TOP 30 Florida vacation rentals by owner in Kissimmee, Florida

Extended Stay America - Orlando - Kissimmee is a comfortable and convenient lodging option located at 7727 West Irlo Bronson Memorial Highway in Kissimmee, Florida. This institution offers spacious and well-equipped rooms that are perfect for long-term stays. Guests can enjoy amenities such as fully equipped kitchens, free Wi-Fi, and on-site laundry facilities. The location is ideal for those looking to explore the attractions of Orlando, as it is close to popular theme parks and shopping areas. Whether visiting for business or leisure, Extended Stay America - Orlando - Kissimmee provides a relaxing and home-like atmosphere for all guests.

Rentals in Emerald Island Resort is a reputable real estate and travel agency located at 8515 Crystal Cove Loop in Kissimmee, Florida, United States. Specializing in vacation rentals within the luxurious Emerald Island Resort, this agency offers a wide range of beautiful properties for guests to choose from. With top-notch customer service and a dedication to providing unforgettable experiences, Rentals in Emerald Island Resort is the perfect choice for those looking to explore the magic of central Florida. Whether you're seeking a cozy villa for a romantic getaway or a spacious home for a family vacation, this agency has something for everyone. Book your stay with Rentals in Emerald Island Resort and make your dream vacation a reality.

Windsor Hills Private Rentals is the official rental website for the Windsor Hills Resort in Kissimmee, Florida. Endorsed and run by the Resort Management Committee, we offer a wide selection of vacation rentals in the most popular resort community in the Orlando area. With no commission or booking fees, you can secure your dream vacation rental directly with the property owner or manager. Our advanced search functionality helps you find the perfect accommodation, whether you're looking for a villa, townhome, or condo. The resort is located just 2 miles from Walt Disney World, making it the ideal location for a family vacation, business event, wedding, or honeymoon. Enjoy the amenities of the Windsor Hills Resort, including a clubhouse, lagoon-style pool, water park, fitness center, playground, and more. With easy access to top golf courses and major theme parks, renting in Windsor Hills puts you in the center of the action. Book your perfect vacation rental property now with Windsor Hills Private Rentals.

Escape to Regal Oaks Resort Vacation Townhomes by IDILIQ, located at 5780 Golden Hawk Way in Kissimmee, Florida, United States. This institution offers lodging, real estate, and travel agency services. Nestled in the heart of Orlando, our resort is the perfect retreat for families, couples, and groups of friends looking for a magical getaway. Enjoy spacious accommodations, world-class amenities, and a range of activities for the whole family. Unwind in a fully equipped kitchen, relax on your private screened patio, and indulge in the resort's pool oasis. With multiple bedrooms, these vacation homes cater to diverse needs, ensuring a truly extraordinary escape. Staycation savings are available exclusively for Florida and Georgia residents. The resort offers a Cabana Pool Bar for tropical beverages, a family-friendly sports bar and grill, and easy access to popular theme parks and attractions. Dive into the expansive pool, challenge your skills on the tennis and pickleball courts, and enjoy the arcade and market on-site. Regal Oaks Resort is part of the IDILIQ Group of companies, offering luxurious accommodations in sought-after holiday destinations. Experience the perfect blend of comfort and family-friendly fun at Regal Oaks Resort Vacation Townhomes by IDILIQ.

Located at 7430 Brooklyn Drive in Kissimmee, Florida, the Magic Village Views, Trademark Collection by Wyndham offers a chic and contemporary sanctuary just a mile away from Disney Parks. With floor-to-ceiling windows providing soothing views of the surrounding gardens, guests can enjoy a magical vacation experience in fully equipped villas that accommodate up to 6 or 8 people comfortably. The spacious accommodations include luxury bedding, furnished patios, free Wi-Fi, and free parking. The institution offers exclusive hotel services, including concierge, clubhouse, multilingual staff, cleaning services, and more to enhance guests' stay. ADA defined service animals are welcome, but no other pets are allowed. Guests must be 21 years of age with a valid ID for check-in, along with a refundable deposit for incidentals and a one-time cleaning fee per villa per stay.

