The Most Luxurious Vacation Home Rentals in Kissimmee

Enter a world of unrivaled opulence at Isolé Villas, one of Central Florida’s most luxurious private estates. Spanning 25,000 square feet, this modern paradise features 15 bedrooms, each outfitted with customized mattresses, fine linens, and en suite bathrooms, accommodating up to 30 guests. The multi-level saltwater pool with sun loungers on the balcony and Jacuzzi offers a serene oasis for relaxation. Indulge in the spa and wellness center complete with a steam room, treatment area, lounge, sauna, and fitness center. For entertainment, the estate includes an indoor basketball court, movie theater, cigar lounge, and piano salon. Access to championship golf courses designed by Jack Nicklaus and Arnold Palmer makes this villa popular for weddings, family reunions, and other grand events.

Blending luxury with natural beauty, the Eagle Modern Oasis at Reunion Resort backs up to a nature preserve, offering a sleek private home with seven bedrooms that can accommodate up to 19 guests. The natural modern furnishings feel like they’re straight off the pages of a design magazine, with indoor and outdoor living spaces adorned with rich woods and stone accents. After a day of adventures, unwind in the stone soaking tubs or take a dip in the ultra-modern pool and hot tub surrounded by lush Florida foliage. The kids will love the camping and adventure-themed bedrooms and the indoor beach-themed drive-in movie theater. Additional amenities include an indoor basketball court and even more through Reunion Resort.

Step into a fairytale at Reunion Château, where modern luxury meets dreamy old-world charm. This 10-bedroom estate sleeps up to 24 guests and features multiple suites and custom rooms for kids. The interior design is highlighted by a four-tier chandelier and many handcrafted elements. Gather around the custom 2,400-pound table in the chef’s kitchen and dining room or relax by the infinity-edge pool with a sundeck and summer kitchen. The private courtyard with fountains, indoor spa, game room with arcade games, and a secret passageway to a play area add to the enchantment.

For those who crave glamour and fun, Pine Valley Paradise at Bear’s Den in Reunion Resort & Golf Club offers a stunning view of the 18th hole of the Jack Nicklaus Golf Course. This sprawling private home includes 8 bedrooms and can sleep up to 18 guests. The large pool and lavish bathrooms with soaking tubs provide relaxation, while the modern furnishings and fully equipped kitchen offer comfort and convenience. A game room with arcade games ensures entertainment for all ages. Guests also have access to the extensive amenities of the resort.

Located next door to Walt Disney World® Resort, Magic Village Views offers modern, elegant condos in a gated community. These three and four-bedroom villas are fully furnished and provide a taste of attainable luxury. Each bedroom comes with its own private complete bathroom, and there’s a half bath on the lower level. The full kitchen, washer, dryer, and private outdoor space with BBQ grill ensure convenience. Onsite amenities include a heated pool, hot tub, tennis court, volleyball court, onsite restaurant, and fitness room. It’s the perfect blend of luxury and proximity to the magic.