A lakeside community with houses and boats.

Find Hotels with a Pool in Windermere, FL from CA $101

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Check availability on Windermere Hotels with a Pool

Tonight
Oct 16 - Oct 17
Tomorrow
Oct 17 - Oct 18
This weekend
Oct 16 - Oct 18
Next weekend
Oct 23 - Oct 25

Our top choices for Windermere hotels with a pool

A pool area with lounge chairs and a building with multiple balconies in the background.
A row of sun loungers by a poolside, with a blue building and a plant in the background.
A modern hotel lobby with a reception desk, multiple TVs, a chandelier, and a seating area.
A modern bar area with a long counter, multiple stools, and a kitchen area with wooden cabinets and a TV.

1. DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel

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 $90
CA $101 total
includes taxes & fees
Nov 9 - Nov 10
DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel
A swimming pool with lounge chairs and a fenced area, surrounded by trees and a bus in the background.
A hotel room with two beds, each with white linens, a headboard, bedside tables with lamps, and a carpeted floor.
A breakfast bar with a chalkboard displaying food items and utensils.
A bathroom with a sink, toilet, and shower curtain.

2. Hampton Inn closest to Universal Orlando

Hampton Inn closest to Universal Orlando
Florida Center
  • Dive into poolside serenity at this Orlando hotel, where sun-drenched relaxation awaits just minutes from Universal Studios.
CA $106
CA $119 total
includes taxes & fees
Nov 1 - Nov 2
Hampton Inn closest to Universal Orlando
A hotel with a large pool, palm trees, and modern buildings.
A hotel room with two beds, a desk, a TV, and a large window offering a city view.
A bathroom with a large mirror, a shower, a sink, and a towel rack.
An outdoor pool area with a covered seating area, surrounded by palm trees and a modern building in the background.

3. 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.
CA $144
CA $161 total
includes taxes & fees
Oct 26 - Oct 27
DoubleTree by Hilton at the Entrance to Universal Orlando
A rectangular pool with a surrounding brick walkway, lounge chairs, and palm trees.
A modern hotel with a large reflective pool in front, palm trees, and a clear blue sky.
A conference room with multiple tables and chairs, a patterned carpet, and modern lighting fixtures.
A modern hotel lobby with a reception desk, a breakfast area, and a seating area with tables and chairs.

4. Holiday Inn Orlando International Dr-ICON by IHG

Holiday Inn Orlando International Dr-ICON by IHG
International Drive District
  • Refreshing outdoor pool beckons with sun loungers and umbrellas, steps away from ICON Park and exciting Orlando attractions.
CA $107
CA $142 total
includes taxes & fees
Oct 18 - Oct 19
Holiday Inn Orlando International Dr-ICON by IHG
A swimming pool with lounge chairs and a building in the background.
A hotel room with a bed, a sofa, a desk, a chair, and a small table.
A spacious dining area with multiple tables and chairs, a central pillar, and a kitchen area in the background.
A spacious lobby with a reception desk, leather sofas, and a large star-patterned floor design.

5. Wingate by Wyndham Convention Ctr Closest Universal Orlando

Wingate by Wyndham Convention Ctr Closest Universal Orlando
Florida Center
  • Splash into Universal thrills at this hotel with a sun-drenched pool and cozy loungers.
CA $119
CA $134 total
includes taxes & fees
Oct 27 - Oct 28
Wingate by Wyndham Convention Ctr Closest Universal Orlando
Pool
Exterior
Exterior
Breakfast area

6. Hilton Garden Inn Millenia near Universal Orlando Resort

Hilton Garden Inn Millenia near Universal Orlando Resort
Florida Center
  • Seasonal poolside bliss awaits at this art deco hotel near Florida's shopping hubs and local attractions.
CA $127
CA $143 total
includes taxes & fees
Nov 1 - Nov 2
Hilton Garden Inn Millenia near Universal Orlando Resort
A swimming pool area with multiple water slides and palm trees.
A child sitting on a blue inflatable pool in a hotel room with a large window, a red armchair, and a suitcase.
A spacious indoor atrium with high ceilings, palm trees, and modern seating areas.
A vibrant lounge area with colorful seating, a bar, and a mural.

