TOP 30 Best Vacation homes with private pools in Kissimmee, Florida

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.

Berkley Lake Townhomes is a luxurious lodging option located at 1049 Park Ridge Circle in Kissimmee, Florida. This institution offers spacious and beautifully designed townhomes for guests looking for a comfortable and convenient stay. With modern amenities, a tranquil lakefront setting, and close proximity to popular attractions in the area, Berkley Lake Townhomes provides a perfect retreat for vacationers and business travelers alike. Enjoy the comforts of home away from home at this charming accommodation in the heart of Kissimmee.

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.

Nestled in the heart of Kissimmee, Florida, Orlando Vacation Rentals Homes at Storey Lake Resort offers luxurious lodging options for visitors to the area. Whether you're looking for a cozy condo or a spacious villa, this real estate and travel agency has a wide selection of vacation rentals to choose from. With its convenient location near popular attractions like Walt Disney World and Universal Studios, Storey Lake Resort is the perfect home base for your Orlando vacation. Experience the comfort and convenience of a home away from home at this beautiful resort community located at 3131 Paradox Circle.

Encantada Resort Vacation Townhomes by IDILIQ is a luxurious lodging option located at 3070 Secret Lake Drive in Kissimmee, Florida. This resort offers spacious and comfortable self-catering townhomes just outside Walt Disney World, making it the perfect choice for vacationers looking for larger spaces and great amenities. Each townhome at Encantada Resort is individually owned and features a fully equipped kitchen, private patio with a hot tub, and all the facilities needed for a perfect vacation in Orlando. The resort is ideal for families and larger groups, with two, three, and four-bedroom options available.

Orbit One Vacation Villas is a charming lodging institution located at 2950 Entry Point Boulevard in Kissimmee, Florida, United States. Nestled in a peaceful and picturesque setting, this vacation villa offers a relaxing escape for guests looking to unwind and rejuvenate. The spacious and well-appointed villas provide all the comforts of home, including fully equipped kitchens, cozy living areas, and private balconies or patios. Guests can also enjoy the resort's amenities such as a swimming pool, hot tub, fitness center, and barbecue area. With its convenient location near popular attractions like Walt Disney World and Universal Studios, Orbit One Vacation Villas is the perfect choice for a memorable and enjoyable vacation experience.

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.

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.

747 Vacation Homes is a premier vacation rental agency located in Kissimmee, Florida. Situated at 8701 West Irlo Bronson Memorial Highway, this institution offers a wide selection of luxurious vacation homes for visitors to enjoy while exploring the attractions of the Orlando area. Whether you're looking for a cozy condo, a spacious villa, or a private pool home, 747 Vacation Homes has the perfect accommodation for your stay. With top-notch amenities and convenient access to popular theme parks and entertainment venues, this institution ensures a comfortable and memorable vacation experience for all guests. Book your dream vacation home with 747 Vacation Homes today and make your stay in Kissimmee truly unforgettable.

Disney Dream Vacation Villa is a luxurious and spacious accommodation located at 2693 Manesty Lane in Kissimmee, Florida, just a short drive away from the magical world of Disney. This stunning villa offers guests a truly unforgettable experience with its modern amenities, stylish decor, and comfortable furnishings. Whether you're looking for a romantic getaway or a fun-filled family vacation, this villa is the perfect choice. Enjoy relaxing by the private pool, cooking in the fully-equipped kitchen, or watching movies in the cozy living room. With its prime location near all the attractions of Disney World, staying at Disney Dream Vacation Villa is sure to make your trip truly magical.

Vacation Villas at Fantasyworld Two is a lodging institution located at 4999 Kyngs Heath Road, Kissimmee, Florida. Just minutes from Orlando's famous attractions, this vacation destination offers a hometown feel with easy access to Disney World, Universal Studios, and SeaWorld. The diverse city of Kissimmee is filled with shopping, dining, and entertainment options, making it a perfect location for families and travelers of all ages. The spacious vacation rentals at Vacation Villas at Fantasyworld Two feature full kitchens, quiet bedrooms, and living areas, perfect for extended family vacations. Unique lockout units offer a private bathroom and kitchenette in the second bedroom. Onsite amenities include an outdoor swimming pool, children's pool and playground, and barbecue area.

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.

DISNEY VACATION RENTALS offers cozy 1 and 2 bedroom cottages for guests looking to experience the magic of Disney while staying in the comfort of a home away from home. Located in Kissimmee, Florida, just a short drive from the theme parks, guests can enjoy the convenience of renting golf carts and campers to explore the area. NEC ENTERPRISES LLC also operates as a real estate agency, RV park, store, and travel agency, providing guests with a one-stop shop for all their vacation needs. Experience the magic of Disney with DISNEY VACATION RENTALS.

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.

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.

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.

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.

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.

