What are the top rated Cottage 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 Cottage Rentals in Winter Park: <a href="/property/great-family-home/HA-321466067" class="class="static-page-link"">Great Family Home</a> <a href="/property/great-location/HA-3212281630" class="class="static-page-link"">GREAT LOCATION 🏡</a> <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/winter-park-pool-home-close-to-lake-virginia-rollins-college-park-ave/HA-3212824954" class="class="static-page-link"">Winter Park Pool home close to Lake Virginia, Rollins College &amp; Park Ave.</a> <a href="/property/just-3-blocks-to-park-ave-shops-restaurants-2-from-the-winter-park-village/HA-3211944157" class="class="static-page-link"">Just 3 Blocks to Park Ave Shops/Restaurants, 2 From The Winter Park Village!</a> <a href="/property/home-away-from-home-in-the-heart-of-charming-winter-park/HA-3213942572" class="class="static-page-link"">Home away from home in the heart of charming Winter Park!</a> <a href="/property/location-cozy-comfort-2-blocks-from-park-ave-w-pool-hot-tub-and-grill-station/HA-3212913776" class="class="static-page-link"">LOCATION! COZY COMFORT 2 BLOCKS FROM PARK AVE W POOL, HOT TUB AND GRILL STATION!</a> <a href="/property/cozy-comfort-just-2-blocks-from-park-ave/HA-3212913809" class="class="static-page-link"">Cozy Comfort Just 2 Blocks From Park Ave!</a> <a href="/property/6-mi-to-downtown-orlando-quiet-home-w-sunroom/HA-1219846580" class="class="static-page-link"">6 Mi to Downtown Orlando: Quiet Home w/Sunroom</a> <a href="/property/you-re-pampered-here-just-3-blocks-from-park-avenue/HA-3212745073" class="class="static-page-link"">You&#39;re Pampered Here - Just 3 Blocks From Park Avenue!</a>

How much does it cost to rent a cottage in Winter Park?

The average cost for a cottage rental in Winter Park is $149 per night. Execstays has a wide list of great cottages near Winter Park that would suit your needs. There are single and multiple rooms for solo trips or family vacations.

Are there any cottages in Winter Park that allow pets?

Yes, here are the top cottage rentals in Winter Park that allow you to bring your pet: A curated stay in the Historic College Quarter Mid Century Modern Cottage in The Heart of Winter Park Modern Elegance In The Heart Of Winter Park - 2 beds/2 baths Tranquil Oasis 4BR Pool Home The Alfond Inn Cute bungalow minutes walk from Park Avenue. <a href="/all/usa/florida/winter-park" class="class="static-page-link"">See all pet-friendly vacation rentals in Winter Park on Execstays</a>

Do you have any rental cottages in Winter Park that are suitable for families?

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

Are there quality cottages in Winter Park that have indoor swimming pools?

As of 2026, the data from Execstays shows that there are Over 2 private swimming pools or cottages with indoor pools in the Winter Park area along with other great amenities.