Longwood Summer Rentals, Cottages & Cabins

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

• Relax by the pool at this retreat near parks, kayaking, and downtown.
• Spacious Family House with Private Pool in Central Florida
• Spacious and relaxing Home - North Of Orlando In Longwood, Florida
• Refreshing Oasis with Massage Chair, Game Garage, Large Fenced Yard +Retro games
• 6 months min
• Cozy Studio – Minutes to Wekiva, Disney & downtown Orl - Netflix - XL parking
• Pool Access! Dog-Friendly Retreat 16 Mi to Orlando
• Resort Like house, 4 bedrooms, 3 bathrooms
• Pool Access! Dog-Friendly Retreat 16 Mi to Orlando
• The American Dream House – Lakefront Luxury with 2 Heated Pools & Hot Tub

In 2026, Holidayrentalvillas offers 68 summer rentals in or around Longwood. 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 Longwood is $289. Check the full list of summer accommodations in Longwood.

There are 68 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 Longwood that have a private or indoor pool:

• Lakefront Home Where You Can Retreat And Relax
• Fire Pit and Private Yard Family Home in Longwood!
• 2BR Dog-friendly Oasis w/Shared Pool & Patio
• Tropical Oasis - Heated Luxury Pool - Game Room

Check all holiday rentals with a pool in Longwood on Holidayrentalvillas.