Vacation Homes for Families in Kissimmee, FL

Family vacation homes in Kissimmee near Disney: 25+ pet-friendly 3 and 4 bedroom townhomes in gated communities, full kitchens, heated pool.

Family vacation homes in Kissimmee work better than connecting hotel rooms for one simple reason: a whole house. Our 25+ pet-friendly townhomes give each family member a real bedroom, a shared living room, and a full kitchen — in two gated communities about 1–5 miles from Walt Disney World. There are both 3 bedroom and 4 bedroom homes, so families of different sizes find a fit.

The practical details matter with kids. A washer and dryer in the home means fewer suitcases and a fresh set of park clothes every morning. A kitchen with dishes and utensils means breakfasts at the table instead of a restaurant queue, and air conditioning keeps the house comfortable after a hot park day. A year-round heated community pool, included at no extra charge, gives the kids somewhere to burn off the evening.

Both communities are gated and quiet, which helps when bedtimes are earlier than the fireworks. Crestwynd Bay, about 1–2 miles from the Disney main gate, has a Walmart and a gas station within walking distance for supplies. Emerald Island Resort, about 5 miles from Disney, is close to Old Town Kissimmee and the restaurants and outlets on US-192. Each home sleeps 7–8 guests, and the pet fee is $25 per night or $100 per month for up to 2 dogs. Booking is direct with the owner: a 20% deposit reserves the home, the balance is due at least 5 days before arrival, and there are no platform service fees. MyOrlandoStay is family-run and has hosted families since 2009, rated 4.8 from 96 verified stays in 2026.

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

Frequently asked questions

How far are the family homes from Disney World?

Crestwynd Bay homes are about 1–2 miles and Emerald Island Resort homes about 5 miles from the Disney main gate — close enough to come home for a midday break.

What does a family stay cost?

You pay the nightly rate plus the cleaning fee ($100 plus tax for 3 bedroom, $120 plus tax for 4 bedroom) and tax. A 20% deposit reserves the home, and the balance is due at least 5 days before arrival.

Is there a washer and dryer in the home?

Yes. Every home has its own washer and dryer, which makes longer family stays much easier.

Are the communities good for children?

Yes. Both communities are gated and quiet residential neighborhoods, and the year-round heated community pool is included for all guests at no extra charge.

Can we bring the family dog?

Yes. Up to 2 well-behaved dogs are welcome in every home; the pet fee is $25 per night or $100 per month.