Luxury rentals in Osceola County

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Top-rated luxury holiday rentals in Osceola County

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Luxe

Villa in Reunion

4.56 out of 5 average rating, 9 reviews

Reunion Pandora

If an epic, unforgettable, Insta-worthy family vacation is on your bucket list, then this villa is a no brainer. Apart from its 12-minute proximity to Disney, and all the over-the-top luxury practically oozing from its walls, the unique draw of this place is the promise of non-stop, high-end entertainment without ever leaving the house! With all of the outstanding amenities, your family is guaranteed an entertaining and restful getaway of a lifetime. Themed Rooms are the name of the game at this epic home, from elaborate kids’ bedrooms to the all-out sports themed arcade room—featuring everything from Dueling Hoop Fevers and Air Hockey, to Snocross and Terminator. The fun continues upstairs at the loft space, where you can grab a drink at the built-in bar while you catch the game on one of six flat screen TVs, or play classics like giant wall scrabble, a variety of board games, poker and pool. If you’re feeling really adventurous, you can even challenge the whole gang to a memorable sing-off using the top-of-the-line karaoke system. Just be careful not to break those martini glasses… For family movie nights, head on over to the two-tiered home theater, where everyone can pile onto the 10 leather recliners and royal purple sofa, facing a large projection screen. In the mood to enjoy the balmy weather while having a good time? Take your gaming skills to the outdoor balcony game station, fully decked out with a shuffleboard table, foosball table, and life-size connect 4. And just downstairs at the pool patio, you can host the annual family ping pong tournament, too! When you’ve just about pinged your last pong and are ready for some R&R, take a dip in your screened-in private swimming pool and jacuzzi, fully shrouded by towering palm trees and lush green nature—basically, your own secluded island oasis. Seven sun loungers surround the pool, so that you can hop out, relax and roast whenever you feel like it. Plus, a covered seating area with cozy sectionals and coffee tables is always available if you’re looking to catch some shade. When dinnertime strikes, gather around the 10-seat patio table, and fire up some poolside cuisine using the summer kitchen grill. You can set the ambiance just right by adjusting the outdoor lighting and music using the Control 4 system displayed on the walls. Just behind the glass patio doors, access your full-size kitchen, which features everything you’ll need to make your own mouthwatering meals.For indoor eating, grab a stool at the granite island-style breakfast bar, or the 14-seat dining table just beside it—with large, sleek, white dining chairs to boot. When you’re ready to wind down, enjoy a glass of wine in the comfort of your sprawling living space, where you can sink into the leather snake-skin armchairs, or stretch out on the velvety suede sofas. Glossy wood beams and rich, modern décor make this room a treat for the eyes. More extravagance awaits in all four king-sized bedrooms on the main floor—including the Master suite, which features its own attached seating area. A quick climb upstairs reveals another six exquisite bedrooms with eye-popping design, plenty of closet space, en suite bathrooms, and for some—balcony access. Even the kids will leap at the sound of “bedtime!” when they get a load of all three, one-of-a-kind themed bedrooms, including the princess-themed room, dinosaur-themed room, and sci-fi adventure-themed room! With all of these outstanding amenities, your family is guaranteed an entertaining and restful getaway of a lifetime.

