Vacation Homes Near Old Town Kissimmee, FL
Vacation homes near Old Town Kissimmee: 25+ pet-friendly homes about 3–5 miles from the classic car cruises, shops and rides on US-192.
Vacation homes near Old Town Kissimmee put one of the area's most relaxed evenings about 3 miles from Emerald Island Resort and about 5 miles from Crestwynd Bay. Old Town is a strip of shops, rides and restaurants along US-192 — entry is free and you pay per ride, so it works for an evening stroll with or without spending much. Distances here are approximate driving distances.
The weekend classic car cruises are the draw most guests remember: chrome and tailfins rolling past the storefronts on Friday and Saturday nights. During the day it is a quieter browse of souvenir shops and casual restaurants, which suits an easy afternoon between park days. Each of our 25+ homes sleeps 7–8 guests, so families and groups of different sizes can base themselves a few minutes from Old Town. Because it sits on US-192, Old Town is on the way home from most places Emerald Island guests drive, so it costs almost no extra time to stop for the evening.
All 25+ of our homes are pet-friendly 3 and 4 bedroom townhomes in gated communities, sleeping 7–8 guests, with a full kitchen, washer and dryer, free Wi-Fi, free parking and the community's year-round heated pool. Each community is gated and quiet, so a late Old Town evening still ends calmly. Check-in is 4:00 PM and check-out is 10:00 AM. Book 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.
Written by Manny, owner-host since 2009 · Updated October 2, 2026
From Crestwynd Bay
≈5 mi · 10 min drive
From Emerald Island Resort
≈3 mi · 7 min drive
Verified guest rating
4.8 / 5
Approximate driving distance
| Community | Miles | Drive time |
|---|---|---|
| Crestwynd Bay | ≈5 mi | ≈10 min |
| Emerald Island Resort | ≈3 mi | ≈7 min |
Distances are approximate and depend on traffic and the parking lot you use.
Our homes near Old Town Kissimmee
21 homes · sleeps 7–8 guests
| Unit | Community | Bedrooms | Bathrooms | Sleeps | Pets | Book |
|---|---|---|---|---|---|---|
| Unit 15 | Emerald Island | 3 | 2.5 | 8 | Yes | Book now |
| Unit 16 | Emerald Island | 3 | 2.5 | 8 | Yes | Book now |
| Unit 18 | Emerald Island | 3 | 2.5 | 8 | Yes | Book now |
| Unit 19 | Emerald Island | 3 | 2.5 | 8 | Yes | Book now |
| Unit 22 | Emerald Island | 3 | 2.5 | 8 | Yes | Book now |
| Unit 25 | Emerald Island | 3 | 2.5 | 8 | Yes | Book now |
| Unit 26 | Emerald Island | 4 | 3.5 | 8 | Yes | Book now |
| Unit 27 | Emerald Island | 4 | 3.5 | 8 | Yes | Book now |
| Unit 29 | Emerald Island | 3 | 2.5 | 8 | Yes | Book now |
| Unit 2 | Crestwynd | 3 | 3 | 8 | Yes | Book now |
| Unit 4 | Crestwynd | 3 | 3 | 8 | Yes | Book now |
| Unit 5 | Crestwynd | 3 | 2.5 | 8 | Yes | Book now |
| Unit 6 | Crestwynd | 3 | 3 | 8 | Yes | Book now |
| Unit 7 | Crestwynd | 3 | 2.5 | 8 | Yes | Book now |
| Unit 8 | Crestwynd | 3 | 3 | 7 | Yes | Book now |
| Unit 9 | Crestwynd | 3 | 3 | 8 | Yes | Book now |
| Unit 10 | Crestwynd | 3 | 3 | 8 | Yes | Book now |
| Unit 14 | Crestwynd | 3 | 3 | 8 | Yes | Book now |
| Unit 20 | Crestwynd | 3 | 2.5 | 8 | Yes | Book now |
| Unit 21 | Crestwynd | 3 | 3 | 8 | Yes | Book now |
| Unit 24 | Crestwynd | 3 | 2.5 | 8 | Yes | Book now |
Frequently asked questions
- How far are the homes from Old Town Kissimmee?
- Emerald Island Resort homes are about 3 miles (7 minutes) and Crestwynd Bay homes about 5 miles (10 minutes) from Old Town Kissimmee by car. Distances are approximate driving distances.
- What fees apply to a stay?
- The cleaning fee is $100 plus tax for 3 bedroom and $120 plus tax for 4 bedroom homes. A 20% deposit reserves the home and the balance is due at least 5 days before arrival.
- Does Old Town cost anything to enter?
- No. Entry is free and you pay per ride or per meal. The weekend classic car cruises are also free to watch.
- Can we bring our dog?
- Yes, every home is pet-friendly. Up to 2 well-behaved dogs are welcome; the pet fee is $25 per night or $100 per month.
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