A lakeside community with houses and boats.

Find Hotels with a Pool in Windermere, FL

Q: 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.

Dates

November 2026

December 2026

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Our top choices for Windermere hotels with a pool

A swimming pool with lounge chairs and a building in the background.

1. 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.

AED 386 total

includes taxes & fees

16 Nov - 17 Nov

A hotel with a swimming pool, outdoor seating, and a stone facade.

2. Holiday Inn Orlando - I-Drive North by IHG

International Drive District

Sparkling pool sanctuary in Orlando offers sun-soaked relaxation near Universal, complete with loungers for all-day enjoyment.

AED 383 total

includes taxes & fees

12 Nov - 13 Nov

A modern hotel with a swimming pool, outdoor seating, and a brick patio.

3. Spark by Hilton Orlando near Universal

Florida Center

Luxurious pool near Universal provides refreshing escape after theme park adventures.

AED 323 total

includes taxes & fees

30 Nov - 1 Dec

An outdoor infinity pool with a clear view of the cityscape, surrounded by lounge chairs and a bar area.

4. Cambria Hotel Orlando Universal Blvd

International Drive District

Dive into sun-soaked vacation bliss at the rooftop pool, offering beautiful panoramic views and a vibrant poolside bar scene.

AED 421 total

includes taxes & fees

12 Nov - 13 Nov

A swimming pool area with multiple water slides and palm trees.

5. Universal's Cabana Bay Beach Resort

Florida Center

Dive into double the fun with 2 outdoor pools, hot tubs, and a lazy river paradise.

AED 674 total

includes taxes & fees

10 Nov - 11 Nov

A pool area with lounge chairs and a building with multiple balconies in the background.

6. 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.

AED 284 total

includes taxes & fees

30 Nov - 1 Dec

A swimming pool with lounge chairs and umbrellas, surrounded by trees and a fence.

7. City Express by Marriott Orlando International Drive

International Drive District

AED 313 total

includes taxes & fees

24 Nov - 25 Nov

A swimming pool with lounge chairs and a small table, surrounded by a fence and palm trees.

8. Hampton Inn & Suites Orlando Intl Dr N

International Drive District

AED 409 total

includes taxes & fees

29 Nov - 30 Nov

A couple in a pool with clear water, a rocky waterfall background, and a tiled pool edge.

9. 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.

AED 317 total

includes taxes & fees

10 Nov - 11 Nov

A swimming pool with steps leading into it, surrounded by a building with a blue roof and white walls.

10. B&B Hotel Orlando International Drive Near Universal - Newly Renovated!

International Drive District

AED 319 total

includes taxes & fees

23 Nov - 24 Nov

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Choose what matters most at hotels with a pool in Windermere

Breakfast included

4 stars

Top Windermere Hotel Reviews

Holiday Inn Orlando - I-Drive North by IHG

International Drive District

10/10 Excellent

Blanca

A hotel pool area with lounge chairs and umbrellas, surrounded by tall buildings and a sunset sky.

Drury Plaza Hotel Orlando - Disney Springs Area

Lake Buena Vista

10/10 Excellent

Amy Dawn

Spark by Hilton Orlando near Universal

Florida Center

10/10 Excellent

Kenneth

A hotel pool area with lounge chairs and umbrellas, surrounded by palm trees and modern buildings.

Universal's Endless Summer Resort - Surfside Inn and Suites

International Drive District

10/10 Excellent

The beginning of a great stay started with Carmen at the front desk. We felt welcomed, informed and appreciated. I read reviews about the hot water, but we had no problem; the shower was great with adequate hot water. The rooms were clean and cleaned daily. The mattresses isn’t plush but I slept well. The shuttle to City Walk and Universal Studios theme parks and early entry into parks was a plus. The restaurant and Starbucks on property were convenient. The property is in a great location and...

Tanya

A pool area with people swimming and relaxing.

Universal's Endless Summer Resort - Dockside Inn and Suites

Florida Center

10/10 Excellent

cynthia

Wingate by Wyndham Convention Ctr Closest Universal Orlando

Florida Center

10/10 Excellent

Lydia

A rectangular pool with a surrounding brick walkway, lounge chairs, and palm trees.

