a pond on a sunny day in kissimee florida

Kissimmee, FL

Twenty minutes south of bustling Orlando, Kissimmee is the perfect vacation rental destination for guests who want proximity to Disney World and other major attractions, but prefer lodging with more of a neighborhood vibe. The town itself entertains families from around the globe with its unique shops, restaurants, and historic Old Town. Guests here are looking for both luxury and escape, with lodging that’s not only comfortable but unique.

Aerial view of Kissimmee, FL

Insider tip

The most successful rental homes in Kissimmee are big enough for families and feature swimming pools, game rooms, outdoor gathering spaces, connected floor plans, tons of natural light, and concept/themed rooms with one-of-a-kind charm. To stand out in a crowded market, consider buying new in a builder community. The property will be built to spec and rental-ready, and will come with full warranties. New builder communities in Kissimmee are located near parks and have best-in-class amenities; some of the builders will even build up to 15-bedroom homes. While large spec vacation rental homes rent well in Kissimmee, they’re expensive. A good thing to keep in mind is that builders here are usually more willing to negotiate near the end of the quarter or fiscal year.

Learn more and compare Kissimmee with other top markets in our insider's guide to the best places to buy a vacation rental.

Market size

24,500+ rental units

Median annual rental revenue


Median home price


Cap rate


Interested in Kissimmee?

Call our local expert Richard Haskins (License #Bk3285669) at 305-783-2909.

Vacasa offers property management and other real estate services directly through Vacasa LLC and through Vacasa LLC's licensed subsidiaries. Click here for more information about Vacasa's licensed real estate brokerage/property manager in your state. Vacasa’s licensed real estate brokerages/property managers include: Vacasa Alabama LLC; Vacasa Arizona LLC; Vacasa Florida LLC; Vacasa Louisiana L.L.C. (licensed in Louisiana); Vacasa Michigan LLC, 947-800-5979; Vacasa Nevada LLC; Vacasa New Hampshire LLC, P.O. Box 283, Conway NH 03818, Dave Grant, Broker of Record; Vacasa New Mexico LLC, 503-345-9399; Vacasa New York LLC, 888-433-0068; Vacasa North Carolina LLC; Vacasa Pennsylvania LLC; Vacasa Real Estate LLC (licensed in Colorado 720-727-9358, Idaho, and Oregon); Vacasa Resort Rentals of Hilton Head Island LLC; Vacasa South Carolina LLC; Vacasa Tennessee LLC; Vacasa Vacation Rentals of Hawaii LLC, 3350 Lower Honoapiilani Road, Suite 600, Lahaina, HI 96761; Vacasa Vacation Rentals of Montana LLC, Rickie Miller, Licensed Property Manager; Vacasa Virginia LLC; Vacasa Wisconsin LLC.

*This document is for information and illustrative purposes only. It is not intended to provide “investment advice” or a “recommendation” regarding a course of action. The discussion is general in nature and has not taken into account your personal financial position or objectives. You should consult a licensed financial advisor or other professional to discuss your specific situation.

Estimated rental income figures and home sale prices are based on historical averages; for any specific property, the actual revenue, purchase price, and cap rate may differ materially from estimated amounts and depend on a wide range of factors outside Vacasa's knowledge or control, such as the property's condition, layout, and furnishings; expenses associated with the acquisition and ownership of the property (such as property taxes, utility fees, HOA fees, insurance fees, and mortgage-related expenses); rental calendar availability; existing and future regulations; current and future economic, social, and political trends and conditions; and weather and environmental factors. These estimates do not take into account the potential impact of state income taxes.

Vacasa makes no representations or warranties, express or implied, about the accuracy of this document. Furthermore, Vacasa has no obligation to update, modify or amend this document or to otherwise notify users in the event that any opinion, assumption, forecast or estimate set forth herein changes or subsequently becomes inaccurate. Therefore, you should not place undue reliance on statements in this document.