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.

Hotels in Truman Annex (Key West) from $196/night

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

...and more

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.

Bundle and saveSave money when you bundle your flight + hotel.

Best hotels in Truman Annex (Key West)

Sunset Key Cottages

9 Wonderful

Truman Annex$1,238+

$1,238+

Free Wi-Fi

Pet friendly

Spa

Lighthouse Hotel - Key West Historic Inns

8.2 Very good

Truman Annex$505+

$505+

Free Wi-Fi

Pool

Pet friendly

Weatherstation Inn - Key West - Living room

Weatherstation Inn

8.9 Very good

Truman Annex$408+

$408+

Parking

Free Wi-Fi

Pool

Caribbean House - Key West - Balcony

Caribbean House

8.6 Very good

Truman Annex$410+

$410+

Free Wi-Fi

Pet friendly

Opal Key Resort & Marina - Key West - Pool

Opal Key Resort & Marina

8.4 Very good

Truman Annex$580+

$580+

Free Wi-Fi

Pool

Pet friendly

Hyatt Residence Club Key West, Sunset Harbor - Key West - Building

Hyatt Residence Club Key West, Sunset Harbor

7.5 Good

Truman Annex$471+

$471+

Free Wi-Fi

Pool

Ocean Breeze At The Truman Annex In Key West - Key West - Living room

Ocean Breeze At The Truman Annex In Key West

Truman Annex$818+

$818+

Free Wi-Fi

Pool

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$196+

$196+

Free Wi-Fi

Pool

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$200+

$200+

Free Wi-Fi

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$1,515+

$1,515+

Parking

Free Wi-Fi

Pool

The PalmsA beautiful space in the perfect place. - Key West - Balcony

The PalmsA beautiful space in the perfect place.

Truman Annex$559+

$559+

Free Wi-Fi

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

9 Wonderful

Truman Annex$883+

$883+

Free Wi-Fi

Pool

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$501+

$501+

Free Wi-Fi

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$439+

$439+

Sun, Sea, And Sky At The Truman Annex In Key West - Key West - Pool

Sun, Sea, And Sky At The Truman Annex In Key West

Truman Annex$389+

$389+

Free Wi-Fi

Pool

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$396+

$396+

Pool

Green Bamboo At The Truman Annex In Key West - Key West - Living room

Green Bamboo At The Truman Annex In Key West

Truman Annex$632+

$632+

Pool

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

9.5 Wonderful

Truman Annex$622+

$622+

Parking

Free Wi-Fi

Pool

Bahama Gardens - Conch House - Key West

Bahama Gardens - Conch House

8 Very good

Truman Annex$974+

$974+

Free Wi-Fi

Pool

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$527+

$527+

Pool

Go to map

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 $263. In comparison, December is the most expensive month, with prices at $753.

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

Tuesday offers the lowest rates in Truman Annex, with an average nightly price of $459. The highest prices are found on Friday, with average rates at $671.

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 $305, while a 4-star hotel the lowest price was $555. The cheapest room found overall was for $305.

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 $351 per night. For the same dates, 3-star hotel rooms have been found for as low as $351 per night and 4-star hotel rooms from $623 per night.

Find deals

2 stars and below

3 stars

4 stars and above

Low season	September
High season	December
Average price (weeknight)	$596
Average price (weekend night)	$660

Cheapest month to stay with an average 55% drop in price.

Most expensive month to stay with an average 30% rise in price.

Average Sun - Thu price over the last 2 weeks.

Average Fri & Sat price over the last 2 weeks.

If you’re looking for a cheap hotel in Truman Annex, you should consider going during the low season. You’ll generally find lower-priced hotels in Truman Annex in September and November.
If you’re looking for a bargain then KAYAK data shows that you’ll find the best hotel deals in Truman Annex (Key West) if you stay on a Tuesday. On the other hand, the most expensive day for hotel bookings is Friday.
If you’re looking for a last minute bargain, the cheapest 3-star hotel in Truman Annex (Key West) found on KAYAK in the last 2 weeks was $274, while the most expensive was $2,146.
Not sure just how much there is to see and do in Truman Annex? KAYAK users usually book their hotel here for 3 days.

See more tips

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.