Hotels with a Pool in Kissimmee

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14 Aug - 16 Aug
Next weekend
21 Aug - 23 Aug

Hotels with a Pool in Kissimmee

Outdoor pool, open 9:00 AM to 9:00 PM, pool loungers

Palazzo Lakeside Hotel

Palazzo Lakeside Hotel
3.0 star property
Kissimmee
  • Outdoor pool
  • Pool loungers
8.4 out of 10, Very good, (5,279 reviews)
Swimming awaits in the outdoor oasis where sun loungers surround refreshing waters between 9:00 AM and 9:00 PM daily. Guests praise the clean pool area, complete with hammocks and cabanas overlooking beautiful lake scenery.
The price is £44
includes taxes & fees
27 Aug - 28 Aug
Palazzo Lakeside Hotel
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.
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Discover your perfect hotel with a pool in Kissimmee

Breakfast included
Hot tub

Hotels with pools and free breakfast in Kissimmee

Water park
Radisson Hotel Orlando Lake Buena Vista South

Radisson Hotel Orlando Lake Buena Vista South

Radisson Hotel Orlando Lake Buena Vista South
3.5 star property
Kissimmee
8.8 out of 10, Excellent, (3932)
The price is £50
includes taxes & fees
2 Sept - 3 Sept
Radisson Hotel Orlando Lake Buena Vista South
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Hotels with pools and hot tubs in Kissimmee

Aerial view
Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

Westgate Vacation Villas Resort
4.0 star property
Kissimmee
8.2 out of 10, Very good, (2046)
The price is £97
includes taxes & fees
13 Aug - 14 Aug
Westgate Vacation Villas Resort
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Hotels with pools and waterparks in Kissimmee

Lobby
Margaritaville Resort Orlando with H2O Waterpark

Margaritaville Resort Orlando with H2O Waterpark

Margaritaville Resort Orlando with H2O Waterpark
4.0 star property
Kissimmee
8.8 out of 10, Excellent, (3708)
The price is £157
includes taxes & fees
24 Aug - 25 Aug
Margaritaville Resort Orlando with H2O Waterpark
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.
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Top neighbourhoods in Kissimmee

A golf course with bunkers, water hazards, and a large lake.

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. Holiday 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.

A street sign reading "Welcome to Kissimmee, Florida" with a mural of horses on a building.

Historic Downtown Kissimmee

Historic City centre Kissimmee captures Florida's past with its stunning 1890s courthouse and Victorian shopfronts 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.

An aerial view of a residential area with numerous houses, roads, and several lakes.

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 holiday rentals ranging from cosy condos to luxury villas. After exhilarating theme park days, this quiet residential haven provides a peaceful retreat. Dining options are limited within the area, 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.

A sunset over a marshy landscape with a wooden pier extending into the water.

Orange Lake

Orange Lake revolves around holiday vibes with the massive Orange Lake Resort at its centre. Championship golf courses, sparkling pools, and family-friendly recreation areas keep visitors entertained without leaving the area. 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. Holiday villas and timeshare units dominate the accommodation scene, offering spacious digs with full kitchens and multiple bedrooms for families.

A lakeside town with a prominent white building, lush greenery, and a distant city skyline.

Lake Berkley

Kissimmee's Lake Berkley neighbourhood offers attractions, including beach near Lake Berkley.

Top landmarks in Kissimmee

A theme park entrance with a Ferris wheel and a roller coaster.

Old Town

8.6/10 (14,011 reviews)
Why not give yourself a treat with a trip to Old Town, one of the most popular family attractions located 7.1 mi (11.4 km) from central Kissimmee? It's also full of great shops and restaurants, so you can spend the afternoon having a wander. If you have fun at Old Town, you'll love Fun Spot America, just a short walk away.
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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 £35 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 25ºC to 33ºC. January sees the coolest weather. It's generally between 12ºC and 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 2 km (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 27,292 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 Holiday Club Polynesian Isles Kissimmee, where you'll have both parking and a pool at your fingertips.

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