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.

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 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

A large resort pool is surrounded by lush palm trees, with a rock formation featuring a waterfall adding a natural element. Lounge chairs are situated around the pool, providing ample space for relaxation amidst a sunny atmosphere.

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.

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.

Superhost

The lobby area features modern seating arrangements, including curved sofas and lounge chairs designed for comfort. A reception counter illuminated with soft lighting is prominently displayed. Large windows allow natural light to brighten the space, creating an open and welcoming environment.

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.

An aerial view captures the resort's layout, featuring multiple buildings surrounded by lush greenery and a serene lake. Two outdoor swimming pools are visible, alongside pathways and palm trees, creating a tranquil and inviting atmosphere.

Resort in Kissimmee

4.68 out of 5 average rating, 314 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.

A cozy movie theater is presented, featuring rows of comfortable, cushioned seating facing a large screen. The dark walls and soft lighting contribute to a relaxed atmosphere, while decorative elements and artwork are visible in the background, enhancing the overall setting.

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 spacious living area is furnished with a large sofa and two armchairs, enhancing comfort. A coffee table sits centrally, while a dining area with wooden chairs and a table is visible in the background. Soft lighting and warm colors create an inviting space.

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 favorite

A bright guest laundry room features multiple stacked washers and dryers along both sides, all equipped with clear controls. The patterned black and white floor tiles add a modern touch, while ample lighting enhances visibility throughout the 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 tranquil pool area is surrounded by lush palm trees, with a fountain creating gentle ripples in the water. Lounge chairs are neatly arranged along the poolside, and the resort's elegant architecture is visible in the background, framed by greenery.

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.