Resort holiday rentals in Osceola County

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Top-rated resort rentals in Osceola County

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

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Superhost

Resort in Kissimmee

4.83 out of 5 average rating, 6 reviews

2 Bedroom Club Wyndham Resort Star Island Disney

2 Bedroom 'lockoff' unit means extra privacy & kitchenette in the 2nd bedroom. Club Wyndham Star Island resort is 10 minutes from WDW yet with a tranquil garden setting. Your unit will be completely your own. It is modern, clean, private, secure, & well stocked. You will have full access to all resort amenities you would expect from a Wyndham Resort including pools, playground, tennis & basketball courts, mini golf, & more. Be sure to check out all the pictures & get excited about your stay!

Resort in Kissimmee

4.67 out of 5 average rating, 3 reviews

Vacation Villas at Fantasy World (by Disney World)

The resort is located about 10 minutes (4 miles) Disney World. This two-story, Mediterranean townhouse features 2-bedrooms, one with a queen-sized bed and the second with two twin-sized beds, two full baths and a fully equipped kitchen, sitting area with pull sofa, dining area, breakfast bar and screened-in patio. Amenities include: 3 swimming pools, 2 lighted tennis courts, an activities center, business center, exercise room, and a pool bar. Complimentary transportation to theme parks.

Superhost

Resort in Kissimmee

Luxury Family Fun Resort/Water Park - Kiss. Fla.

Family Water Park and Resort - Safe, Fence enclosed resort,guided activities for the family, 1-2 Bedroom with Jaccuzzi hot tub. Westgate Town Center Resort · Ship Wreck Island Water Park · Villas range. Furnished, full kitchen, washer/dryer, sleeper sofa for 2, Sports Bar, Restaurants, Pizza, Ice Cream, Gaming Area, basketball, movie theater, discount area theme park tickets, swan paddle boats, swimming pools, bicycle rentals and more. NO TOUR REQUIRED *like cheaper prices require.

Superhost

Resort in Kissimmee

Star Island Resort, Beautiful 1-bedroom condo FL!

This resort is located just 4 miles from Disney's Magic Kingdom, is the ideal vacation destination. Whether your plans call for a family getaway or a secluded honeymoon trip, our resort’s all-suite accommodations will serve as your home away from home. Star Island combines the comfort of luxury living with our own version of the “star treatment”. Our brand new Pool Bar and upstairs Star Bar will offer you the best entertainment experience and vacation atmosphere money can buy.

Superhost

Resort in Celebration

4.6 out of 5 average rating, 5 reviews

MYSTIC DUNES RESORT & GOLF CLUB 1bd

Minutes from Disney World. An international tourism hub, the markedly picturesque sun-drenched landscape and lush wetlands of Orlando beckon visitors to discover its subtropical climate and natural beauty. With beautiful lakes and swamps comprising much of the scenery, diverse wildlife and vegetation flourish. This vibrant city, deemed the epicenter of theme park entertainment, offers the ultimate setting for year-round family friendly activities, adventure and exploration.

Resort in Kissimmee

4.72 out of 5 average rating, 425 reviews

WorldMark Reunion Three Bedroom

Just seven miles from Walt Disney World Resort, Club Wyndham Reunion is an exclusive 2,300-acre resort that features spacious three-bedroom suites that comfortably sleep eight guests. You will appreciate private bedrooms, a full kitchen, living/dining area, balcony, washer/dryer and Wi-Fi. Enjoy the five-acre water park with eleven pools, seven hot tubs and a lazy river. Amenities include three golf courses, six tennis courts, three bars, three restaurants and a spa!

Superhost

Resort in Kissimmee

Standard Villa 5 at Westgate Resorts Town Center

Westgate Town Center Resort in Kissimmee, FL, offers all the comforts for the whole family. It is within minutes of Kissimmee's world-famous theme parks and attractions. Reservations must be booked for at least seven nights and made one month in advance. Enjoy easy access to popular shops and restaurants from this charming place to stay. Note: Kindly submit an inquiry prior to making a reservation request, so I can check the availability of dates at the resort.

Hotel room in Kissimmee

4.8 out of 5 average rating, 5 reviews

Nature Escape! Outdoor Pool, Parking, Playground!

Surrounded by lakes and trees, but close to attractions and outdoor recreation, this peaceful retreat provides the perfect setting for a getaway or a fun vacation. Within minutes of the property, guests can enjoy horseback riding, airboat rides, golfing, and fishing, along with plenty of attractions, like the Disney Wilderness Preserve. Take advantage of this quiet and relaxing property while still enjoying convenience to everything the area has to offer!

Guest favourite

Resort in Kissimmee

4.92 out of 5 average rating, 13 reviews

Wyndham Star Island

Two-bedroom Lockout. A 10-minute drive from a Walt Disney World. Set alongside a scenic fountain lake, there are two pools, one with a waterfall, and indoor and outdoor hot tubs. Jet Ski and paddle boat rentals available. A spa providing massages and a sauna are onsite. There are nine tennis courts, a basketball and volleyball court, a putting green, and golf and tennis pro are available for lessons. A game room and arcade are available for children.

Resort in Kissimmee

4.9 out of 5 average rating, 10 reviews

Westgate Town Center Studio One-Bedroom Deluxe

Property is located just a mile from Walt Disney World. Start with 14 heated outdoor swimming pools and hot tubs, arcade, paddle boats, a Disney movie theater, miniature golf, playgrounds, tennis, basketball, sand volleyball, a fitness center, and scheduled activities. Ship Wreck Island water park featuring multiple slides, tunnel slides, fountains, play areas and a lazy river is available for $25 dollars a day per person.

Superhost

Resort in Kissimmee

4.8 out of 5 average rating, 5 reviews

Holiday Inn Club Vacations at Orange Lake Resort

Please arrange the room at least 7 days before. Available floor-plans: 1Bedroom(King)1Bath/2Bedroom(King+2Queen)2Bath/3Bedroom(King+Queen+2Queen)3Bath. PRICE VARIES FROM FLOORPLANS AND DATES. LISTING PRICE IS FOR A 3BEDROOM UNIT. Perfect for a large group/groups of families and friends. Please MESSAGE FIRST to CONFIRM AVAILABILITY before making an reservation. Thanks for the cooperation and understanding.

Guest favourite

Resort in Kissimmee

4.93 out of 5 average rating, 15 reviews

Celebration Suites - 2 Miles from Disney - For 4

1-bedroom PRIVATE apartment suite with a full kitchen including all cookware/utensils, and 2 TVs in this suite in total. The room includes 1 king-sized bed and 1 full-sized bed. We also offer a great fitness center and guest laundry rooms so you can wash/dry clothing. You can pick up keys easily as our Front desk staff is on-site 24-hours per day and speaks English, Spanish, and Portuguese.