What are the top rated Cottage Rentals in Truman Annex?

There are a lot of options in Truman Annex. If you plan on staying in the Truman Annex area, consider making a reservation for a few nights at one of these properties as these have been rated the top Cottage Rentals in Truman Annex: <a href="/property/condo-in-old-town-key-west-s-truman-annex-pool-bicycle-free-parking-and-wifi/HA-321297241" class="class="static-page-link"">Condo in Old Town Key West&#39;s Truman Annex - Pool, Bicycle, Free Parking and WiFi</a> <a href="/property/bright-modern-condo-7-minwalk-to-the-beach-pool-bikes-2-furnished-porches/HA-1214841080" class="class="static-page-link"">Bright &amp; Modern Condo—7 MinWalk to the Beach! Pool, Bikes &amp; 2 Furnished Porches!</a> <a href="/property/old-town-2-bicycles-grill-wifi-1st-floor-pool-rent-30-days-get-20-discount/HA-121279213" class="class="static-page-link"">Old Town 2 Bicycles, Grill, WiFi, 1st Floor, Pool! Rent 30 days get 20% discount</a> <a href="/property/sea-breeze-cottage-2-large-decks-pool-free-parking-wifi-in-truman-annex/HA-121987489" class="class="static-page-link"">Sea Breeze Cottage 2 Large Decks, pool, free parking/wifi in Truman Annex</a> <a href="/property/key-west-hen/HA-1214218064" class="class="static-page-link"">Key West Hen</a> <a href="/property/quaint-island-escape-condo-w-spacious-balcony-deck-in-beautiful-truman-annex/HA-121934388" class="class="static-page-link"">Quaint Island Escape Condo w/Spacious Balcony Deck in Beautiful Truman Annex</a> <a href="/property/key-west-rooster/HA-1214018549" class="class="static-page-link"">Key West Rooster</a> <a href="/property/starfish-sunny-townhome-in-quiet-truman-annex-two-blocks-from-duval-st/HA-1213813999" class="class="static-page-link"">STARFISH - SUNNY TOWNHOME in QUIET TRUMAN ANNEX TWO BLOCKS FROM DUVAL ST.</a> <a href="/property/enjoy-more-privacy-in-a-truman-annex-end-unit-townhome/HA-1213552474" class="class="static-page-link"">Enjoy More Privacy in a Truman Annex End Unit Townhome</a> <a href="/property/heart-of-downtown-key-west-cottage-with-off-street-parking/HA-3211713230" class="class="static-page-link"">Heart of Downtown Key West Cottage With Off-Street Parking</a>

How much does it cost to rent a cottage in Truman Annex?

The average cost for a cottage rental in Truman Annex is $742 per night. Cruisevacations has a wide list of great cottages near Truman Annex that would suit your needs. There are single and multiple rooms for solo trips or family vacations.

Do you have any rental cottages in Truman Annex that are suitable for families?

Most of our listed cottages are suitable for families. Check out the complete list of cottages in Truman Annex to find one that works for you.

Are there quality cottages in Truman Annex that have indoor swimming pools?

As of 2026, the data from Cruisevacations shows that there are Over 495 private swimming pools or cottages with indoor pools in the Truman Annex area along with other great amenities.

Truman Annex Cottage Rentals By Owner

MAJESTIC PARADISE @ Truman Annex - Heart of Old Town, Key West

From US $269

10.0 (189 Reviews)

Condo

MAJESTIC PARADISE @ Truman Annex - Heart of Old Town, Key West

Air Conditioner
Parking
Pool

Truman Annex Cottage Rentals & Holiday Homes

Find the best cottages in Truman Annex - We found 495 exact matches

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