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Check availability on Windermere Hotels with a Pool

Tonight
Sep 22 - Sep 23
Tomorrow
Sep 23 - Sep 24
This weekend
Sep 25 - Sep 27
Next weekend
Oct 2 - Oct 4

Our top choices for Windermere hotels with a pool

A hotel pool area with multiple lounge chairs and umbrellas, a water slide, and palm trees.
An outdoor patio area with a fire pit, yellow and blue seating, and a covered section with a pergola.
A modern hotel room with a dining area, a living space with a sofa and coffee table, and a kitchenette.
A hotel with a prominent "HOME 2" sign, a stone facade, and an arched entrance.

1. Home2 Suites by Hilton Orlando at Flamingo Crossings

Home2 Suites by Hilton Orlando at Flamingo Crossings
Bay Lake
  • Splash into vacation mode at this family resort featuring a sun-soaked pool area and thrilling waterslide.
₩134,051
₩150,809 total
includes taxes & fees
Oct 4 - Oct 5
Home2 Suites by Hilton Orlando at Flamingo Crossings
A swimming pool with lounge chairs and a building in the background.
A spacious dining area with multiple tables and chairs, a central pillar, and a kitchen area in the background.
A hotel room with a bed, a sofa, a desk, a chair, and a small table.
A hotel entrance with a sign reading "Wingate by Wyndham."

2. 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.
₩128,446
₩144,501 total
includes taxes & fees
Sep 27 - Sep 28
Wingate by Wyndham Convention Ctr Closest Universal Orlando
A swimming pool with lounge chairs and a small table, surrounded by a fence and palm trees.
A hotel room with a bed, desk, and chair, a mirror, and a door leading to another room.
A hotel room with a grey sofa, a small table, a desk with a chair, a mirror, and a picture on the wall.
A modern dining area with round tables and chairs, a long counter, and a patterned rug.

3. Hampton Inn & Suites Orlando Intl Dr N

Hampton Inn & Suites Orlando Intl Dr N
International Drive District
₩121,440
₩136,619 total
includes taxes & fees
Oct 18 - Oct 19
Hampton Inn & Suites Orlando Intl Dr N
A swimming pool with lounge chairs and palm trees, surrounded by a building with large windows.
Two high-rise buildings with reflections in a calm body of water, surrounded by greenery and palm trees.
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.

4. 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.
₩126,385
₩142,183 total
includes taxes & fees
Sep 27 - Sep 28
DoubleTree by Hilton at the Entrance to Universal Orlando
A swimming pool area with multiple water slides and palm trees.
A spacious indoor atrium with high ceilings, palm trees, and modern seating areas.
A child sitting on a blue inflatable pool in a hotel room with a large window, a red armchair, and a suitcase.
A vibrant lounge area with colorful seating, a bar, and a mural.

5. 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.
₩206,063
₩231,821 total
includes taxes & fees
Sep 23 - Sep 24
Universal's Cabana Bay Beach Resort
A swimming pool with a water slide, lounge chairs, umbrellas, and palm trees.
A large hotel with a central entrance, multiple floors, and a sign indicating 'Homewood Suites by Hilton.'
A hotel room with a large window, a pool view, a chair, a table, a lamp, and a bed.
A modern kitchen with a large island, bar stools, pendant lighting, and a flat-screen TV.

6. Homewood Suites by Hilton Orlando at Flamingo Crossings

Homewood Suites by Hilton Orlando at Flamingo Crossings
Bay Lake
  • Dive into poolside bliss with loungers and a thrilling waterslide at this spotless Orlando retreat.
₩156,580
₩176,153 total
includes taxes & fees
Oct 6 - Oct 7
Homewood Suites by Hilton Orlando at Flamingo Crossings
A rectangular pool with a surrounding brick walkway, lounge chairs, and palm trees.
A modern kitchen with a large dining table, chairs, and a built-in bookshelf with various items.
A spacious indoor area with a counter, seating, and large windows.
A modern hotel with a large reflective pool in front, palm trees, and a clear blue sky.

7. 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.
₩100,284
₩133,424 total
includes taxes & fees
Oct 20 - Oct 21
Holiday Inn Orlando International Dr-ICON by IHG
A swimming pool with lounge chairs and palm trees, a Ferris wheel in the background, and a modern building to the right.
An outdoor seating area with wicker furniture and a central fire feature.
A modern living area with a sectional sofa, round ottomans, and a flat-screen TV mounted on a wooden wall.
A modern hotel lobby with a mix of seating areas, including tables and chairs, and a central seating area with sofas.

8. Element by Marriott Orlando Universal Blvd.

Element by Marriott Orlando Universal Blvd.
International Drive District
₩121,440
₩136,621 total
includes taxes & fees
Sep 27 - Sep 28
Element by Marriott Orlando Universal Blvd.
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.

9. 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.
₩105,889
₩119,125 total
includes taxes & fees
Sep 29 - Sep 30
Spark by Hilton Orlando near Universal
A Wyndham Garden hotel with a swimming pool, lounge chairs, and palm trees.
A modern hotel room with two beds, a desk, and a chair.
A modern lounge area with a fireplace, seating, and a bar.
A modern lobby with a seating area, a reception desk, and a large window providing a view of the outdoors.

10. Wyndham Garden Orlando Universal / I Drive

Wyndham Garden Orlando Universal / I Drive
International Drive District
  • Sparkling pool sanctuary in Orlando offers sun-soaked relaxation near Universal, complete with loungers for all-day enjoyment.
₩122,268
₩137,553 total
includes taxes & fees
Sep 28 - Sep 29
Wyndham Garden Orlando Universal / I Drive
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Choose what matters most at hotels with a pool in Windermere

Breakfast included
4 stars
Hot tub
5 stars
Spa

Top Windermere Hotel Reviews

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

10/10 Excellent
"Absolutely great stay. The grounds were well kept, the staff was so friendly and accommodating especially TaTa who maintained great service in the rain!! We had a great time and definitely will be back!!"
Sharntivia 3-night trip
Posted 6 hours ago
The Grove Resort & Water Park Orlando
Drury Plaza Hotel Orlando - Disney Springs Area

Drury Plaza Hotel Orlando - Disney Springs Area

10/10 Excellent
"It’s a great hotel with a great breakfast and two every person who is over 21 receives two free drinks. The rooms are nice and roomy and clean"
Milagros 3-night trip
Posted 8 hours ago
Drury Plaza Hotel Orlando - Disney Springs Area
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

10/10 Excellent
"Great staff and very clean room. Will stay again!"
Abbigail 1-night trip
Posted 8 hours ago
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
DoubleTree by Hilton at the Entrance to Universal Orlando

DoubleTree by Hilton at the Entrance to Universal Orlando

10/10 Excellent
"Very bright and clean facilities. Easy walk to Universal City Walk."
Jessica 4-night trip
Posted 8 hours ago
DoubleTree by Hilton at the Entrance to Universal Orlando
Hyatt Regency Orlando International Airport

Hyatt Regency Orlando International Airport

10/10 Excellent
"Clean friendly"
Dulce 1-night trip
Posted 12 hours ago
Hyatt Regency Orlando International Airport
Rosen Inn Lake Buena Vista

Rosen Inn Lake Buena Vista

10/10 Excellent
"Clean and helpful staff"
Alejandra 1-night trip
Posted 17 hours ago
Rosen Inn Lake Buena Vista

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. Universal's Endless Summer Resort - Dockside Inn and Suites: Hotel located near Universal Orlando Resort. Features 2 outdoor pools, a children's pool, and 3 bars. 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.
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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