Explore top 2025 5 Star Hotels in Winter Park

Name: Gorgeous 2 Bedroom Apartment Close to Disney 305 3191
Rating: 9

Seize Your Someday with our amazing deals for the whole family!

Save an extra 10% or more on select hotels with Member Discounts

Access exclusive hotel deals, only with the Travelocity app

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

Top Winter Park 5 Star hotels

Waldorf Astoria Orlando - An Official Walt Disney World® Hotel

14200 Bonnet Creek Resort Lane, Orlando, FL

Fully refundableReserve now, pay when you stay

$406 nightly

$457 total

Oct 3 - Oct 4

Total with taxes and fees

This luxury resort features a golf course, a full-service spa, and 12 restaurants. There's fun for all ages with a lazy river and a children's club, and families ...

9.2/10 Wonderful! (364 reviews)

"Great"

Reviewed on Sep 26, 2025

Conrad Orlando at Evermore

1500 Eastbeach Way, Orlando, FL

Fully refundableReserve now, pay when you stay

$433 nightly

$488 total

Oct 30 - Oct 31

Total with taxes and fees

This luxury resort features a private beach, a golf course, and a full-service spa. Relax with beach cabanas, sun loungers, and beach umbrellas. Bring the family ...

9.4/10 Exceptional! (294 reviews)

"Amazing resort. Will go again."

Reviewed on Sep 27, 2025

The Ritz-Carlton Orlando, Grande Lakes

4012 Central Florida Parkway, Orlando, FL

$546 nightly

$614 total

Sep 30 - Oct 1

Total with taxes and fees

This smoke-free hotel features a golf course, a full-service spa, and 7 restaurants. There's fun for all ages with a lazy river and a children's club, and families ...

9.2/10 Wonderful! (1,011 reviews)

"Stayed here for a few days. Staff was great and upgraded my room for my birthday and sent me a bottle of wine and macarons. Very sweet! Room was clean and comfortable. Slept well. Spa was relaxing and pool was clean and good service. Recommend for a relaxing stay!"

Reviewed on Sep 28, 2025

Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort

10100 Dream Tree Blvd., Lake Buena Vista, FL

Fully refundableReserve now, pay when you stay

$1,040 nightly

$1,170 total

Oct 1 - Oct 2

Total with taxes and fees

This luxury resort features a golf course, free water park access, and a full-service spa. There's fun for all ages with a lazy river and a children's pool, ...

9.6/10 Exceptional! (869 reviews)

"An amazing stay at the Four Seasons Orlando! The service was outstanding, the pools (especially the lazy river) were fantastic, and the on-site restaurants offered excellent dining options. Truly a perfect experience from start to finish."

Reviewed on Sep 14, 2025

Luxurious 2 Bd Close to Disney @ Storey Lake 204 3131

3131 Paradox Circle, Unit 204, Kissimmee, FL

A golf course, free water park access, and 2 outdoor pools are all featured at this smoke-free vacation home. There's fun for all ages with a lazy river and ...

10/10 Exceptional! (4 reviews)

"It was a clean and nice"

Reviewed on Sep 13, 2025

Get rates

Gorgeous 4 Bedroom w/ Pool Close to Disney 4836

4836 Dedication Street, Kissimmee, FL

Free water park access and an outdoor pool are featured at this luxury vacation home. Bring the family and enjoy the lazy river, children's pool, and waterslide. ...

9.4/10 Exceptional! (12 reviews)

"Clean, loved the pool"

Reviewed on Sep 18, 2025

Get rates

Stunning 4Bd With Pool At Storey Lake Resort 4821

4821 Dedication St, Kissimmee, FL

A golf course, free water park access, and 3 outdoor pools are all featured at this luxury vacation home. There's fun for all ages with a lazy river and mini ...

7.4/10 Good! (3 reviews)

"They ripp you off with the cleaning and ma"

Reviewed on Sep 7, 2025

Get rates

2 Bedroom l Waterpark & Resort Amenities Included, Themed Rooms

3191 Sea World Court, Kissimmee, FL

Free water park access and an outdoor pool are featured at this luxury villa. Bring the family and enjoy the free kid's club, waterslide, and playground. Enjoy ...

8.2/10 Very Good! (15 reviews)

"Everything during our stay was amazing definitely will stay again"

Reviewed on Sep 7, 2025

Get rates

Marvelous 5Bd w/ Pool Close to Disney @ Storey Lake 2629

2629 Reading Trail, Kissimmee, FL

Free water park access and an outdoor pool are featured at this luxury vacation home. Bring the family and enjoy the lazy river, children's pool, and waterslide. ...

8.6/10 Excellent! (3 reviews)

"Nice"

Reviewed on Jun 13, 2025

Get rates

Gorgeous 2 Bedroom Apartment Close to Disney 305 3191

3191 Paradox Circle, Unit 305, Kissimmee, FL

Free water park access and an outdoor pool are featured at this smoke-free condo. There's fun for all ages with a lazy river and a waterslide, and barbecue grills ...

9/10 Wonderful! (6 reviews)

Great location for anything Disney

"Great location, beautiful spacious apartment, comfortable beds/space. It was well appointed with kitchen items, bathroom, and laundry. The apartment floors were a little dirty and there really needed to be a fan in the 2nd bedroom. It was pretty stuffy in there with the thermometer limited to 72 ..."

Reviewed on Feb 10, 2025

Get rates

Don't see what you're looking for?

See all available properties in Winter Park

View all properties

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.

Winter Park Resorts & 5 Star Hotels

Looking for your own little slice of heaven during your next trip? Check out all the best 5-star hotels in Winter Park to make sure your trip is as extravagantly comfortable as you expect.

Whether you plan on staying in your room the whole time or getting out and enjoying the city, you’ll be living the life while staying at your luxury accommodation. With so many amenities at your beck and call, you might try to turn your stay into a staycation!

Many of the 5-star hotels have award-winning restaurants you can dine at, as well as plush bedding and a concierge service to take care of your every need. Most also offer pools and modern fitness centers, not to mention high-speed Wi-Fi.

For your next trip, book a hotel that can be your own little hideaway, whether you’re in town for business or leisure. Winter Park 5-star hotels provide you with all the comforts and amenities you expect from a sophisticated hotel, with a staff that’s happy to ensure you have everything you need to feel at home.

Whether you’re a first-time guest, or you’ve stayed in 5-star hotels in Winter Park before, you’ll have no shortage of options to choose from on your next trip when you book with Travelocity. Browse our vast selection and find great deals on luxury lodging.