Hotels with a Pool in Kissimmee

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Hotels with a Pool 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 hotels with a pool in Kissimmee?
One of the best Kissimmee hotels with a pool based on guest reviews is Marriott's Cypress Harbour Villas. Make the most of a sauna and a tennis court here. You can also turn any day into a relaxing pool day at Marriott's Lakeshore Reserve, another highly rated option.
What are the cheapest hotels with a pool in Kissimmee?
It's easy to find some of the cheapest hotels in Kissimmee with a pool from $68 for your next trip. One of the most budget-friendly is Candlewood Suites Orlando - Lake Buena Vista, an IHG Hotel. It offers a terrace and a barbecue grill too. Holiday Inn Express & Suites Orlando - Lake Buena Vista, an IHG Hotel is another place that offers poolside perks at a price you'll love.
What is the best time to stay in a hotel with a pool in Kissimmee?
July is the warmest month, with temperatures ranging from 77ºF (25ºC) to 91ºF (33ºC). January sees the coolest weather. It's generally between 54ºF (12ºC) and 70ºF (21ºC) during this time. September is a good month to enjoy a more relaxed pace and potentially score cheaper Kissimmee hotels with a pool.
What hotels with a pool are closest to Old Town?
With a terrace and a garden, Comfort Suites Maingate East is one of the closest hotels with a pool to Old Town. Barefoot Suites is another option just a short drive away. Strike the perfect balance of adventure and leisure when you book a hotel in Kissimmee with a pool near this attraction.
What hotels with a pool are closest to Orlando Intl. Airport (MCO)?
Around 1 mile east of Orlando Intl. Airport (MCO), Hyatt Regency Orlando International Airport is a great option. Enjoy a leisurely swim after a day of travel and take advantage of pillow top mattresses and hypo-allergenic bedding here. Homewood Suites by Hilton Orlando Airport is another property nearby. Choose a Kissimmee hotel with a pool close to the airport that offers both comfort and convenience.
What are the best 5-star hotels with a pool in Kissimmee?
The Ritz-Carlton Orlando, Grande Lakes will take your getaway to new heights. This 5-star hotel in Kissimmee with a pool comes with windsurfing and room service.
Are there any hotels with a pool in Kissimmee with parking?
You'll find 26,811 Kissimmee hotels with a pool and parking. Pull in and go for a dip at Marriott's Lakeshore Reserve. A barbecue grill and a waterslide are included in your stay too. Or, head to Hilton Vacation Club Polynesian Isles Kissimmee, where you'll have both parking and a pool at your fingertips.
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.