Holiday rentals with a pool in Kissimmee

Game Room/HeatedPool/Piano Upscale Waterfront Home

Welcome to one-of-a-kind upscale contemporary waterfront oasis, where luxury meets comfort. This stunning house is nestled in a tranquil neighborhood, just moments away from the airport and all the attractions you desire. Step inside to find a beautifully renovated space: fully equipped open kitchen, game room, gym, pool table, grand piano etc Outside: private screened in heated pool($20/night heating fee)with breathtaking waterviews, patio equipped with grill, dining table, ping pong and more!

Big Disney Home! Heated Priv Pool-5 Beds Lake View

This gorgeous updated pool home is perfect for families and friends for a Florida vacation! Located just 5 mi from Disney! Close to Universal Studios! Over 2000 sq ft. Updated themed rooms. Chill in your own heated private pool or enjoy the club house pool of Veranda Palms complete with a water park and splash pad! Work out in the fitness center or walk the gated neighborhood to the new community center, just steps away. Enjoy your private game room with Skee Ball, pool table, and ping pong!

House by the Mouse: Something for Everyone!

Welcome to our completely remodeled solar four bedroom, three bath villa, less then four miles to Disney World, and only a short drive to Universal, Sea World, Lego Land, and other local attractions. Designed themed bedrooms include Harry Potter, Mickey and Minnie Mouse, Star Wars, and a romantic master bedroom that allows you to relax in comfort. The pool, spa, and the entire villa is just for you, no need to share with anyone else, so kick back and enjoy!

192 & Formosa • Private Soft Pool • 14-min Disney

🌴 What Makes This Stay Special ✅ Private salt-softened splash pool (screened-in for privacy) ✅ 3 bedrooms — each with its own full ensuite bathroom ✅ FREE parking right at your door ✅ NO resort fees ✅ 14 minutes to Disney (approx. 3.5 miles) ✅ 5 minutes to groceries, Walmart & restaurants ✅ Located inside Windsor Palms gated resort community This is a private townhome, not a hotel — which means more space, more privacy, and room for everyone to spread out.

Waterfront Wizarding Near Universal's Harry Potter

This spellbound stay, situated in the prestigious Lake Berkley Resort, boasts lake views & private pool. With 6 bedrooms, 3 bathrooms, well equipped kitchen & comfy living spaces, this thematic home is ideal for families & friends seeking an immersive vacation. A 10min drive to Disney, 15min to Sea World & 20min to Universal's Wizarding World of Harry Potter, this magical manor provides a convenient home base for exploring Orlando's famous attractions.

☀️THE☀️ SUNSHINE☀️ HOUSE☀️ (3BD/2BA/3 Smart TVs)☀️

⚠️ BOOKING REQUIREMENTS: (please do not book if you dont meet or do not agree with the requirements) ✔️Minimum age of 25 yo is required to book this unit and be ready to present photo ID when requested. Must attend the trip. ✔️Be one single family living outside Orlando area and visiting parks. ✔️Be kind, clean, and well-organized. ✔️Must carefully read and agree with (1) listing description, (2) house rules and (3) checkout instructions.iona

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

Retreat w/ Pvt Pool + Club Access | Disney 15min

Experience luxury in this spacious 5-bedroom, 5.5-bathroom home located just 15 minutes from Disney. Relax in elegant living areas with Smart TVs and an Xbox One, or step outside to your private pool with stylish patio furniture and BBQ grill. The open-concept kitchen and dining area are perfect for gathering, while the Windsor at Westside resort offers a lazy river, pools, fitness center, playgrounds, and sports courts, all just steps away.

Disney Area| Private Pool| Resort Waterpark 2956

Minutes from Disney, this spacious 4-bedroom townhome is located in the sought-after Storey Lake Resort. Relax in your private screened pool after a day at the parks and enjoy access to amazing resort amenities including water slides, lazy river, clubhouse, fitness center and kayak rentals. Comfortably sleeps up to 12 guests with a full kitchen, fast WiFi and free parking. Perfect for families visiting Disney and Orlando attractions.

The Real Florida Whispering Oaks

The Oaktree home is a favorite among returning guests. Once you have stayed in this home you cannot wait to return. The spacious pool /spa and deck area, game room and provides all you could ask for to make your stay one to remember. Recently remodeled kitchen with updated appliances make this home shine! Partially fenced in yard with no rear neighbors offer you a quiet retreat. T.V. on pool deck! Complimentary Hot Tub Heat!

8052 Heated Pool Grill House Kissimmee by Disney

Relax with the whole family at this peaceful HEATED POOL & GRILL house in Kissimmee, just minutes from Disney Parks and Margarita Ville Water Park. Master Suite has a great view to screened Pool & Lanai. 3 bedrooms, 2 bathrooms, fully equipped kitchen, 4 Smart TV's and strong Wi-Fi all around the house. Enjoy our Games Room with a Foosball table and a Pool table located in the garage!

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.