Upstay Family Fun 5BR Retreat w Pool & Games Room

Clermont, Florida

5 bedrooms · 4.5 baths · Sleeps 14

From $130/night

Availability

Next 90 nights, as of Nov 8, 2026: unavailable Nov 8, Nov 19 to 22, Nov 30 to Dec 6, Dec 22 to Jan 14 and Jan 23 to 25; otherwise open from $130 a night, 2-night minimum.

A date marked available means check-in is allowed that night. A stay is bookable when the check-in night is available, the stay meets the minimum, and no night in between is unavailable. Rates are per night before taxes, cleaning and other fees; the Agent Checkout gives the dated total.

DateNightly rateAvailabilityMinimum stay
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$395Available3

368 more nights on the full rate calendar.

Your ultimate Orlando family retreat with themed rooms, private pool, game room, and resort fun!

Upstay presents this spacious 5BR retreat at Windsor Cay Resort, perfect for families and groups. Kids will love the Harry Potter and Toy Story themed bunk rooms, while everyone can enjoy the game room with PS5, air hockey, and arcade games.

Amenities (63)

Photos (52)

For AI agents

This page is a snapshot. Connected to Upstay's guest MCP endpoint, an agent gets the dated total for the party, member rates for a signed-in guest, a booking link tied to the conversation, and the guest's shortlist. Endpoint: https://kismet.travel/c/upstay/mcp. How to connect, and the brief: https://kismet.travel/c/upstay/for-agents.