Hotels in Truman Annex, Key West

KAYAK searches hundreds of travel sites at once for hotels in Truman Annex

Here is why travelers choose KAYAK

Free to useThere are no hidden charges or fees.

Filter your dealsFilter by free cancellation, free breakfast and more.

Millions of reviewsCheck ratings based on millions of real guest reviews.

Recommended by KAYAK
Booking Insights
Recommended by KAYAK

Best hotels in Truman Annex (Key West)

Go to map

Search by stars

2+ stars3+ stars4+ stars

Search by review score

6+ Okay7+ Good8+ Great9+ Excellent

Search by price

318 ﷼ - 4,608 ﷼4,608 ﷼ - 8,898 ﷼8,898 ﷼ - 13,188 ﷼13,188 ﷼ - 17,475 ﷼17,475 ﷼+ per night

Search by freebies

Free cancellationFree breakfastFree parkingFree internet

Most recommended Truman Annex hotels

Show all
Sunset Key Cottages - Key West - Restaurant
Sunset Key Cottages
Truman Annex
9.0Wonderful(202)
Free Wi-Fi
Pet friendly
Air Conditioning
4,638 ﷼+
Check availability
Weatherstation Inn - Key West - Living room
Weatherstation Inn
Truman Annex
8.9Very good(393)
Parking
Free Wi-Fi
Pool
Air Conditioning
1,013 ﷼+
Check availability
Caribbean House - Key West - Balcony
Caribbean House
Truman Annex
8.8Very good(1141)
Free Wi-Fi
Pet friendly
Air Conditioning
1,042 ﷼+
Check availability
Opal Key Resort & Marina - Key West - Building
Opal Key Resort & Marina
Truman Annex
8.4Very good(2463)
Free Wi-Fi
Pool
Pet friendly
Air Conditioning
1,316 ﷼+
Check availability
Ocean Breeze At The Truman Annex In Key West - Key West - Living room
Ocean Breeze At The Truman Annex In Key West
Truman Annex
Free Wi-Fi
Pool
Air Conditioning
2,818 ﷼+
Check availability
Shipyard Truman Annex; 620 Thomas St. 1st Floor Available December & Sept 2025 - Key West - Pool
Shipyard Truman Annex; 620 Thomas St. 1st Floor Available December & Sept 2025
Truman Annex
Free Wi-Fi
Pool
Air Conditioning
858 ﷼+
Check availability
The PalmsA beautiful space in the perfect place. - Key West - Balcony
The PalmsA beautiful space in the perfect place.
Truman Annex
Free Wi-Fi
Air Conditioning
1,261 ﷼+
Check availability
Key West Found by AvantStay Close to Shops w Patio Shared Pool Week Long Stays Only - Key West - Bedroom
Key West Found by AvantStay Close to Shops w Patio Shared Pool Week Long Stays Only
Truman Annex
9.0Wonderful(18)
Free Wi-Fi
Pool
Air Conditioning
2,069 ﷼+
Check availability
A Conch Escape At The Truman Annex In Key West - Key West - Pool
A Conch Escape At The Truman Annex In Key West
Truman Annex
Free Wi-Fi
Air Conditioning
1,768 ﷼+
Check availability
Upscale End Unit Home @ Truman Annex Close To Duval St - Key West - Balcony
Upscale End Unit Home @ Truman Annex Close To Duval St
Truman Annex
Air Conditioning
1,203 ﷼+
Check availability
Key West, Gated Truman Annex Condo, new Waterfront Park, and Ft. Zach Beach. - Key West - Pool
Key West, Gated Truman Annex Condo, new Waterfront Park, and Ft. Zach Beach.
Truman Annex
Pool
Air Conditioning
1,176 ﷼+
Check availability
Green Bamboo At The Truman Annex In Key West - Key West - Living room
Green Bamboo At The Truman Annex In Key West
Truman Annex
Pool
Air Conditioning
1,637 ﷼+
Check availability
Beach House Condo by AvantStay Communal Pool Gated Community Great Location Week Long Stays - Key West - Beach
Beach House Condo by AvantStay Communal Pool Gated Community Great Location Week Long Stays
Truman Annex
9.5Wonderful(12)
Parking
Free Wi-Fi
Pool
Air Conditioning
1,945 ﷼+
Check availability
Hemingway Hideaway in the Truman Annex - Key West - Living room
Hemingway Hideaway in the Truman Annex
Truman Annex
Free Wi-Fi
Pool
Air Conditioning
2,319 ﷼+
Check availability
Hyatt Vacation Club at Sunset Harbor - Key West - Pool
Hyatt Vacation Club at Sunset Harbor
Truman Annex
7.7Good(34)
Air Conditioning
4,301 ﷼+
Check availability
Island Time At The Truman Annex In Key West - Key West
Island Time At The Truman Annex In Key West
Truman Annex
Free Wi-Fi
Pool
Air Conditioning
1,588 ﷼+
Check availability
Bahama Gardens - Conch House - Key West
Bahama Gardens - Conch House
Truman Annex
8.0Very good(10)
Free Wi-Fi
Pool
Air Conditioning
3,166 ﷼+
Check availability
Southard Pearl @ The Annex Condo Near Duval & Beach Last Key Services - Key West
Southard Pearl @ The Annex Condo Near Duval & Beach Last Key Services
Truman Annex
Pool
Air Conditioning
1,975 ﷼+
Check availability
Seashore at the Shipyard - Key West
Seashore at the Shipyard
Truman Annex
7.0Good(16)
Pool
Air Conditioning
1,181 ﷼+
Check availability
Keys to Paradise - Shipyard Truman Annex - Key West
Keys to Paradise - Shipyard Truman Annex
Truman Annex
Free Wi-Fi
Pool
Air Conditioning
2,091 ﷼+
Check availability
Booking Insights

