Winter Garden Summer Rentals, Cottages & Cabins

There are a lot of options in Winter Garden. If you plan on staying in the Winter Garden area, consider making a reservation for a few nights at one of these properties as these have been rated the top Summer Rentals in Winter Garden:

• Orange Lake Resort 2 BR/2 BA Condo East Village
• DELUXE 2 BR Villa at Orange Lake Gold Crown Resort
• Amazing Orange Lake Resort - 2 BR River Island Luxury Condo. Near Disney
• Orange Lake Resort - Orlando, FL close to beaches and theme parks
• 3 Bedroom/3 Bath Villa Orange Lake Resort Near Disney. 4/5/25-4/12/25
• 3 Bedroom Villa At Orange Lake Resorts
• 3 getaway weeks available for rent!
• Ultimate Family & Business Getaway: Spacious 2BR villa, pool, golf, & much more.
• 2 BR Condo At Orange Lake. 1 wk Available, Flexible Through 2022, Sleeps 8
• Spring Break 2 Bedroom East Village

In 2026, Holidayrentalvillas offers 57 summer rentals in or around Winter Garden. Find unique home rentals for your summer holiday or a weekend getaway with family and friends.

The average price per night for a summer rental in Winter Garden is $282. Check the full list of summer accommodations in Winter Garden.

There are 57 summer rentals, cabins, cottages and properties that are available to rent. Book for your next trip with Holidayrentalvillas.

Yes, here are some popular summer holiday rentals in Winter Garden that have a private or indoor pool:

• Ultimate Orlando Adventure: Orange Lake Resort - Disney, Universal, Sea World!
• Holiday Inn Club Vacation Resort Orlando
• Ultimate Orlando Adventure: Orange Lake Resort - Disney, Universal, Sea World!
• Ultimate Orlando Adventure: Orange Lake Resort - Disney, Universal, Sea World!

Check all holiday rentals with a pool in Winter Garden on Holidayrentalvillas.