Titan Vacation Homes is a premier real estate agency located at 5047 West Irlo Bronson Memorial Highway in Kissimmee, Florida. Specializing in luxury vacation rental properties, our team of experienced agents are dedicated to helping clients find the perfect home for their dream getaway. Whether you're looking for a cozy cabin in the woods or a beachfront villa, Titan Vacation Homes has a wide range of options to choose from. With exceptional customer service and a commitment to excellence, let us help you make your vacation dreams a reality.

Atlas Vacation Homes is a premier institution located at 3211 Vineland Road, Kissimmee, Florida, United States. As a general contractor, real estate agency, and travel agency all in one, we offer a unique and enchanting getaway experience in the heart of Florida. Our properties are situated just minutes away from Walt Disney World® Resort, providing a luxurious place to vacation surrounded by the beauty of nature. At Storey Lake, guests can choose from 5 to 7-bedroom homes and 4 to 5-bedroom town homes built around a picturesque lake. Enjoy water amenities such as sand beach areas, canoe & kayak rentals, fishing, and more. The Retreat at ChampionsGate offers 4 to 9-bedroom vacation rental homes and 4-bedroom town homes with access to resort-style amenities at the Oasis Club, including discounted golf rates at the ChampionsGate Country Club.

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.

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.

Vacation Homes for Rent offers a wide selection of beautiful and comfortable vacation homes in Kissimmee, Florida. Located at 8681 West Irlo Bronson Memorial Highway, our properties are perfect for families, groups, and couples looking for a relaxing and memorable getaway. Each home is fully equipped with modern amenities and features, including private pools, spacious living areas, and fully equipped kitchens. Our convenient location allows easy access to popular attractions such as Walt Disney World, Universal Studios, and SeaWorld. Whether you're looking for a cozy retreat or a luxurious escape, Vacation Homes for Rent has the perfect accommodation for your next vacation in sunny Florida.

Florida Fantasy Homes is a premier lodging institution located in the heart of Kissimmee, Florida. Situated at 1050 East Osceola Parkway, our luxurious vacation homes offer the perfect blend of comfort and convenience for travelers visiting the Sunshine State. Whether you're looking for a cozy retreat for a romantic getaway or a spacious accommodation for a family vacation, Florida Fantasy Homes has a variety of options to suit your needs. With top-notch amenities, stunning decor, and proximity to popular attractions like Disney World and Universal Studios, our institution provides the ultimate home away from home experience for guests. Book your stay with us and make your Florida dream vacation a reality.

Experience luxury and comfort at our Private Heated Pool House with Office near Disney World in Orlando. This stunning 5-bedroom, 3-bathroom property is perfect for families or groups of up to 11 guests. With 2317 ft² of space, this entire place offers plenty of room to relax and unwind. Located at 1037 Lake Berkley Drive in Kissimmee, Florida, our property is just a short drive away from all the attractions that Orlando has to offer. The exact location will be shared before your arrival, ensuring a smooth check-in process.

Elite Vacation Homes is a premier real estate agency located in Kissimmee, Florida. Our team specializes in providing luxurious vacation rental homes for visitors looking to experience the magic of Orlando. Situated at 7 North Vernon Avenue, our properties are conveniently located near all the major attractions, including Walt Disney World, Universal Studios, and SeaWorld. With a wide range of accommodations to choose from, we cater to families, couples, and large groups alike. Our expert staff is dedicated to ensuring that your stay is nothing short of exceptional, offering top-notch customer service and personalized recommendations for your vacation needs. Experience the ultimate in comfort and convenience with Elite Vacation Homes.

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! ⭐️⭐️⭐️⭐️⭐️

Apart Orlando Hotel is a lodging institution located at 3001 Limbo Lane in Kissimmee, Florida, United States. Offering excellent furnished apartments in a gated resort complex, guests can choose from 1, 2, or 3 bedroom accommodations depending on the number of visitors. Situated just a 5-minute drive from Disney parks and a short distance from Walmart and major outlets, Apart Orlando Hotel provides convenient and comfortable accommodation for travelers exploring the area.

Solara Resort Clubhouse is a luxurious lodging option located at 1575 Carey Palm Circle in Kissimmee, Florida. This resort offers vacation home rentals near popular attractions such as Disney World, SeaWorld, and Universal Orlando. The clubhouse features a splash pad, volleyball court, fitness center, poolside Tiki bar, private poolside cabanas, and more for guests to enjoy. Whether you prefer sports or relaxation, Solara Resort has something for everyone. The resort's central location provides easy access to theme parks, dining, shopping, and entertainment. With a variety of amenities and activities available, Solara Resort Clubhouse is the perfect destination for a memorable Orlando vacation experience.

Reunion Resort Water Park, located at 7593 Gathering Drive in Kissimmee, Florida, is a top tourist attraction and amusement park for visitors of all ages. With a variety of exclusive amenities and features, including private swimming pools and movie theaters, our vacation homes offer a unique and luxurious stay. The Water Park at Reunion Resort features a zero entry pool, 1,000 foot lazy river, large waterslide, kids splash zone, beach area, cabanas for rent, and a full bar with frozen drinks. Guests can enjoy complimentary tubes for the lazy river and participate in family-friendly contests for prizes.