and more in this vibrant area.

Smathers Beach showing a bay or harbor, tropical scenes and windsurfing

Beachside

When in Beachside, you can plan a visit to Duval Street and Smathers Beach, some noteworthy sights in the nearby area.

Audubon House and Tropical Gardens featuring a house

Key West Historic District

Old Town Key West boasts a rich history with 2485 historic buildings, and is home to popular attractions like Ernest Hemingway House and Mallory Square. Enjoy the lively atmosphere in the central business district.

Key West featuring a marina, a coastal town and general coastal views

Downtown Key West

If you're spending some time in Downtown Key West, Duval Street and Ernest Hemingway Home and Museum are top sights worth seeing.

New Town

Though New Town might not have many top sights, you can venture to the surrounding area to see attractions like Smathers Beach and Key West Tropical Forest and Botanical Garden.

Top Truman Annex Hotel Reviews

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

10/10 Excellent
"The balcony was not private it was outside our front door located outside. Other then that it was a great stay!"
Danielle 4-night trip
Posted 2 days ago
Southernmost Beach Resort and Guesthouses

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Frequently asked questions

What is Truman Annex like?
You'll be sure to have fun visiting Key West's Truman Annex neighborhood. Be sure to check out Harry S. Truman Little White House and Mel Fisher Maritime Museum as part of your Truman Annex travel plans.
Where is the best place to stay in Truman Annex?
Based on our traveler 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 can I expect to 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 353 Truman Annex hotels and other accommodations to choose from.
If I need to cancel my hotel reservation in Truman Annex, will I receive a refund?
Yes! Most room reservations are refundable provided that you cancel before the hotel's cancellation deadline, which often is within 24-48 hours of your check-in date. If you have a non-refundable reservation, it may still be possible to cancel it and be given a refund within a 24-hour period of your booking. Add dates, click "Search", then filter by "fully refundable" to view top deals in Truman Annex.
Where can I learn more about changing or cancelling my trip to Truman Annex?
To find more details about changing or cancelling your trip to Truman Annex, go to https://www.expedia.com/service/.
What is there to do in this Key West neighborhood?
Harry S. Truman Little White House, Mel Fisher Maritime Museum, and USCGC Ingham Maritime Museum feature captivating exhibits to peruse while you're checking out Truman Annex. Jackson Square and Roy John-Karl Gallery are also a couple of places to visit in the neighborhood. 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.