Hotels with Rooftop Pools in Kissimmee

Just off US-441, we are within two miles of several restaurants and shops at The Crosslands and Loop West. Gatorland Amusement Park is just five minutes away. Orlando International Airport, Walt Disney World, and Universal Studios are all within 16 miles of our hotel. We have a fitness center, outdoor pool, meeting space, and on-site dining at First Watch Café.

Welcome to the SpringHill Suites Orlando Lake Buena Vista South, A Walt Disney World Good Neighbor® hotel located 10 minutes from Walt Disney World theme parks, and 15 minutes from Universal Orlando and SeaWorld.Our beautiful guest suites all include a sofa bed, microwave, mini-fridge, large work desk, Free hot breakfast, Free wireless high-speed internet and are 25% bigger than your average hotel room. Relax and enjoy complimentary access with no resort fee to the adjacent resort amenities (owned and operated by Calypso Cay) to include 3 resort style pools, waterslides, pool bar, mini-golf, sports courts, and fitness center.-There is also an Adventure Park onsite that includes zip lining, rock climbing, inflatable slide and bungee jumping for an additional fee.

When it comes to the best places to stay in Orlando for Disney World, our hotel is a trusted pick. We are a Walt Disney World Good Neighbor® Hotel and a Tripadvisor Traveler's Choice "Best of the Best" 2025 Award Winner.Enjoy our scheduled shuttle service to nearby attractions like Walt Disney World® Resort, Universal Studios Florida, and Epic Universe®. Fuel your adventure with our free Express Start™ Breakfast and enjoy our Tiki Bar and Calypso Island Market for snacks and drinks. Have fun in the sun at our three pools with waterslides and a splash pad, or play on our 18-hole mini-golf course. Discover endless fun and adventure in Orlando at our 1-bedroom suite close to Disney World!

Located in Kissimmee, Seasons Florida Resort is within a 15-minute drive of Old Town and Disney Springs™. This hotel is 7.6 mi (12.3 km) from Disney's Hollywood Studios® and 9.4 mi (15.1 km) from Epcot®. Take advantage of recreation opportunities such as an outdoor pool, or other amenities including complimentary wireless internet access and a vending machine. Featured amenities include multilingual staff, laundry facilities, and an elevator. Free self parking is available onsite. Make yourself at home in one of the 125 guestrooms featuring refrigerators and microwaves. Flat-screen televisions with premium TV channels are provided, while complimentary wireless internet access keeps you connected. Private bathrooms with shower/tub combinations feature complimentary toiletries and hair dryers. Conveniences include desks and coffee/tea makers, as well as phones with free local calls.

With a stay at Hotel MonteCarlo in Kissimmee, you'll be a 5-minute drive from Old Town and 8 minutes from Orlando Vineland Premium Outlets. This motel is 6.1 mi (9.8 km) from Disney Springs™ and 7.1 mi (11.5 km) from Walt Disney World® Resort. Enjoy recreation amenities such as an outdoor pool or take in the view from a garden. Additional amenities at this motel include complimentary wireless internet access and a vending machine. Featured amenities include multilingual staff, lockers, and a vending machine. Free self parking is available onsite. Stay in one of 23 guestrooms featuring LED televisions. Complimentary wireless internet access keeps you connected, and digital programming is available for your entertainment. Private bathrooms with showers feature hair dryers and toothbrushes and toothpaste. Conveniences include safes and desks, and housekeeping is provided daily.

The Embassy Suites by Hilton Orlando Lake Buena Vista South hotel offers an ideal location in Orlando, Florida. We are just 3.5 miles from the Walt Disney World Resort and a short, 20-minute drive from Orlando International Airport. Located one block east of US 192, numerous restaurants, shopping malls, golf courses, world-class attractions and all of the excitement that Orlando has to offer surround the hotel. As Orlando's largest Embassy Suites convention hotel, we feature modern conveniences for business guests attending a meeting or convention, and a great location and recreational amenities to please leisure guests. Spacious two-room suites include a number of amenities such as a generous workspace and the luxurious Sweet Dreams Bed Experience. Take advantage of our many amenities including a sparkling outdoor pool and whirlpool, well-equipped Fitness Center, game room, jogging paths, nearby golf, restaurants and two outlet malls. Enjoy our complimentary made-to-order breakfast and evening reception. Relax in our inviting Lobby Lounge, The Oasis, or dine at our casual, American bistro-style restaurant, Kyng's Grille, serving lunch and dinner daily. Stop by The Marketplace for coffee-to-go, snacks and other sundries. Embassy Suites by Hilton Orlando Lake Buena Vista South has 40,000 sq. ft. of flexible meeting and banquet facilities. This includes the 15,000-sq. ft. Palms Ballroom, the 5,000- sq. ft. Magnolia Ballroom and 15 flexible breakout rooms. Our ten small boardrooms accommodate meetings for up to eight people. Planners will appreciate the modern A/V services, business center and our professional convention services and catering staff. Whether it's business, a meeting, vacation or weekend getaway brings you to Orlando, our experienced hotel staff looks forward to welcoming you to our hotel.

