Luxury Hotels in Kissimmee

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Luxury 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

Frequently asked questions

What are the best luxury hotels in Kissimmee?
With a sauna, a tennis court and lavish surroundings, Marriott's Cypress Harbour Villas is a hit with travelers. Marriott's Royal Palms is another popular Kissimmee luxury hotel.
What are the cheapest luxury hotels in Kissimmee?
Choose one of the affordable luxury hotels in Kissimmee from $57 that offer chic stays at savvy prices. Simply select the "Luxury Property" box, then fine-tune your search by setting the maximum price you want to pay. Also, consider your timing. Traveling during off-peak and shoulder seasons can help you save. To unlock Member Prices and earn discounts on future travel, sign up to become a member of our rewards program.
What is the best time to stay in a luxury hotel in Kissimmee?
July is the warmest month, with temperatures ranging from 77ºF (25ºC) to 91ºF (33ºC). If you prefer cooler weather, go in January. It's generally between 54ºF (12ºC) and 70ºF (21ºC) during this time. September is a great month to escape the crowds and potentially get more affordable luxury hotels in Kissimmee.
What luxury hotels in Kissimmee have a pool?
Marriott's Cypress Harbour Villas is a popular Kissimmee luxury hotel with a pool. You can access a firepit and windsurfing during your stay. Alternatively, spend your days lounging poolside in the lavish setting of Marriott's Royal Palms.
What are the closest luxury hotels to Orlando Intl. Airport (MCO)?
Go from your plane seat to ultimate comfort at Rosen Shingle Creek. It's around 8 miles west of Orlando Intl. Airport (MCO). Make the most of a dock and a view of the golf course here. Another stylish getaway near the airport is Grand Bohemian Orlando, Autograph Collection. Book either of these properties, or check out other luxury hotels in Kissimmee to find your ideal stay.
What are the best 5-star luxury hotels in Kissimmee?
The Ritz-Carlton Orlando, Grande Lakes is a top 5-star luxury Kissimmee hotel. From windsurfing to a swimming pool and service that goes the extra mile, everything you need is right here.
Are there any luxury hotels in Kissimmee with parking?
Choose from 26,811 Kissimmee luxury hotels with parking. At Marriott's Royal Palms, it's the little extras that make all the difference. This escape comes with parking, windsurfing and a firepit. Or, pull up and relax in style at Hyatt Regency Grand Cypress.
Are all taxes and fees included in the Kissimmee hotel prices shown on Hotels.com?
Hotels.com provide upfront pricing so you can relax knowing you won't be met with surprise additional fees or taxes when you're ready to confirm your booking. From the time you start your search on Hotels.com, the price you see is what you pay. This makes it much easier to compare properties and secure our best deal for your next getaway.