Resort vacation rentals in Osceola County

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Top-rated resorts 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

4.8 out of 5 average rating, 5 reviews

Vacation Villas at Fantasyworld

PLEASE READ I want to make the booking experience as efficient as possible. Therefore, the pricing/payment structure requires a separate charge for the booking cost thru my resort membership. Please send me your dates. I'll respond with availability and the amount of the additional booking cost that can fall between $400- $1,950 USD based on resort category and dates (season/holidays). This resort charges resort fees that are included in the rate you see. Parking is free.

Resort in Kissimmee

4.64 out of 5 average rating, 159 reviews

Club Wyndham Cypress Palms One-Bedroom Suite

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 (interior view only). 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

4.91 out of 5 average rating, 11 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.

Superhost

Resort in Kissimmee

Near Orlando Theme Parks - 2 Bedrooms - 2 Baths

This stylish Resort is close to must-see destinations, including Disney World, Sea World and Universal Studios. Or, you can choose to just relax and enjoy all the resort has to offer from the beautiful pool and jacuzzi, fun playground for the kids, and the poolside bar & grill. There are other local places to visit including The Fossil Fun Games, Cross Country Creek, Old Town Sling Shot, and Lonely Dog Immersive Experience. Don't forget LegoLand!

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.

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Resort in Kissimmee

4.92 out of 5 average rating, 13 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

Resort in Kissimmee

Star Island Resort- 1 bedroom

This getaway is only a 10-minute drive from a defining Orlando vacation experience, Walt Disney World. The resort redefines vacation accommodations with its tranquil garden setting, premier amenities and elegant living spaces set alongside a scenic fountain lake. However you choose to define your family’s Orlando experience, this oasis can accommodate it.

Superhost

Resort in Celebration

5.0 out of 5 average rating, 3 reviews

Perfect Sanctuary in Orlando 2-BR

This unit is located within a resort, just five miles from the entrance to Walt Disney World. Celebration Town Center is seven miles away, and SeaWorld and Universal Orlando are within 20 miles. Enjoy one- to three-bedroom suites, each with a kitchenette or full kitchen and living area. Cool off in the pool complex with a water slide.

Resort in Osceola County

5.0 out of 5 average rating, 3 reviews

3 Bedroom Deluxe Suite on Beautiful Florida Resort

In a town where pixie dust sprinkles the air and wizards walk the halls of Hogwarts, magical moments evolve effortlessly - IF you can bare leaving this beautiful gated golf community's water play centre - if so, go to a universe of fantasy worlds at four world-renowned theme park complexes.

Guest favourite

Resort in Kissimmee

4.97 out of 5 average rating, 39 reviews

Amazing Townhome with Private Pool (SL4839)

Exceptional 5-Bedroom Townhome with Private Pool and Themed Rooms (SL4839) This stunning 5-bedroom, 4-bathroom retreat spans, accommodating up to 10 guests. Please note that parties and pets are not allowed on this property, ensuring a serene and enjoyable stay.