Maitland Summer Rentals, Cottages & Cabins

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

• Temporary living that feels like home where you can relax and be yourself.
• Stylish Boutique Guest house in Winter Park
• SPRING LAKE GETAWAY SUITE (Detached Guest House)
• Casa Feliz
• A curated stay in the Historic College Quarter
• nIncredible Private Lakefront Cottage Retreat
• Beautiful Lakefront Gem ~ Pool ~ Fishing ~ 5 Star Location
• Wana Chill Spot w/Pool, Spa, Bar ,Ping Pong, BBQ
• Orlando Poolside Oasis
• Remodeled Home in the Orlando area w/Fire Pit! Close to Universal and Disney!

In 2026, Holidayrentalvillas offers 5 summer rentals in or around Maitland. 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 Maitland is $229. Check the full list of summer accommodations in Maitland.

There are 5 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 Maitland that have a private or indoor pool:

• Beautiful Lakefront Home w/Pool in delightful Altamonte Springs
• Stylish and Spacious Winter Park Retreat Close to Dining, Shopping and Rollins College
• Winter Park College quarters historic district
• Cozy Gated Nature Walk to MallParkPublix 2Story
• Relaxing 3BR Home Near Orlando Downtown & Parks
• The Alfond Inn
• Casa Bella
• Affordable, convenient pet-friendly family space

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