Hotels with a Pool in Winter Garden

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Nov 3 - Nov 4
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Nov 4 - Nov 5
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Nov 6 - Nov 8
Next weekend
Nov 13 - Nov 15

Hotels with a Pool in Winter Garden

A swimming pool with clear blue water, surrounded by lounge chairs and yellow umbrellas.

1. Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
3.0 star property
Bay Lake
  • Outdoor pool
  • Poolside bar
  • Pool loungers
9.4 out of 10, Exceptional, (5,703 reviews)
Families dive into poolside bliss with dedicated shallow areas for little ones while adults sip refreshing cocktails from the swim-up bar. Sports enthusiasts appreciate nearby basketball courts and a well-equipped 24-hour fitness center after Disney park explorations.
The price is $76
$85 total
includes taxes & fees
Nov 24 - Nov 25
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
A hotel pool area with multiple lounge chairs and umbrellas, a water slide, and palm trees.

2. Home2 Suites by Hilton Orlando at Flamingo Crossings

Home2 Suites by Hilton Orlando at Flamingo Crossings
3.0 star property
Bay Lake
  • Outdoor pool
  • Pool loungers
9.4 out of 10, Exceptional, (6,247 reviews)
Swimmers delight in the outdoor pool complex featuring an exhilarating waterslide and abundant sun loungers. Beyond aquatic adventures, families appreciate the hotel's spacious rooms with full kitchens, convenient fire pits, and complimentary theme park shuttle service.
The price is $98
$110 total
includes taxes & fees
Nov 24 - Nov 25
Home2 Suites by Hilton Orlando at Flamingo Crossings
A swimming pool with lounge chairs and a view of a building in the background.

3. Home2 Suites By Hilton Winter Garden

Home2 Suites By Hilton Winter Garden
3.0 star property
Winter Garden
  • Outdoor pool
9.4 out of 10, Exceptional, (532 reviews)
Poolside relaxation awaits at this modern retreat featuring an outdoor swimming haven complemented by a well-equipped fitness center. Spacious rooms offer laptop-friendly workspaces, designer toiletries, and 55-inch LCD TVs for complete comfort.
The price is $110
$123 total
includes taxes & fees
Nov 29 - Nov 30
Home2 Suites By Hilton Winter Garden
A hotel pool area with lounge chairs, a fire pit, and a large pool.

4. Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance
3.0 star property
Bay Lake
  • Outdoor pool
  • Poolside bar
  • Pool loungers
9.6 out of 10, Exceptional, (2,313 reviews)
Poolside perfection awaits with comfortable loungers under shady umbrellas and refreshing drinks from the bar. After swimming, guests appreciate the spotless facilities, 24-hour fitness center, and quick 10-minute drive to Disney parks.
The price is $94
$105 total
includes taxes & fees
Nov 29 - Nov 30
Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance
A pool area with lounge chairs, a fire pit, and palm trees.

5. SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance

SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
3.5 star property
Bay Lake
  • Outdoor pool
  • Poolside bar
  • Hot tub
9.0 out of 10, Wonderful, (2,350 reviews)
Poolside paradise awaits at this freshly remodeled retreat. Swimmers enjoy a spacious, heated outdoor pool with gradual entry while the hot tub provides perfect relaxation. A convenient poolside bar, free theme park shuttle, and hearty breakfast buffet complete the experience.
The price is $95
$107 total
includes taxes & fees
Nov 24 - Nov 25
SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
A swimming pool with a slide and a small waterfall feature, surrounded by lounge chairs and umbrellas.

6. Homewood Suites by Hilton Orlando at Flamingo Crossings

Homewood Suites by Hilton Orlando at Flamingo Crossings
3.0 star property
Bay Lake
  • Outdoor pool
  • Pool loungers
9.4 out of 10, Exceptional, (2,769 reviews)
Swimming enthusiasts adore the outdoor pool complex featuring a thrilling waterslide, sun loungers, and poolside entertainment area. Spacious rooms with kitchenettes provide homey comfort after days exploring nearby theme parks, accessible via complimentary shuttle.
The price is $114
$128 total
includes taxes & fees
Nov 29 - Nov 30
Homewood Suites by Hilton Orlando at Flamingo Crossings
A pool area with lounge chairs, a fire pit, and palm trees.

7. TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance

TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
3.5 star property
Bay Lake
  • Outdoor pool
  • Poolside bar
  • Hot tub
9.0 out of 10, Wonderful, (1,917 reviews)
Swimming enthusiasts love the well-maintained outdoor pool area, complete with a refreshing hot tub and convenient poolside bar service. After exploring nearby theme parks via the complimentary shuttle, families appreciate returning to spotlessly clean accommodations.
The price is $95
$107 total
includes taxes & fees
Nov 24 - Nov 25
TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
A swimming pool with a rock feature, a covered seating area, and a building with balconies in the background.

8. Hilton Vacation Club Aqua Sol Orlando West

Hilton Vacation Club Aqua Sol Orlando West
4.0 star property
Winter Garden
  • 2 outdoor pools
  • Poolside bar
  • Pool loungers
  • Hot tub
8.8 out of 10, Excellent, (3,947 reviews)
Poolside adventures await at this family-friendly paradise featuring a water park, waterslides, and multiple swimming spots. Lazy days unfold with paddle boats, tennis courts, and a poolside bar serving delicious drinks and reasonably priced meals.
The price is $103
$143 total
includes taxes & fees
Nov 10 - Nov 11
Hilton Vacation Club Aqua Sol Orlando West
A resort with multiple swimming pools, lounge areas, and a view of the sea.

9. The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando
4.0 star property
Winter Garden
  • 6 outdoor pools
  • 3 poolside bars
  • Pool loungers
  • 2 hot tubs
8.2 out of 10, Very good, (10,934 reviews)
Splash into refreshment at the expansive water complex, where families create lasting memories between waterslides and pool cabanas. Three poolside bars serve tropical drinks while the immaculately landscaped grounds provide a peaceful retreat after Disney adventures.
The price is $208
$289 total
includes taxes & fees
Dec 2 - Dec 3
The Grove Resort & Water Park Orlando
Interior

10. Upstay - Large Condo Near Disney w Pool and Gym

Upstay - Large Condo Near Disney w Pool and Gym
4.0 star property
Winter Garden
  • Outdoor pool
The price is $71
$248 total
includes taxes & fees
Nov 30 - Dec 1
Upstay - Large Condo Near Disney w Pool and Gym
An aerial view of a resort with a large swimming pool, sun loungers, and palm trees.

11. Upstay Condo w Pool Sauna Sleeps 8

Upstay Condo w Pool Sauna Sleeps 8
2.0 star property
Winter Garden
  • Free parking
  • Free WiFi
  • Non-smoking
8.0 out of 10, Very good, (1 review)
The price is $83
$269 total
includes taxes & fees
Nov 4 - Nov 5
Upstay Condo w Pool Sauna Sleeps 8
A pool area with lounge chairs and a small pool.

12. Upstay Large Family Condo w Pool, Sauna

Upstay Large Family Condo w Pool, Sauna
3.5 star property
Winter Garden
  • Outdoor pool
The price is $95
$275 total
includes taxes & fees
Nov 10 - Nov 11
Upstay Large Family Condo w Pool, Sauna
Room

13. Upstay - Condo Near Disney w Pool Hot tub Sauna

Upstay - Condo Near Disney w Pool Hot tub Sauna
2.0 star property
Winter Garden
  • Pet friendly
  • Free parking
  • Free WiFi
The price is $80
$236 total
includes taxes & fees
Nov 30 - Dec 1
Upstay - Condo Near Disney w Pool Hot tub Sauna
Interior

14. Modern 3BR Resort Condo With Pool Near Disney

Modern 3BR Resort Condo With Pool Near Disney
4.0 star property
Winter Garden
  • Outdoor pool
The price is $69
$245 total
includes taxes & fees
Nov 4 - Nov 5
Modern 3BR Resort Condo With Pool Near Disney
An aerial view of a resort with a large swimming pool, sun loungers, and palm trees.

