Resort vacation rentals near Old Town Kissimmee

Find and book unique resort rentals on Airbnb

Top-rated resort rentals near Old Town Kissimmee

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

0 of 0 items showing

1 of 3 pages

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.

Top guest favorite

A resort pool area features a large, curving swimming pool surrounded by palm trees and lounge chairs. A pirate ship play structure is positioned nearby, complemented by a lake view in the background. The scene is set against a backdrop of resort buildings.

Resort in Orlando

5 out of 5 average rating, 11 reviews

Wyndham Bonnet Creek Resort: 2-Bedroom Deluxe

Experience the ultimate Orlando getaway at Club Wyndham Bonnet Creek's 2-bedroom suite, accommodating up to eight guests. The master bedroom features a king bed, the second bedroom offers two double beds, and a queen sleeper sofa is in the living area. Enjoy a fully equipped kitchen, two bathrooms, and a private balcony. Resort amenities include five outdoor pools, two lazy rivers, six hot tubs, and a fitness center. It is adjacent to Disney World, minutes from Orlando's top attractions.

Superhost

A resort’s elegant architecture is showcased with structured balconies adorned by greenery. An inviting pool reflects the surrounding palm trees and blue sky, creating a serene outdoor space for relaxation. The atmosphere suggests easy access to leisure activities and comfortable accommodations.

Resort in Orlando

5 out of 5 average rating, 4 reviews

Bonnet Creek Resort 1 bdrm

Discover a magical resort less than a mile from the gates of Walt Disney World®. Bonnet Creek Resort offers everything you need for a memorable adventure, including transportation to and from the Disney® theme parks. When it's time to take a day off from the parks, chill out at the resort's five pools, lazy rivers and private cabanas or schedule time for some pampering at the spa. Ranked No. 10 on Condé Nast Traveler's "Best Resorts in Orlando, Florida: Readers' Choice Awards 2015."

Guest favorite

A resort-style pool area is surrounded by lush palm trees and tropical landscaping. Lounge chairs are positioned around the pool, with a fountain adding a serene element. The building in the background features a Mediterranean-inspired design.

Resort in Orange County

5 out of 5 average rating, 33 reviews

Cozy Orlando Condo 4Mi from Disney

Get ready for a memorable vacation when you stay at this 2-bedroom, 2-bathroom rental on Floridays Resort Drive. This condo is located in a beautiful 4.5 star rated resort community where you experience upscale living at its finest. Spend your days visiting local attractions like Universal Studios, Walt Disney World, Sea World, and many more. After a day of fun, return home to hang by the pool, have a family game night in the arcade, or enjoy the Florida scenery from your balcony.

Guest favorite

An outdoor swimming pool is surrounded by palm trees and lounge chairs under a clear blue sky. Water cascades gently from stone structures into the pool, which features a gradual entry. The resort building stands in the background, complementing the tranquil scenery.

Resort in Orlando

4.85 out of 5 average rating, 48 reviews

By Universal Orlando Marriott Grande Vista studio

Explore popular attractions, including Walt Disney World®, Universal Orlando and SeaWorld®, Start your day with a few swings at the Grande Vista Golf Club or a lesson from the experts at Marriott Golf Academy. Refresh yourself in the outdoor swimming pools and reenergize at our fitness center. Find tasty American cuisine at The Grill at Grande Vista and delectable poolside fare at Copa Loca Bar & GrilL. 8 miles to Disney World 8.3 miles to Universal Orlando 2.4 miles to Sea World

Guest favorite

A spacious resort building is set against a clear blue sky, featuring multiple balconies and a mix of brick and stucco exteriors. Lush greenery and tall grasses frame the front, enhancing the structure's welcoming presence within the landscaped grounds.

Resort in Kissimmee

4.74 out of 5 average rating, 482 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!

Guest favorite

A spacious studio suite features a king-size bed and a comfortable couch, complemented by large sliding glass doors opening to a private balcony. Natural light filters through the windows, highlighting a minimalist aesthetic with light wood flooring and subtle decor.

Resort in Orlando

4.84 out of 5 average rating, 50 reviews

Updated Suite Near Universal Studios

Guests 21+ Only. You really can't beat the location of The Enclave Resort and Suites with good amenities and easy access to local hot spots from this newly owned unit. Your stay includes a step-out balcony, onsite breakfast and lunch restaurant, convenience store and gift shop from 7 to 11 a.m., Indoor heated pool and jacuzzi, two outdoor pools and whirlpools, fitness room and laundry facilities right around the corner of your suite plus a tennis court.

Top guest favorite

An aerial view captures the resort's vibrant landscape, featuring palm trees and an outdoor pool. The unique lighthouse structure is highlighted near the waterfront, where lounge chairs are arranged along the pathway. A colorful sky complements the serene setting, showcasing the property’s inviting atmosphere.

Resort in Orlando

4.97 out of 5 average rating, 29 reviews

Studio Close to Disney Marriott Grand Vista

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.

A bird's-eye view showcases the sprawling Wyndham Bonnet Creek Resort, featuring a tranquil lake surrounded by palm trees. The surrounding high-rise buildings reflect the warm hues of sunset against a clear sky, creating a harmonious blend of nature and architecture.

Resort in Orlando

5 out of 5 average rating, 3 reviews

Disney-Wyndham Bonnet Creek Resort

Closest to Disney Magic! Located in Lake Buena Vista, Wyndham Bonnet Creek Resort is mere minutes from the gates of Walt Disney World®. You’ll will enjoy a very rewarding stay on site. From the full activities calendar to special touches like the tranquil Lazy River, beautiful pool and private lake, this is no ordinary stay. Shuttle available directly to Disney World for a fee.