Luxury rentals in Osceola County

Find and book unique accommodations on Airbnb

Top-rated luxury vacation rentals in Osceola County

Guests agree: these stays are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

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

4.81 out of 5 average rating, 27 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 Reunion

4.8 out of 5 average rating, 5 reviews

Reunion Blue Moon

Flights of fancy fill this fairy-tale-inspired, gorgeously appointed Orlando home with all-ages appeal. Not only are there outdoor entertaining areas built for day and night, there’s even a secret playroom. It all overlooks the golf course in the Reunion gated resort community, 6 miles from Disney World and a short drive from Universal Studios. Bask in the Florida sunshine on a hotel-worthy deck that has a swimming pool and hot tub, an outdoor kitchen with a barbecue, and even ping-pong and foosball tables—all shaded by day and heated by night. After a day at the theme parks, stretch out in the private gym before unwinding by the bar, games room, and home theater or challenging friends and family in the superhero-themed arcade. Polished marble floors and oversized chandeliers make a dramatic statement in the entry, and the sleek style carries through to a spacious great room with living and dining areas and a fully equipped kitchen. The bedrooms and playroom show off the villa’s fun side, though, with themes taken from classic kids’ movies. For theme-park fun, it’s a 9-minute drive to Walt Disney World Resort and less than 20 miles to both Universal Studios Florida. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM • Bedroom 1: King size bed, Ensuite bathroom with stand-alone rain shower & bathtub, Dual vanity, Walk-in closet, Safe, Television, Direct access to pool area • Bedroom 2: King size bed, Ensuite bathroom with stand-alone rain shower & bathtub, Dual vanity, Walk-in closet, Safe, Television, Private balcony, Outdoor furniture, Pool view • Bedroom 3: King size bed, Ensuite bathroom with stand-alone rain shower, Walk-in closet, Television, Balcony • Bedroom 4: King size bed, Ensuite bathroom with stand-alone rain shower, Walk-in closet, Television, Balcony • Bedroom 5: King size bed, Ensuite bathroom with stand-alone rain shower, Dual vanity, Walk-in closet, Ceiling fan, Television • Bedroom 6: King size bed, Ensuite bathroom with stand-alone rain shower, Walk-in closet, Television • Bedroom 7: 2 Queen size beds, Ensuite bathroom with stand-alone rain shower, Television • Bedroom 8 - Aladdin Kids Room: 2 Twin size bunk beds, Ensuite bathroom with stand-alone rain shower, Walk-in closet, Television • Bedroom 9 - Avengers Kids Room: 2 Twin size bunk beds, Ensuite bathroom with shower/bathtub combo, Walk-in closet, Television FEATURES & AMENITIES • Home theater • Wet bar • Karaoke OUTDOOR FEATURES • Swimming pool - heating at extra cost • Hot tub - heating at extra cost • Sun beds • Foosball table • Heat lamps SHARED ACCESS TO AMENITIES AT THE REUNION RESORT Included: • Community pools • Waterpark • Rental bikes Extra Cost (advance notice may be required): • Playground • Shuttle service • Salon & spa • Restaurants • Golf • Fitness centre & activities

Luxe

Villa in Kissimmee

4.3 out of 5 average rating, 10 reviews

The Palm

Staying true to its name, lush palm trees fringe this Florida escape. Foosball, a pool, shuffleboard, an arcade room—there’s endless entertainment for the whole family. Kids will love the Frozen and Star Wars bunk bed rooms as well as a glow-in-the-dark playroom. Sink into the bubbling hot tub after a day of adventure. The plush cinema room invites everyone to gather around for a favourite film. 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, Ceiling fan • Bedroom 2: King size bed, Ensuite bathroom with stand-alone shower, Television, Ceiling fan • Bedroom 3: 2 Queen size beds, Ensuite bathroom with stand-alone shower, Television, Ceiling fan • Bedroom 4: King size bed, Ensuite bathroom with stand-alone shower & bathtub, Dual vanity, Television, Ceiling fan • Bedroom 5: King size bed, Ensuite bathroom with stand-alone shower, Television, Ceiling fan, Shared access to terrace • Bedroom 6: King size bed, Ensuite bathroom with stand-alone shower, Television, Ceiling fan • Bedroom 7 - Kids room: 2 Twin size beds, Double size bed, Ensuite bathroom with shower/bathtub combo, Television, Shared access to terrace • Bedroom 8 - Kids room: Double size bunk bed, Twin size bunk bed, Ensuite bathroom with stand-alone shower, Television FEATURES & AMENITIES • Wine cooler • Home theater • Shuffleboard • More under “What this place offers” below OUTDOOR FEATURES • Outdoor living space • Terrace • Lanai STAFF & SERVICES Extra Cost (advance notice may be required): • Activities and excursions • More under “Add-on services” below

Luxe

Villa in Four Corners

4.83 out of 5 average rating, 6 reviews

Kempa Park

Located on the 6th hole of the Jack Nicklaus Golf Course in the Reunion Resort, this villa is a golfer’s dream. Go ahead and plan that big getaway. There are accommodations for 16 at Kempa Park, including 2 themed rooms for the kids. Spend your mornings on the course, afternoons in the pool, and nights hanging out in the games room. If you feel like getting out, check out Four Corners downtown. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM • Bedroom 1 - Primary: King size bed, Ensuite bathroom with stand-alone shower & bathtub, Television • Bedroom 2: King size bed, Ensuite bathroom with stand-alone shower & bathtub, Television • Bedroom 3: King size bed, Ensuite bathroom with stand-alone shower & bathtub, Television • Bedroom 4: King size bed, Ensuite bathroom with stand-alone shower, Television • Bedroom 5: King size bed, Ensuite bathroom with stand-alone shower, Television • Bedroom 6: King size bed, Ensuite bathroom with stand-alone shower, Television • Bedroom 7: King size bed, Ensuite bathroom with stand-alone shower, Television • Bedroom 8: King size bed, Ensuite bathroom with stand-alone shower, Television • Bedroom 9: 2 Queen size beds, Ensuite bathroom with stand-alone shower, Television • Bedroom 10: 2 Queen size beds, Ensuite bathroom with stand-alone shower, Television • Bedroom 11: 3 Twin size bunk beds, Ensuite bathroom with showers, Television • Bedroom 12: 3 Twin size bunk beds, Ensuite bathroom with stand-alone showers, Television STAFF & SERVICES Extra Cost (advance notice may be required): • Activities and excursions

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

Home in Four Corners

4.5 out of 5 average rating, 6 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 065

Just outside of the theme parks in Orlando, this stunning vacation rental has everything you could hope for in an exciting getaway. Golfers will love working on their game in the simulator. Kids, and the young at heart, are sure to spend hours in the games rooms, arcades, and home theater. The little ones will also appreciate the themed bedrooms, enclosed swimming pool, and hot tub. Copyright © Luxury Retreats. All rights reserved.

Luxe

Villa in Davenport

4.5 out of 5 average rating, 4 reviews

Villatel 062

Set within Davenport, just outside Orlando's theme parks, this stunning vacation rental is the perfect spot for large families with kids of all ages. There’s never a dull moment in the home theatre, casino, or games room. If you’re keeping up with daily routines, there’s a home gym and plenty of space to get some work done. You’ll also love the covered swimming pool and hot tub. Copyright © Luxury Retreats. All rights reserved.