A lakeside community with houses and boats.

Find Hotels with a Pool in Windermere, FL

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Check availability on Windermere Hotels with a Pool

Tonight
Oct 23 - Oct 24
Tomorrow
Oct 24 - Oct 25
This weekend
Oct 23 - Oct 25
Next weekend
Oct 30 - Nov 1

Our top choices for Windermere hotels with a pool

A swimming pool with a waterfall feature, lounge chairs, and a gazebo.
An aerial view of a resort with multiple swimming pools, palm trees, and lounge areas.
A modern hotel room with a dining area, a sofa, a chair, and a large window with curtains.
Bar (on property)

1. Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
Orlando
$111 nightly
$125 total
Nov 16 - Nov 17
Total with taxes and fees
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
A swimming pool area with multiple water slides and palm trees.
A vibrant lounge area with colorful seating, a bar, and a mural.
A modern hotel room with a large window, a sofa, a TV, a desk, and a bed.
A child sitting on a blue inflatable pool in a hotel room with a large window, a red armchair, and a suitcase.

2. Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort
Florida Center
  • Dive into double the fun with 2 outdoor pools, hot tubs, and a lazy river paradise.
$153 nightly
$172 total
Nov 23 - Nov 24
Total with taxes and fees
Universal's Cabana Bay Beach Resort
A resort pool area with palm trees, lounge chairs, and umbrellas.
A resort with a waterfront, a pool, and a gazebo area.
A courtyard with a fountain, outdoor seating, and string lights.
A waterfront hotel with a fountain, dock, and multiple boats.

3. Marriott's Grande Vista

Marriott's Grande Vista
Orlando
$96 nightly
$108 total
Nov 15 - Nov 16
Total with taxes and fees
Marriott's Grande Vista
A resort with a large pool, a water slide, and multiple buildings with balconies.
An outdoor patio area with tables and chairs, string lights, and a fire feature.
A hallway with a patterned carpet, chandeliers, and framed pictures on the walls.
A Starbucks coffee shop with a counter, menu boards, and a display case with pastries.

4. Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area
Orlando
  • Splash into aquatic paradise with 7 pools, a lazy river, and waterslides at this family resort.
$120 nightly
$135 total
Oct 27 - Oct 28
Total with taxes and fees
Westgate Lakes Resort & Spa Universal Studios Area
A large indoor pool with a water slide and a rock formation.
A miniature golf course entrance with a wooden archway labeled "Bogey Beach Mini Golf".
Two people seated in wicker chairs, reading magazines, with a black wall and a hanging light fixture in the background.
A spacious lobby with modern furniture, a reception desk, and indoor plants.

5. Coco Key Hotel & Water Park Resort

Coco Key Hotel & Water Park Resort
International Drive District
  • Splash into pool paradise with 3 outdoor pools and waterslide at this family resort.
$123 nightly
$138 total
Nov 23 - Nov 24
Total with taxes and fees
Coco Key Hotel & Water Park Resort
A resort pool with a central water feature, surrounded by palm trees and lounge chairs.
A modern restaurant with a bar area, outdoor seating, and a view of the outdoors.
A spacious lobby with a high ceiling, a central chandelier, a reception desk, and a large seating area.
A resort with a central pool, multiple buildings, and a fountain.

6. Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando
International Drive District
$104 nightly
$117 total
Nov 18 - Nov 19
Total with taxes and fees
Sheraton Vistana Villages Resort Villas, I-Drive/Orlando
A swimming pool with lounge chairs and palm trees, surrounded by a building with large windows.
An outdoor pool area with a covered seating area, surrounded by palm trees and a modern building in the background.
A modern hotel room with a sectional sofa, a small ottoman, a glass coffee table, and a flat-screen TV.
A hotel room with two beds, a desk, a TV, and a large window offering a city view.