Villa By The Castle is a top-rated luxury vacation rental located at 2608 Daulby Street in Kissimmee, Florida. This 6-bedroom, 4-bathroom villa is just 2 miles from Disney World in the beautiful Windsor Hills Resort. The villa is equipped with a private pool and spa, a game room with a pool table and air hockey, and a great room with a 70" 3D LED Smart TV. With amenities like TVs in every bedroom, baby gear, and a fully equipped kitchen, Villa By The Castle provides a comfortable and welcoming home for your Disney vacation. As owner-operated, you'll have direct communication with us throughout your stay. Windsor Hills is the closest resort community to Disney World, offering resort-style amenities and a convenient location. Book your stay at Villa By The Castle and experience the best of Kissimmee and Orlando.

Experience the ultimate in luxury at this stunning 6 bedroom, 4 bath villa located in the prestigious Windsor Hills Resort in Kissimmee, Florida. This spacious and beautifully appointed home features top-of-the-line amenities, including a private pool and spa, fully equipped gourmet kitchen, and multiple living and dining areas. Perfect for families or large groups, this villa offers plenty of space to relax and unwind after a day of exploring all that Orlando has to offer. With easy access to theme parks, shopping, and dining, this is the perfect home base for your next vacation in the Sunshine State.

Florida Vacation Villas is a premier lodging, real estate, and travel agency located at 2777 North Poinciana Boulevard in Kissimmee, Florida, United States. Our villas offer luxurious accommodations for vacationers looking to experience the magic of Florida. Whether you're looking for a relaxing getaway or an action-packed adventure, our team is dedicated to providing top-notch service to ensure your stay is unforgettable. With a prime location near popular attractions like Disney World and Universal Studios, Florida Vacation Villas is the perfect choice for your next vacation in the Sunshine State. Book your stay with us today and experience the ultimate Florida getaway!

Poinciana Vacation Management is a premier vacation rental management company located at 500 Cypress Parkway in Kissimmee, Florida, United States. Our team specializes in providing top-notch services for property owners looking to rent out their vacation homes in the popular tourist destination of Kissimmee. With years of experience in the industry, we offer personalized and professional management services to ensure that your property is well-maintained and consistently booked by guests. From marketing and advertising to guest communication and property maintenance, Poinciana Vacation Management handles every aspect of vacation rental management with efficiency and expertise. Trust us to maximize your rental income and provide an exceptional experience for both you and your guests.

Central Florida Holiday Homes is a reputable real estate and travel agency located at 3333 Bartlett Boulevard in Orlando, Florida. Specializing in the Reunion, Davenport, Kissimmee, Champions Gate, and Disney regions of Central Florida, we have been providing expert vacation home services for over 25 years. Our comprehensive vacation home management services include marketing your property on our website and other high-traffic platforms such as VRBO, Flipkey, and AirBnB. We also conduct weekly checks on your home to ensure everything is in order, even when there are no guests present.

Apex Vacation Homes is a one-stop destination for all your vacation needs in Kissimmee, Florida. Located at 7816 West Irlo Bronson Memorial Highway, our institution offers a range of services including car rentals, finance, real estate agency, and travel agency. Whether you're looking to rent a car for your trip, secure financing for your dream vacation home, buy or sell real estate in the area, or plan your next getaway, our expert team is here to assist you every step of the way. Experience top-notch service and personalized attention at Apex Vacation Homes.

Disney Dreams Vacation Rentals is a real estate and travel agency located at 2577 Maneshaw Lane, Kissimmee, Florida, United States. Our vacation home is situated in the prestigious Windsor Hills Resort, just two miles away from Disney World. Our fully furnished 3 bedroom, 3 bath town home offers a private pool/spa, fully equipped kitchen, Free Wi-Fi, and plasma TVs throughout. Perfect for families and extended families, our vacation rental provides a luxurious setting for a memorable Disney vacation. Explore Central Florida's popular attractions easily from our location, with driving directions provided for each park from Windsor Hills. Eat, swim, shop, or play - all within reach from Disney Dreams Vacation Rentals. Make lasting memories with a Disney Dreams vacation.

Epic Florida Rentals is a premier real estate and travel agency located at 7862 West Irlo Bronson Memorial Highway in Kissimmee, Florida. We specialize in providing luxurious vacation rentals in the heart of Florida's most popular tourist destinations. Our team is dedicated to helping clients find the perfect rental property for their dream getaway, whether it be a cozy condo near Disney World or a spacious beachfront villa. With a wide selection of properties to choose from and exceptional customer service, Epic Florida Rentals is your go-to agency for an unforgettable vacation experience in the Sunshine State.

