Compare Cottages, Resorts, & Rentals in Kissimmee, Florida, USA
About Kissimmee Vacation Rentals
There are over 45156 amazing vacation rentals available in Kissimmee. Choose from a variety of options including villas, hotels, and other rental properties. Explore a vast selection of luxury amenities at unbeatable prices, providing you with the ideal spot for your next getaway. Life is Better at the Cottage with Vacation Cottage, where you can discover fantastic stays in Kissimmee.
Vacation Cottage offers numerous last-minute deals on villas, hotels, and rentals, both near you and across the globe. Whether you need accommodations for a group or event, such as a hotel or vacation rental (including cabins and private luxury villas), let us assist you. With Vacation Cottage in Kissimmee, you can easily compare options from multiple suppliers with just a click to find the perfect price point, amenities, and style of stay for you. Whether you're seeking group discounts, private pools, hot tubs, pet-friendly options, or spacious master suite bedrooms with open-air showers, you can find it all with Vacation Cottage vacation rentals, resorts, and Airbnb-style properties in Kissimmee. The average size of places to stay near Kissimmee is approximately 1739.46 ft², with prices averaging US $396 per night.
Vacation Cottage helps you discover the perfect holiday rental to create lasting travel memories in Kissimmee. Prices listed often feature discounts compared to rack rates. Simply search for your destination and secure your ideal place to stay today.
Find Vacation Cottage Rentals in these Cities and Neighborhoods Kissimmee, FL
Frequently Asked Questions About Kissimmee?
What are the top cottages, summer homes, and lake houses in Kissimmee?
- Top-Rated Amazing Villa! Salt💧Pool, Game Room + Pool Heat, BBQ & Baby Gear
- 4 Bedroom Villa 2 Miles from Disney Entrance Kissimmee off Us192
- Water View - Pool & Spa - 3.5 miles to Disney - BBQ
- Windsor Poolside Escape with Stunning Pool View-Perfect for Families!
- Amazing villa close to Disney with 5* Reviews
- Quiet, Clean, Disney-3.5 miles, Well kept home! Free Pool/spa Heat!
- Conservation View - Hot Tub - Free Pool Heat - Very Private
- Our DisneyDreamVilla - minutes to DisneyWorld!
- BEAUTIFUL LAKEVIEW TOWNHOME, 5 MILES TO DISNEY. FULLY EQUIPED
- Close to Disney! NO Extra Fees! Gated! Clean & Comfy! Family Friendly!
How many rentals, hotels, or resorts are available in Kissimmee?
Vacation Cottage consistently updates its selection, offering a blend of new options alongside well-established accommodations in prime locations. Currently, there are over 45156 properties listed by Vacation Cottage in the Kissimmee area for the year 2026, with this number increasing daily. By aggregating listings from various websites and travel providers, Vacation Cottage ensures a diverse array of choices for the best luxury stays in Kissimmee.
Nearby Neighborhood (16)
| Neighborhood | Property Count |
|---|---|
| West Kissimmee Rental Cottages and Private Getaways in Orlando, Florida | 16949 |
| Historic Downtown Kissimmee Rental Cottages and Private Getaways in Orlando, Florida | 8131 |
| Windsor Hills Rental Cottages and Private Getaways in Orlando, Florida | 1648 |
| Bay Lake Rental Cottages and Private Getaways in Orlando, Florida | 929 |
| Windsor Palms Rental Cottages and Private Getaways in Orlando, Florida | 901 |
| Bellavida Rental Cottages and Private Getaways in Orlando, Florida | 264 |
| Lake Berkley Rental Cottages and Private Getaways in Orlando, Florida | 175 |
| Orange Lake Rental Cottages and Private Getaways in Orlando, Florida | 127 |
| Crescent Lakes Rental Cottages and Private Getaways in Orlando, Florida | 96 |
| Crystal Cove Rental Cottages and Private Getaways in Orlando, Florida | 89 |
| Indian Point Rental Cottages and Private Getaways in Orlando, Florida | 59 |
| Trafalgar Village Rental Cottages and Private Getaways in Orlando, Florida | 54 |
| Crestwynd Bay Rental Cottages and Private Getaways in Orlando, Florida | 52 |
| Calabria Rental Cottages and Private Getaways in Orlando, Florida | 41 |
| Windward Cay Rental Cottages and Private Getaways in Orlando, Florida | 15290 |
| Mill Run Rental Cottages and Private Getaways in Orlando, Florida | 765 |
