Search
Best hotels
Insights
Best value
Tips
FAQs
Map

Hotels in Truman Annex, Key West

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

Here is why travellers 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.

Best hotels in Truman Annex (Key West)

Most recommended Truman Annex hotels

Show all
Sunset Key Cottages - Key West - Living room
Sunset Key Cottages
Truman Annex
9.0Wonderful(202)
Free Wi-Fi
Pet friendly
Spa
$2,080+
Check availability
Weatherstation Inn Circa 1911 - Key West - Living room
Weatherstation Inn Circa 1911
Truman Annex
8.9Very Good(373)
Parking
Free Wi-Fi
Pool
$542+
Check availability
Caribbean House - Key West - Balcony
Caribbean House
Truman Annex
8.6Very Good(1115)
Free Wi-Fi
Pet friendly
$585+
Check availability
Opal Key Resort & Marina - Key West - Pool
Opal Key Resort & Marina
Truman Annex
8.4Very Good(2431)
Free Wi-Fi
Pool
Pet friendly
$803+
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
$1,248+
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
$329+
Check availability
Pineapple Cottage ~ Adorable, Updated Cottage In Old Town With Heated Pool! - Key West - Living room
Pineapple Cottage ~ Adorable, Updated Cottage In Old Town With Heated Pool!
Truman Annex
Free Wi-Fi
$336+
Check availability
Easy Livin By Avantstay Key West Home W Pool Bbq Week Long Stays Only - Key West - Kitchen
Easy Livin By Avantstay Key West Home W Pool Bbq Week Long Stays Only
Truman Annex
Parking
Free Wi-Fi
Pool
$2,525+
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
$773+
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(17)
Free Wi-Fi
Pool
$1,373+
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
$761+
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
$568+
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
$595+
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
$1,050+
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
$709+
Check availability
Hemingway Hideaway in the Truman Annex - Key West - Living room
Hemingway Hideaway in the Truman Annex
Truman Annex
Free Wi-Fi
Pool
$1,109+
Check availability
Hyatt Vacation Club at Sunset Harbor - Key West - Building
Hyatt Vacation Club at Sunset Harbor
Truman Annex
8.3Very Good(34)
Free Wi-Fi
$724+
Check availability
Bahama Gardens - Conch House - Key West
Bahama Gardens - Conch House
Truman Annex
8.0Very Good(10)
Free Wi-Fi
Pool
$1,462+
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
$885+
Check availability
Seashore at the Shipyard - Key West
Seashore at the Shipyard
Truman Annex
7.6Good(15)
Pool
$688+
Check availability
Go to map

Search by stars

2+ stars3+ stars4+ stars

Search by review score

6+ Okay7+ Good8+ Great9+ Excellent

Search by price

$143 - $1,971$1,971 - $3,799$3,799 - $5,627$5,627 - $7,454$7,454+ per night

Search by freebies

Free cancellationFree breakfastFree parkingFree internet

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 September, with average rates of $736. In comparison, March is the most expensive month, with prices at $2,342.

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

Wednesday offers the lowest rates in Truman Annex, with an average nightly price of $1,050. The highest prices are found on Monday, with average rates at $1,378.

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 $298, while a 4-star hotel the lowest price was $669. The cheapest room found overall was for $314.

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 $454 per night. For the same dates, 3-star hotel rooms have been found for as low as $454 per night and 4-star hotel rooms from $972 per night.
Find deals

How much is a Truman Annex hotel?

Here are our most popular & best value hotels

2 stars and below

3 stars

4 stars and above

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 2 days.

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, Caribbean House, and Lighthouse Hotel - Key West Historic Inns 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

Hotels about topic

Show all
Weatherstation Inn Circa 1911 - Key West - Living room
Weatherstation Inn Circa 1911
Truman Annex
8.9Very Good(373)
Parking
Free Wi-Fi
Pool
$542+
Check availability
Sunset Key Cottages - Key West - Living room
Sunset Key Cottages
Truman Annex
9.0Wonderful(202)
Free Wi-Fi
Pet friendly
Spa
$2,080+
Check availability

Popular topics

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, car hires and package deals with KAYAK.