Upstay

12/31/2024

As we welcome 2025, we want to thank you for choosing our homes for your getaways this year. It's been a joy to be part of your travel stories and we're looking forward to making your stays even more comfortable and memorable in the year ahead.

Wishing you a wonderful New Year filled with great adventures!

Warmly,
The Upstay Team

12/28/2024

Orlando is a city that dares you to take risks, embrace adventure, and find joy in the unexpected. Upstay properties strike the perfect balance—close enough to all the action of Orlando’s theme parks, but nestled in peaceful settings so you can recharge in tranquility.

12/27/2024

This gorgeous mansion is designed with families and groups in mind, offering spacious living areas, modern conveniences, and private amenities. The home features 10 spacious bedrooms, a fully equipped kitchen, a private pool and hot tub with a screened-in lanai, and plenty of comfortable lounging spaces to unwind after a day at Orlando's theme parks.

Book Direct and Save!
https://www.upstay.com/rentals/2176

12/27/2024

This 2-bedroom home in East Austin is the perfect spot for your next getaway! Enjoy the backyard firepit, BBQ grill, and modern design of this contemporary retreat.

Book Direct and Save!
https://www.upstay.com/rentals/2127

12/27/2024

Looking for the perfect place to stay for your next Orlando family vacation? Then look no further! This gorgeous 5 bedroom home is big enough to host up to 12 guests at a time, and there's plenty of space for everyone.

Book Direct and Save!
https://www.upstay.com/rentals/2122

12/27/2024

Orlando isn’t just a destination for thrills—it’s also a haven for indulgence. No matter how you choose to spoil yourself, Orlando has endless opportunities to make every moment feel extraordinary. Whether you're looking for a cozy condo for two or a spacious villa for a group, Upstay offers a range of accommodations to suit your needs and preferences.

12/26/2024

Orlando is the ultimate playground for the young at heart! Whether you're riding the Hogwarts Express, hugging Mickey Mouse, or flying with dragons, every corner is a chance to relive childhood dreams. When it comes to finding the perfect place to stay in Orlando, Upstay has you covered with a blend of comfort, convenience, and style that makes every trip unforgettable.

12/24/2024

From our home to yours, here's wishing you a happy holiday season!

12/11/2024

Book Now for SXSW Festival in Austin!

From it's spacious open concept design, large windows, and modern finishings, this contemporary home is the perfect spot for your next Austin getaway.

Book direct and save!
https://www.upstay.com/rentals/2127

11/28/2024

Wishing everyone a happy holiday, and a heartfelt thank you to all of our homeowners and guests for another great year.

11/27/2024

Check out our feature on Staycation Sports! Watch the full episode on IGTV Thursday, November 28th at 11am PST on The Destination Channel

11/27/2024

Catch us on the newest episode of on
IGTV: Thursday, November 28th at 11am PST on .channel

Send a message to learn more

11/19/2024

MARK YOUR CALENDARS and be sure to watch our feature in the upcoming Magic of Orlando episode on Staycation Sports!

premieres November 24th at 1:30 PM EST, on WKCF Channel 18 and on IGTV Thursday, November 28th at 11am PST on The Destination Channel

Staycation Sports takes you on a journey through top sports cities, showcasing stylish vacation rentals perfect for fans looking for a dream stay. Join host Charlie Boots as he explores the best places to stay, giving viewers an insider look at incredible homes tailored for the ultimate sports experience.

Upstay offers the best vacation rentals with unique design. Browse our rentals in Orlando, Colorado, Canada & More.

11/18/2024

If you're heading to Orlando for the Pro Bowl in February, or planning a group vacation during the Super Bowl LIX, Upstay offers the best home features for football fans. With group friendly layouts and plenty of seating, Upstay lets fans replicate the stadium experience in a private setting, with the comfort of lounging at home. Imagine catching the big plays on your own projector screen from your private home theater, or sizzling up game-day snacks on your BBQ grill. Upstay makes it easy to relax and enjoy your favorite sports teams in style.

Book direct to save up to 20% at upstay.com

11/15/2024

New Property Alert!
Modern Home with Pool in New Development

Planning a sun-filled family vacation? This 4-bedroom, 3-bathroom home by Upstay has everything you need. Enjoy the Florida sunshine from your private back sundeck with a sparkling pool, plus free onsite parking, WiFi, and all the essentials. Located in Clermont, just a short drive from Walt Disney World in Lake County, it’s also a great spot for fishing, boating, and wakeboarding.

Book direct and save up to 20%
https://www.upstay.com/rentals/2168

11/15/2024

New Property Alert!
Sunny Clermont Getaway with Private Pool

Soak up that Florida sunshine while relaxing by your private pool, at this beautiful four bedroom townhome. One of the newest additions to our Florida collection, this Lake County home can host up to 8 guests at a time, and you'll be just a short drive from Disney, golfing, and more.

Book direct and save up to 20%
https://www.upstay.com/rentals/2163

11/13/2024

BREAKING NEWS: Upstay to be featured on Staycation TV!

On behalf of The Destination Channel, we are excited to announce that, Staycation: Magic of Orlando will be airing in Orlando on Sunday, November 24th, 2024 at 1:30pm EST on WKCF Channel 18. Or, you can watch via IGTV on Thursday, November 28th at 11am PST on .channel

channel .tv



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