What are the top rated Pet Friendly Vacation 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 Pet Friendly Vacation Rentals in Old Town: <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/eyebrow-suite-2bd-1-5ba-suite-off-duval/HA-3214063154" class="class="static-page-link"">Eyebrow Suite - 2bd/1.5ba Suite off Duval</a> <a href="/property/oasis-in-old-town-our-special-home/HA-32135288" class="class="static-page-link"">Oasis in Old Town - our special home</a> <a href="/property/margarita-cottage-bask-in-sunshine-and-lounge-by-your-pool-in-paradise/HA-3214459196" class="class="static-page-link"">~MARGARITA COTTAGE~ Bask in sunshine and lounge by your pool in paradise.</a> <a href="/property/the-ivy-cottage-private-home-in-key-west/HA-3214599522" class="class="static-page-link"">The Ivy Cottage - Private Home in Key West</a> <a href="/property/havana-lane-an-updated-classic-conch-cottage-with-still-a-rustic-edge/HA-321475033" class="class="static-page-link"">Havana Lane: An updated classic conch cottage with still a rustic edge!</a> <a href="/property/cozy-cottage-with-private-hot-tub-tranquil-garden-parking-dogs-ok/HA-3211204474" class="class="static-page-link"">Cozy Cottage with Private Hot Tub, Tranquil Garden &amp; Parking - Dogs OK</a> <a href="/property/courtney-s-place-historic-cottages-inns/BC-508589" class="class="static-page-link"">Courtney&#39;s Place Historic Cottages &amp; Inns</a> <a href="/property/dog-friendly-cottage-with-private-hot-tub-garden-great-downtown-location/HA-3211204475" class="class="static-page-link"">Dog-Friendly Cottage with Private Hot Tub &amp; Garden - Great Downtown Location</a> <a href="/property/find-your-zen-at-hidden-treasure/HA-3214056308" class="class="static-page-link"">Find your zen at HIDDEN TREASURE</a>

How many pet-friendly vacation rentals are available in Old Town on Cottageromance?

There are more than 61 pet-friendly rentals available on Cottageromance. Check prices and availability in Old Town and last updated on January 2026. Check an individual property if they have restrictions on the size or numbers of pets.

Which is the best dog-friendly place to stay in Old Town?

There are many dog-friendly vacation homes available in Old Town. Here are the most popular pet-friendly places, ranked by their guest rating as listed in Old Town: Two Rustic Cottages with Private Hot Tubs & Private Parking - Dogs OK Villa Angelita by Last Key Realty ~ Chick-A-Pea Cottage ~ Enjoy Key West’s charisma, with a pool, and parking! Old Town Garden Villas - Abaco Suite

Do you have any luxury vacation homes that allow pets in or near Old Town?

Most definitely! There are many luxury places to stay in Old Town. Use our search filter to discover all of our luxury accommodations where pets are welcome, then choose the one that matches your taste. Sorting by price is another way to find the most expensive dog-friendly home in Old Town. Though note, more expensive is not always better.