Luxury Hotels in Winter Garden

November 2026
December 2026

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Next weekend
Oct 30 - Nov 1
In two weeks
Nov 6 - Nov 8

Luxury Hotels in Winter Garden

1. Hilton Vacation Club Aqua Sol Orlando West

Hilton Vacation Club Aqua Sol Orlando West
Winter Garden
  • Hot tub
  • Poolside bar
  • Concierge services
$94
$134 total
includes taxes & fees
Oct 31 - Nov 1
Hilton Vacation Club Aqua Sol Orlando West

2. Rosen Shingle Creek

Rosen Shingle Creek
Orlando
  • 11 restaurants
  • Full-service spa
  • Poolside bar
  • Concierge services
$119
$134 total
includes taxes & fees
Oct 30 - Oct 31
Rosen Shingle Creek

3. Disney's Beach Club Resort

Disney's Beach Club Resort
Bay Lake
  • 2 restaurants
  • 3 hot tubs
  • Poolside bar
  • Concierge services
$1,501
$1,689 total
includes taxes & fees
Nov 7 - Nov 8
Disney's Beach Club Resort

4. Hilton Orlando/Altamonte Springs

Hilton Orlando/Altamonte Springs
Altamonte Springs
  • Hot tub
  • Outdoor pool
  • Concierge services
$118
$136 total
includes taxes & fees
Nov 1 - Nov 2
Hilton Orlando/Altamonte Springs

5. Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort

Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort
Golden Oak
  • 5 restaurants
  • Full-service spa
  • Poolside bar
  • Concierge services
$1,405
$1,648 total
includes taxes & fees
Nov 1 - Nov 2
Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort

6. Orlando Marriott Lake Mary

Orlando Marriott Lake Mary
Lake Mary
  • 3 restaurants
  • Hot tub
  • Outdoor pool
  • Concierge services
$119
$135 total
includes taxes & fees
Nov 22 - Nov 23
Orlando Marriott Lake Mary

7. The Westin Lake Mary, Orlando North

The Westin Lake Mary, Orlando North
Lake Mary
  • 2 bars
  • Hot tub
  • Outdoor pool
  • Concierge services
$127
$145 total
includes taxes & fees
Nov 8 - Nov 9
The Westin Lake Mary, Orlando North

8. Conrad Orlando at Evermore

Conrad Orlando at Evermore
Orlando
  • On private beach
  • 5 restaurants
  • Full-service spa
  • Poolside bar
  • Concierge services
$422
$525 total
includes taxes & fees
Oct 30 - Oct 31
Conrad Orlando at Evermore

9. Caribe Royale Orlando, WorldHotels Elite

Caribe Royale Orlando, WorldHotels Elite
Orlando
  • 5 restaurants
  • Full-service spa
  • Poolside bar
  • Concierge services
$174
$239 total
includes taxes & fees
Nov 19 - Nov 20
Caribe Royale Orlando, WorldHotels Elite

10. Hyatt Regency Orlando

Hyatt Regency Orlando
International Drive District
  • 4 restaurants
  • Full-service spa
  • Poolside bar
  • Concierge services
$143
$217 total
includes taxes & fees
Oct 29 - Oct 30
Hyatt Regency Orlando

11. The Alfond Inn

The Alfond Inn
Winter Park
  • Poolside bar
  • Concierge services
  • Boutique feel
$304
$373 total
includes taxes & fees
Nov 24 - Nov 25
The Alfond Inn

12. The Cabins at Disney's Fort Wilderness Resort

The Cabins at Disney's Fort Wilderness Resort
Bay Lake
  • Poolside bar
The Cabins at Disney's Fort Wilderness Resort

13. Disney's Contemporary Resort

Disney's Contemporary Resort
Bay Lake
  • 3 restaurants
  • Hot tub
  • Poolside bar
  • Concierge services
$708
$797 total
includes taxes & fees
Nov 3 - Nov 4
Disney's Contemporary Resort

14. The Tiny Cottage in The Springs

The Tiny Cottage in The Springs
Altamonte Springs
  • Free parking
  • Free WiFi
$178
$749 total
includes taxes & fees
Oct 26 - Oct 27
The Tiny Cottage in The Springs

15. The Ritz-Carlton Orlando, Grande Lakes

The Ritz-Carlton Orlando, Grande Lakes
Orlando
  • 7 restaurants
  • Full-service spa
  • Poolside bar
  • Concierge services
$479
$601 total
includes taxes & fees
Nov 25 - Nov 26
The Ritz-Carlton Orlando, Grande Lakes

