The Best Hotels with a Pool in Windermere, FL 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. The Grove Resort & Water Park Orlando : Resort located near Flamingo Crossings Town Center. Offers 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. Provides a lazy river, 2 outdoor pools, and 2 restaurants. Kompose Boutique Resort at Theme Parks : Resort located near Walt Disney World® Resort. Features 2 hot tubs, an outdoor pool, and a sauna. Wyndham I-Drive Avanti Resort & Conference Center : Hotel, 7-minute walk from CoCo Key Water Resort. Offers a children's pool, an outdoor pool, and 2 bars.

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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.

₩141,746 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.

₩142,270 total

includes taxes & fees

Jul 14 - Jul 15

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.

₩154,925 total

includes taxes & fees

Jun 28 - Jun 29

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.

₩130,346 total

includes taxes & fees

Jul 19 - Jul 20

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.

₩168,377 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.

₩200,334 total

includes taxes & fees

Jul 6 - Jul 7

DoubleTree by Hilton Orlando Airport

Airport North

Dive into sun-kissed relaxation with a perfect outdoor pool oasis in this airport-adjacent retreat.

₩142,459 total

includes taxes & fees

Jul 6 - Jul 7

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.

₩144,944 total

includes taxes & fees

Jun 25 - Jun 26

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Choose what matters most at hotels with a pool in Windermere

Breakfast included

4 stars

Top Windermere Hotel Reviews

Holiday Inn Resort Orlando Suites - Waterpark by IHG

10/10 Excellent

"Very clean and nice staff very helpful"

Lake Buena Vista Resort Village & Spa

10/10 Excellent

"The rooms have always been very clean and comfortable. We travel with kids so to have our own room and a full kitchen is awesome. I was however alittle disappointed in the arcade they have since it was like walking into an arcade from the 1980s. Some of the games weren’t working but overall the hotel is a great stay for what you pay."

Walt Disney World Swan

10/10 Excellent

"It was a great experience in every way. Since my first visit to Disney property in 1986 I have always stayed at a Disney owned property, maybe 16 times? This time my husband and I decided to go for a few days and just visit Epcot and Hollywood studios . We decided to try the Swan and we were pleasantly surprised! The proximity to the parks we could visit without bus transportation was the main factor but there is so much more to enjoy. Great pools, a variety of wonderful restaurants, clean rooms and helpful staff were just the start. A walk to the Boardwalk at sunset was lovely.Although I would prefer a Disney resort with small children, this felt like a grown up , luxury hotel. My only complaints…. was there was no fan in the bathroom and the additional fees when my adult daughter joined us for two nights. We had two queen beds , why do I need to pay more? Besides that, I would definitely recommend a stay at the Swan."

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. The Grove Resort & Water Park Orlando: Resort located near Flamingo Crossings Town Center. Offers 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. Provides a lazy river, 2 outdoor pools, and 2 restaurants. Kompose Boutique Resort at Theme Parks: Resort located near Walt Disney World® Resort. Features 2 hot tubs, an outdoor pool, and a sauna. Wyndham I-Drive Avanti Resort & Conference Center: Hotel, 7-minute walk from CoCo Key Water Resort. Offers a children's pool, an outdoor pool, and 2 bars.

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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