What are the top rated Vacation Rentals in Historic Downtown Kissimmee?

There are a lot of options in Historic Downtown Kissimmee. If you plan on staying in the Historic Downtown Kissimmee area, consider making a reservation for a few nights at one of these properties as these have been rated the top Vacation Rentals in Historic Downtown Kissimmee: <a href="/property/park-all-day-recharge-in-style-10min-to-disney-clean-revamped-w-resort-pool/HA-1214831807" class="class="static-page-link"">Park all day, recharge in style- 10min to Disney, clean, revamped w/resort pool</a> <a href="/property/2816-simile-storey-lake-10br-fire-pit-pool-hot-tub-game-evchrg/HA-3212991932" class="class="static-page-link"">2816 Simile · Storey Lake 10BR Fire Pit Pool Hot Tub Game EVChrg</a> <a href="/property/spacious-1-bedroom-loft-in-disney-area-5-star-rated-mill-creek-resort-2769/HA-3213738501" class="class="static-page-link"">SPACIOUS 1 BEDROOM LOFT IN DISNEY AREA 5 STAR RATED MILL CREEK RESORT 2769</a> <a href="/property/2933-fable-street-storey-lake-9br-fire-pit-pool-hot-tub-game-ev/HA-3212729123" class="class="static-page-link"">2933 Fable Street · Storey Lake 9BR Fire Pit Pool Hot Tub Game EV</a> <a href="/property/home-away-from-home-vacation-villa/HA-3213356904" class="class="static-page-link"">HOME AWAY FROM HOME -VACATION VILLA</a> <a href="/property/brand-new-lake-view-9br-dream-vacation-house-w-everything-storey-lake/HA-3212866732" class="class="static-page-link"">Brand-new Lake-view 9BR Dream Vacation House w/Everything @ Storey Lake</a> <a href="/property/amazing-bella-vida-resort-270bd-5-bedrooms-5-bathrooms-10-guests-lake-view/HA-1219698246" class="class="static-page-link"">AMAZING BELLA VIDA RESORT 270BD-5 BEDROOMS - 5 BATHROOMS - 10 GUESTS- LAKE VIEW</a> <a href="/property/5-star-exceptional-luxury-villa-at-storey-lake-mins-to-disney/BC-11558577" class="class="static-page-link"">5 Star Exceptional Luxury Villa at Storey Lake mins to Disney</a> <a href="/property/grand-opening-9bd-5ba-storey-lake-resort-lake-view-gameroom/HA-3213259416" class="class="static-page-link"">Grand Opening! 9BD/5BA-Storey Lake Resort/Lake View/GameRoom</a> <a href="/property/great-villa-10min-from-disney-with-private-pool-direct-from-owner/HA-3213602098" class="class="static-page-link"">Great Villa, 10min from Disney with Private Pool - direct from owner</a>

Which is the best family rental in Historic Downtown Kissimmee?

There are many large, family-friendly vacation homes available in Historic Downtown Kissimmee; however, here are the most popular family rentals listed on our site: Luxury 4 Bedroom Villa on the gated Bellavida Resort close to the Theme parks Multi Resorts at Fantasy World 2780 Bookmark Drive Special rates available in Sep and Oct of 2025

Can we get self-catering vacation rentals in Historic Downtown Kissimmee?

Yes, there are 2254 self-catering vacation homes in Historic Downtown Kissimmee that have hot tubs, swimming pools, & other amenities.

What are the best luxury vacation rentals near Historic Downtown Kissimmee?

There are more than 2254 luxury villas and vacation homes in or near Historic Downtown Kissimmee. Filter by price to compare find the most expensive places to stay on Castleinhawaii.