Holiday rentals with a pool in Kissimmee

Your Happy Place at Tuscana Resort

Tuscana Resort 2 bedroom 2 bath condo - New Listing - Special Rates Accommodates the needs of all types of travelers that want a cozy place to relax after a long day out and about. Close to Theme Parks, Golfing and many of Orlandos attractions. Sleeps 6 guests in this spacious open concept condo. 65" Smart flat screen TV in the living room. Both bedrooms have TV's Fully equipped kitchen for dining at home. Located on the first floor for easy access and a minute walk to the community pool.

Waterfront Escape/Private Hot Tub/3 miles 2 Disney

Discover the ultimate vacation experience in this freshly updated waterfront townhome, where comfort meets breathtaking views from your private lanai, hot tub and dining area. Wake up to serene water vistas from the spacious primary suite, featuring a plush king bed and a private ensuite bath. The guest bedroom offers two inviting double beds and 3-piece ensuite. The open-concept kitchen is a chef's dream, outfitted with modern appliances and flowing seamlessly into the dining and living areas.

Luxury 5BR free heat private pool Disney Universal

Welcome to this gem near all major attractions: Disney (5 miles), SeaWorld (7 miles), Universal (12 miles), Convention Center (9 miles), and Airport (20 miles). Nearby are outlets, restaurants, and supermarkets. This luxurious home features 5 bedrooms, 4 bathrooms, a private heated pool/spa, fully equipped kitchen, laundry, and free stroller, playpen, and highchair. Resort amenities include a water complex, lazy river, bar, fitness center, mini golf, kayaking, and more! Pets friendly & welcome!

Disney World Area Executive Villa *Sleeps 10* Pool

Luxury Villa in the Disney Area of Orlando. 3 bedrooms and second floor living room with sofa bed, sleeping up to 10 guests Situated in the fabulous Highlands Reserve, Walt Disney World is only 25 minutes drive. The villa features a private screened pool with sundeck, perfect for outdoor dining Spacious accommodation and featuring a master suite with bathroom and walk in closet, children's rooms and games room Infant pushchair, highchair & cot/pac 'n' play Laundry & fully equipped kitchen

Luxury Themed 5BR-Pool-Game Room

This newly-built townhome in Solara Resort is boasting a perfect location near all of the famous amusement parks and attractions this area is known for, you will have no delay in spoiling the whole family with a day at Disney or Universal Studios. Take a relaxing dip in the private pool, grill up a few burgers on the grill, or simply reminisce with loved ones. Inside you will be spoiled by the modern touches throughout. The kiddos will absolutely love the Marvel and Disney-themed bedrooms.

VerandaPalms/HeatedPool/Carpet free/NearDisney

This beautiful 4 bedroom home is 10 minutes from the Disney parks !!! Walking distance from Shingle Creek Reg. Park, just in the corner of Veranda Palms main entrance. This home has 2 suites, a private heated pool and is located near Sams Club and restaurants. Complimentary XBOX and Nespresso Coffee machine. ROKU in all bedrooms. Non smoking policy. Clubhouse with large swimming pool and gym. Well-maintained home, with new appliances. Superhost awarded 34 times in a row !!!

"Paradise Found" Sensational 6 Bed Home W/Peloton

Discover 'Paradise Found' at Windsor at Westside, a 6-bed fantasy home near Disney. This 3,300 sq ft gem offers an open-plan living space, gourmet kitchen, and a private pool oasis with a BBQ, dining and lounge. Enjoy a king suite with pool access, a fun-filled garage gym/games area, and a vast upstairs lounge with Xbox. Dream in themed children's rooms or one of the three king bedrooms. Perfect for families seeking a magical retreat! Free resort access, pool heat and BBQ.

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

Premium 6BR | Theater, Games & Heated Pool

Welcome to your 3,400 sq ft luxury escape just minutes from Disney World! Perfect for families and friends, our villa sleeps 12 with ensuite bathrooms in every bedroom. Enjoy the home theater, game room, and a fully equipped kitchen—plenty of space to gather or relax. Close to shopping, dining, and all the Orlando magic. Book now for unforgettable memories in your private Disney-area villa.

2-104 Legacy Dunes, Lake View, Heated Pool, Gym

Two Bedrooms 1 King Sized Bed 1 Queen Sized Bed 1 Queen Sized Sleeper Sofa Bed Sleeps up to 6 Guests 2 Full Bathrooms Ground Floor, No Stairs to Climb Close to Walt Disney World Screened Patio with a Lake View Washer and Dryer Roku TV's Free Wi-Fi Free Parking Heated Outdoor Swimming pool Tennis Court, Basketball, Pickleball, Volleyball Game Room Playground Gym Gated Community

Haunted Mansion Retreat with pool 7 min to Disney

Our Haunted Mini Mansion is a delightful ghostly retreat where every room has wall-to-wall creeps! Enjoy this spooky 3 bedroom, 3 full bathroom private townhouse inspired by Disney’s Haunted Mansion. Hurry back to make your final arrangements!

4 Bd/3 Ba Sleeps 10! Lucaya Village (25-108)

• Community: Lucaya Village • 4 Bedrooms/3 Bathrooms/Sleeps 10 • Disney (5 miles) Sea World (7 miles) Universal (12 miles) • Convention Center (6 miles) Legoland (31 miles) • Location: Polynesian Isle Blvd, Kissimmee FL 34746