Luxe

Villa in Kissimmee

4.82 out of 5 average rating, 34 reviews

Magical Mansion

Watch the golfers on the Jack Nicklaus Course from the sunny patio of this modern mini-mansion in Kissimmee. Grill up something fresh for dinner while the kids splash around in the pool. Later, melt any leftover stress away in the hot tub while you watch the sunset. In the morning, set out to explore Walt Disney World, 8-miles from Reunion Resort. Built for big families, Magical Mansion puts a little extra thought into making everyone comfortable with its generous amount of seating in each area. The spacious kitchen has a large breakfast bar island with stools, which is a great place to gather before heading out for the night. If you’re staying in, throw the big game on the widescreen and gather on the 2 L-shaped couches. Mix up a few drinks at the wet bar and challenge a friend to a game of pool or see who can beat the high score on pinball. During your stay, you’ll have shared access to the amenities at Reunion Resort. The Jack Nicklaus Golf Course, of which you’ll have a green-view, is just a 2-minute walk from home. After the course, take the kids to the Reunion Waterpark or out for a shopping trip in Orlando. Once you’ve spent a few days enjoying the magic of Disney, venture on to Universal Studios which is within 20-miles. If you’d rather take it easy, check yourself into Reunion’s spa and enjoy a secluded afternoon to yourself. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM • Bedroom 1 - Primary: King size bed, Ensuite bathroom with stand-alone rain shower & bathtub, Dual vanity, Television • Bedroom 2: King size bed, Ensuite bathroom with stand-alone shower & bathtub, Television • Bedroom 3: King size bed, Ensuite bathroom with shower/bathtub combo, Television • Bedroom 4: King size bed, Ensuite bathroom with stand-alone shower, Television • Bedroom 5: Queen size bed, Ensuite bathroom with stand-alone shower, Television • Bedroom 6: 2 Double size beds, Ensuite bathroom with stand-alone shower, Television • Bedroom 7 - Kids Room: 2 Twin over double size bunk beds, Ensuite bathroom with stand-alone shower, Television • Bedroom 8 - Kids Room: 2 Twin size beds, Ensuite bathroom with stand-alone shower, Television OUTDOOR FEATURES • Terrace • More under “What this place offers” below STAFF & SERVICES Extra cost (advance notice may be required): • Pool heating • Activities and excursions SHARED ACCESS TO AMENITIES AT THE REUNION RESORT Included: • Access to 10 Community pools throughout the Resort • Access to Seven Eagles Fitness Center • Access to 5 acres Water Park with Lazy River • Shuttle to Walt Disney World • Shuttle Service throughout the Resort • Access to 3 Signature Golf course( Arnold Palmer, Tom Watson and Jack Nicklaus) - fees apply At extra cost (advance notice may be required): • Miniature golf course • Tennis court access • On-site restaurants and bars - Eleven Rooftop Bar/Restaurant

Luxe

Villa in Davenport

5 out of 5 average rating, 4 reviews

Villatel 081

This impressive villa in dreamy Orlando can comfortably host up to 18 guests. Nestled into a fun-filled resort, there is an activity for everyone, from a movie theater to an arcade, billiards, and more. Plunge into the capacious swimming pool before relaxing in the bubbling hot tub with a cocktail. A day trip can be spent exploring nearby amusement parks, beaches, and mouth-watering restaurants. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM • Bedroom 1 - Primary: King size bed, Ensuite bathroom with stand-alone shower & bathtub • Bedroom 2: King size bed, Ensuite bathroom with stand-alone shower • Bedroom 3: King size bed, Ensuite bathroom with stand-alone shower & bathtub, Walk-in closet • Bedroom 4: 2 Queen size beds, Ensuite bathroom with stand-alone shower • Bedroom 5: King size bed, Ensuite bathroom with stand-alone shower Additional Bedding • Bedroom 6 - Kids Room: 6 Twin size beds, Ensuite bathroom with stand-alone shower

Luxe

Villa in Davenport

Villatel 050

This 6-bedroom Orlando mansion features fun for the whole family. A pool and patio area, enclosed in glass, looks out to the verdant yard. The bubbling hot tub is the perfect place to sip a cocktail. Amusement parks, beaches, and restaurants are nearby. Access to the resort’s tennis courts, waterpark, hiking trails, and more are yours to enjoy. Relax in the cinema room with your favorite movie. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM • Bedroom 1 - Primary: King size bed, Ensuite bathroom with stand-alone shower • Bedroom 2: King size bed, Ensuite bathroom with stand-alone shower & bathtub • Bedroom 3: King size bed, Ensuite bathroom with stand-alone shower & bathtub, Walk-in closet • Bedroom 4: 2 Queen size beds, Ensuite bathroom with stand-alone shower • Bedroom 5: King size bed, Ensuite bathroom with stand-alone shower Additional Bedding • Bedroom 6 - Kids Room: 6 Twin size beds, Ensuite bathroom with stand-alone shower

Luxe

Home in Celebration

Isole Villa: 25K Sq Ft Luxury Grand Estate

Isole Villa is a 25,000 sq. ft. luxury estate with 15 bedrooms, 17 bathrooms, and accommodations for 30 guests. Highlights include two Presidential Suites, a Grand Dining Room, a private spa with ESPA treatments, and a multi-level saltwater pool. Entertainment options abound with a private theater, sports court, arcade, and piano salon. The estate also offers an executive boardroom and fitness center. Perfect for retreats or family getaways, Isole Villa promises an unforgettable luxury experienc

