Holiday rentals with a pool in Kissimmee

Lakeside Paradise, 15 min Disney + Saltwater Pool

Welcome to Lakeside Paradise – Discover the perfect blend of tranquility and excitement at Lakeside Paradise. Enjoy the serenity of our lakeside retreat, just moments from Central Florida’s top attractions: Disney Parks – 8 miles (15 mins) Universal Studios – 16 miles (25 mins) SeaWorld – 13 miles (20 mins) ESPN Sports Complex – 6 miles (10 mins) Margaritaville/Island H2O – 3 miles (10 mins) Walmart/Target – 6 miles (10 mins) Optional heated pool and spa available for an added fee of $40/day

Waterfront next to Resort by Disney Game &Theater

Lakefront Luxury Everything is Completely remodeled 5 bdrms\5 bthrms luxury villa – Located in the gated Paradise Palms Resort,which is just around the corner from Disney. Only a few steps away from the Clubhouse amenities & nature path,this home offers privacy & lake\nature views from the sun soaked south facing color changing pool\spa.Enjoy , New home theater, two 1st floor master bdrms & 2 bthrms + another master & immersive themed rooms on 2nd floor. AC Arcade TV gameroom & billiards Loft

8BR Lakefront themed Villa•Pool•GameRoom•GolfCart

Stay minutes from Disney in a spacious 8BR, 4.5BA villa designed for families & groups! Kids will love the Mario Kart, Frozen, Toy Story, Small World & Royal themed rooms, plus a Harry Potter game room with pool table & arcades. Adults will enjoy the private pool, lanai patio, gourmet kitchen, Beauty & the Beast dining room, and the convenience of a golf cart included with your stay. Perfect for: • Multi-family Disney trips • Large groups (sleeps 16+) • Guests wanting both space & magic

Luxurious 5BR w/ Pool, Spa, Game Room & BBQ Grill

Step into your dream getaway at Windsor Island Resort, a stunning vacation retreat in Kissimmee with a private pool, relaxing spa, and full resort-style amenities. Just 10 miles from Disney and close to Orlando’s top attractions, this spacious home is perfect for families and friends. Whether you’re floating down the lazy river, enjoying a game of basketball, or simply unwinding in your own private oasis, this villa combines comfort, fun, and convenience for an unforgettable vacation.

Gorgeous 5BR @ Encore Next to Disney - 305

Modern 3,000sf luxury home, with 5 bedrooms, at world's renowned Encore Resort at Reunion. Featuring 5 bedrooms, 5 1/2 bathrooms, a game room, a beautiful backyard, a private pool and spa. 6 Minutes away from Super Walmart and Publix supermarket 15 Minutes away from Disney Parks 15 minutes away from Disney Springs 15 Minutes away from Premium Outlets 20 Minutes away from Universal Studios 20 Minutes away from International Drive attractions *PLEASE MAKE SURE TO READ THE HOUSE RULES*

Luxury Townhouse Near Disney | 3BR

Enjoy a brand new, beautifully designed townhouse located in the exclusive Magic Village community, just minutes away from Disney Parks. What you’ll love: • Private patio with outdoor furniture • Free Wi-Fi • Fresh towels & linens • Fully equipped kitchen • BBQ grill (no additional fee) • Free parking (no extra cost) The pool, tennis court and fitness center should pay $100 extra fee per group per day. ✨ Book now and enjoy a memorable stay near the magic!

Upstay-Luxury 3BR Home w Private Pool & Games Room

Escape to your own resort retreat—just 17 miles from Disney! Splash in the private screened-in pool, unwind in the chic living area, or challenge the crew to games upstairs. This vibrant 3-bedroom home features a King and Queen bedroom and a fun Minions-themed bunk room, full kitchen, Smart TVs, and in-home laundry. With BBQ, resort-style clubhouse access, and family-friendly vibes, it's the ultimate Florida getaway! Your dream adventure starts right here.

Contemporary Stay 10 min to Parks Pets Friendly

Welcome to Your Magical Gateway – Just 10 Minutes from Orlando's Magical Parks! Location: Perfectly located for Disney and Universal, our apartment offers a peaceful retreat with all the comforts of home. Whether you’re here to explore the magic unwind, or even stay for longer terms, you’ll love every moment of our cozy space. The property sleeps 4 people! PLEASE CONTACT US TO INQUIRY ABOUT ADDITIONAL POTENTIAL DISCOUNTS FOR MULTIPLE DAYS STAY

Heated pool~Lazy River~Mini Golf~Near DisneyResort

Welcome to Lazy Lagoon, your ultimate vacation retreat in the heart of Kissimmee, FL! Our inviting 4-bedroom, 3-bathroom home offers the perfect blend of comfort and adventure, making it ideal for families, friends, or any group getaway. With space to accommodate up to 10 guests, you'll find everything you need for an unforgettable stay just minutes from Orlando's top attractions.

4Bd/ 4.5 Ba Sleeps 12! Solara Resort (2378ZP)

• Community: Solara Resort • 4 Bedrooms/ 4.5 Bathrooms/ Sleeps 12 • Clubhouse (0.9 miles) Walmart (4.1 miles) Publix (4.1 miles) • Disney World® (7.3 miles) SeaWorld (16.4 miles) • Convention Center (17.5 miles) ICON Park (19.5 miles) • Universal Studios (20.2 miles) Epic Universe (19.2 miles)i) • Location: Zaballina Place, Kissimmee FL 34747

Cozy Modern 1 Bedroom Apartment

Warm welcome to our modern one bedroom apartment. We are happy to be your host for your stay. Located minutes away from attractions such as Walt Disney World and Universal Studios. During your stay you will find comfort with a brew of a delicious cup of coffee as the sun rises. Book your next stay with us. We would love to be your host!

Boutique Luxury Home, Private Pool Close to Disney

Spend a unique boutique experience, just minutes from Walt Disney World theme parks, in this stylish 6-bedroom, 6-bathroom home that can comfortably accommodate 12 people. The house features a private pool, an Al fresco dining area with a BBQ and a lovely view to the golf court at Reunion Resort.