A lakeside community with houses and boats.

Find Hotels with a Pool in Windermere, FL

Check availability on Windermere Hotels with a Pool

Tonight
Oct 8 - Oct 9
Tomorrow
Oct 9 - Oct 10
This weekend
Oct 9 - Oct 11
Next weekend
Oct 16 - Oct 18

Our top choices for Windermere hotels with a pool

A swimming pool with a waterfall feature, lounge chairs, and a gazebo.
A modern hotel room with a dining area, a sofa, a chair, and a large window with curtains.
A turtle in a landscaped area with palm trees and a water feature.
Bar (on property)

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

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
Orlando
$137 nightly
$154 total
Oct 29 - Oct 30
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 modern hotel room with a large window, a sofa, a TV, a desk, and a bed.
A vibrant lounge area with colorful seating, a bar, and a mural.
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.
$150 nightly
$169 total
Nov 4 - Nov 5
Total with taxes and fees
Universal's Cabana Bay Beach Resort
A resort with a large pool, a water slide, and multiple buildings with balconies.
A hallway with a patterned carpet, chandeliers, and framed pictures on the walls.
An aerial view of a resort with multiple swimming pools, palm trees, and a large building with a red-tiled roof.
An outdoor patio area with tables and chairs, string lights, and a fire feature.

3. 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 18 - Oct 19
Total with taxes and fees
Westgate Lakes Resort & Spa Universal Studios Area
A resort pool area with palm trees, lounge chairs, and umbrellas.
A courtyard with a fountain, outdoor seating, and string lights.
A waterfront hotel with a fountain, dock, and multiple boats.
A spacious dining area with high ceilings, wooden beams, and a bar with a variety of liquor bottles.

4. Marriott's Grande Vista

Marriott's Grande Vista
Orlando
$96 nightly
$108 total
Oct 29 - Oct 30
Total with taxes and fees
Marriott's Grande Vista
A swimming pool with lounge chairs and palm trees, surrounded by a building with large windows.
A modern hotel room with a sectional sofa, a flat-screen TV, a large window with curtains, a dining table, and a radiator.
A hotel room with two beds, a desk, a TV, and a large window with a view.
Two high-rise buildings with reflections in a calm body of water, surrounded by greenery and palm trees.

5. 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.
$101 nightly
$114 total
Oct 18 - Oct 19
Total with taxes and fees
DoubleTree by Hilton at the Entrance to Universal Orlando
A large indoor pool with a water slide and a rock formation.
A spacious lobby with modern furniture, a reception desk, and indoor plants.
Two people seated in wicker chairs, reading magazines, with a black wall and a hanging light fixture in the background.
A miniature golf course entrance with a wooden archway labeled "Bogey Beach Mini Golf".

6. 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.
$134 nightly
$151 total
Oct 19 - Oct 20
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 spacious lobby with a high ceiling, a central chandelier, a reception desk, and a large seating area.
A modern restaurant with a bar area, outdoor seating, and a view of the outdoors.
A resort with a central pool, multiple buildings, and a fountain.

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

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando
International Drive District
$96 nightly
$108 total
Nov 2 - Nov 3
Total with taxes and fees
Sheraton Vistana Villages Resort Villas, I-Drive/Orlando
A resort with a large pool, water slides, palm trees, and beach umbrellas.
A waterfront property with a dock, a gazebo, and a row of modern buildings in the background.
A couple walking past a surfboard and a 'Longboard Bar and Grill' sign.
A modern lobby with a reception desk, seating area, and a bar.

8. The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando
Winter Garden
  • Splash into paradise at this resort with 6 outdoor pools, a lazy river, and a complimentary water park for endless aquatic fun.
$228 nightly
$257 total
Oct 9 - Oct 10
Total with taxes and fees
The Grove Resort & Water Park Orlando
A pool area with people swimming and relaxing.
A spacious lobby with a central reception desk, a large mural, and a modern ceiling design.
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.

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.
$141 nightly
$159 total
Nov 2 - Nov 3
Total with taxes and fees
Universal's Endless Summer Resort - Dockside Inn and Suites
A resort with a large pool, a water slide, and a beach area.
An outdoor dining area with a wooden roof and glass walls, featuring tables and chairs arranged for guests.
A modern multi-story hotel with balconies, palm trees, and a clear sky.
A beach volleyball game in front of a modern hotel with multiple balconies and palm trees.

10. Evermore Orlando Resort

Evermore Orlando Resort
Orlando
Evermore Orlando Resort
View all properties

Choose what matters most at hotels with a pool in Windermere

Breakfast included
Hot tub
4 stars
5 stars
Water park

Top Windermere Hotel Reviews

Rosen Inn Lake Buena Vista

Rosen Inn Lake Buena Vista

8/10 Good
"The location and the actual room was great. I had an issue with the lock on my door but it was fixed very quickly. The only thing I found outrageous was that they charge for holding a package (envelope) delivered from Amazon. Aside from that I loved our stay."
Aracelis 7-night trip
Posted 10 hours ago
Rosen Inn Lake Buena Vista
DoubleTree by Hilton at the Entrance to Universal Orlando

DoubleTree by Hilton at the Entrance to Universal Orlando

10/10 Excellent
"Everything here was amazing from the time we checked in. Hakeem was incredible and had us start our trip off amazing so shout out to him!! We loved our stay here, everything was so clean cozy and all the amenities and extras were great. Definitely will be back"
hailey 2-night trip
Posted 11 hours ago
DoubleTree by Hilton at the Entrance to Universal Orlando
Fairfield Inn & Suites Lake Buena Vista in Marriott Village

Fairfield Inn & Suites Lake Buena Vista in Marriott Village

10/10 Excellent
"El lugar es perfecto, es tal como lo ofrecen. Son claros con lo que ofrecen. Vale mucho la pena si vas de compras todo queda cerca. Si vas a Disney tienen bus y vale mucho la pena. El desayuno paso mis expectativas es mucho mejor de lo que yo esperaba."
lisandro 2-night trip
Posted 13 hours ago
Fairfield Inn & Suites Lake Buena Vista in Marriott Village
Hyatt Regency Orlando International Airport

Hyatt Regency Orlando International Airport

10/10 Excellent
"Excellent"
Myriam 1-night trip
Posted 14 hours ago
Hyatt Regency Orlando International Airport
The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

10/10 Excellent
"La piscina estaba limpia"
Hanoy 2-night trip
Posted 2 days ago
The Grove Resort & Water Park 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 $60 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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