Master Vacation Homes is a real estate and travel agency located at 2801 North Poinciana Boulevard in Kissimmee, Florida, United States. Our institution specializes in providing vacation rental homes for travelers looking for a comfortable and convenient accommodation option. We offer a wide range of properties to choose from, ensuring that our guests have a memorable and enjoyable stay in the Sunshine State. Our website uses Cookies to enhance user experience, but rest assured that we do not store sensitive personal information. If you have any questions or concerns about our Cookies Policy, please feel free to contact us. Thank you for considering Master Vacation Homes for your next getaway!

American Star Vacation Homes is a premier real estate and travel agency located at 2107 Clay Street in Kissimmee, Florida. We specialize in providing luxurious vacation homes for rent in the beautiful Sunshine State. Our properties are meticulously maintained and equipped with all the amenities you need for a comfortable and memorable stay. Whether you're looking for a cozy cottage or a spacious villa, we have a wide range of options to suit your needs. Let us help you plan the perfect getaway in Florida!

Search Florida Rentals by Owners is a travel agency located at Colonial Court in Fort Myers, Florida, United States. The institution offers a variety of vacation rental properties in popular destinations across Florida, such as Kissimmee, Naples, St. Augustine, and Daytona Beach. From beachfront condos to luxurious villas, Search Florida Rentals provides fully-equipped and strategically located accommodations to suit every traveler's needs and budget. One of the highlights of booking with Search Florida Rentals is the transparency in pricing, as there are no hidden costs or commissions charged to guests. The institution prides itself on offering state-of-the-art amenities and hotel-level hospitality to ensure a luxurious vacation experience for all. Flexible check-in policies make it convenient for travelers to plan their holiday rentals with ease.

Blue Travel - Vacation Homes is a premier real estate and travel agency located at 2960 Loopdale Lane, Kissimmee, Florida, United States. If you are searching for luxury lifestyle vacation homes in Orlando, look no further. Our agency offers a wide variety of luxury vacation rentals in Orlando that are perfect for short-term stays. Our vacation homes are inspired by Disney Vacation Homes and are located near Walt Disney World, making them the ideal choice for your Orlando getaway. Stay with us and experience the beauty and magic of Orlando in style.

USA House Vacations is a premier travel agency located in Kissimmee, Florida, offering a wide range of vacation rental homes in the United States. Our properties are meticulously selected to provide the perfect accommodation for your next holiday getaway. Whether you are looking for a cozy beach house, a luxurious villa, or a spacious family-friendly home, we have something for everyone. Our dedicated team is committed to providing exceptional customer service and ensuring that your vacation experience is unforgettable. Book your dream getaway with USA House Vacations today and make lasting memories with your loved ones.

Unno Boutique Hotel is a charming lodging establishment located at 2095 East Irlo Bronson Memorial Highway in Kissimmee, Florida. This boutique hotel offers a unique and intimate atmosphere for guests looking for a personalized experience during their stay in the United States. With stylish and modern rooms, excellent amenities, and attentive staff, Unno Boutique Hotel is the perfect choice for travelers seeking a comfortable and memorable stay in Kissimmee.

Villas At Fortune Place is a charming lodging institution located at 1201 Simpson Road in Kissimmee, Florida, United States. Nestled in a serene and picturesque setting, this resort-style property offers spacious and well-appointed villas perfect for families and groups looking for a comfortable and relaxing vacation getaway. Guests can enjoy a range of amenities including a swimming pool, hot tub, fitness center, and outdoor recreational facilities. With its convenient location near popular attractions such as Walt Disney World and Universal Studios, Villas At Fortune Place is the ideal choice for a memorable and enjoyable stay in the Sunshine State.

The Riviera Motel is a charming lodging establishment located at 2248 East Irlo Bronson Memorial Highway in Kissimmee, Florida. Situated in the heart of the Sunshine State, this cozy motel offers comfortable and affordable accommodations for travelers looking to explore all that Florida has to offer. With its convenient location near popular attractions such as Walt Disney World and Universal Studios, the Riviera Motel is the perfect home base for your Florida vacation. Whether you're visiting for business or pleasure, the friendly staff at the Riviera Motel is dedicated to ensuring you have a pleasant and memorable stay. Book your room today and experience the warmth and hospitality of this delightful motel in Kissimmee.

Acadia Estates Villa is a stunning 6-bedroom, 4.5-bathroom, 2-story house located at 8025 Acadia Estates Court, Kissimmee, Florida. This beautiful property features a pool, attached hot tub/spa, theater room, and much more. Recently remodeled, the theater room is a highlight of the house, providing a luxurious entertainment experience. Conveniently located near Disney, Acadia Estates Villa offers a fantastic vacation experience for families and groups. The property is situated in a quiet, gated community and is just a short drive away from major attractions such as Universal Studios and SeaWorld. Additionally, it is only a little over an hour away from the stunning beaches of Florida.

