Resort vacation rentals in Osceola County

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Top-rated resort rentals in Osceola County

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A large swimming pool is framed by palm trees and lounge chairs, with umbrellas providing shade. Colorful water slides are visible in the background, adjacent to a spacious area for sunbathing. Clear blue skies enhance the inviting atmosphere of the resort's outdoor space.

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.

A detailed map of the resort is displayed, highlighting various amenities and layouts. Key features include pools, playgrounds, dining options, and activity areas. Landmarks are marked for easy navigation, emphasizing the resort's layout and nearby attractions.

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.

Superhost

A guest room features two beds with light bedding and decorative blue throws. A bedside table with a lamp stands between the beds. Soft green walls and a framed abstract artwork provide a calming atmosphere, while the patterned carpet adds texture.

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

A large multi-story building is surrounded by lush palm trees and well-maintained landscaping. A peaceful lake, featuring a fountain, is positioned in the foreground, reflecting the blue sky and scattered clouds above.

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.

The exterior of the resort features multiple levels, surrounded by lush greenery and tall palm trees. A paved walkway leads through the vibrant landscaping, creating a welcoming atmosphere. Bright blue skies and scattered clouds enhance the tropical ambiance.

Resort in Kissimmee

4.8 out of 5 average rating, 980 reviews

Club Wyndham Cypress Palms Two Bedroom Suite

Spacious two-bedroom family suites with kitchen and living/dining areas offer whimsical touches of tropical splendor. Unwind in one of the two outdoor heated swimming pools or squeeze in a morning workout at the fitness center. Kids will enjoy playing at the arcade game room, or participating in all the fun-filled activities packed in the 'Play Days' program. Discover a host of activities like golf, tennis, water skiing and boating right at their doorstep.

A well-appointed hotel room features two double beds with light-colored linens and accent pillows. The walls are adorned with framed artwork, and a table lamp sits between the beds on a wooden nightstand. A patterned curtain partially covers a window, allowing natural light to enter.

Hotel room in Kissimmee

4.83 out of 5 average rating, 6 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 favorite

A scenic view of a tranquil fountain lake is captured at dusk, reflecting the surrounding architecture. Spacious balconies overlook the water, surrounded by lush greenery and palm trees. The soft glow of evening lights enhances the serene atmosphere.

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.

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

A sprawling resort area is presented, featuring multiple pools and lounging areas surrounded by lush greenery. Palm trees and bright umbrellas offer shade, while guests can be seen enjoying the outdoors. A manicured landscape extends in the background, with hints of nearby attractions visible.

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

The exterior of the hotel features a colorful façade with a welcoming reception area. A round sign highlights the hotel's recognition as one of the best family hotels in the USA. Chairs and tables are arranged outside beneath umbrellas, providing a casual gathering space.

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

A serene waterway reflects the modern multi-story buildings, which feature balconies and large windows. Lush landscaping and palm trees enhance the tranquil environment, while soft evening light creates a calm and inviting scene along the scenic fountain lake.

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.