7. DoubleTree by Hilton at the Entrance to Universal Orlando

DoubleTree by Hilton at the Entrance to Universal Orlando
Florida Center
  • Splash into Florida sunshine at the entrance to Universal Orlando with a poolside cocktail and refreshing hot tub.
$93 nightly
$104 total
Nov 16 - Nov 17
Total with taxes and fees
DoubleTree by Hilton at the Entrance to Universal Orlando
A resort with a large pool, a water slide, and a beach area.
A beach volleyball game in front of a modern hotel with multiple balconies and palm trees.
An outdoor dining area with a wooden roof and glass walls, featuring tables and chairs arranged for guests.
A spacious restaurant with a high ceiling, wooden beams, and a central bar area with stools.

8. Evermore Orlando Resort

Evermore Orlando Resort
Orlando
Evermore Orlando Resort
A pool area with people swimming and relaxing.
A spacious lobby with a high ceiling, seating areas, and a bar.
A covered outdoor seating area with wooden tables and chairs, a pool in the background, and a ceiling fan.
A hotel with a modern design, featuring a large building with multiple floors and a covered outdoor area with seating.

9. Universal's Endless Summer Resort - Dockside Inn and Suites

Universal's Endless Summer Resort - Dockside Inn and Suites
Florida Center
  • Splash into a family adventure at Universal's Endless Summer Resort with 2 outdoor pools, loungers, and a refreshing poolside bar.
$146 nightly
$164 total
Nov 11 - Nov 12
Total with taxes and fees
Universal's Endless Summer Resort - Dockside Inn and Suites
A couple in a pool with clear water, a rocky waterfall background, and a tiled pool edge.
A high-rise building with multiple balconies, surrounded by lush greenery and palm trees.
A woman relaxing on a sun lounger by a pool with a building in the background.
A lush indoor garden with a variety of tropical plants, a small water feature, and a building with balconies in the background.

10. Wyndham I-Drive Avanti Resort & Conference Center

Wyndham I-Drive Avanti Resort & Conference Center
International Drive District
  • Splash into ultimate vacation vibes at this Orlando oasis featuring a family-friendly pool paradise just steps from your room.
$73 nightly
$82 total
Nov 23 - Nov 24
Total with taxes and fees
Wyndham I-Drive Avanti Resort & Conference Center
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Choose what matters most at hotels with a pool in Windermere

Breakfast included
Hot tub
4 stars
5 stars
Water park

Find out more about Windermere

Discover top Windermere attractions

Windermere offers a captivating blend of natural beauty and thrilling activities that will delight any traveler. Start your day by exploring the stunning lakeside, where you can enjoy leisurely strolls along the shore, taking in the breathtaking views of the surrounding hills and shimmering waters. For those seeking adventure, consider embarking on a scenic boat tour, allowing you to soak in the area's picturesque landscapes from the water while learning about its rich history. Families will appreciate the opportunity to engage in outdoor pursuits, such as cycling on scenic trails that wind through lush parks and charming villages. Art enthusiasts can discover local galleries showcasing the region's vibrant artistic community, providing a unique glimpse into the cultural fabric of Windermere. Finally, unwind at one of the many cozy cafés or upscale dining spots, where you can indulge in delightful local cuisine while enjoying the warm hospitality that this charming area is known for. After a day full of exploration, you'll find luxurious accommodations that cater to your every need, ensuring a restful retreat amidst this enchanting environment.

Top Windermere Hotel Reviews

Marriott's Grande Vista

Marriott's Grande Vista

10/10 Excellent
"I enjoyed my stay. I was here for a conference and I stayed 6 nights. The room was spacious, clean, and quiet. I had a view of the golf course that was perfect! Oh...the bed was one of the most comfortable beds ever!"
Demetra 7-night trip
Posted less than an hour ago
Marriott's Grande Vista
Fairfield Inn & Suites Lake Buena Vista in Marriott Village

Fairfield Inn & Suites Lake Buena Vista in Marriott Village

10/10 Excellent
"Convenient to the parks. Room was great and spacious with the bunk beds! ( So glad I got that!) Property was wonderful and loved the playground for the kids. Weather was a little chilly for swimming and since driving all day the playground allowed them to get out their wiggles! Breakfast was amazing! Will definitely stay here again"
Carmel 1-night trip
Posted 1 hour ago
Fairfield Inn & Suites Lake Buena Vista in Marriott Village
Drury Plaza Hotel Orlando - Disney Springs Area

