The Best Winter Park Hotels with Pools from $77 - Hotels with indoor pools in Winter Park, FL

A two-story house with a balcony, surrounded by lush greenery and trees.

Upfront pricing
Our total price for your stay includes taxes and fees
Treat yourself
Save 10% or more on over 100,000 hotels worldwide with Member Prices
Learn about One Key
Be picky
Search almost a million properties worldwide

Check availability on Winter Park Hotels with a Pool

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for Winter Park hotels with a pool

1. The Alfond Inn

Winter Park

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

$326 nightly

$367 total

Sep 20 - Sep 21

Total with taxes and fees

4 bedrooms, desk, iron/ironing board, WiFi (free)

Coffee/tea maker, fridge, microwave, oven

2. The Canopy on Periwinkle- A Home Away From Home

Goldenrod

$315 nightly

$350 total

Sep 20 - Sep 21

Total with taxes and fees

1 bedroom, iron/ironing board, WiFi (free), bed sheets

3. 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.

$148 nightly

$164 total

Oct 4 - Oct 5

Total with taxes and fees

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

Orlando

$267 nightly

$296 total

Sep 20 - Sep 21

Total with taxes and fees

5. Winter Park Charmer - Heated Pool Home - Close to everything

Winter Park

$342 nightly

$379 total

Oct 6 - Oct 7

Total with taxes and fees

Outdoor pool, open 6:00 AM to 11:00 PM, pool umbrellas, sun loungers

6. Courtyard by Marriott Orlando Downtown

Ivanhoe Village

Float in sunshine at downtown Orlando's chic hotel pool, surrounded by plush loungers and umbrellas.

$110 nightly

$123 total

Sep 20 - Sep 21

Total with taxes and fees

Suite, 2 Double Beds, Non Smoking | Desk, blackout drapes, iron/ironing board, WiFi (free)

7. Comfort Suites Downtown

Ivanhoe Village

Make a splash in downtown Orlando with this hotel's seasonal outdoor pool and relaxing hot tub for post-exploration recovery.

$121 nightly

$136 total

Sep 28 - Sep 29

Total with taxes and fees

Deluxe Suite, 1 King Bed, Non Smoking, Pool View | Premium bedding, down comforters, pillowtop beds, desk

8. La Quinta Inn & Suites by Wyndham Orlando UCF

Orlando

Sun-soaked outdoor pool offers refreshing escapes and hot tub relaxation near the University of Central Florida campus.

$88 nightly

$99 total

Sep 20 - Sep 21

Total with taxes and fees

View all properties

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

Breakfast included

Hot tub

Water park

Spa

4 stars

Top Winter Park Hotel Reviews

Hyatt Regency Orlando International Airport

10/10 Excellent

"Close ness"

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

10/10 Excellent

"They are so helpful here. It’s a beautiful property too."

DoubleTree by Hilton at the Entrance to Universal Orlando

10/10 Excellent

"Everything was perfect"

Wyndham I-Drive Avanti Resort & Conference Center

8/10 Good

"La localización del hotel está accesible a todo"

Marriott's Grande Vista

10/10 Excellent

"👍👍👍"

Fairfield Inn & Suites Lake Buena Vista in Marriott Village

8/10 Good

"Excelente"

Holiday Inn Resort Orlando Suites - Waterpark by IHG

10/10 Excellent

"Great location, with clean rooms, and nice staff. Will definitely be back!"

Universal's Cabana Bay Beach Resort

10/10 Excellent

"."

Rosen Inn Lake Buena Vista

10/10 Excellent

"It was a very good stay..."

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 $77 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.

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.

Explore a world of travel with Expedia

Things to do in Orlando

Room 1

Upfront pricing

Treat yourself

Be picky

Check availability on Winter Park Hotels with a Pool

Our top choices for Winter Park hotels with a pool

1. The Alfond Inn

2. The Canopy on Periwinkle- A Home Away From Home

3. 1-bedroom vacation room just 12 minutes from University of Central Florida

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

5. Winter Park Charmer - Heated Pool Home - Close to everything

6. Courtyard by Marriott Orlando Downtown

7. Comfort Suites Downtown

8. La Quinta Inn & Suites by Wyndham Orlando UCF

9. Hampton Inn & Suites Orlando Airport @ Gateway Village

10. La Quinta Inn & Suites by Wyndham Orlando Airport

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

Top Winter Park Hotel Reviews

Hyatt Regency Orlando International Airport

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

DoubleTree by Hilton at the Entrance to Universal Orlando

Wyndham I-Drive Avanti Resort & Conference Center

Marriott's Grande Vista

Fairfield Inn & Suites Lake Buena Vista in Marriott Village

Holiday Inn Resort Orlando Suites - Waterpark by IHG

Universal's Cabana Bay Beach Resort

Rosen Inn Lake Buena Vista

Frequently asked questions

Explore a world of travel with Expedia

Find Hotels with a Pool in Winter Park, FL

Upfront pricing

Treat yourself

Be picky

Check availability on Winter Park Hotels with a Pool

Our top choices for Winter Park hotels with a pool

1. The Alfond Inn

2. The Canopy on Periwinkle- A Home Away From Home

3. 1-bedroom vacation room just 12 minutes from University of Central Florida

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

5. Winter Park Charmer - Heated Pool Home - Close to everything

6. Courtyard by Marriott Orlando Downtown

7. Comfort Suites Downtown

8. La Quinta Inn & Suites by Wyndham Orlando UCF

9. Hampton Inn & Suites Orlando Airport @ Gateway Village

10. La Quinta Inn & Suites by Wyndham Orlando Airport

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

Top Winter Park Hotel Reviews

Hyatt Regency Orlando International Airport

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

DoubleTree by Hilton at the Entrance to Universal Orlando

Wyndham I-Drive Avanti Resort & Conference Center

Marriott's Grande Vista

Fairfield Inn & Suites Lake Buena Vista in Marriott Village

Holiday Inn Resort Orlando Suites - Waterpark by IHG

Universal's Cabana Bay Beach Resort

Rosen Inn Lake Buena Vista

Frequently asked questions

Explore a world of travel with Expedia