The Best Windermere Hotels with Pools from $80 - Hotels with indoor pools in Windermere, FL

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Our top choices for Windermere hotels with a pool

Kompose Boutique Resort at Theme Parks

Kissimmee

Splash down the waterslide or bask poolside at this modern family resort with two hot tubs.

$84 nightly

Jun 3 - Jun 4

Total with taxes and fees

Vacation Village Orlando, Celebration

Kissimmee

Float through 7 outdoor pools or unwind in hot tubs at this family-friendly resort.

$96 nightly

Jun 3 - Jun 4

Total with taxes and fees

Outdoor pool, pool umbrellas, sun loungers

Ramada by Wyndham Suites Orlando Airport

Airport North

Poolside paradise awaits with sun loungers, umbrellas, and a refreshing outdoor oasis.

$75 nightly

Jun 3 - Jun 4

Total with taxes and fees

Wingate by Wyndham - Orlando International Airport

Airport North

Refreshing outdoor pool oasis with sun loungers offers relaxation after exploring nearby shopping and dining options.

$79 nightly

Jun 3 - Jun 4

Total with taxes and fees

Outdoor pool, open 8:00 AM to 9:00 PM, cabanas (surcharge)

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.

$82 nightly

Jun 29 - Jun 30

Total with taxes and fees

La Quinta Inn & Suites by Wyndham Orlando Airport

Airport North

Relaxing poolside retreat awaits with sun loungers, umbrellas, and a luxurious hot tub experience.

$82 nightly

Jun 30 - Jul 1

Total with taxes and fees

Outdoor pool, open 8:00 AM to 11:00 PM, pool umbrellas, sun loungers

Fairfield Inn By Marriott Orlando Airport

Airport North

Splash into this refreshing outdoor retreat with crystal-clear waters and a rejuvenating hot tub after airport arrivals.

$72 nightly

Jun 15 - Jun 16

Total with taxes and fees

Westgate Lakes Resort & Spa Universal Studios Area

Orlando

Splash into aquatic paradise with 7 pools, a lazy river, and waterslides at this family resort.

$127 nightly

Jun 3 - Jun 4

Total with taxes and fees

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Breakfast included

Hot tub

Top Windermere Hotel Reviews

Drury Plaza Hotel Orlando - Disney Springs Area

10/10 Excellent

"The service from the Hotel Staff was beyond what we expected. My wife accidentally forgot her Beats Headphones in the room after we checked out and were already at the airport. She called the hotel and spoke with Grace at Guest Services. Housekeeping found my wife's headphones; Grace's team created a shipping label and had them shipped next day air back to our home in Texas. She was so pleased and grateful for their hospitality. This was our second time staying at the hotel and won't be our last. We enjoy getting early access to all the Disney theme parks, taking advantage of the shuttle buses and the staff at the front desk are always so helpful. Rooms are clean and well maintained, lobby area is well maintained. When I get asked where we stay when coming to Disney, I proudly say Drury! Thank you!"

Westgate Lakes Resort & Spa Universal Studios Area

2/10 Terrible

"I hate everything about this place. It's not what it says on the website we went there for a three night trip we couldn't even enjoy ourselves. All the amenities were closed. No access to pools. No access to the door to the pools. Gates are locked front desk telling you different different things every time you call them .I'll never go back to this place. I hate it. They close the main doors to access the Adult pool and they want you to walk around the building where all the garbage stinks. Disgusting when you ask them questions they have something to cover their behind. Nobody's owning up to anything there is no parking please there is no parking you have to stay and wait for a trolley or a bus to take you to your building . It's so frustrating. From Desk will tell you OK will send the trolley then I call another day. They said no no trolley will come. They never sent out a trolley. You have to wait for a bus every time they have a different story to tell the hallway is nasty dirty filthy."

Holiday Inn Resort Orlando Suites - Waterpark by IHG

10/10 Excellent

"the rooms were clean and staff members including the " Capitan" were very helpful and kind. Pools were clean and nice . We went back on February. That's my second time in this hotel and i highly recommend. Keep the amazing job keeping the hotel clean and for the nice workers you guys have. i will be coming back to this hotel next year. Thank you for your services and kindness. Highly recommended for family stay."

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 $80 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.

How can I save on a Windermere hotel with a pool with Expedia?

Before booking your Windermere hotel, remember to join One Key™, Expedia's free travel rewards program. Just sign up and sign in to access our lowest Member Prices as well as members-only perks. Booking your hotel in advance will typically help you save, but there are last-minute deals to explore too.

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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Check availability on Windermere Hotels with a Pool

Our top choices for Windermere hotels with a pool

Kompose Boutique Resort at Theme Parks

Vacation Village Orlando, Celebration

Ramada by Wyndham Suites Orlando Airport

Wingate by Wyndham - Orlando International Airport

DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel

La Quinta Inn & Suites by Wyndham Orlando Airport

Fairfield Inn By Marriott Orlando Airport

Westgate Lakes Resort & Spa Universal Studios Area

Wyndham Garden Orlando Airport

Hampton Inn & Suites Orlando Airport @ Gateway Village

Choose what matters most at hotels with a pool in Windermere

Top Windermere Hotel Reviews

Drury Plaza Hotel Orlando - Disney Springs Area

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

Westgate Lakes Resort & Spa Universal Studios Area

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Caribe Royale Orlando

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

The Grove Resort & Water Park Orlando

Marriott's Grande Vista

Holiday Inn Resort Orlando Suites - Waterpark by IHG

Frequently asked questions

Explore a world of travel with Expedia

Find Hotels with a Pool in Windermere, FL

Upfront pricing

Treat yourself

Be picky

Check availability on Windermere Hotels with a Pool

Our top choices for Windermere hotels with a pool

Kompose Boutique Resort at Theme Parks

Vacation Village Orlando, Celebration

Ramada by Wyndham Suites Orlando Airport

Wingate by Wyndham - Orlando International Airport

DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel

La Quinta Inn & Suites by Wyndham Orlando Airport

Fairfield Inn By Marriott Orlando Airport

Westgate Lakes Resort & Spa Universal Studios Area

Wyndham Garden Orlando Airport

Hampton Inn & Suites Orlando Airport @ Gateway Village

Choose what matters most at hotels with a pool in Windermere

Top Windermere Hotel Reviews

Drury Plaza Hotel Orlando - Disney Springs Area

Frequently asked questions

Explore a world of travel with Expedia