16. Rosen Plaza on International Drive

Rosen Plaza on International Drive
International Drive District
  • 5 restaurants
  • Hot tub
  • Poolside bar
  • Concierge services
$111
$128 total
includes taxes & fees
Nov 24 - Nov 25
Rosen Plaza on International Drive

17. Waldorf Astoria Orlando - An Official Walt Disney World® Hotel

Waldorf Astoria Orlando - An Official Walt Disney World® Hotel
Orlando
  • 6 restaurants
  • Full-service spa
  • Poolside bar
  • Concierge services
$348
$447 total
includes taxes & fees
Nov 22 - Nov 23
Waldorf Astoria Orlando - An Official Walt Disney World® Hotel

18. Rosen Centre Hotel

Rosen Centre Hotel
International Drive District
  • 7 restaurants
  • Full-service spa
  • Poolside bar
  • Concierge services
$122
$138 total
includes taxes & fees
Oct 29 - Oct 30
Rosen Centre Hotel

19. Hotel Beauden, Autograph Collection

Hotel Beauden, Autograph Collection
Downtown Orlando
  • Poolside bar
  • Concierge services
$195
$219 total
includes taxes & fees
Nov 22 - Nov 23
Hotel Beauden, Autograph Collection

20. Encore Resort and Water Park at Reunion by Rentyl

Encore Resort and Water Park at Reunion by Rentyl
Kissimmee
  • 2 restaurants
  • Full-service spa
  • Poolside bar
  • Concierge services
$310
$885 total
includes taxes & fees
Oct 26 - Oct 27
Encore Resort and Water Park at Reunion by Rentyl
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Top neighborhoods in Winter Garden

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.

Horizon West

Winter Garden's Horizon West neighborhood has a host of places to visit such as Walt Disney World® Resort and Orange County National Golf Club.

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.

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.

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

8.6/10 (131 reviews)
If you want to give your credit card some exercise, head out to Flamingo Crossings Town Center in Bay Lake.
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Disney's Palm Golf Course

8.4/10 (457 reviews)
You might want to practice your swing at Disney's Palm Golf Course, a golf course located 11.2 mi (18.1 km) from central Winter Garden. If Disney's Palm Golf Course doesn't quite scratch your golfing itch, Grand Cypress Golf Club, and Orange Lake Golf are also nearby.
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Orange County National Golf Club

8.4/10 (647 reviews)
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 Palm Golf Course, and Disney's Magnolia Golf Course are also nearby.
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Disney's Magnolia Golf Course

8.4/10 (552 reviews)
You might want to play some rounds at Disney's Magnolia Golf Course, located 11.1 mi (17.9 km) from central Winter Garden. If Disney's Magnolia Golf Course doesn't quite scratch your golfing itch, Disney's Palm Golf Course, and Orange Lake Golf are also nearby.
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Surfari Water Park

9.0/10 (2,086 reviews)
If thrills are what you're after, head to Surfari Water Park, located 2.3 mi (3.8 km) from central Four Corners. If you have fun at Surfari Water Park, you'll love Disney's Animal Kingdom® Theme Park and Island H2O Live!, both located nearby.
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West Orange Trail

8.4/10 (337 reviews)
Downtown Winter Garden is home to West Orange Trail, so why not stop by during your stay in Winter Garden. Winter Garden has lots of other activities such as Camping World Stadium and Kia Center.
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Garden Theatre

8.4/10 (219 reviews)
If you want to see a show while you're in town, try and grab some tickets at Garden Theatre in Downtown Winter Garden. If you want to experience more of the culture Winter Garden has to offer, head to Winter Garden Heritage Museum, West Orange Trail, and AdventHealth Winter Garden.
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Oakland Nature Preserve

8.8/10 (82 reviews)
If you like quiet time surrounded by flowers and greenery, hang out at Oakland Nature Preserve in Killarney. Want to stretch your legs some more? Head to East Ridge High School Football Stadium, located nearby.
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About the destination

Winter Garden is a family-friendly place known for its theme park and waterparks. Simply book an excursion to enjoy your stay a little more. Plan a fun excursion to Orange County National Golf Club and Disney's Magnolia Golf Course while here. Popular sights in the surrounding area include Universal Studios Florida and The Wizarding World of Harry Potter™.