TOP 30 Vacation rental properties in Kissimmee, Florida

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Located in Kissimmee, Florida, Quality Vacation Homes offers a range of beautiful and comfortable lodging options for those looking to enjoy a relaxing and luxurious vacation. Our vacation homes are fully equipped with all the amenities needed for a comfortable stay, including spacious living areas, fully equipped kitchens, and private pools. Whether you're looking for a cozy retreat for a romantic getaway or a spacious home for a family vacation, Quality Vacation Homes has the perfect accommodation for you. Our prime location allows easy access to all the attractions and activities that Kissimmee has to offer, making it the ideal choice for your next vacation. Book your stay with us today and experience the ultimate in quality vacation living.

Reunion Vacation Homes is a lodging, real estate, and travel agency located at 7531 Osceola Polk Line Road in Davenport, Florida, United States. Specializing in bringing friends and family together in Orlando Vacation Home Rentals and Anna Maria Island Rentals, Reunion Vacation Homes offers a wide range of vacation rentals in select Orlando area resorts close to Disney® such as Reunion Resort, The Retreat at Champions Gate, Windsor at Westside, and more. With options ranging from 2-3 bedroom condos to 10-14 bedroom luxury villas, there is something for everyone. Whether you're looking for top villa rentals near Disney World® in Kissimmee & Davenport, or luxury mansions in Reunion Resort, Reunion Vacation Homes has you covered. With over 300 luxury villas and condos to choose from, guests can enjoy amenities such as private pools, golf course views, and proximity to major attractions.

Orlando Short Term Rentals is a premier real estate and travel agency located at 1050 Plaza Drive in Kissimmee, Florida. Specializing in providing top-notch short term rental properties in the Orlando area, our agency offers a wide range of accommodations to suit every traveler's needs. Whether you're visiting for a family vacation, business trip, or special event, our team is dedicated to helping you find the perfect rental property to make your stay unforgettable. With a focus on customer satisfaction and personalized service, Orlando Short Term Rentals is your go-to destination for a seamless and enjoyable rental experience in the Sunshine State.

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.

Bella Vida Vacation Homes is a luxurious lodging option located in Kissimmee, Florida. As a real estate and travel agency, they offer a wide range of vacation homes for rent, providing guests with the ultimate comfort and convenience during their stay. Situated at 1172 Marcello Boulevard, Bella Vida Vacation Homes is the perfect choice for travelers looking for a home away from home experience in the Sunshine State. With top-notch amenities and a prime location near popular attractions, Bella Vida Vacation Homes ensures a memorable and enjoyable stay for all guests.

Located at 8900 Legacy Court in Kissimmee, Florida, Go Disney Vacation is a top accommodation choice for those visiting Disney World. Offering spacious vacation home condo rentals with amenities such as a living room, dining room, fully equipped kitchen, separate bedrooms, balcony, and free WiFi, our properties provide a comfortable and affordable alternative to staying at Disney's resort hotels. With resort-style amenities, security, and a convenient location near all the major theme parks and attractions, our vacation homes offer a peaceful retreat for families looking to relax and unwind after a day at the parks. Skip the expensive dining options at Disney and enjoy preparing meals in your own kitchen. Book with us and experience the top 10 benefits of staying at a vacation home instead of a Disney resort hotel. With our high guest satisfaction ratings on TripAdvisor, Go Disney Vacation is your number one choice for a magical Disney vacation in Kissimmee, Florida.

Breeze Kissimmee is a vibrant and lively bar located at 7 East Dakin Avenue in the heart of Kissimmee, Florida. Known for its relaxed atmosphere and friendly staff, Breeze Kissimmee offers a wide selection of beverages, including craft cocktails, beer, and wine. Guests can enjoy live music, DJ nights, and special events throughout the week. Whether you're looking for a fun night out with friends or a place to unwind after a long day, Breeze Kissimmee is the perfect spot to kick back and enjoy the breeze.

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!

Experience luxury at its finest in this stunning 3 bedroom, 2 bath condo located in the prestigious Windsor Hills community in Kissimmee, Florida. This beautifully appointed accommodation features modern amenities, high-end furnishings, and a spacious layout perfect for families or groups of friends. Enjoy the convenience of a fully equipped kitchen, plush bedding, and a private balcony with breathtaking views. Take advantage of the resort-style amenities including a pool, fitness center, and clubhouse. With its prime location near Disney World and other major attractions, this condo is the perfect choice for your next vacation 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.

Viva Orlando Rentals is a premier real estate agency located at 610 Sycamore Street in Kissimmee, Florida. Specializing in vacation rentals in the Orlando area, Viva Orlando Rentals offers a wide range of properties to choose from, including luxury villas, condos, and townhomes. With a commitment to providing top-notch customer service and personalized attention to each client, Viva Orlando Rentals is dedicated to helping visitors find the perfect accommodation for their stay in the sunshine state. Whether you're planning a family vacation, a romantic getaway, or a group trip, Viva Orlando Rentals has the perfect property for you. Book your dream vacation rental with Viva Orlando Rentals today and experience the magic of Orlando in style and comfort.

