Own a Piece of Orlando
From Anywhere in the World.
A trusted, remote-friendly path to vacation home ownership at Windsor Hills Resort — guard-gated, short-term-rental zoned, and less than 3 miles from the gates of Walt Disney World.
Built for the way overseas families actually buy.
Second Homes
A Florida holiday home you can use year-round.
Vacation Homes
Turnkey, fully furnished, ready for family stays.
Overseas Owners
UK, Canadian & global buyers welcome — remote-friendly.
STR Investment
Short-term rental zoned, minutes from Walt Disney World.
3 miles from Disney. A world away from ordinary.
Windsor Hills Resort sits less than 3 miles from the main gates of Walt Disney World — one of the closest guard-gated resort communities you can own in. For overseas buyers, that proximity translates directly into year-round rental demand and a globally recognized location your guests already know.
Unlike many Florida neighborhoods, Windsor Hills is zoned and approved for short-term rentals. Use the home for your own family holidays and offset ownership costs by renting it nightly when you're not visiting — the model most UK and Canadian buyers are looking for.
The community offers a clubhouse, resort-style pool with lazy river and waterslide, movie theater, fitness center, sports courts, and 24/7 manned security gate — a full resort experience that drives reviews and repeat bookings.
What UK & Canadian buyers should know.
This page provides general real estate guidance only and is not legal or tax advice. Always confirm details with a qualified cross-border attorney and CPA.
Cross-border ownership, demystified.
FIRPTA, EINs & Ownership Structure
FIRPTA withholding typically applies when foreign owners sell U.S. real estate — not at purchase. We help you raise the right LLC, EIN, and tax questions early — before you go under contract.
Licensing & Rental Rules
Short-term rentals in Florida involve state and local licensing. You'll need a Florida DBPR vacation rental license and Osceola County tourist tax registration. We walk you through every step.
Management Companies
For owners overseas, a reliable property manager is essential. We introduce you to vetted Windsor Hills companies handling bookings, guest check-in, cleaning, pool & lawn care, and 24/7 emergencies.
Remote Buying Process
We routinely close transactions for buyers in London, Toronto, Vancouver, Manchester, and beyond — using virtual tours, e-signatures, video walkthroughs, and Power of Attorney where needed.
Common questions from international buyers.
Can UK or Canadian citizens buy a home in Windsor Hills?
+
Yes. International buyers regularly purchase property at Windsor Hills Resort. There is no U.S. residency requirement to own real estate in Florida.
Can I rent my Windsor Hills home short-term (Airbnb / VRBO)?
+
Yes. Windsor Hills is one of the few guard-gated resorts inside the 3-mile Disney radius that is fully approved for nightly short-term rentals.
Do I need an LLC to buy?
+
Not necessarily. Some buyers purchase personally; others use an LLC for liability or tax-planning reasons. We'll connect you with cross-border attorneys and CPAs who specialize in international ownership.
What is FIRPTA and does it affect me?
+
FIRPTA is U.S. tax withholding that applies when a foreign owner sells U.S. real estate — not when buying. We'll make sure you understand the full ownership timeline from purchase to eventual resale.
Do I need a management company?
+
Almost always, yes. A professional manager handles bookings, guest check-in, housekeeping, pool/lawn care, and emergencies while you're overseas. We can introduce you to vetted Windsor Hills specialists.
Can I complete the purchase remotely from the UK or Canada?
+
Yes. We routinely close transactions remotely using e-signatures, virtual tours, video walkthroughs, and Power of Attorney where needed.
Speak with a Windsor Hills specialist.
Tell us about your goals — second home, vacation home, or rental investment — and we'll send a curated shortlist suited to international buyers.
Prefer to browse first? View all Windsor Hills properties for sale →
Let's Talk
Ready to Find Your Dream Vacation Home?
Contact Holiday Realty LLC today for a free consultation. We'll help you buy or sell your Windsor Hills Resort property.