5 Star Hotels in Kissimmee

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5 Star Hotels in Kissimmee

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Top neighborhoods in Kissimmee

Historic Downtown Kissimmee

Historic Downtown Kissimmee captures Florida's past with its stunning 1890s courthouse and Victorian storefronts along Broadway Street. Stroll under heritage oaks while exploring unique shops filled with antiques and local crafts. Weekend farmers markets and street festivals bring the area to life, celebrating the region's cowboy heritage and diverse community. The lakefront area offers peaceful fishing spots and scenic views of Lake Tohopekaliga. A mix of Southern comfort food, Cuban cafes, and barbecue joints fuel your adventures. Most attractions are within the walkable six-block historic core, making it easy to explore this charming slice of old Florida.

Windsor Hills

Windsor Hills offers a perfect home base for Disney adventures with resort-style amenities just minutes from major attractions. Families love the gated communities with pools, game rooms, and themed vacation rentals ranging from cozy condos to luxury villas. After exhilarating theme park days, this quiet residential haven provides a peaceful retreat. Dining options are limited within the neighborhood, so most visitors drive 10-15 minutes to nearby tourist areas for meals. Rental cars are essential for getting around, though rideshares are readily available. The Mediterranean-style properties with private pools make Windsor Hills ideal for groups seeking comfort between park visits.

Reunion

Reunion is a golfer's paradise just outside Orlando with three legendary courses designed by Palmer, Nicklaus, and Watson. After teeing off, splash around at the resort water park or lounge by multiple pools scattered throughout this upscale community. When you're ready for theme parks, Disney and Universal are just 20 minutes away. Vacation homes with private pools dominate the accommodation scene, giving families plenty of space to spread out. Resort restaurants serve upscale meals, though you'll need a car to explore beyond the community's Mediterranean-style grounds. The quiet, manicured setting feels worlds away from Orlando's tourist bustle.

Orange Lake

Orange Lake revolves around vacation vibes with the massive Orange Lake Resort at its center. Championship golf courses, sparkling pools, and family-friendly recreation areas keep visitors entertained without leaving the neighborhood. Disney World is just minutes away, making this Four Corners spot perfect for theme park enthusiasts who want amenities galore after a day of adventure. Resort shuttles and rideshares make getting to attractions easy since public transit is limited. Dining options stick mostly to resort restaurants and nearby chains. Vacation villas and timeshare units dominate the accommodation scene, offering spacious digs with full kitchens and multiple bedrooms for families.

Bellavida

Bellavida delivers Mediterranean-style luxury without the hassle of crowded resorts. This gated Kissimmee community serves as your perfect home base for Disney World and Universal adventures just 10-15 minutes away. After thrilling theme park days, retreat to spacious vacation homes with private pools, or lounge at the resort-style community pool surrounded by palm-lined streets. Cook family meals in fully-equipped rental kitchens or drive to nearby Kissimmee restaurants in minutes. Most visitors find rental cars essential for exploring Orlando's attractions, though rideshares are readily available. The peaceful, manicured grounds offer a welcome respite from theme park excitement.

Top landmarks in Kissimmee

Find out more about 5 Star Hotels in Kissimmee

Find out more about 5 Star Hotels in Kissimmee

What can I expect from 5-star hotels in Kissimmee?

When you stay at 5-star hotels in Kissimmee during 2025, you can expect exceptional service, luxurious rooms, and all the high-end amenities you could possibly want from your stay. From the moment you arrive, you'll feel like a VIP. The attentive service and exceptional hospitality of the hotel staff and concierge will take care of your every need, whether it's round-the-clock room service, childcare, or a reservation at one of Kissimmee's top restaurants. Then there are the rooms. A 5-star hotel in Kissimmee typically includes opulent furnishings, personalized welcome kits, and premium bedding. Remember, the search filters on Hotels.com help you find specific amenities or extras you're seeking.

What makes the best 5-star hotels in Kissimmee stand out?

Some of the best 5-star hotels in Kissimmee stand out for their distinct features and extras, often inspired by local traditions and culture. These add a touch of authenticity to your stay. Kissimmee's most high-end properties typically boast several on-site restaurants serving up extraordinary fusion dishes showcasing the local cuisine in elegant settings. Some of the most popular luxury hotels in Kissimmee include special extras in their rooms and suites, too. Think hot tubs, exceptional views, and the latest technology. The detailed and up-to-date property descriptions on Hotels.com explain what you can expect, while verified reviews give you real-life insights into what the guest experience is like.

How much does a 5-star hotel in Kissimmee typically cost?

In 2025, the cost of five-star hotels in Kissimmee varies and depends on factors like the time of year and room type. To get a feel for average prices, take advantage of the Hotels.com search wizard. Simply enter your dates and destination to view real-time rates for luxury properties in Kissimmee.

Are there special deals or discounts for 5-star hotels in Kissimmee?

Yes, on Hotels.com you'll find some of the best deals and biggest discounts for five-star hotels in Kissimmee. As one of the world's largest websites for hotel bookings, we're able to negotiate exceptional deals, and we then pass the savings on to you. Then there's One KeyOpens in a new window—Hotels.com's generous reward program. Members can access instant discounts on thousands of hotels simply by signing in. Keep a look out for the blue savings label in the search results. One Key rewards you with OneKeyCash for most stays, too. You can then use this reward currency to save on future bookings. Plus, as you move up the tier levels, you'll unlock special perks, such as VIP Access to select hotels, free room upgrades, and even early check-in. Best of all, One Key is free to join. As if all that wasn't enough, you can save on 5-star hotels in Kissimmee by searching and booking through the Hotels.com app. 

How can I verify if a hotel in Kissimmee is rated 5 stars?

There are two really easy ways to confirm if a Kissimmee hotel is five stars on Hotels.com. You can check the “5-star rating” filter to view a list of all properties rated as 5 stars in Kissimmee. Or you can look for the star rating above the property name on the hotel's dedicated page. Hotels.com keeps all its descriptions up to date, so you can feel confident that what you see is what you book.

Do Kissimmee 5-star hotels offer free cancellation options?

Yes, Kissimmee 5-star hotels booked through Hotels.com usually come with free cancellation. This means you can change your mind as much as you like when booking on Hotels.com. Just keep in mind that each property has different booking conditions, though. It's always a good idea to glance over these before confirming your stay. The good news is that all this information is easy to find on Hotels.com—just look out for the “free cancellation” label or use the “fully refundable” filter when searching.

What amenities do 5-star hotels in Kissimmee provide?

Most 5-star hotels in Kissimmee boast high-end amenities like luxury spas and several upscale restaurants. Stay at one of these opulent properties if you're seeking full-body massages, holistic treatments, and rejuvenating therapies. When it comes to dining, you can expect exquisite cuisine prepared by some of Kissimmee's best chefs. More luxury amenities include elegant bars serving signature cocktails prepared by expert mixologists, state-of-the-art fitness centers, and even yoga classes.

Are there family-friendly 5-star hotels in Kissimmee?

The “family-friendly” search filter will reveal all the 5-star hotels in Kissimmee that will welcome you and your little ones with open arms. Kid-friendly 5-star hotels typically feature all you need for a relaxing stay, including children's facilities like shallow-water pools, changing facilities, and even dedicated day-care facilities with an expertly trained staff member. You'll also often find luxurious family suites and interconnecting rooms, as well as cribs and special beds for children.

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