Drury Plaza Hotel Orlando - Disney Springs Area

10/10 Excellent
"Traveled as a family of 4. The breakfast was great. The evening snacks and beverages were super convenient especially after a long day at the parks. Free shuttle to Disney parks was great! Just know it's 1st come so arrive early. There aren't any stores nearby for minor things so you would have to drive or Uber to someplace if you forgot something from home. Disney springs is about a 15 min walk from property. Overall it was a great place to stay. This will be a place to stay for future visits to Orlando. It was convenient between both Universal and Disney parks. About equal distance to both."
Jill 6-night trip
Posted 1 hour ago
Drury Plaza Hotel Orlando - Disney Springs Area
Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort

10/10 Excellent
"Clean, great pool and close to Universal with free shuttles."
Theodore 3-night trip
Posted 2 hours ago
Universal's Cabana Bay Beach Resort
Holiday Inn Resort Orlando Suites - Waterpark by IHG

Holiday Inn Resort Orlando Suites - Waterpark by IHG

10/10 Excellent
"It was my first time here and we had a great experience, the rooms are well maintained and the room service are on time and all the amenities are as described.. The only thing I would complain about is there was some flooding waters by the hallway near our room which is a risk for the kids."
Purity 2-night trip
Posted 3 hours ago
Holiday Inn Resort Orlando Suites - Waterpark by IHG
Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

10/10 Excellent
"Everything was great. Loved how the bedroom had its own door unlike a standard hotel. Pools were really nice, check in was extremely smooth. Only minor annoyance was we got called at least once a day about a “departure gift”. Once at 9 am when we were trying to get some sleep. After the 3rd time it got a bit annoying. No complaints about amenities"
Jacob 3-night trip
Posted 3 hours ago
Sheraton Vistana Villages Resort Villas, I-Drive/Orlando
DoubleTree by Hilton at the Entrance to Universal Orlando

DoubleTree by Hilton at the Entrance to Universal Orlando

10/10 Excellent
"Good breakfast"
Guillermo 2-night trip
Posted 4 hours ago
DoubleTree by Hilton at the Entrance to Universal Orlando

Frequently asked questions

How much does a hotel with outdoor pool in Windermere cost?
Enjoy staying in a hotel in Windermere with an outdoor pool. You can find a great deal from $77 on Expedia. If you're leaning toward a little luxury, prices can rise, and may vary depending on the location, season, and hotel amenities. Be sure to book in advance to enjoy more options and potentially better rates, especially if you're planning a trip during weekends or around public holidays.
Are there hotels in Windermere with outdoor pool activities or events?
Windermere, Florida, is an enchanting destination known for its picturesque lakes and charming small-town ambiance. Travellers seeking relaxation and family-friendly fun will be pleased to discover that several hotels in the area offer exciting outdoor pool activities. The Windermere - Pool Lazy River & Waterslides stands out with its inviting private outdoor pool, lazy river, and thrilling waterslides, making it a favorite among families looking for a splash-filled getaway.For those who desire even more water adventures, nearby Orlando hotels like The Grove Resort & Water Park provide an array of outdoor pool options and water activities. This resort features multiple pools, a water park, and various recreational amenities that cater to guests of all ages.Families will particularly appreciate the engaging atmosphere and convenience of these accommodations, as they combine relaxation with plenty of opportunities for fun-filled days by the water. Whether you're floating down a lazy river or enjoying a thrilling slide, Windermere ensures a memorable stay for everyone.
Is it cheaper to book flights and a Windermere hotel with a pool as a package?
Booking a hotel and flight package on Expedia can be cheaper than booking flights and hotels separately. Bundling can lead to significant savings, especially for international travel or when booking well in advance. However, savings vary depending on factors like destination, travel dates and availability, so it's wise to compare options. With access to over 300,000 hotels worldwide, Expedia makes it easy to build the perfect vacation package.
Can I cancel my hotel reservation on Expedia?
Expedia has plenty of refundable hotels. In many cases, you need to cancel your booking 24-48 hours ahead of your arrival date. Remember to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use Expedia's "Fully refundable property" filter during your search to find the right hotel in Windermere for you.

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