Direct Booking Vacation Homes Near Disney World

Book direct with the owner of 25+ pet-friendly vacation homes near Disney World in Kissimmee — no platform service fees, secure online calendar.

Direct booking vacation homes near Disney World are exactly what MyOrlandoStay offers: 25+ pet-friendly 3 and 4 bedroom townhomes in the gated Crestwynd Bay and Emerald Island Resort communities in Kissimmee, Florida. When you book on this site you deal with the owner, not a marketplace, so you pay no booking-platform service fees. Every home sleeps 7–8 guests and sits about 1–5 miles from the Disney main gate.

Booking works the same way as the big platforms, minus the middleman. Check live availability on our secure online booking calendar, reserve your dates with a 20% deposit, and pay the balance at least 5 days before arrival. The cleaning fee is $100 plus tax for 3 bedroom and $120 plus tax for 4 bedroom homes — listed plainly with no hidden extras. Check-in is 4:00 PM and check-out is 10:00 AM. If plans change, the cancellation terms are simple: cancel 30 or more days before arrival for a full refund minus processing fees; inside 30 days the 20% deposit is kept.

You can also talk to the owner before you book. Call (407) 557-8999 with any question about the homes, the communities or the area — you reach the people who actually maintain the houses, not a call center. Every home includes a fully equipped kitchen, washer and dryer, free Wi-Fi, free parking and the community's year-round heated pool. Weekly and monthly stays are welcome in every home, and well-behaved dogs can come too. MyOrlandoStay is a family-run company that has welcomed guests since 2009, with a 4.8 average rating from 96 verified stays in 2026.

Written by Manny, owner-host since 2009 · Updated October 2, 2026

Frequently asked questions

How do I book direct?

Check live availability on our secure online booking calendar and reserve online, or call (407) 557-8999. A 20% deposit reserves the home and the balance is due at least 5 days before arrival.

What fees do I pay when booking direct?

The cleaning fee is $100 plus tax for 3 bedroom and $120 plus tax for 4 bedroom homes. There is no booking-platform service fee. If you bring dogs, the pet fee is $25 per night or $100 per month.

How far are the homes from Walt Disney World?

Crestwynd Bay homes are about 1–2 miles and Emerald Island Resort homes about 5 miles from the Disney main gate.

What is the cancellation policy?

Cancel 30 or more days before arrival: 100% refund minus processing fees. Cancel within 30 days of arrival: the 20% reservation deposit is kept. On or after arrival: no refunds.

Can I talk to someone before I book?

Yes. Call (407) 557-8999 and you will reach the owner, who can answer questions about any home, the communities and the booking process.