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

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Our top choices for Winter Park hotels with a pool

1-bedroom vacation room just 12 minutes from University of Central Florida

Orlando

Relax poolside at a cozy retreat with both private and outdoor pools, just 12 minutes from University of Central Florida.

$149 nightly

May 12 - May 13

Total with taxes and fees

Quiet and safe neighborhood come to this great place with lots of room for relax

Orlando

$265 nightly

May 3 - May 4

Total with taxes and fees

2 outdoor pools, open 10:00 AM to 5:00 PM, cabanas (surcharge)

The Alfond Inn

Winter Park

Soak up poolside perfection at this luxury hotel with loungers, umbrellas, and a refreshing bar.

$329 nightly

May 25 - May 26

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.

$71 nightly

May 31 - Jun 1

Total with taxes and fees

Outdoor pool, open 9:00 AM to 10:00 PM, pool umbrellas, sun loungers

Universal's Stella Nova Resort

Orlando

$150 nightly

Jun 1 - Jun 2

Total with taxes and fees

Outdoor pool, pool umbrellas, sun loungers

Hyatt House Orlando International Drive

International Drive District

Sun-kissed relaxation awaits at this poolside oasis with loungers and shade umbrellas.

$101 nightly

May 17 - May 18

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.

$125 nightly

May 13 - May 14

Total with taxes and fees

Hilton Vacation Club Grande Villas Orlando

Orlando

Poolside paradise awaits with 2 sparkling outdoor pools and luxurious cabanas for ultimate relaxation.

$104 nightly

May 5 - May 6

Total with taxes and fees

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Choose what matters most at hotels with a pool in Winter Park

Breakfast included

Hot tub

Top Winter Park Hotel Reviews

Marriott's Grande Vista

8/10 Good

"We thought the room was nice and tidy. Unfortunately, we didn't really get a chance to explore the hotel and amenities. The staff were nice and helpful, and we had an overall pleasant stay."

DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel

4/10 Poor

"The property looked OK and smelled OK, but it was not clean in my room. The shower I actually needed shower shoes that was a first for me. There was hair all over the room. The bed was clean. The air conditioner was super loud and the shower leaked all over the floor. The room looks as it’s pictured, but there is a parking fee that is not disclosed and Expedia makes it sound like parking is included with the price. The location was the best thing about the property. It was close to everything. I wouldn’t stay here again just because this isn’t my cup of tea. I guess you get what you pay for. The pool also said it closed at nine, but there were people outside in the pool up and down the corridors all night."

Frequently asked questions

How much does a hotel with outdoor pool in Winter Park cost?

Enjoy staying in a hotel in Winter Park 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.

Which Winter Park hotels offer poolside service for food and drinks?

The Alfond Inn is a fantastic option for travellers seeking a hotel in Winter Park with poolside service for food and drinks. This elegant 4-star hotel boasts an outdoor pool where guests can soak up the sun while enjoying delicious refreshments from the poolside bar. With a remarkable traveller rating of 9.6, guests frequently rave about the top service and friendly staff, making it an inviting retreat for travellers.

In addition to the inviting pool, The Alfond Inn offers a range of luxurious amenities, including a spa with various treatments that can rejuvenate your body after a day of exploration. Its comfortable and beautifully designed rooms ensure a relaxing stay, while the fabulous dining options keep visitors coming back for more.

Is it cheaper to book flights and a Winter Park 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 Winter Park hotel with a pool with Expedia?

Before booking your Winter Park 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 Winter Park for you.

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Check availability on Winter Park Hotels with a Pool

Our top choices for Winter Park hotels with a pool

1-bedroom vacation room just 12 minutes from University of Central Florida