7. 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.
CA $228
CA $257 total
includes taxes & fees
Nov 10 - Nov 11
Universal's Cabana Bay Beach Resort
A modern hotel with a swimming pool, outdoor seating, and a brick patio.
A hotel room with a bed, a chair, a desk, and a lamp.
A spacious room with wooden flooring, large windows, and a green carpet. There are two orange rocking chairs and a round table.
A reception desk with a modern design, featuring a wooden finish and a green carpet.

8. Spark by Hilton Orlando near Universal

Spark by Hilton Orlando near Universal
Florida Center
  • Luxurious pool near Universal provides refreshing escape after theme park adventures.
CA $119
CA $134 total
includes taxes & fees
Nov 2 - Nov 3
Spark by Hilton Orlando near Universal
A clear blue pool with lounge chairs and umbrellas, surrounded by palm trees and a building with a balcony.
A hotel lobby with a reception desk, a TV mounted on the wall, and a seating area with sofas.
A grocery store interior with refrigerated sections, a checkout counter, and a beverage section.
An outdoor patio with wicker furniture, green umbrellas, and brick walls.

9. Rosen Inn International

Rosen Inn International
International Drive District
  • Soak up the sun at this family-friendly hotel with 2 outdoor pools, poolside loungers, and a dedicated children's splash area.
CA $82
CA $92 total
includes taxes & fees
Oct 18 - Oct 19
Rosen Inn International
A swimming pool with clear blue water, surrounded by lounge chairs and yellow umbrellas.
A breakfast bar with various food dispensers, a seating area with a table and chairs, and large windows with a view of greenery.
A hotel room with a large window overlooking a swimming pool and a landscaped area with trees and a building in the background.
A lobby with a central seating area, wooden ceiling, and patterned carpet.

10. Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
Bay Lake
  • Splash into endless fun with an outdoor pool and sunny loungers just steps from Disney magic.
CA $107
CA $121 total
includes taxes & fees
Nov 2 - Nov 3
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
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Choose what matters most at hotels with a pool in Windermere

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Windermere Hotel Reviews

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

10/10 Excellent
"Loved my stay there, staff was amazing and the resort was beautiful"
Usomine 3-night trip
Posted 6 hours ago
The Grove Resort & Water Park Orlando
Seasons Florida Resort

Seasons Florida Resort

10/10 Excellent
"Great ac"
Emily 4-night trip
Posted 6 hours ago
Seasons Florida Resort
DoubleTree by Hilton at the Entrance to Universal Orlando

DoubleTree by Hilton at the Entrance to Universal Orlando

10/10 Excellent
"Good location. Clean room. Great breakfast buffet. Friendly staff."
Carla M Garayua 3-night trip
Posted 8 hours ago
DoubleTree by Hilton at the Entrance to Universal Orlando
Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

10/10 Excellent
"Front desk was excellent, really friendly and helpful. Everyone wa truly helpful and definitely friendly and polite."
ralph 1-night trip
Posted 8 hours ago
Westgate Lakes Resort & Spa Universal Studios Area
Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort

10/10 Excellent
"Good"
sally Lisa 3-night trip
Posted 11 hours ago
Universal's Cabana Bay Beach Resort
Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

10/10 Excellent
"I would like to see breakfast added as an amenity especially considering parking is not included and is pretty costly at $35 per day."
Tamara 2-night trip
Posted 13 hours ago
Sheraton Vistana Villages Resort Villas, I-Drive/Orlando
Fairfield Inn & Suites Lake Buena Vista in Marriott Village

Fairfield Inn & Suites Lake Buena Vista in Marriott Village

10/10 Excellent
"good"
Elliot 2-night trip
Posted 13 hours ago
Fairfield Inn & Suites Lake Buena Vista in Marriott Village

Frequently asked questions

What are some hotels with pools in Windermere?
Hyatt Regency Orlando International Airport: Features 2 restaurants, an outdoor pool, and complimentary wireless internet access. Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando: Aparthotel located near Orlando Vineland Premium Outlets. Offers 6 outdoor pools, a children's pool, and 3 restaurants. Marriott's Grande Vista: Aparthotel located near Orlando Vineland Premium Outlets. Provides 4 outdoor pools, a children's pool, and 3 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 Cabana Bay Beach Resort: Hotel, 5-minute walk from Universal Orlando Resort. Offers a lazy river, 2 outdoor pools, and 2 restaurants.
What is there to see and do in Windermere?
Explore places like Universal Studios Florida, Universal Orlando Resort, and Magic Kingdom® Park 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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