Florida

November through April is the most generous stretch of weather in the state, and the months our guests return to year after year. December and January carry the snowbird premium and book up earliest. April and November are the value sweet spots: warm, dry, and well outside hurricane season. May and October still feel like summer in Florida, with longer pool days and gentler pricing.

The official Atlantic hurricane season runs June 1 through November 30. The serious risk window is mid-August through mid-October, with September the busiest month. For most travellers in those months, the practical answer is to book travel insurance, watch the five-day forecast in the week before arrival, and plan flexibly. Most summer storms are tropical rain rather than evacuation events, but we will always help you understand your options if a forecast changes around your dates.

Our directly-stewarded home sits in a gated community on the south side of Clermont, fifteen minutes from Walt Disney World by car and roughly twenty-five minutes from Universal Orlando. The location was chosen for that exact balance: theme parks within easy reach, but a real residential pace at the front door so the day still feels like a vacation when you come back.

One of the homes on this page is stewarded directly by Everyday Luxury (our Clermont property). The rest are in the careful hands of partner operators we work alongside while our Florida portfolio grows. We list them because the owners and their guests share the same standards we do, and we want guests browsing Florida to see the full breadth of what is available. As we steward more homes directly, you will see that reflected here.

Yes. The home is in Weston Hills, a gated short-term-rental community in south Clermont with assisted entry, two community pools, a children's aquatic centre, tennis and volleyball courts, walking paths, and a fitness area. Most homes in the community (including ours) have private pools as well.

Most of the Florida homes in this collection sleep eight or more, and many sleep ten to twelve. Florida vacation rentals are built for the way American families travel: shared meals, separate bedrooms for the adults and the kids, and a private pool that turns the time between activities into the part of the trip everyone remembers.

Several of the Florida homes welcome pets, with a small additional cleaning fee. Filter the homes above by Pet-friendly, or tell us about your dog and we will help match you with the right home. Florida is a remarkably easy state to travel through with a dog: most state parks, many restaurants, and almost every coastal boardwalk are dog-friendly outside of summer beach hours.

Clermont is inland Central Florida, so the closest open Gulf beach is Clearwater (about two hours by car) and the closest Atlantic beach is Cocoa or New Smyrna (about an hour). Many guests pair a Clermont base with one or two day trips to the coast. If a beach-front stay is the priority for the whole trip, look at our Gulf Coast and Emerald Coast partner homes above.

Most homes in the Florida collection have private pools, and most homes that offer heating treat it as an optional add-on with an additional fee. Pricing varies by home and season. We will always tell you the exact cost before you book and help you decide whether your dates need it. December through February are the months heating most often pays off; June through September almost never require it.

It is about a six-hour drive south to Key Largo and another two-and-a-half hours to Key West along the Overseas Highway. Most guests who include the Keys in a Florida trip set up a separate base for those nights rather than driving back the same day. We are happy to help you sequence a multi-base itinerary.

Plans change, and a thoughtful cancellation policy is part of how we look after every guest. Terms vary by home and by season, so the policy that applies to your stay is shown in full on the reservation page when you begin a booking for any Everyday Luxury Curated listing. You can also read it in advance on our cancellation policy page (opens in a new tab). If your dates need to move, reach out early and we will do everything we can to reschedule or re-accommodate.

We are honoured by every home we steward, and grateful to the owners who continue to choose us. If you own a property in Florida and want to learn more about how we look after homes, our team would love to hear from you. Read more on our property management page.