KAYAK’s insights for hotels in Truman Annex

Discover seasonal trends, ideal booking windows, and other data-driven tips to plan your stay in Truman Annex with confidence.

Which month has the cheapest hotel rates in Truman Annex?

Hotels are cheapest in Truman Annex in August, with average rates of 2,653 ﷼. In comparison, March is the most expensive month, with prices at 11,434 ﷼.

What is the cheapest day of the week to book a hotel in Truman Annex?

Monday offers the lowest rates in Truman Annex, with an average nightly price of 4,365 ﷼. The highest prices are found on Thursday, with average rates at 5,338 ﷼.

How much is a hotel in Truman Annex for tonight?

The best deal for a 3-star hotel room in Truman Annex found by KAYAK users in the last 3 days was 499 ﷼, while a 4-star hotel the lowest price was 1,152 ﷼. The cheapest room found overall was for 526 ﷼.

How much is a hotel in Truman Annex for this weekend?

The cheapest hotel room in Truman Annex for the upcoming weekend found on KAYAK in the last 3 days was for 709 ﷼ per night. For the same dates, 3-star hotel rooms have been found for as low as 709 ﷼ per night and 4-star hotel rooms from 1,423 ﷼ per night.
Find deals

How much is a Truman Annex hotel?

Here are our most popular & best value hotels

Top tips for finding a hotel deal in Truman Annex

  • Not sure just how much there is to see and do in Truman Annex? KAYAK users usually book their hotel here for 1 day.

FAQs when booking a hotel in Truman Annex

  • What are the best hotels in Truman Annex?

    Truman Annex is a great part of Key West to make your base. If you’re staying in Truman Annex area then Opal Key Resort & Marina, Lighthouse Hotel - Key West Historic Inns, and Caribbean House are all recommended on KAYAK.

  • Which hotels in Truman Annex are romantic?

    If you’re looking for a romantic break with your partner in Truman Annex, then why not stay at Opal Key Resort & Marina, Lighthouse Hotel - Key West Historic Inns, or Caribbean House, which have been recommended by KAYAK users as great for couples.

Where to stay in Truman Annex?

Our map will help you find the perfect hotel in Truman Annex, Key West by showing you the exact location of each hotel.

What Truman Annex hotel guests are talking about

Show all

Popular topics

Hotels about topic

Show all
Weatherstation Inn - Key West - Living room
Weatherstation Inn
Truman Annex
8.9Very good(393)
Parking
Free Wi-Fi
Pool
Air Conditioning
1,013 ﷼+
Check availability
Sunset Key Cottages - Key West - Restaurant
Sunset Key Cottages
Truman Annex
9.0Wonderful(202)
Free Wi-Fi
Pet friendly
Air Conditioning
4,638 ﷼+
Check availability

Everything you need to know for your stay in Key West

Hotels near airports in Key West

Hotels near Key West Airport

Truman Annex hotel deals. Search for hotels in Truman Annex. Find cheap hotel rooms in Truman Annex. KAYAK searches hundreds of travel sites to help you find cheap hotels and book the room that suits you best.

Not what you’re looking for? Find thousands of other hotels, flights and car rentals with KAYAK.