The Best Winter Park Hotels with Pools from $103 - 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.

$162 nightly

Apr 6 - Apr 7

Total with taxes and fees

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

Orlando

$260 nightly

Apr 5 - Apr 6

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.

$324 nightly

Apr 5 - Apr 6

Total with taxes and fees

Wyndham Grand Orlando Resort Bonnet Creek

Orlando

Splash into aquatic bliss at this resort with 5 outdoor pools, a lazy river, and poolside cabanas.

$201 nightly

Mar 20 - Mar 21

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.

$93 nightly

Apr 1 - Apr 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.

$118 nightly

Mar 22 - Mar 23

Total with taxes and fees

Outdoor pool, a heated pool, pool umbrellas, sun loungers

Universal's Endless Summer Resort - Surfside Inn and Suites

International Drive District

$154 nightly

Mar 22 - Mar 23

Total with taxes and fees

Hampton Inn & Suites Orlando Airport @ Gateway Village

Airport North

Vibrant pool oasis near Orlando Airport beckons travelers to dive in after a day exploring nearby attractions.

$106 nightly

Mar 30 - Mar 31

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

Caribe Royale Orlando

10/10 Excellent

"We truly enjoyed our stay until the morning when house keeping "

DoubleTree by Hilton at the Entrance to Universal Orlando

8/10 Good

"Overall it was a good stay. All the staff are helpful and friendly. Shout out to the older Asian looking gentleman (wasn’t able to get his name), our server at Sunshine cafe. He was probably the best server we’ve ever had. Food at the restaurants are just ok. They are, in my opinion quite pricey. The hotel is old. Our door won’t shut all the way. Sink was clogged but the got it fixed immediately. Shuttle service to the theme parks was great. If you missed the shuttle, you can walk to the park and back to the hotel. We will definitely stay there again."

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

10/10 Excellent

"We arrived late, so did not get to experience many amenities. We also did not eat breakfast here. Other than that, the hotel was very clean and kept nicely. The staff was kind. Our room was clean, spacious, and decorated great! This is a secret hidden gem! An amazing price point for what you get. We will be back if we’re in the area again. "

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 $103 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