Luxe

Home in Kissimmee

Legends Palazzo: Theater, Arcade, Theming, Golf

Legends Palazzo is a 9-bedroom, 8-bathroom luxury estate in Reunion Resort, spanning 10,637 sq. ft. and sleeping 24 guests. Highlights include a two-story Toy Story-themed kids’ room, private theater, game room with a pool table and arcade, and modern design with stainless steel appliances. The outdoor patio features ample seating, a summer kitchen, an infinity spillover hot tub, and more. With luxurious touches and resort amenities, Legends Palazzo is the ultimate destination for an unforgettab

Luxe

Home in Kissimmee

The Azure Haven at Liberty Bluff: Golf View, Pool

This luxurious 8-bedroom Reunion Resort home sleeps 24 and offers six king bedrooms and two themed twin bunk rooms (Lion King and Minions). Entertainment includes a garage theater, billiards, table tennis, gaming loft, pool basketball, corn hole, and a splash pad. The large pool patio features ample luxury seating and a fire pit for relaxing evenings. With stainless steel appliances, cozy spaces, and access to Reunion Resort amenities, this home is perfect for an unforgettable Florida getaway.

Luxe

Home in Reunion

4.83 out of 5 average rating, 6 reviews

Mansion w Arcade, Theater, Game Loft, Huge Balcony

Welcome to your dream group getaway spot in Orlando—big enough to host the whole crew, cozy enough for everyone to feel at home, and fun enough that you'll never want to leave. Lounge in the private pool and spa, test your skills in the arcade and game loft, or stage a family dance-off in the open living areas. With imaginative themed bedrooms, plenty of spots to spread out, and playful touches around every corner, this home turns group vacationing into an adventure everyone will remember.

Luxe

Villa in Kissimmee

4.3 out of 5 average rating, 10 reviews

The Palm

Welcome to our Villa. Highlights: ✔ 8 Luxury Bedroom Suites (All with En-Suite Bathrooms) ✔ 9 Bathrooms ✔ Themed Kids Bedrooms ✔ Pool, attached Spa, and Kids Splash Pad ✔ Incredible rooftop party patio with Jacuzzi + 240 degree breathtaking views ✔ Games room with 4 racing arcades, Classic Arcades, PlayStation, and XBOX ✔ Pool Table, Foosball, Shuffleboard ✔ 150" Dolby Surround Sound Movie Theater ✔ Fire pit and outdoor lounge area ✔ Professional Natural Gas BBQ No Parties or events

Luxe

Home in Four Corners

4.8 out of 5 average rating, 5 reviews

Legends Palace: Private Bowling, Theater, Arcade

Legends Palace is a 13-bedroom, 15-bathroom luxury estate in Reunion Resort, spanning 22,000 sq. ft. and sleeping 32 guests. Highlights include a private bowling alley, gym, movie theater, Harry Potter-themed suite, arcade room, and a bar with a golf simulator. The outdoor patio features a summer kitchen, ample seating, and dining areas. With luxurious finishes, expansive living spaces, and access to Reunion Resort’s amenities, Legends Palace offers an unparalleled high-end getaway.

Luxe

Home in Four Corners

4.7 out of 5 average rating, 10 reviews

Sager Reunion

A truly impressive luxurious modern mansion in Reunion Resort & Club, complete with South facing golf views, infinity pool and a kid's rock waterslide! The high ceilings and open layout, includes designs that truly impress throughout the entire home. The exquisite double height hallway and stunning staircases set the tone as soon as you step into this luxury vacation home. Take a few minutes to picture yourself in this luxury home next vacation!

Luxe

Villa in Davenport

5 out of 5 average rating, 3 reviews

Villatel 047

This elegant Davenport escape features plush décor with pops of royal blue and sumptuous fabrics. A glass-enclosed swimming pool includes a ping-pong table and spacious terrace. After watching the vivid sunset, curl up in the cinema with a favorite flick. Spend a day exploring local lakes, play a round of golf, tour a vineyard, or picnic in one of the nearby parks. Arcade games keep the fun going. Copyright © Luxury Retreats. All rights reserved.