Resort holiday rentals in Kissimmee

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Top-rated resort rentals in Kissimmee

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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.

Top guest favourite
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 large pool is surrounded by lush palm trees and lounge chairs, reflecting the vibrant blue sky. The resort building stands in the background, featuring multiple stories with a blend of yellow and terracotta hues.
Resort in Orlando
5 out of 5 average rating, 7 reviews

Bonnet Creek Resort 2 bd

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 favourite
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 favourite
A bright and airy room features a spacious bed and a comfortable seating area, including a sofa and a chair. Natural light streams through sliding glass doors, leading to a private balcony. A television is positioned across from the bed, contributing to a functional layout.
Resort in Orlando
5 out of 5 average rating, 31 reviews

Disney World - Studio Marriott Grande Vista

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

Resort in Orlando
5 out of 5 average rating, 5 reviews

Holiday Week Special! Luxury Westgate Lakes Villa

Perfect for families spending the holidays at Disney or Universal Avoid $300–$500/night hotel prices Full resort access (pools, waterpark, mini golf) The wonderfully decorated and spacious Three-Bedroom Villa at Westgate Resorts in Orlando offers astonishing spaciousness – 1,690 square feet of space and room for up to 12 guests. The Three-Bedroom Villa gives families plenty of room to spread out and enjoy the space. Relax and unwind on your private balcony or patio!

The exterior of the resort showcases a multi-story building with soft green hues and large windows. Lush palm trees and manicured shrubs frame a winding pathway, leading to a structured gazebo area adorned with decorative columns.
Resort in Orlando
4.83 out of 5 average rating, 18 reviews

WorldMark Orlando Kingstown Reef Studio Deluxe

Located on popular International Drive, WorldMark Orlando - Kingstown Reef is just minutes away from Orlando's theme parks, water parks, dinner theaters, fabulous shopping, golfing, restaurants and nightlife. This spacious Studio Deluxe resort suite comfortably sleeps up to two guests in 430 square feet and features one queen murphy bed. You will appreciate the convenience of a partial kitchen, a washer/dryer, private balcony/terrace and Wi-Fi throughout.

Guest favourite
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
4.86 out of 5 average rating, 59 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.

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.

An aerial view of a resort complex showcases several multi-story buildings arranged around a vibrant water park. Colorful water slides and play structures are visible near a large swimming pool, surrounded by lounge chairs and patios. A picturesque lake reflects the surrounding landscape.
Resort in Kissimmee
4.76 out of 5 average rating, 21 reviews

Luxury Westgate Resort Villa near Disney! 1B/1Ba

This 510 sq ft deluxe villa is located at Westgate Resorts Town Center. It includes 1 bedroom & 1 bath while accommodating up to 4 guests. It features a king bed, a queen sleeper sofa, separate living and sleeping areas, a small equipped kitchen, and a washer/dryer. Enjoy access to all the usual amenities like a 27-inch color TV, a large flat screen television in the living area, DVD player, WiFi, and more.

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.

Popular amenities for resort rentals in Kissimmee

Quick stats about resort rentals in Kissimmee

  • Total holiday rentals

    Explore 30 holiday rentals in Kissimmee

  • Nightly prices starting at

    Kissimmee holiday rentals start at $52 SGD per night before taxes and fees

  • Verified guest reviews

    Over 40 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space & child-friendly amenities

  • Holiday rentals with a pool

    30 properties feature pools

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    30 of Kissimmee holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Kissimmee rentals

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