What are the top rated Cottage Rentals in Old Town?

There are a lot of options in Old Town. If you plan on staying in the Old Town area, consider making a reservation for a few nights at one of these properties as these have been rated the top Cottage Rentals in Old Town: <a href="/property/admirals-gold-key-west-truman-annex-villa-close-to-beach-and-duval-w-parking-and-pool-access/HA-3213670891" class="class="static-page-link"">Admirals Gold Key West - Truman Annex Villa - Close to Beach and Duval w Parking and Pool Access</a> <a href="/property/tropical-cottage-by-rent-key-west-vacations-quiet-gated-pool-deck-pet-frien/HA-3214047861" class="class="static-page-link"">TROPICAL COTTAGE by RENT KEY WEST VACATIONS - Quiet &amp; gated. Pool/Deck/Pet frien</a> <a href="/property/last-minute-availability-architect-designed-oasis-in-old-towne-on-a-quiet-lane/HA-121385102" class="class="static-page-link"">LAST MINUTE AVAILABILITY! architect designed OASIS in OLD TOWNE on a quiet lane!</a> <a href="/property/robinson-crusoe-cottage-delight-in-island-vibes-in-this-home-with-a-pool/HA-3214459197" class="class="static-page-link"">~ROBINSON CRUSOE COTTAGE~ Delight in island vibes in this home with a pool.</a> <a href="/property/villa-bella-an-exceptional-5-4-island-home-convenient-to-old-town/HA-3212056313" class="class="static-page-link"">VILLA BELLA - AN EXCEPTIONAL 5/4 ISLAND HOME-Convenient to Old Town</a> <a href="/property/ceasar-s-paradise-a-modern-luxury-retreat-w-4-bedrooms-5-5-baths/HA-3212063207" class="class="static-page-link"">CEASAR&#39;S PARADISE - A MODERN LUXURY RETREAT W/4+ Bedrooms/5.5 Baths</a> <a href="/property/conch-cottages-enjoy-your-next-island-vacation-with-friends-right-here/HA-3214459194" class="class="static-page-link"">~CONCH COTTAGES~ Enjoy your next island vacation with friends right here!</a> <a href="/property/old-town-key-west-compound-with-pool-parking-and-privacy-one-block-off-duval/HA-3212980215" class="class="static-page-link"">Old Town Key West Compound with Pool, Parking and Privacy One Block Off Duval!</a> <a href="/property/poolside-king-room-steps-from-duval/HA-3212721474" class="class="static-page-link"">Poolside King Room Steps from Duval!</a> <a href="/property/old-town-key-west-cottage-3bed-2bath/HA-3213210646" class="class="static-page-link"">Old Town Key West Cottage 3bed/2bath</a>

How much does it cost to rent a cottage in Old Town?

The average cost for a cottage rental in Old Town is $589 per night. Cottageromance has a wide list of great cottages near Old Town that would suit your needs. There are single and multiple rooms for solo trips or family vacations.

Are there any cottages in Old Town that allow pets?

Yes, here are the top cottage rentals in Old Town that allow you to bring your pet: Two Rustic Cottages with Private Hot Tubs & Private Parking - Dogs OK Old Town Garden Villas Tranquility by Avantstay Close to Duval St w/BBQ & Shared Pool PINEAPPLE COTTAGE ~ Adorable, Updated Old Town Cottage w/Shared Heated Pool! <a href="/all/usa/florida/key-west/old-town" class="class="static-page-link"">See all pet-friendly vacation rentals in Old Town on Cottageromance</a>

Do you have any rental cottages in Old Town that are suitable for families?

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

Are there quality cottages in Old Town that have indoor swimming pools?

As of 2026, the data from Cottageromance shows that there are Over 156 private swimming pools or cottages with indoor pools in the Old Town area along with other great amenities.

Old Town Cottage Rentals By Owner

Two Rustic Cottages with Private Hot Tubs & Private Parking - Dogs OK

From US $1,019

9.2 (98 Reviews)

Cabin

Two Rustic Cottages with Private Hot Tubs & Private Parking - Dogs OK

Air Conditioner
Parking
Pet Friendly

Old Town Cottage Rentals & Holiday Homes

Find the best cottages in Old Town - We found 156 exact matches

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