Upstay Family Retreat w Pool, Theater & Games Room

Kissimmee, Florida

9 bedrooms · 6 baths · Sleeps 20

From $154/night

Availability

Next 90 nights, as of Nov 8, 2026: 45 of 90 nights booked, first open night Nov 8; open nights from $154 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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368 more nights on the full rate calendar.

Upstay presents this newly renovated 9-bedroom home at the sought-after Windsor at Westside Resort—just 8 miles from Disney! Recently updated to include a brand-new movie theater and an upgraded games room with a PlayStation, this home offers even more space for fun and relaxation.

Amenities (74)

Photos (54)

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.