Resort holiday rentals in Osceola County

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Top-rated resort stays in Osceola County

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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.

Resort in Kissimmee

4.75 out of 5 average rating, 8 reviews

Timeshare at Westgate town center

This a comfort friendly hotel, 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) ,several swimming pools, rental bikes, tennis courts, basketball courts and activity center (games/arts&crafts). In addition there is an onsite convenience store.

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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.

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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.

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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.

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.

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

4.93 out of 5 average rating, 14 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.

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Resort in Kissimmee

New place to stay

Wyndham Cypress Palms 2BR – Near Disney & Pool

Discover the perfect blend of comfort and convenience at Club Wyndham Cypress Palms! This spacious 2 Bedroom Suite features a full kitchen, living room, washer/dryer, and screened balcony—ideal for families and groups. Just minutes from Walt Disney World® and Orlando’s top attractions, enjoy two outdoor pools, hot tubs, a fitness center, and BBQ areas. Tucked in a peaceful tropical setting, it’s your relaxing retreat close to all the magic.

Resort in Kissimmee

4.69 out of 5 average rating, 322 reviews

Club Wyndham Cypress Palms One Bedroom

This spacious one-bedroom resort suite measures approximately 513 square feet. You will enjoy a king bed in the master bedroom and one queen sleeper sofa in the living room. Additional amenities include a kitchenette and dining area. Unwind in one of the two outdoor heated swimming pools or squeeze in a morning workout at the fitness center. Discover a host of activities like golf, tennis, water skiing and boating right at their doorstep.

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.

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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.