Stays of a month or longer are welcome in MyOrlandoStay's Kissimmee vacation homes.
Monthly and Extended Stay Vacation Rentals in Kissimmee
Stays of a month or longer are welcome in MyOrlandoStay's 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 3 miles away. Well-behaved cats and dogs are welcome — the pet fee is $100 per month for monthly stays.
Monthly stays include an electricity allowance of $200 and a water allowance of $50 per month; usage above the allowance is billed to the guest. Emerald Island Resort homes have a maximum stay of six months. We rent entire homes only — no individual rooms. The pet fee for monthly stays is $100 per month.
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 | 6–8 | Yes | Book now |
| Unit 3 | Emerald Island | 3 | 2.5 | 6–8 | Yes | Book now |
| Unit 4 | Crestwynd | 3 | 3 | 6–8 | Yes | Book now |
| Unit 5 | Crestwynd | 3 | 2.5 | 6–8 | Yes | Book now |
| Unit 6 | Crestwynd | 3 | 3 | 6–8 | Yes | Book now |
| Unit 7 | Crestwynd | 3 | 2.5 | 6–8 | Yes | Book now |
| Unit 8 | Crestwynd | 3 | 3 | 5–7 | Yes | Book now |
| Unit 9 | Crestwynd | 3 | 3 | 6–8 | Yes | Book now |
| Unit 10 | Crestwynd | 3 | 3 | 6–8 | Yes | Book now |
| Unit 14 | Crestwynd | 3 | 3 | 6–8 | Yes | Book now |
| Unit 15 | Emerald Island | 3 | 2.5 | 6–8 | Yes | Book now |
| Unit 16 | Emerald Island | 3 | 2.5 | 6–8 | Yes | Book now |
| Unit 17 | Emerald Island | 3 | 2.5 | 6–8 | Yes | Book now |
| Unit 18 | Emerald Island | 3 | 2.5 | 6–8 | Yes | Book now |
| Unit 19 | Emerald Island | 3 | 2.5 | 6–8 | Yes | Book now |
| Unit 20 | Crestwynd | 3 | 2.5 | 6–8 | Yes | Book now |
| Unit 21 | Crestwynd | 3 | 3 | 6–8 | Yes | Book now |
| Unit 22 | Emerald Island | 3 | 2.5 | 6–8 | Yes | Book now |
| Unit 24 | Crestwynd | 3 | 2.5 | 6–8 | Yes | Book now |
| Unit 25 | Emerald Island | 3 | 2.5 | 6–8 | Yes | Book now |
| Unit 26 | Emerald Island | 4 | 3.5 | 6–8 | Yes | Book now |
| Unit 27 | Emerald Island | 4 | 3.5 | 6–8 | Yes | Book now |
| Unit 29 | Emerald Island | 3 | 2.5 | 6–8 | 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 an outdoor community pool, heated from about November to March. Monthly stays include an electricity allowance of $200 and a water allowance of $50 per month; usage above the allowance is billed to the guest.
- Is there a maximum stay?
- Emerald Island Resort homes have a maximum stay of six months. Ask us about longer stays in Crestwynd Bay.
- Can I bring my pet on a monthly stay?
- Yes — well-behaved cats and dogs are welcome. For monthly stays the pet fee is $100 per month.
- Do you offer extended stay rentals shorter than a month?
- Yes — weekly stays are welcome in every home. See our weekly vacation rentals in Kissimmee page for 7-night stays, or this page for a month or longer.
- How close are the homes to Disney World?
- Our Crestwynd homes are about 1–2 miles and our Emerald Island homes about 3 miles from Walt Disney World, in Kissimmee, Florida.
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Check real-time availability and reserve your preferred home today.