What are the top rated Pet Friendly Vacation Rentals in Winter Park?

There are a lot of options in Winter Park. If you plan on staying in the Winter Park 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 Winter Park: <a href="/property/amazing-lakefront-mid-modern-3-bed-winter-park-home-surrounded-by-natural-beauty/HA-3214514306" class="class="static-page-link"">Amazing lakefront mid-modern 3-bed Winter Park home surrounded by Natural Beauty</a> <a href="/property/mid-century-modern-cottage-in-the-heart-of-winter-park/HA-321919138" class="class="static-page-link"">Mid Century Modern Cottage in The Heart of Winter Park</a> <a href="/property/coastal-feel-modern-appeal/HA-321450575" class="class="static-page-link"">Coastal Feel - Modern Appeal</a> <a href="/property/the-alfond-inn/BC-585163" class="class="static-page-link"">The Alfond Inn</a> <a href="/property/stylish-3br-2ba-home-in-lake-view-retreat-near-to-park-trails-pickleball-golf/HA-3214853220" class="class="static-page-link"">Stylish 3BR/2BA Home in Lake View Retreat, near to Park,Trails,Pickleball,Golf.</a> <a href="/property/winter-park-3b-2b-home-with-king-bed-gym-fenced-yard/HA-3214346827" class="class="static-page-link"">Winter Park: 3B 2B Home with King Bed, Gym, &amp; Fenced Yard</a> <a href="/property/winter-park-charmer-heated-pool-home-close-to-everything/HA-3213732296" class="class="static-page-link"">Winter Park Charmer - Heated Pool Home - Close to everything</a> <a href="/property/luxury-living-just-3-blocks-from-park-ave/HA-3212620321" class="class="static-page-link"">Luxury Living Just 3 Blocks From Park Ave!</a> <a href="/property/charming-2-bedroom-apartment-with-ac-and-wifi-in-enchanting-winter-park/HA-3213769401" class="class="static-page-link"">Charming 2-bedroom apartment with AC and WiFi in enchanting Winter Park</a> <a href="/property/park-plaza-hotel-orlando-winter-park/BC-517837" class="class="static-page-link"">Park Plaza Hotel Orlando - Winter Park</a>

How many pet-friendly vacation rentals are available in Winter Park on Execstays?

There are more than 87 pet-friendly rentals available on Execstays. Check prices and availability in Winter Park 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 Winter Park?

There are many dog-friendly vacation homes available in Winter Park. Here are the most popular pet-friendly places, ranked by their guest rating as listed in Winter Park: Modern Elegance In The Heart Of Winter Park - 2 beds/2 baths Tranquil Oasis 4BR Pool Home Cute bungalow minutes walk from Park Avenue. Spacious Modern Japandi Retreat - Winter Park

Do you have any luxury vacation homes that allow pets in or near Winter Park?

Most definitely! There are many luxury places to stay in Winter Park. 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 Winter Park. Though note, more expensive is not always better.