Book the Best Hotels with POOL in Windermere 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. Hyatt Regency Orlando International Airport : Offers 2 restaurants, an outdoor pool, and complimentary wireless internet 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. The Grove Resort & Water Park Orlando : Resort located near Flamingo Crossings Town Center. Features 6 outdoor pools, a children's pool, and free water-park access. Universal's Endless Summer Resort - Dockside Inn and Suites : Hotel located near Universal CityWalk. Offers 2 outdoor pools, a children's pool, and 3 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.

CA $118 total

includes taxes & fees

Jun 3 - Jun 4

Vacation Village Orlando, Celebration

Kissimmee

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

CA $149 total

includes taxes & fees

Jun 22 - Jun 23

Outdoor pool, pool umbrellas, sun loungers

Ramada by Wyndham Suites Orlando Airport

Airport North

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

CA $116 total

includes taxes & fees

Jun 3 - Jun 4

Wingate by Wyndham - Orlando International Airport

Airport North

Refreshing outdoor pool oasis with sun loungers offers relaxation after exploring nearby shopping and dining options.

CA $119 total

includes taxes & fees

Jun 3 - Jun 4

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.

CA $128 total

includes taxes & fees

Jul 1 - Jul 2

La Quinta Inn & Suites by Wyndham Orlando Airport

Airport North

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

CA $127 total

includes taxes & fees

Jun 30 - Jul 1

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.

CA $111 total

includes taxes & fees

Jun 21 - Jun 22

Westgate Lakes Resort & Spa Universal Studios Area

Orlando

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

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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

"Enjoyed our stay. Highly recommended"

Westgate Lakes Resort & Spa Universal Studios Area

2/10 Terrible

"I hate everything about this place. It's not what it says on the website we went there for a three night trip we couldn't even enjoy ourselves. All the amenities were closed. No access to pools. No access to the door to the pools. Gates are locked front desk telling you different different things every time you call them .I'll never go back to this place. I hate it. They close the main doors to access the Adult pool and they want you to walk around the building where all the garbage stinks. Disgusting when you ask them questions they have something to cover their behind. Nobody's owning up to anything there is no parking please there is no parking you have to stay and wait for a trolley or a bus to take you to your building . It's so frustrating. From Desk will tell you OK will send the trolley then I call another day. They said no no trolley will come. They never sent out a trolley. You have to wait for a bus every time they have a different story to tell the hallway is nasty dirty filthy."

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. Hyatt Regency Orlando International Airport: Offers 2 restaurants, an outdoor pool, and complimentary wireless internet 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. The Grove Resort & Water Park Orlando: Resort located near Flamingo Crossings Town Center. Features 6 outdoor pools, a children's pool, and free water-park access. Universal's Endless Summer Resort - Dockside Inn and Suites: Hotel located near Universal CityWalk. Offers 2 outdoor pools, a children's pool, and 3 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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