The Best Hotels with a Pool in Windermere, FL from AED 313 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. Universal's Cabana Bay Beach Resort : Hotel, 5-minute walk from Universal Orlando Resort. Offers a lazy river, 2 outdoor pools, 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. DoubleTree by Hilton at the Entrance to Universal Orlando : Hotel, 3-minute walk from Universal Orlando Resort. Features a children's pool, an outdoor pool, and 2 restaurants. Westgate Lakes Resort & Spa Universal Studios Area : Hotel located near The Orlando Eye. Offers 7 outdoor pools, a children's pool, and a water park.

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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.

AED 434 total

includes taxes & fees

11 May - 12 May

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.

AED 313 total

includes taxes & fees

4 Jun - 5 Jun

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.

AED 323 total

includes taxes & fees

2 Jun - 3 Jun

Ramada by Wyndham Suites Orlando Airport

Airport North

Poolside paradise awaits with sun loungers, umbrellas, and a refreshing outdoor oasis.

AED 409 total

includes taxes & fees

12 May - 13 May

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.

AED 451 total

includes taxes & fees

10 May - 11 May

Hyatt House Orlando International Drive

International Drive District

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

AED 384 total

includes taxes & fees

31 May - 1 Jun

Westgate Lakes Resort & Spa Universal Studios Area

Orlando

Splash into aquatic paradise with 7 pools, a lazy river, and waterslides at this family resort.

AED 527 total

includes taxes & fees

10 May - 11 May

4 outdoor pools, open 5:30 AM to midnight, cabanas (surcharge)

Rosen Shingle Creek

Orlando

Swim in luxury with four sparkling pools and poolside cabanas at this golf resort haven.

AED 399 total

includes taxes & fees

10 May - 11 May

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Choose what matters most at hotels with a pool in Windermere

Breakfast included

4 stars

Top Windermere Hotel Reviews

Four Points by Sheraton Orlando International Drive

10/10 Excellent

"Staff was friendly and the room was nice, clean with comfortable beds. "

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

10/10 Excellent

"This was a beautiful property. We stayed in a one bedroom villa, which was small but comfortable. It was nice having a washer and dryer! We didn’t use the kitchen, but enjoyed the lanai. The pool was great (we used the Key West pool because that’s where our room was). The activities were fun and my husband even won at Bingo! The staff was very welcoming and we are already planning our next stay in a two bedroom this time."

Wyndham I-Drive Avanti Resort & Conference Center

4/10 Poor

"The rooms and building look nothing like pictured. The bathrooms are gross and outdated. When we arrived there was hair in the sink and stains on the towels. The area by the elevators smelled like weed and it overall looked terrible. The pillows were the worst I’ve ever seen and the bedding was not comfy. "

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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. Universal's Cabana Bay Beach Resort: Hotel, 5-minute walk from Universal Orlando Resort. Offers a lazy river, 2 outdoor pools, 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. DoubleTree by Hilton at the Entrance to Universal Orlando: Hotel, 3-minute walk from Universal Orlando Resort. Features a children's pool, an outdoor pool, and 2 restaurants. Westgate Lakes Resort & Spa Universal Studios Area: Hotel located near The Orlando Eye. Offers 7 outdoor pools, a children's pool, and a water park.

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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