15. Upstay - Modern Family Apartment w Pool Hot Tub

Upstay - Modern Family Apartment w Pool Hot Tub
2.0 star property
Winter Garden
  • Pet friendly
  • Free parking
  • Free WiFi
The price is $88
$245 total
includes taxes & fees
Nov 4 - Nov 5
Upstay - Modern Family Apartment w Pool Hot Tub
Interior

16. Upstay Condo Near Disney w Pool & Sauna

Upstay Condo Near Disney w Pool & Sauna
3.0 star property
Winter Garden
  • Outdoor pool
8.0 out of 10, Very good, (1 review)
The price is $83
$261 total
includes taxes & fees
Nov 18 - Nov 19
Upstay Condo Near Disney w Pool & Sauna
An aerial view of a resort with a large, irregularly shaped pool surrounded by lounge chairs and umbrellas, set against a backdrop of palm trees and a multi-story building.

17. Modern 3BR Condo Near Disney- Pool and Hot Tub

Modern 3BR Condo Near Disney- Pool and Hot Tub
2.0 star property
Winter Garden
  • Pet friendly
  • Free parking
  • Free WiFi
  • Gym
The price is $80
$236 total
includes taxes & fees
Nov 30 - Dec 1
Modern 3BR Condo Near Disney- Pool and Hot Tub
Interior

18. Near Disney - Family Condo w Pool, Games, and More

Near Disney - Family Condo w Pool, Games, and More
3.0 star property
Winter Garden
  • Outdoor pool
6.0 out of 10, Good, (1 review)
The price is $75
$252 total
includes taxes & fees
Nov 30 - Dec 1
Near Disney - Family Condo w Pool, Games, and More
An aerial view of a resort with a large swimming pool, sun loungers, and palm trees.

19. Upstay Tropical Style Family Condo w Pool

Upstay Tropical Style Family Condo w Pool
2.0 star property
Winter Garden
  • Free parking
  • Free WiFi
The price is $79
$264 total
includes taxes & fees
Nov 4 - Nov 5
Upstay Tropical Style Family Condo w Pool
A pool area with lounge chairs and a small pool.

20. Upstay: Condo Near Disney w Pool, Sauna

Upstay: Condo Near Disney w Pool, Sauna
4.0 star property
Winter Garden
  • Outdoor pool
10.0 out of 10, Exceptional, (2 reviews)
The price is $69
$245 total
includes taxes & fees
Nov 30 - Dec 1
Upstay: Condo Near Disney w Pool, Sauna
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.
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Discover your perfect hotel with a pool in Winter Garden

Breakfast included
Hot tub

Hotels with pools and free breakfast in Winter Garden

A breakfast bar with various food dispensers, a seating area with a table and chairs, and large windows with a view of greenery.
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
3.0 star property
Bay Lake
9.4 out of 10, Exceptional, (5703)
The price is $76
$85 total
includes taxes & fees
Nov 24 - Nov 25
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
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Hotels with pools and hot tubs in Winter Garden

A pool area with lounge chairs, a fire pit, and palm trees.
SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance

SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance

SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
3.5 star property
Bay Lake
9.0 out of 10, Wonderful, (2350)
The price is $95
$107 total
includes taxes & fees
Nov 24 - Nov 25
SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
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4-star hotels with pools in Winter Garden

A resort with multiple buildings, a central swimming pool, and a waterway.
Hilton Vacation Club Aqua Sol Orlando West

Hilton Vacation Club Aqua Sol Orlando West

Hilton Vacation Club Aqua Sol Orlando West
4.0 star property
Winter Garden
8.8 out of 10, Excellent, (3947)
The price is $103
$143 total
includes taxes & fees
Nov 10 - Nov 11
Hilton Vacation Club Aqua Sol Orlando West
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.
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Top neighborhoods in Winter Garden

A tree-lined sidewalk with parked cars and a clear sky.

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.

A city skyline at dusk with illuminated buildings reflecting on a calm body of water.

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.

A sunset over a body of water with silhouetted land in the distance and tall grasses in the foreground.

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.

A wooden pier extending into a calm body of water, surrounded by lush greenery and a distant forest.

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.

A wooden pier extending into a calm body of water, surrounded by lush greenery and a distant forest.

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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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™.