Holiday Inn Orlando International Dr-ICON by IHG

International Drive District

10/10 Excellent

Julie

Universal's Cabana Bay Beach Resort

Florida Center

10/10 Excellent

When I booked, I honestly wasn’t sure what to expect, but Cabana Bay exceeded our expectations. Friendly staff, a charming theme, great communal areas and lovely rooms. We ended up with a volcano view room in the Beachside building and it was a 10/10. We had an awesome view of Volcano Bay which we ended up deciding to do on our last day (also recommend!). We explored the pools, enjoyed s’mores by the fire pits, played in the arcade, enjoyed early park access and transportation to the parks, ate...

Amanda

Hampton Inn & Suites Orlando Intl Dr N

International Drive District

10/10 Excellent

Pui chi

A hotel pool area with lounge chairs, a fire pit, and a large pool.

Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

Bay Lake

10/10 Excellent

We had an excellent stay! The hotel is clean, modern, and very well-appointed, with comfortable rooms that made us feel right at home. Traveling with our toddler, we found everything to be exceptional—the accommodations were spacious and family-friendly. The free breakfast was a fantastic bonus, with a variety of options, including some vegan-friendly choices, which we really appreciated. The staff was welcoming and attentive, ensuring we had everything we needed for a great stay. We would...

Nicolette

A swimming pool with clear blue water, surrounded by lounge chairs and yellow umbrellas.

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

Bay Lake

10/10 Excellent

Bharat

A swimming pool with a stone facade, lounge chairs, and a covered seating area.

Hyatt House Orlando International Drive

International Drive District

10/10 Excellent

jordan

Rosen Shingle Creek

Orlando

10/10 Excellent

Narciso

A hotel pool area with multiple lounge chairs and umbrellas, a water slide, and palm trees.

Home2 Suites by Hilton Orlando at Flamingo Crossings

Bay Lake

10/10 Excellent

Joel

B&B Hotel Orlando International Drive Near Universal - Newly Renovated!

International Drive District

10/10 Excellent

Travis

DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel

International Drive District

10/10 Excellent

GRACE

A swimming pool with a slide and a small waterfall feature, surrounded by lounge chairs and umbrellas.

Homewood Suites by Hilton Orlando at Flamingo Crossings

Bay Lake

10/10 Excellent

The property was amazing it is 10 mins away from Disney parks and 5 mins away from the Disney entrance gates. There is a target, 5-below, lime fresh Mexican grill, and a Starbucks at walking distance. The pool is very large and amazing for kids. The hotel rooms are very large with pull couches, comfortable beds, and a fully stocked kitchen perfect cooking. The hotel staff is on another level they offer top-tier service at all hours. The free breakfast is great. Parking is 20 dollars per day and...

Jada

City Express by Marriott Orlando International Drive

International Drive District

10/10 Excellent

Stephen

Pestana Orlando Suites - Lake Buena Vista

Orlando

10/10 Excellent

Christopher

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.

Find Hotels with a Pool in Windermere, FL

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Windermere hotels with a pool

1. Wingate by Wyndham Convention Ctr Closest Universal Orlando

2. Holiday Inn Orlando - I-Drive North by IHG

3. Spark by Hilton Orlando near Universal

4. Cambria Hotel Orlando Universal Blvd

5. Universal's Cabana Bay Beach Resort

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

7. City Express by Marriott Orlando International Drive

8. Hampton Inn & Suites Orlando Intl Dr N

9. Wyndham I-Drive Avanti Resort & Conference Center

10. B&B Hotel Orlando International Drive Near Universal - Newly Renovated!

Choose what matters most at hotels with a pool in Windermere

Top Windermere Hotel Reviews

Holiday Inn Orlando - I-Drive North by IHG

10/10 Excellent

Frequently Asked Questions

What are some hotels with pools in Windermere?

What is there to see and do in Windermere?

When is the best time to book a hotel with a pool in Windermere?