Find Hotels with a Pool in Winter Park, FL from CA $114

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

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

    Search almost a million properties worldwide

Check availability on Winter Park Hotels with a Pool

This weekend
Next weekend

Our top choices for Winter Park hotels with a pool

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

1-bedroom vacation room just 12 minutes from University of Central Florida
Orlando
9.4 out of 10, Exceptional, (3 reviews)
  • cleanliness
    Relax poolside at a cozy retreat with both private and outdoor pools, just 12 minutes from University of Central Florida.
The price is CA $75
CA $227 total
includes taxes & fees
May 12 - May 13
1-bedroom vacation room just 12 minutes from University of Central Florida

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

Quiet and safe neighborhood come to this great place with lots of room for relax
Orlando
10.0 out of 10, Exceptional, (2 reviews)
The price is CA $181
CA $400 total
includes taxes & fees
May 3 - May 4
Quiet and safe neighborhood come to this great place with lots of room for relax

The Alfond Inn

The Alfond Inn
4.0 star property
Winter Park
9.6 out of 10, Exceptional, (1,000 reviews)
  • cleanliness
    Soak up poolside perfection at this luxury hotel with loungers, umbrellas, and a refreshing bar.
The price is CA $368
CA $453 total
includes taxes & fees
May 25 - May 26
The Alfond Inn

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
8.6 out of 10, Excellent, (1,250 reviews)
  • cleanliness
    Splash into fun at this Orlando oasis with pool cabanas, a hot tub, and a poolside bar.
The price is CA $101
CA $114 total
includes taxes & fees
May 11 - May 12
DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel

Universal's Stella Nova Resort

Universal's Stella Nova Resort
3.0 star property
Orlando
9.2 out of 10, Wonderful, (735 reviews)
The price is CA $230
CA $259 total
includes taxes & fees
Apr 30 - May 1
Universal's Stella Nova Resort

Hyatt House Orlando International Drive

Hyatt House Orlando International Drive
4.0 star property
International Drive District
9.4 out of 10, Exceptional, (1,752 reviews)
  • cleanliness
    Sun-kissed relaxation awaits at this poolside oasis with loungers and shade umbrellas.
The price is CA $138
CA $155 total
includes taxes & fees
May 7 - May 8
Hyatt House Orlando International Drive

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area
4.0 star property
Orlando
8.4 out of 10, Very good, (6,278 reviews)
  • cleanliness
    Splash into aquatic paradise with 7 pools, a lazy river, and waterslides at this family resort.
The price is CA $133
CA $196 total
includes taxes & fees
May 3 - May 4
Westgate Lakes Resort & Spa Universal Studios Area

Hilton Vacation Club Grande Villas Orlando

Hilton Vacation Club Grande Villas Orlando
3.5 star property
Orlando
9.2 out of 10, Wonderful, (2,862 reviews)
  • cleanliness
    Poolside paradise awaits with 2 sparkling outdoor pools and luxurious cabanas for ultimate relaxation.
The price is CA $115
CA $160 total
includes taxes & fees
May 21 - May 22
Hilton Vacation Club Grande Villas Orlando

Wyndham Grand Orlando Resort Bonnet Creek

Wyndham Grand Orlando Resort Bonnet Creek
4.0 star property
Orlando
9.0 out of 10, Wonderful, (2,920 reviews)
  • cleanliness
    Splash into aquatic bliss at this resort with 5 outdoor pools, a lazy river, and poolside cabanas.
The price is CA $217
CA $308 total
includes taxes & fees
May 28 - May 29
Wyndham Grand Orlando Resort Bonnet Creek

Drury Plaza Hotel Orlando - Disney Springs Area

Drury Plaza Hotel Orlando - Disney Springs Area
3.0 star property
Lake Buena Vista
9.8 out of 10, Exceptional, (5,819 reviews)
  • cleanliness
    Dive into a cool-down oasis with a spacious outdoor pool, hot tub, and poolside bar service.
The price is CA $207
CA $233 total
includes taxes & fees
May 30 - May 31
Drury Plaza Hotel Orlando - Disney Springs Area
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.

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

Top Winter Park Hotel Reviews

Frequently asked questions

What are the best hotels in Winter Park with outdoor pools?
The Alfond Inn is a great choice for travellers seeking a delightful stay in Winter Park, featuring a stunning outdoor pool that invites relaxation under the Florida sun. Rated 9.4 by guests, this 4-star hotel is not only known for its beautiful accommodations but also for its exceptional amenities, such as a poolside bar where you can enjoy refreshing drinks while soaking up the atmosphere.

Families will appreciate the spacious sun loungers surrounding the pool, making it a superb spot to unwind after a day of exploring local attractions. Beyond the pool, The Alfond Inn offers an extensive spa experience, including body scrubs, facial treatments, and various types of massages to rejuvenate your senses.

With its excellent and friendly staff, guests often rave about the service, making you feel right at home. The location is another highlight, placing you in close proximity to Winter Park's charming downtown area, where you can enjoy shopping, dining, and cultural experiences.
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 CA $114 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 in Winter Park is a fantastic choice for travellers seeking a blend of relaxation and convenience, especially if you're looking for poolside service. This 4-star hotel features an inviting outdoor pool complemented by a delightful poolside bar, where guests can enjoy refreshing drinks and snacks while basking in the sun on comfortable loungers.

Guests rave about the top service at The Alfond Inn, with a stellar review rating of 9.4. Many appreciate the friendly staff who go above and beyond to ensure a memorable experience. The hotel's location is also described as perfect, making it a great base for exploring the charm of Winter Park.

In addition to the pool amenities, The Alfond Inn offers a range of spa treatments, including massages and body scrubs, allowing for a truly indulgent getaway.
Are there hotels with outdoor pools that are close to Lake Rose?
The Alfond Inn is a charming 4-star hotel that features a beautiful outdoor pool, great for families seeking relaxation under the Florida sun. With a review rating of 9.4, guests consistently praise the excellent and friendly staff, alongside the hotel's great location that makes it easy to enjoy nearby attractions, including Lake Rose.

This hotel not only offers a refreshing outdoor pool surrounded by comfortable sun loungers but also boasts a poolside bar, allowing for leisurely afternoons with a drink in hand. For those looking to unwind further, The Alfond Inn includes a spa where visitors can indulge in a range of treatments like body scrubs, massages, and facial treatments, ensuring a rejuvenating experience for parents and a fun environment for kids alike.
Is it cheaper to book flights and a hotel in Winter Park 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 travel package.
How can I save on a hotel in Winter Park with Expedia?
Before booking your Winter Park hotel, remember to join Expedia's free travel rewards program—One Key™. 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 with an outdoor pool in Winter Park for you.

Explore a world of travel with Expedia