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Holidays in Kissimmee by TailorMadeFlorida.com

Holidays in Kissimmee, Orlando

Staying in Kissimmee places you in just about the perfect mid-point between the noise, fun and excitement of the Disney theme parks and the tranquil countryside of central Florida. Just outside of the Walt Disney World Resort yet offering a much quieter and relaxed setting compared to International Drive or Lake Buena Vista.

The focal point for tourists staying in the Kissimmee area is US Highway 192, this road runs east to west just below Walt Disney World and is home to a huge choice of hotels, a wealth of restaurants, shopping plazas, dinner shows and smaller attractions. Just a few minutes drive from US192 are a wide selection of private villa communities, these fabulous homes with own swimming pool offer a spacious living space in a peaceful location close to major theme parks and entertainment.

Old Town is one of Kissimmee's most popular tourist attractions, at this 19th century style shopping and entertainment village you can browse speciality shops, brave a haunted mansion and have fun at a fantastic family fairground. For evening entertainment Kissimmee boasts two famous dinner show venues, Arabian Nights and Medieval Times.

Kissimmee is an ideal vacation choice for anyone looking to experience everything Orlando has to offer.

Villa Resorts in Kissimmee

Windsor Palms Resort Florida

Windsor Palms Resort Florida Our holiday villas and apartments at Windsor Palms Resort in Kissimmee provide an ideal base for a wonderful family holiday. This gated villa resort is located just 2 miles from Disney and a very short drive from a wide selection of shops, bars and restaurants. » More

Indian Creek Villas

Indian Creek Villas Indian Creek has long been a very popular villa resort with TailormadeFlorida guests attracted by the high quality accommodation and exceptional location. Indian Creek boasts a superb central Kissimmee position, one of the closest villa resorts to the Disney theme parks and only 2-3 minutes from the shopping plazas and family restaurants on Highway 192. » More

Tuscany Resort

Tuscany Resort in Kissimmee is a wonderfully stylish, Italian themed villa community surrounded by wetlands and natural conservation. This tranquil villa resort provides a peaceful place to relax after a busy day at the theme parks. » More

Emerald Island Resort

The Fabulous Emerald Island Resort boasts a superb location in central Kissimmee, just 10 minutes from the Disney theme parks, and offers a stunning selection of oversized holiday villas. Emerald Island is a real favourite of ours and our clients, the area is immaculately kept and the moment you drive through the entrance the feeling of grandeur is really present, a great way to begin your Florida Holiday. » More

Windsor Hills Resort

Windsor Hills Resort offers everything you could possibly need for a perfect family villa holiday. A great choice of accommodation options, an incredible range of onsite amenities and one of the closest villa resorts to the Disney theme parks. The central Kissimmee location is virtually unbeatable. » More

Terra Verde Resort

Terra Verde Resort is a stunning, idyllic retreat offering high-end accommodation and superb on-site amenities. Offering a choice of villas with pool and townhouses plus a wealth of onsite amenities Terra Verde is an ideal vacation resort for families and one of Orlando's most sought after villa holiday locations. » More

Hotels in Kissimmee

Best Western Lakeside

Best Western Lakeside The Maingate Lakeside has been a top selling Kissimmee hotel for many years, holidaymakers are consistently drawn to the superb location, great value and comfortable rooms. » More

Ramada Plaza Gateway Hotel

Ramada Plaza Gateway Hotel Located just 1 mile west of Walt Disney World Resort in a lively area surrounded by popular family restaurants and shopping plazas, the Ramada Plaza Gateway provides an excellent base for exploring the Orlando attractions. » More

Seralago Hotel

Specifically aimed at families, this bright, fun-filled holiday hotel offers comfortable accommodation and a friendly atmosphere. The Seralago Hotel has an excellent Kissimmee location, just a short drive from Walt Disney World and within walking distance of a wide selection of shops and restaurants. » More

Radisson Worldgate Resort

The Radisson Worldgate Resort offers spacious, modern rooms, a relaxed, friendly atmosphere and a superb Kissimmee location just 1 mile from Walt Disney World and around 15-20 minutes from Seaworld, Aquatica and Universal Orlando. The Radisson Worldgate Resort has plenty of excellent family restaurants and popular big chain stores in the immediate area. » More

Radisson Resort Orlando Celebration

Radisson Resort Orlando Celebration Set in over 20 acres of lush landscaped gardens, tall palm trees and water fountains, the Radisson Resort Orlando offers a wealth of activities and amenities and a warm, welcoming family atmosphere. » More

Condos in Kissimmee

Mystic Dunes Resort

Mystic Dunes Resort has been a massive favourite with TailormadeFlorida guests for several years. Boasting a virtually unbeatable location - Mystic Dunes is set just 2-3 minutes back from a huge selection of restaurants and shops on US192 in Kissimmee and a very easy 10 minute drive from the Disney theme parks. » More

Bahama Bay Resort

Bahama Bay is a luxury development of 2 and 3 Bedroom Condos. The resort is close to Disney World Resort Florida and is ideal for a family or larger group of friends wanting a self catering holiday in superior accommodations. » More

Townhomes in Kissimmee

Lucaya Village Resort

A recent addition to the ever expanding TailormadeFlorida portfolio of Orlando resorts, Lucaya Village Resort has rapidly become one of our most in-demand accommodation options. Well suited to the discerning traveller, Lucaya Village Resort is an ideal choice for both families and smaller parties looking for high quality accommodation and the freedom and flexibility offered by spacious self catering accommodation. » More

All of our offers and prices are subject to our terms and conditions and availability at the time of booking. Various travel dates apply, and offers are normally based on maximum occupancy for accommodation. If any offer is not exactly what you are looking for, or you would like alternative hotels/locations/airports, please contact us and one of our specialist travel consultants will create your holiday to suit your requirements.