Windermere Hotel Guide - Hotels with Pool in Windermere, Orlando

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Windermere Hotels with Pool

Top Windermere Hotels with Pool

Fridge, microwave, oven, stovetop
Last Minute Disney Getaway! Luxury Villa with Private patio. Book Now! #115911

Last Minute Disney Getaway! Luxury Villa with Private patio. Book Now! #115911

Orlando
  • Pool
  • Kitchen
  • Washer
  • Pet-friendly
  • Air conditioning
  • Gym
Last Minute Disney Getaway! Luxury Villa with Private patio. Book Now! #115911
Fridge, microwave, oven, stovetop
Last Minute Disney Getaway! Private patio & Themed Bedrooms. Book Now! #115909

Last Minute Disney Getaway! Private patio & Themed Bedrooms. Book Now! #115909

Orlando
  • Pool
  • Kitchen
  • Washer
  • Pet-friendly
  • Air conditioning
  • Gym
Last Minute Disney Getaway! Private patio & Themed Bedrooms. Book Now! #115909
Outdoor pool, open 8:00 AM to 9:00 PM, pool cabanas (surcharge)
DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel

DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel

3.0 star property
International Drive District
  • Outdoor pool
  • Poolside bar
  • Pool loungers
  • Hot tub
8.8 out of 10, Excellent, (605)
Poolside luxury awaits at this pristine retreat near Universal Studios. Families appreciate the dedicated children's pool, while adults relax in cabanas with cocktails from the poolside bar after invigorating workouts in the 24-hour fitness centre.
The price is €74
includes taxes & fees
11 Dec - 12 Dec
DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel
Outdoor pool, pool umbrellas, pool loungers
Kompose Boutique Resort at Theme Parks

Kompose Boutique Resort at Theme Parks

3.0 star property
Kissimmee
  • Outdoor pool
  • Poolside bar
  • Pool loungers
  • 2 hot tubs
9.4 out of 10, Exceptional, (1807)
Vibrant poolside experiences await with a thrilling waterslide, luxurious hot tubs, and refreshing drinks served at the bar. Families love the spacious, modern rooms while the sauna and 24-hour fitness centre provide additional relaxation options.
The price is €81
includes taxes & fees
1 Dec - 2 Dec
Kompose Boutique Resort at Theme Parks
Royal Room, 2 Queen Beds, Pool View | Pool
Magic Moment Resort & Kids Club, Dazzler Select by Wyndham

Magic Moment Resort & Kids Club, Dazzler Select by Wyndham

3.0 star property
Kissimmee
  • Outdoor pool
  • Pool loungers
8.4 out of 10, Very good, (2646)
Splashing in the heated outdoor pool proves a highlight for families after Disney adventures. Kids delight in the playground, arcade, and bouncy castle while adults relax in free cabanas amid the thoughtfully designed recreational spaces.
Magic Moment Resort & Kids Club, Dazzler Select by Wyndham
Outdoor pool, pool umbrellas, pool loungers
DoubleTree by Hilton Orlando Airport

DoubleTree by Hilton Orlando Airport

4.0 star property
Airport North
  • Outdoor pool
  • Pool loungers
8.8 out of 10, Excellent, (2079)
Sparkling outdoor pool creates a peaceful sanctuary amid the hustle of Orlando Airport. Guests appreciate the clean waters, comfortable loungers, and convenient towel service while enjoying proximity to Florida Mall and complimentary airport shuttles.
The price is €78
includes taxes & fees
27 Nov - 28 Nov
DoubleTree by Hilton Orlando Airport
4 outdoor pools, open 5:30 AM to midnight, pool cabanas (surcharge)
Rosen Shingle Creek

Rosen Shingle Creek

4.5 star property
Orlando
  • 4 outdoor pools
  • Poolside bar
  • Pool loungers
  • 2 hot tubs
9.4 out of 10, Exceptional, (4245)
Swimming paradise unfolds across 4 inviting outdoor pools surrounded by swaying palms and luxurious cabanas. Refreshing poolside drinks complement sun-drenched days while nearby hot tubs offer evening relaxation after golf rounds on the 18-hole course.
The price is €108
includes taxes & fees
25 Nov - 26 Nov
Rosen Shingle Creek
Outdoor pool, pool umbrellas, pool loungers
La Quinta Inn & Suites by Wyndham Orlando Airport North

La Quinta Inn & Suites by Wyndham Orlando Airport North

3.0 star property
Airport North
  • Outdoor pool
  • Pool loungers
  • Hot tub
7.4 out of 10, Good, (697)
Swimming and relaxation await at the inviting outdoor pool, perfectly complemented by a soothing hot tub. Fitness enthusiasts appreciate the well-equipped exercise centre, while the convenient airport shuttle and delicious free breakfast enhance every stay.
The price is €53
includes taxes & fees
3 Dec - 4 Dec
La Quinta Inn & Suites by Wyndham Orlando Airport North
Outdoor pool
Seasons Florida Resort

Seasons Florida Resort

2.0 star property
Kissimmee
  • Outdoor pool
8.8 out of 10, Excellent, (3240)
Soak in the warm, clean outdoor pool surrounded by well-maintained grounds after exciting park adventures. Located near Disney Springs and Epcot, this recently renovated retreat offers peaceful accommodation with premium bedding.
The price is €60
includes taxes & fees
23 Nov - 24 Nov
Seasons Florida Resort
Outdoor pool
Country Inn & Suites by Radisson, Orlando Airport, FL

Country Inn & Suites by Radisson, Orlando Airport, FL

3.0 star property
Airport North
  • Outdoor pool
  • Hot tub
7.8 out of 10, Good, (4239)
Poolside tranquility awaits at this conveniently located retreat, featuring a pristine outdoor swimming area and soothing hot tub. Guests appreciate the spotless pool area, friendly staff, and convenient shuttle service to nearby attractions and the airport.
The price is €68
includes taxes & fees
16 Dec - 17 Dec
Country Inn & Suites by Radisson, Orlando Airport, FL
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties

Top Windermere Hotel Reviews

Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort

10/10 Excellent
"Clean and beautiful "
Ektaa Sanjay 4-night trip
Posted 2 days ago
Universal's Cabana Bay Beach Resort

Explore a world of travel with Expedia

Frequently asked questions

What are some hotels with pools in Windermere?
Universal's Cabana Bay Beach Resort: Hotel, 5-minute walk from Universal Orlando Resort. Features a lazy river, 2 outdoor swimming pools and 2 restaurants. Rosen Inn at Pointe Orlando: Hotel, 2-minute walk from Pointe Orlando. Offers 2 coffee shops/cafes, 3 outdoor swimming pools and complimentary wireless Internet access. Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando: Hotel located near Disney Springs™. Provides 6 outdoor swimming pools, a children's pool and 3 restaurants. DoubleTree by Hilton at the Entrance to Universal Orlando: Hotel, 2-minute walk from Universal Orlando Resort. Features a children's pool, an outdoor pool and 2 restaurants. Wyndham I-Drive Avanti Resort & Conference Center: Hotel, 7-minute walk from CoCo Key Water Resort. Offers a children's pool, an outdoor pool and 2 bars.
What is there to see and do in Windermere?
Explore places such as 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 accommodation that has an outdoor pool if you're planning to visit Windermere in the driest months of November, February or December, when the average rainfall is 49 mm. Accommodation 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 194 mm.