Vista Del Lago Rentals is a premier real estate agency located at 16594 Avenue del Lago in Kissimmee, Florida, United States. Specializing in vacation rentals, long-term rentals, and property management services, Vista Del Lago Rentals offers a wide range of properties to suit every need and budget. With a team of experienced professionals dedicated to providing exceptional service, clients can trust Vista Del Lago Rentals to help them find the perfect rental property or manage their investment with care and expertise. Whether you are looking for a cozy vacation home or seeking assistance in renting out your property, Vista Del Lago Rentals is the go-to agency in the Kissimmee area.

Innovare Vacation Homes is a premier real estate and travel agency located in Kissimmee, Florida, United States. We specialize in providing luxurious vacation homes for rent in the Orlando area, catering to tourists and travelers looking for a comfortable and convenient accommodation during their stay. Our properties are meticulously maintained and fully equipped with modern amenities to ensure a relaxing and enjoyable experience for our guests. Whether you are visiting for a family vacation or a romantic getaway, Innovare Vacation Homes offers a wide range of options to suit your needs. Book with us and make your stay in Florida truly unforgettable.

Tropical Villas Orlando Vacation Rentals & Property Management is a premier real estate and travel agency located at 2950 Loopdale Lane in Kissimmee, Florida, United States. We specialize in providing luxurious vacation rentals in the tropical paradise of Orlando, offering a wide range of properties to suit every traveler's needs. Our dedicated team of professionals is committed to ensuring a seamless and unforgettable vacation experience for our guests, from booking to check-out. Whether you're looking for a cozy condo or a spacious villa, we have the perfect accommodation for your dream vacation in Orlando. Contact us today to start planning your next getaway!

Vacation Alchemy is a premier real estate and travel agency located in Kissimmee, Florida. Our team of experienced professionals specializes in crafting unforgettable vacation experiences for our clients. Whether you're looking to buy or rent a vacation home in the Sunshine State, or you need assistance planning the perfect getaway, Vacation Alchemy has you covered. With a prime location near all of the attractions that Florida has to offer, including Disney World and Universal Studios, we are your one-stop shop for all of your vacation needs. Contact us today to start planning your dream vacation!

The Diamond on the Island at Emerald Island Resort is a luxurious vacation rental house located in Kissimmee, Florida. Situated in the prestigious Emerald Island Resort, this stunning property offers the perfect combination of comfort, style, and convenience for your Disney vacation. With spacious accommodations, modern amenities, and a prime location just minutes away from Walt Disney World, this rental house is the ideal choice for families and groups looking to experience the magic of Orlando. Book your stay at The Diamond on the Island and make unforgettable memories on your next Florida getaway. Contact our real estate and travel agency located at 8578 Sunrise Key Drive to learn more about our exclusive vacation rental options.

Emerald Island Resort offers luxurious villa and townhouse rentals in the heart of Kissimmee, Florida. Situated on Emerald Island Boulevard, this stunning property is the perfect choice for travelers looking for a memorable vacation experience. Whether you're looking for a relaxing getaway or an action-packed adventure, Emerald Island Resort has something for everyone. With top-notch amenities, spacious accommodations, and a convenient location near all the attractions, this resort is the ideal destination for your next vacation. Book your stay with Emerald Island Resort today and make unforgettable memories in the Sunshine State.

Blue Sky Villas is a luxurious vacation home rental agency located at 7862 West Irlo Bronson Memorial Highway in Kissimmee, Florida. Our stunning properties offer guests the ultimate in comfort and style, with spacious accommodations and top-of-the-line amenities. Whether you're looking for a relaxing getaway or a fun-filled family vacation, Blue Sky Villas has the perfect home for you. Our dedicated team of professionals is here to ensure that your stay is nothing short of perfect. Book your dream vacation with us today and experience the luxury and convenience of Blue Sky Villas.

Sunrise 2 Sunset Vacation Homes is a real estate and travel agency located at 7828 West Irlo Bronson Memorial Highway in Kissimmee, Florida, United States. As a partner with CiiRUS, they offer more than just vacation rental software - they provide real solutions to drive efficiency and grow revenue for your business. With elite reservation management tools for hosts of all sizes, they make it easy to handle rates, quotes, and reservations from multiple channels including Airbnb, Vrbo, and your own website. Their software allows you to centrally track all income and expenses, pay owners, charge vendors, and distribute branded owner statements directly. You can easily distinguish payouts, expenses, and commissions with ongoing reconciliation and advanced reports. The software also offers real-time full-data sync with Airbnb, Vrbo, and more without the need for third parties.

