The Best Hotels with a Pool in Windermere, FL from ￥8,811 in 2026

Q: What are some hotels with pools in Windermere?

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando : Aparthotel located near Disney Springs™. Features 6 outdoor pools, a children's pool, and 3 restaurants. DoubleTree by Hilton at the Entrance to Universal Orlando : Hotel, 3-minute walk from Universal Orlando Resort. Offers a children's pool, an outdoor pool, and 2 restaurants. The Grove Resort & Water Park Orlando : Resort located near Flamingo Crossings Town Center. Provides 6 outdoor pools, a children's pool, and free water-park access. Universal's Cabana Bay Beach Resort : Hotel, 5-minute walk from Universal Orlando Resort. Features a lazy river, 2 outdoor pools, and 2 restaurants. Walt Disney World Dolphin : Hotel, 8-minute walk from Walt Disney World® Resort. Offers 3 outdoor pools, a children's pool, and a private beach.

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Our top choices for Windermere hotels with a pool

Kompose Boutique Resort at Theme Parks

Kissimmee

Splash down the waterslide or bask poolside at this modern family resort with two hot tubs.

￥15,225 total

includes taxes & fees

Jun 16 - Jun 17

Outdoor pool, pool umbrellas, sun loungers

La Quinta Inn & Suites by Wyndham Orlando Airport

Airport North

Relaxing poolside retreat awaits with sun loungers, umbrellas, and a luxurious hot tub experience.

￥13,790 total

includes taxes & fees

Jun 29 - Jun 30

Hampton Inn & Suites Orlando Airport @ Gateway Village

Airport North

Vibrant pool oasis near Orlando Airport beckons travelers to dive in after a day exploring nearby attractions.

￥17,590 total

includes taxes & fees

Jun 16 - Jun 17

Outdoor pool, open 8:00 AM to 11:00 PM, pool umbrellas, sun loungers

Fairfield Inn By Marriott Orlando Airport

Airport North

Splash into this refreshing outdoor retreat with crystal-clear waters and a rejuvenating hot tub after airport arrivals.

￥12,893 total

includes taxes & fees

Jun 29 - Jun 30

Outdoor pool, open 8:00 AM to 9:00 PM, cabanas (surcharge)

DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel

International Drive District

Splash into fun at this Orlando oasis with pool cabanas, a hot tub, and a poolside bar.

￥14,439 total

includes taxes & fees

Jun 28 - Jun 29

7 outdoor pools, pool umbrellas, sun loungers

Vacation Village Orlando, Celebration

Kissimmee

Float through 7 outdoor pools or unwind in hot tubs at this family-friendly resort.

￥16,284 total

includes taxes & fees

Jun 28 - Jun 29

Hyatt House Orlando International Drive

International Drive District

Sun-kissed relaxation awaits at this poolside oasis with loungers and shade umbrellas.

￥19,308 total

includes taxes & fees

Jun 21 - Jun 22

Wyndham Garden Orlando Airport

Belle Isle

Make a splash at this hotel's outdoor oasis, where pool loungers provide the perfect perch for sunny Florida days.

￥15,720 total

includes taxes & fees

Jun 14 - Jun 15

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Choose what matters most at hotels with a pool in Windermere

Breakfast included

4 stars

Top Windermere Hotel Reviews

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

10/10 Excellent

"The Sheraton Vistana is clean an room service is very good.close to all restaurants, supermarket, Mall."

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

6/10 Okay

"We lost something there and it has been very hard to communicate with staff as they like to do everything by text and A?I assistant...not the homey feel it used to have as I've been going there my whole life as an owner and a guest."

Frequently asked questions

What are some hotels with pools in Windermere?

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando: Aparthotel located near Disney Springs™. Features 6 outdoor pools, a children's pool, and 3 restaurants. DoubleTree by Hilton at the Entrance to Universal Orlando: Hotel, 3-minute walk from Universal Orlando Resort. Offers a children's pool, an outdoor pool, and 2 restaurants. The Grove Resort & Water Park Orlando: Resort located near Flamingo Crossings Town Center. Provides 6 outdoor pools, a children's pool, and free water-park access. Universal's Cabana Bay Beach Resort: Hotel, 5-minute walk from Universal Orlando Resort. Features a lazy river, 2 outdoor pools, and 2 restaurants. Walt Disney World Dolphin: Hotel, 8-minute walk from Walt Disney World® Resort. Offers 3 outdoor pools, a children's pool, and a private beach.

What is there to see and do in Windermere?

Explore places like Universal Studios Florida, Universal Orlando Resort, and Universal's Volcano Bay while you're in the area. Spend some time experiencing the great outdoors at Lake Butler and Tibet Butler Preserve.

When is the best time to book a hotel with a pool in Windermere?

You may want to consider an accommodation with an outdoor pool if you're planning to visit Windermere in the driest months of November, February, or December when the average rainfall is 2 inches. Lodging with an indoor pool may be what you want if you come to town during the rainiest months of August, July, and September when the average rainfall is 8 inches.

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