Luxury Hotels in Winter Garden

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Luxury Hotels in Winter Garden

Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort
3 outdoor pools, cabanas (surcharge), pool umbrellas

Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort

5.0 star property
9.6 out of 10, Exceptional, (867)
$945 nightly
The price is $1,063
Sep 1 - Sep 2
Total with taxes and fees
Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort
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.

Top neighborhoods in Winter Garden

March 25, 2023, Winter Garden, FL: The West Orange bicycle trail through Winter Garden, Florida

Downtown Winter Garden

Plant Street bursts with small-town charm in Downtown Winter Garden. The restored 1935 Garden Theatre anchors the brick-lined pedestrian zone where locals and visitors stroll past historic storefronts. Hop on the West Orange Trail for a scenic bike ride or browse the weekly farmers market for fresh Florida citrus and artisanal goods. Farm-to-table restaurants with outdoor seating line the main drag, while boutique bed & breakfasts offer cozy accommodations in restored buildings. The pedestrian-friendly layout means you can park once and explore everything on foot, from antique shops to the Central Florida Railroad Museum.

Orange sunset over distant hills on Lake Apopka near Orlando, Florida.

Vista del Lago

Vista del Lago is a peaceful retreat just minutes from Orlando's major attractions. Vacation homes with private pools and resort amenities offer the perfect landing spot after action-packed theme park days. Disney's Animal Kingdom and Magic Kingdom are just a short drive away, while community pools provide refreshing breaks between adventures. Dining options require a quick drive to nearby Championsgate or Disney Springs, where choices range from casual to upscale. Most travelers appreciate having rental cars to navigate between the quiet neighborhood and Orlando's entertainment districts. Many vacation rentals feature full kitchens and game rooms, creating the ideal home base for family theme park trips.

At the Oakland Preserve. Nice Boardwalk plus an animal sanctuary
Photo by Gregg Yutko
Open Photo by Gregg Yutko

Oakland

Oakland's historic charm lives on through preserved Victorian homes and oak-canopied streets. Wander downtown to discover the 1889 Healthy House Museum and local artisan shops. The 128-acre Oakland Nature Preserve invites you to explore cypress wetlands and spot some of the 200+ bird species that call Lake Apopka home. Southern comfort food dominates the dining scene with most spots closing early. The area is best explored by car, though downtown remains pleasantly walkable. Cozy bed and breakfasts in historic homes offer an intimate alternative to Orlando's bustling tourist accommodations just 15 minutes away.

Panoramic view of Lake Apopka and nature Florida.

Killarney

Killarney offers a peaceful retreat from Orlando's tourist bustle while keeping adventure within reach. The Oakland Nature Preserve invites you to explore scenic trails while the nearby West Orange Trail is perfect for morning bike rides. Lake Apopka provides a serene backdrop for fishing or simply watching the sunset paint the Florida sky. When you're ready for more action, Winter Garden's charming downtown is just minutes away. Accommodation options include budget-friendly extended-stay hotels and vacation homes with pools and kitchenettes. A car is essential for getting around, though rideshare services are readily available. The quiet suburban streets make evening strolls pleasant after busy days exploring nearby attractions.

Top landmarks in Winter Garden

Flamingo Crossings Town Center

Flamingo Crossings Town Center

If you want to give your credit card some exercise, head out to Flamingo Crossings Town Center in Bay Lake.

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Orange County National Golf Club

Orange County National Golf Club

You might want to play some rounds at Orange County National Golf Club, located 8.9 mi (14.4 km) from central Winter Garden. If Orange County National Golf Club doesn't quite scratch your golfing itch, Disney's Magnolia Golf Course, and Disney's Oak Trail Golf Course are also nearby.

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Frequently asked questions

What are the cheapest luxury hotels in Winter Garden?
Enjoy the finer things for less when you stay in an affordable luxury hotel in Winter Garden on your next adventure. If you're on a budget, try our "Price: low to high" tool to search for upscale properties within your price range. Be on the lookout for discounts that'll help you save even more. You can also become a member of our rewards program to access Member Prices and earn discounts on future travel.
What is the best time to stay in a luxury hotel in Winter Garden?
If you're after the warmest weather, organize your trip for July. The temperatures are around 77ºF (25ºC) to 91ºF (33ºC) at this time. January has the coolest temperatures between 54ºF (12ºC) and 68ºF (20ºC). For a more relaxed vibe and potentially more affordable luxury hotels in Winter Garden, visit in September when it's less busy.
What are the closest luxury hotels to Orlando Intl. Airport (MCO)?
Treat yourself to the best that life has to offer at Rosen Shingle Creek. It's located around 8 miles west of Orlando Intl. Airport (MCO). You can take advantage of a dock, a view of the golf course and more here. Grand Bohemian Orlando, Autograph Collection is another option close by designed to leave a lasting impression. Whether you stay at a luxury hotel in Winter Garden or somewhere else, you'll enjoy an instant upgrade to your travel experience.
Are there any luxury hotels in Winter Garden with parking?
Select the "Parking" filter to find a luxury hotel in Winter Garden, then check the listing for the specifics. Perfect for road trippers, these properties give you the freedom to come and go as you please. Plus, you can rest easy knowing your car is safe and accessible during your stay.
Are all taxes and fees included in the Winter Garden hotel prices shown on Hotels.com?
Hotels.com provide upfront pricing so you can relax knowing you won't be met with surprise additional fees or taxes when you're ready to confirm your booking. From the time you start your search on Hotels.com, the price you see is what you pay. This makes it much easier to compare properties and secure our best deal for your next getaway.