Disney Luxury Rental is a top-rated real estate and travel agency located at 2672 Manesty Lane in Kissimmee, Florida, United States. We specialize in providing luxury vacation rentals for those looking to experience the magic of Disney in complete comfort. Our properties are meticulously maintained and equipped with all the amenities you need for a memorable stay. Whether you're planning a family vacation or a romantic getaway, Disney Luxury Rental is here to help you create the ultimate Disney experience. Book with us today and start making memories that will last a lifetime! Welcome to Disney Luxury Rental! ⭐️⭐️⭐️⭐️⭐️

Vacation Pool Homes is a premier real estate and travel agency located in Kissimmee, Florida. Situated at 7799 Styles Boulevard, this institution specializes in providing luxurious vacation rental homes with private pools for visitors to the Sunshine State. With a wide range of properties to choose from, Vacation Pool Homes offers the perfect accommodation for families, couples, and groups looking to enjoy a relaxing and memorable vacation in Florida. Whether you're planning a theme park adventure or simply seeking a peaceful retreat, Vacation Pool Homes has the perfect property for you. Book your dream vacation home today and experience the ultimate in comfort, convenience, and relaxation.

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.

M&M Legacy Rentals LLC is a real estate and travel agency located at 2613 Daulby Street in Kissimmee, Florida, United States. Our luxurious lakeview villa offers 6 bedrooms and a new massage chair for ultimate relaxation. With stunning pool views and newly updated features, our villa aims to provide a tranquil and rejuvenating experience for our guests. We offer overflow parking with prior approval, fully stocked kitchen supplies, new appliances, and entertainment options such as a Star Wars mini theater game room and massage chairs. Additionally, we provide complimentary pool heat, BBQ, and essential household items. Our payment schedule and cancellation policy ensure a seamless booking process, and we highly recommend travel insurance. Guests can communicate with us via email or text, and we provide a secure numeric door lock for easy access. Our property is located in a gated community with security measures in place, including Ring cameras and a security fence around the pool. We also offer a safe for valuables and assistance with planning Walt Disney World trips. Guests must obtain wristbands for access to community amenities, and day visitors are subject to approval and an additional fee. Amazon delivers packages to the community regularly, ensuring convenience for our guests. Visit our website to book your stay and experience the ultimate resort vacation at M&M Legacy Rentals LLC.

Located at 7588 Excitement Drive in Kissimmee, Florida, My Orlando Vacation Escape is a top-rated real estate and travel agency specializing in luxury themed vacation rentals. Our properties include themed bowling villas and stunning view mansions throughout Florida, providing guests with an immersive and unforgettable experience. At My Orlando Vacation Escape, we take pride in hosting guests from around the globe who come to celebrate life's special moments. Our commitment to exceptional customer service is reflected in our numerous 5-star reviews, as we strive to ensure each guest has a memorable and enjoyable stay.

Advantage Vacation Homes is a premier lodging option in Kissimmee, Florida, offering luxurious vacation homes for rent. Situated at 7799 Styles Boulevard, this real estate agency provides travelers with spacious and well-appointed accommodations, perfect for families and large groups. Each vacation home is fully furnished and equipped with modern amenities, ensuring a comfortable and convenient stay. Guests can enjoy the privacy and flexibility of a home away from home, while still having access to resort-style amenities and services. Whether you're visiting the nearby theme parks or simply looking to relax in the Sunshine State, Advantage Vacation Homes is the ideal choice for your next getaway.

Welcome to Big R House, managed by Big R Vacations LLC! Located at 8891 Menton Loop in Kissimmee, Florida, our institution is a real estate and travel agency specializing in vacation rentals. After a fun-filled day at Disney, Seaworld, and Universal, come back to our home to relax and unwind. Originally owned by us, we have put a lot of thought and care into the design of this property to ensure your comfort and enjoyment.

Experience the ultimate Star Wars adventure at the #1 Rated Vacation Rental in Kissimmee, Florida. This 5-star Villa is perfect for fans of the iconic franchise, with themed rooms and decor that will transport you to a galaxy far, far away. Located at 2608 Bowring Street, our real estate and travel agency offers a unique and unforgettable experience for guests of all ages. Book your stay now and immerse yourself in the magic of Star Wars!

Love Rentals is a reputable real estate agency located at 1142 Celebration Boulevard in Kissimmee, Florida. Specializing in vacation rentals and property management, Love Rentals offers a wide range of luxurious and affordable properties for short-term stays or long-term leases. Our experienced team is dedicated to providing exceptional customer service and ensuring a seamless rental experience for both tenants and property owners. Whether you are looking for a cozy apartment, a spacious family home, or a beachfront villa, Love Rentals has the perfect property to suit your needs. Contact us today to find your dream rental property in beautiful Kissimmee, Florida.