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Our top choices for Southwest Orlando cottages

Upstay: Bright Family-friendly Retreat With Patio

Chatham Park

₩404,850 total

includes taxes & fees

Jan 6 - Jan 7, 2026

Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema

Kissimmee

₩1,777,820 total

includes taxes & fees

Dec 29 - Dec 30

Watersong Swanky

Davenport

Fire Pit & Yard: Updated Winter Garden Home!

Winter Garden

₩751,511 total

includes taxes & fees

Dec 28 - Dec 29

Upstay: 6BR Resort Home w Pool & Basketball Court

Kissimmee

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Top Southwest Orlando Hotel Reviews

DoubleTree by Hilton at the Entrance to Universal Orlando

10/10 Excellent

"Staff was amazing, we stayed 3 nights and room was cleaned and restocked every night very nice!!! Amenities were amazing all in all a wonderful place to stay and so close to Universal!!!!"

Residence Inn by Marriott Near Universal Orlando™

10/10 Excellent

"The room was okay. We expected them to have the blankets and pillows needed for our stay since our daughter was sleeping on the couch, but they ran out of sheets and pillows. Thankfully we had a sleeping bag with us from the long trip. "