Deep Magical Memories is a unique institution located at 2301 Butterfly Palm Way in Kissimmee, Florida, United States. As a lodging, real estate, and travel agency all rolled into one, we specialize in creating unforgettable experiences for our guests. Whether you are looking for a cozy place to stay, a dream vacation home to buy, or a magical trip to Disney World, we are here to make it happen. Our team of experts is dedicated to providing top-notch service and ensuring that every guest leaves with lasting memories. Come visit us at Deep Magical Memories and let us help you create the vacation of your dreams.

Kinsman Pointe is a premier real estate agency offering a selection of beautiful homes for rent in Kissimmee, Florida. Located at 2150 Ranch Side Road, our properties are meticulously maintained and feature modern amenities to ensure a comfortable living experience. Whether you are looking for a cozy apartment or a spacious family home, our dedicated team is here to help you find the perfect rental property to suit your needs. Contact us today to schedule a viewing and start your search for your dream home in Kissimmee.

The Valencian apartments are located at 1400 West Donegan Avenue in Kissimmee, Florida. These modern and spacious apartments offer a luxurious living experience in the heart of the Sunshine State. With a range of amenities including a sparkling swimming pool, fitness center, and beautifully landscaped grounds, residents can enjoy a resort-style lifestyle right at home. The Valencian apartments are conveniently located near shopping, dining, and entertainment options, making it the perfect place to call home in Kissimmee.

St. Cloud Village is a reputable real estate agency located at 201 Saint Cloud Village Court in Kissimmee, Florida. Our dedicated team of professionals is committed to helping clients find their dream home or investment property in the vibrant and diverse community of St. Cloud. With a wealth of experience and expertise in the local real estate market, we strive to provide personalized service and guidance to ensure a smooth and successful transaction for all parties involved. Whether you are buying, selling, or renting, St. Cloud Village is your trusted partner in navigating the real estate market in Kissimmee and beyond.

Fernandas BnB is a charming lodging establishment located at 2498 Sweetwater Club Circle in Kissimmee, Florida, United States. As a combination of a real estate agency and a travel agency, Fernandas BnB offers guests a unique experience in a beautiful and relaxing setting. Whether you are looking for a short-term rental or a vacation home, Fernandas BnB has a variety of options to suit your needs. With personalized service and attention to detail, Fernandas BnB is the perfect choice for your next stay in Kissimmee.

Star Lake Manor is a premier real estate and travel agency located in the heart of Kissimmee, Florida. Situated at the picturesque address of 7944 Sea Pearl Circle, our institution offers a wide range of services to cater to all your property and vacation needs. Whether you are looking to buy or sell a property in the area, or planning a dream vacation to Florida, our dedicated team of professionals is here to assist you every step of the way. With our expertise and knowledge of the local market, you can trust Star Lake Manor to help you find the perfect property or plan an unforgettable trip. Visit us today and let us turn your real estate and travel dreams into reality.

The Jerry Barker Group is a reputable real estate agency located at 16050 Vetta Drive, Montverde, Florida, United States. Specializing in helping buyers identify and purchase short term rental vacation homes in the Orlando / Kissimmee area near Disney, our team provides guidance with property management and oversees everything needed for a smooth transition into property ownership. We also assist current owners who are building or selling their portfolio. Our website offers three great ways to help you immediately:

Heron Holiday Homes is a boutique real estate and travel agency located at 1420 Celebration Boulevard in Celebration, Florida, United States. We offer a collection of seasonal and vacation rentals in Orlando, Kissimmee, Clermont, and Davenport, allowing you to live like a local while enjoying the best that Central Florida has to offer. Our properties are ideally located near award-winning beaches, golf courses, shopping, entertainment, and dining options. Stay at BellaVida Resort, just 5 miles from Walt Disney World, or enjoy the proximity to Universal Studios, Sea World, and more at Emerald Island Resort. Themed bedrooms, two ensuites, and recently renovated properties are available for your comfort. Experience 2nd Heaven at Reunion Resort, with views of the Jack Nicklaus-designed Tradition Golf Course and close proximity to all Orlando attractions. Come and stay with us for a memorable vacation experience in Central Florida."