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Resort holiday rentals in Osceola County

Find and book unique resort stays on Airbnb

Top-rated resort stays in Osceola County

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

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Resort in Kissimmee
4.7 out of 5 average rating, 10 reviews

Timeshare at Westgate 1 bedroom

This a 1 bedroom comfort friendly resort, just a few minutes from Disney world with a fully furnished area with a balcony. There are a great number of activities on site that are free or for a low cost. These activities include swan boats, arcade, mini-golf, movie theater (disney movies), different dining options,water park(for a COST) ,many swimming pools, rental bikes, tennis courts, basketball courts and activity center (games/arts&crafts). In addition there is an onsite convenience store.

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
The exterior of the Westgate Vacation Villas Resort is displayed, showcasing a multi-story building with a classical architectural style. Lush palm trees and manicured landscaping are visible in the foreground, enhancing the welcoming atmosphere. Bright sky with scattered clouds can be seen above.
Resort in Kissimmee

Luxury Family Resort/Water Park - Kissimmee, Fla.

Family Water Park and Resort - Close to Disney NO TOUR REQUIRED - as with cheaper prices Book w/ ME = VIP Access * Enclosed resort * Activities for the family * Water Park * Washer/dryer * Sleeper sofa for 2 * Sports Bar * Restaurants * Gaming Area * Basketball Court * Movie Theater * Discount area theme park tickets, * Swan paddle boats * Swimming pools * Bicycle rentals Cancellation: Guests who cancel 7 – 30 days before check-in get 50% back. After that, the trip is non-refundable.

Resort in Kissimmee
4.73 out of 5 average rating, 521 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!

The inviting bedroom features a spacious bed adorned with plush pillows and decorative throws. Framed ocean-themed artwork hangs above the headboard. Soft lighting from the bedside lamps complements the warm curtains, creating a comfortable atmosphere. A seating area is visible next to the bed.
Resort in Kissimmee
4.93 out of 5 average rating, 27 reviews

Westgate Town Center Resort & Spa

Resort, 5 minutes from Disney world and 20 minutes from Universal. Space for 4 persons one-bedroom apartment Suite. Full Kitchen. TV. Ac. Pool. Gym, Water Park, Mini Golf and a lot more. Lake. It has one bedroom with king bed, one living room with queen size sofa bed and one bathroom. Everything you need is provided 7 nights check in on Friday, Saturday or Sunday after 4pm. $110/night w/o jacuzzi and $120/night with jacuzzi. Holiday booking may be more.

An aerial view captures an expansive resort area featuring a large water park with multiple slides, a lazy river, and vibrant play areas. Surrounding lounging chairs in various colors provide ample seating. The warm tones of the buildings complement the sunlit pool areas.
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.

Superhost
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.

Superhost
Aerial view of Westgate Town Center Resort includes vibrant water features and pools surrounded by colorful waterslides. The surrounding buildings exhibit terracotta roofs and lush landscaping, with a lagoon reflecting the scenic backdrop. The layout highlights ample outdoor space for recreation and leisure.
Resort in Kissimmee

One Bedroom Deluxe Westgate Resorts

Note: Kindly submit an inquiry at least 72 hours before making a reservation request. 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.

Resort in Kissimmee
4.83 out of 5 average rating, 6 reviews

Disney Experience

Relax with the whole family in this Disney house. Looking for the perfect place for your family vacation? Our home, located in the Paradise Palms Resort, just 15 minutes from Disney, is the ideal spot for comfort, convenience, and unforgettable memories!

A large outdoor pool is surrounded by a textured stone patio, with several lounge chairs arranged nearby. Tropical trees and shrubbery provide a lush backdrop, while shaded umbrellas offer comfort in the sun. A thatched roof gazebo stands in the distance.
Resort in Kissimmee
5 out of 5 average rating, 5 reviews

Cypress Palms - 2 Bedroom Condo

Tropical Lagoon Pools & Hot-Tubs Wonderland – Kissimmee FL Splash into morning at winding lagoon-style pools, crunch French fries by the barbecue grotto, head to nearby theme parks, and return to unwind in your washer/dryer-equipped suite.

Resort in Kissimmee
5 out of 5 average rating, 8 reviews

Condo in Kissimmee – Standard

Fully Furnished 4 Sleeper Condo. - 1 King Bed or Double Bed Room - Queen Sleeper Sofa Bed in the Living Room - 1 Kitchenette ( Microwave, Toaster, Coffee/Tea Maker, Refrigerator, Dishwasher) - Washer, Dryer, Iron, Ironing Board

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