Located in Kissimmee, Magic Moment Resort and Kids Club is within a 10-minute drive of Orlando Vineland Premium Outlets and Disney Springs™. This family-friendly hotel is 5.7 mi (9.2 km) from Disney's Hollywood Studios® and 8.4 mi (13.5 km) from Epcot®. Take advantage of recreation opportunities including an outdoor pool and a 24-hour fitness center. This hotel also features complimentary wireless internet access, concierge services, and an arcade/game room. Spending a day of fun is easy with the complimentary theme park shuttle. At Magic Moment Resort and Kids Club, enjoy a satisfying meal at the restaurant. A complimentary continental breakfast is served daily from 7:00 AM to 9:30 AM. Featured amenities include a business center, multilingual staff, and luggage storage. Planning an event in Kissimmee? This hotel has 797 square feet (74 square meters) of space consisting of conference space and a meeting room. Free self parking is available onsite. Make yourself at home in one of the 170 air-conditioned rooms featuring flat-screen televisions. Your pillowtop bed comes with Egyptian cotton sheets. Cable television is provided for your entertainment. Private bathrooms with shower/tub combinations feature designer toiletries and hair dryers.

Located in Kissimmee, Club Wyndham Cypress Palms is in the entertainment district, within a 15-minute drive of Walt Disney World® Resort and Disney's Hollywood Studios®. This aparthotel is 6.2 mi (10 km) from Disney Springs™ and 8.6 mi (13.8 km) from Orange County Convention Center. Dip into one of the 2 outdoor swimming pools or 2 hot tubs and enjoy other recreational amenities, which include a 24-hour fitness center. This aparthotel also features complimentary wireless internet access, concierge services, and a picnic area. Featured amenities include a business center, a 24-hour front desk, and luggage storage. Free self parking is available onsite. Make yourself at home in one of the 366 guestrooms featuring refrigerators and microwaves. 32-inch flat-screen televisions with cable programming provide entertainment, while complimentary wireless internet access keeps you connected. Conveniences include phones, as well as separate sitting areas and coffee/tea makers.

Located in Kissimmee, Comfort Suites Maingate East is in the entertainment district, a 4-minute walk from Fun Spot America and 5 minutes by foot from Old Town. This family-friendly hotel is 1.6 mi (2.6 km) from Falcon's Fire Golf Club and 2.7 mi (4.4 km) from Celebration Golf Club. Enjoy a range of recreational amenities, including an outdoor pool, a hot tub, and a 24-hour fitness center. Additional amenities at this hotel include complimentary wireless internet access, concierge services, and an arcade/game room. Spending a day of fun is easy with the complimentary theme park shuttle. You can enjoy a meal at the restaurant serving the guests of Comfort Suites Maingate East, or stop in at the snack bar/deli. Relax with your favorite drink at the bar/lounge or the poolside bar. A complimentary buffet breakfast is served daily from 6:30 AM to 9:30 AM. Featured amenities include a 24-hour business center, express check-out, and a 24-hour front desk. Free self parking is available onsite. Make yourself at home in one of the 198 air-conditioned rooms featuring refrigerators and microwaves. Wired and wireless internet access is complimentary, and flat-screen televisions with cable programming provide entertainment. Bathrooms feature shower/tub combinations, complimentary toiletries, and hair dryers. Conveniences include safes and desks, and housekeeping is provided once per stay.

Embark on a magical getaway at the Holiday Inn & Suites Orlando SW - Celebration Area, located just steps from Old Town in Kissimmee and less than three miles from Walt Disney World®.As a Walt Disney World Good Neighbor® Hotel, enjoy a free shuttle to Disney World®, SeaWorld®, and Universal Orlando®. Relax in spacious rooms and suites with mini-fridges for your favorite treats, inviting flat-screen TVs for cozy family movie nights, and plush bedding for added comfort.Make a splash at our outdoor pool, enjoy family moments in the 24-hour game room, and savor delicious meals at our on-site restaurants, where kids under 12 eat free. Your unforgettable Orlando vacation starts here!