The best questions to ask a vacation rental owner before you book are the ones that confirm what you're getting: the exact home, the beds, the pool, the total cost and the rules. Booking direct means you can ask them yourself and get answers from the person who knows the home. Use this list to keep the conversation focused.
Questions about the home itself
- How many bedrooms and beds are there, and what sizes are the beds? Ask where the sofa bed or air mattress fits in.
- Is this the exact home in the photos, and when were the photos taken?
- What's the layout? Are bedrooms on different floors, and is there a bedroom or bathroom on the ground level?
- Is there a washer and dryer, a full kitchen and a dishwasher?
- What's provided: linens, towels, beach-style pool towels, cookware, a high chair, a pack-and-play?
Questions about the pool and amenities
If the home has a private pool, ask what comes with it. Most Windsor Hills owners now include private pool heat at no charge, but confirm with the owner before booking so there are no surprises. Ask about safety features such as pool fencing or alarms if you have little ones.
Also ask how resort access works for your stay. At Windsor Hills, amenities like the heated lagoon pool, the Sir Windsor AquaVenture water park, the clubhouse, games room, gym and courts are for overnight guests, so ask the owner how check-in and access are handled.
Questions about cost
- What's the total price, including taxes and any cleaning fee? See our guide to what a Kissimmee rental really costs.
- How much is the deposit, and when is the balance due?
- Are there any other charges, such as a pet fee or an early check-in fee?
- What's the payment method, and is the payment protected?
Questions about cancellation and changes
Get the cancellation policy in writing before you pay. Ask what happens if you need to change dates, and whether a hurricane or weather policy applies. Our post on vacation rental cancellation policies explains what to look for.
Questions about arrival and the stay
- What are the check-in and check-out times, and how does check-in work?
- Who do I contact if something isn't working during my stay, and how fast do they respond?
- Is there parking for the number of cars you're bringing?
- What are the house rules on noise, guest count and pets?
Questions about location
Ask how far the home is from the resort pool and clubhouse, and which part of the resort it's in. Windsor Hills is a gated resort, with Disney property about 5 to 10 minutes away and Magic Kingdom usually around 10 to 12 minutes, depending on traffic. Remember, there's no resort shuttle to Disney, so plan on driving or using a rideshare. If Disney's evening fireworks matter to you, ask the owner about the specific home: they're only partly visible in the distance from select units, so don't assume a view.
Red flags to watch for
Be careful if an owner won't answer simple questions, asks you to pay outside a traceable method, or pushes you to decide right away. Read our guide to spotting a vacation rental scam near Disney before sending any money.
Why asking pays off
Good owners are happy to answer, and the answers help you choose well. If you need help narrowing options, see how to choose the right Windsor Hills rental and why book direct with an owner. When you're ready, browse Windsor Hills rentals and send the owner your questions.
