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/charming-home-3-blocks-from-historic-park-avenue-one-block-from-lake-virginia/HA-3212423558" class="class="static-page-link"">Charming home 3 blocks from historic Park Avenue &amp; one block from Lake Virginia</a> <a href="/property/award-winning-boutique-hotel-close-to-parks-rollins-college-rooftop-pool/HA-1219713912" class="class="static-page-link"">Award Winning Boutique Hotel Close to Parks &amp; Rollins College, Rooftop Pool</a> <a href="/property/lakefront-condo-w-sunroom-office-lakeside-pool/HA-3212066118" class="class="static-page-link"">Lakefront Condo w/Sunroom, Office, &amp; Lakeside Pool</a> <a href="/property/amazing-location-walk-to-everything/HA-3211986130" class="class="static-page-link"">Amazing location- walk to everything</a> <a href="/property/winter-park-bungalow-outdoor-oasis-rollins-college-park-ave-fenced-yard/HA-3211060352" class="class="static-page-link"">Winter Park Bungalow &amp; Outdoor Oasis - Rollins College, Park Ave &amp; Fenced Yard</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>

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

The average cost for a cottage rental in Winter Park is $228 per night. Cruisevacations 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: 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 Cruisevacations</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 Cruisevacations shows that there are Over 184 private swimming pools or cottages with indoor pools in the Winter Park area along with other great amenities.

Winter Park Cottage Rentals By Owner

Modern Elegance In The Heart Of Winter Park - 2 beds/2 baths

From US $180

New

Apartment

Modern Elegance In The Heart Of Winter Park - 2 beds/2 baths

Air Conditioner
Parking
Pet Friendly

Winter Park Cottage Rentals & Holiday Homes

Find the best cottages in Winter Park - We found 184 exact matches

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