Monthly Rentals
Extended Stays
Monthly Vacation Rentals in Kissimmee, FL
Stays of a month or longer are welcome in our Kissimmee vacation homes. Every home is fully furnished with a full kitchen, washer and dryer, free Wi-Fi and free parking — an easy, comfortable base for a longer visit to the Disney area.
Choose from pet-friendly 3 and 4 bedroom homes in two gated communities: Crestwynd, about 1–2 miles from Walt Disney World, and Emerald Island Resort, about 5 miles away. Well-behaved dogs are welcome — the pet fee is $100 per month for monthly stays.
For monthly availability and rates, call (407) 557-8999 or email crestwynd@earthlink.net.
Our furnished homes
| Unit | Community | Bedrooms | Bathrooms | Sleeps | Pets | Book |
|---|---|---|---|---|---|---|
| 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 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 20 | Crestwynd | 3 | 2.5 | 8 | Yes | Book now |
| Unit 21 | Crestwynd | 3 | 3 | 8 | Yes | Book now |
| Unit 22 | Emerald Island | 3 | 2.5 | 8 | Yes | Book now |
| Unit 24 | Crestwynd | 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 |
Frequently asked questions
- Do you offer monthly or extended stays?
- Yes — stays of a month or longer are welcome in our Kissimmee vacation homes. Call (407) 557-8999 or email us for monthly availability and rates.
- What is included in a monthly rental?
- Every home is fully furnished with a full kitchen, washer and dryer, free Wi-Fi, free parking, air conditioning and a smart TV, plus access to a year-round heated outdoor pool.
- Can I bring my pet on a monthly stay?
- Yes — well-behaved dogs are welcome. For monthly stays the pet fee is $100 per month.
- How close are the homes to Disney World?
- Our Crestwynd homes are about 1–2 miles and our Emerald Island homes about 5 miles from Walt Disney World, in Kissimmee, Florida.
Ready to book your Orlando vacation?
Check real-time availability and reserve your preferred home today.