What are the top rated Villa 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 Villa Rentals in Winter Park: <a href="/property/newly-updated-topflr-views-of-foothills-river-private-balcony-hideaway-park/HA-3211989957" class="class="static-page-link"">Newly Updated TopFlr Views Of FootHills River Private Balcony Hideaway Park</a> <a href="/property/enjoy-a-front-row-seat-to-all-winter-park-downtown-activities/HA-1214585147" class="class="static-page-link"">Enjoy a front row seat to all Winter Park downtown activities!</a> <a href="/property/updated-winter-park-condo-w-indoor-heated-pool/HA-1219879645" class="class="static-page-link"">Updated Winter Park Condo w/Indoor Heated Pool!</a> <a href="/property/the-slopeside-building-on-the-mountian-ski-down-110-ft-to-the-gondola/HA-121234948" class="class="static-page-link"">THE SLOPESIDE BUILDING! ON THE MOUNTIAN! SKI DOWN 110 FT TO THE GONDOLA!</a> <a href="/property/luxury-condo-414-i-pool-i-club-house-i-hot-tub-i-best-price-i-discounted-attractions/HA-1219883855" class="class="static-page-link"">Luxury Condo 414 I Pool I Club House I Hot Tub I Best Price I Discounted Attractions</a> <a href="/property/beautiful-two-bedroom-condo-in-winter-park-pool-hot-tub-free-transportation/HA-3211304932" class="class="static-page-link"">Beautiful two bedroom condo in Winter Park! Pool, hot tub, free transportation.</a> <a href="/property/wp-base-zephyr-mtn-ldge-1br-ski-in-out-smart-tvs-solo-wifi-new-bath/HA-3211473926" class="class="static-page-link"">WP Base! Zephyr Mtn Ldge 1BR Ski In/Out, Smart TVs, solo WiFi, NEW BATH</a> <a href="/property/zephyr-mtn-lodge-slopeside-true-ski-in-ski-out-at-wp-base-many-upgrades/HA-321872914" class="class="static-page-link"">Zephyr Mtn Lodge Slopeside - True ski-in/ski-out at WP base - many UPGRADES</a> <a href="/property/enjoy-the-vibe-of-the-village-of-winter-park-steps-from-3br-ultra-clean-condo/HA-3211652172" class="class="static-page-link"">Enjoy the vibe of the village of Winter Park- steps from 3BR ultra-clean condo!</a> <a href="/property/true-ski-in-out-dont-hit-request-to-book-without-asking-please-use-contact-host/HA-32173502" class="class="static-page-link"">True ski in out.Don’t hit request to book without asking please,use contact host</a>

What is the rate per night for renting a villa near Winter Park?

At Isleofpalmsresorts, the average rental fee for standard villas in Winter Park is $498 per night. Isleofpalmsresorts has a large database of quality villas near Winter Park that are suitable for families, a romantic getaway, or a solo trip with single or multiple bedrooms.

Do you have a villa in Winter Park that allows pets?

Yes, here are the top villas rentals in Winter Park that are pet friendly: Best Value Luxury Townhome in Lakota across from Ski Resort, Private Hot Tub! Ski-In and Out Zephyr Mtn Lodge Condo with Hot Tub Access Convenient Winter Park, Colorado, Vacation Rental! Large Glass Front with Beautiful Mountain Views See all pet-friendly vacation rentals in Winter Park on Isleofpalmsresorts

Are there any rental villas in Winter Park that are suitable for families?

Most of our listed villas are suitable for families. The number of rooms varies, and you can check out the complete list of villas in Winter Park to find what works for you.

Do your rental villas in Winter Park have indoor swimming pools?

Based on the 2026 data from our Isleofpalmsresorts site, there are more than 2422 private swimming pools or villas with indoor pools in or near Winter Park.

Winter Park Villa Rentals【 LUXURY 】

Best Value Luxury Townhome in Lakota across from Ski Resort, Private Hot Tub!

From US $619

10.0 (94 Reviews)

House

Best Value Luxury Townhome in Lakota across from Ski Resort, Private Hot Tub!

Parking
Pet Friendly
TV

Winter Park Villa Rentals & Homes

Find villas near Winter Park - We found 2422 exact matches

When do you want to travel?