Winter Garden Hotel Guide - Hotels with Pool in Winter Garden, Florida

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Winter Garden Hotels with Pool

Tonight
22 Nov - 23 Nov
Tomorrow
23 Nov - 24 Nov
Next weekend
28 Nov - 30 Nov
In two weeks
5 Dec - 7 Dec

Top Winter Garden Hotels with Pool

Outdoor pool, open 8:00 AM to 11:00 PM, pool umbrellas, pool loungers
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

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

2.5 star property
Bay Lake
  • Outdoor pool
  • Poolside bar
  • Pool loungers
9.4 out of 10, Exceptional, (4255)
Vibrant pool area welcomes families with comfortable loungers, refreshing drinks, and attentive bar service just minutes from Disney parks. Sports enthusiasts appreciate the basketball court while parents value the shallow pool section perfect for young swimmers.
The price is €109
includes taxes & fees
9 Dec - 10 Dec
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
Outdoor pool, a heated pool
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, (2244)
Sparkling waters beckon at this hotel's expansive outdoor pool area, complete with a relaxing hot tub and convenient poolside bar. A complimentary shuttle whisks guests to theme parks while the freshly remodeled spaces provide a comfortable respite.
The price is €99
includes taxes & fees
10 Dec - 11 Dec
SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
Outdoor pool, a heated pool
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, (1633)
Swimmers splash in the spacious outdoor pool while others relax in the steaming hot tub nearby. A poolside bar serves cold drinks, creating a perfect retreat after park adventures. The hotel's complimentary Disney shuttle, breakfast buffet, and fitness centre complete this family escape.
The price is €104
includes taxes & fees
15 Dec - 16 Dec
TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
Outdoor pool, open 9:00 AM to 10:00 PM, pool umbrellas, pool loungers
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
9.2 out of 10, Wonderful, (4981)
Spacious rooms with full kitchens welcome families after exciting pool adventures with waterslides and sun loungers. Beyond the sparkling waters, guests enjoy firepit gatherings, a 24-hour fitness centre with Peloton bikes, and complimentary theme park shuttles.
The price is €101
includes taxes & fees
30 Nov - 1 Dec
Home2 Suites by Hilton Orlando at Flamingo Crossings
Exterior
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, (4071)
Splash into aquatic bliss at a resort boasting multiple swimming options, from thrilling waterslides to tranquil pool loungers. Beyond water adventures, guests enjoy tennis courts, mini golf, paddle boats, and convenient poolside dining.
The price is €128
includes taxes & fees
2 Dec - 3 Dec
Hilton Vacation Club Aqua Sol Orlando West
Outdoor pool, open 8:00 AM to 11:00 PM, pool umbrellas, pool loungers
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, (1964)
Sparkling waters beckon at this family-friendly retreat featuring an inviting outdoor pool complete with sun loungers and refreshing poolside bar service. Located just 10-15 minutes from Disney theme parks, this spotless hotel offers spacious accommodation with fully equipped kitchens.
The price is €122
includes taxes & fees
14 Dec - 15 Dec
Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance
Outdoor pool, open 9:00 AM to 10:00 PM, pool loungers
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, (2090)
Splash into holiday bliss at the outdoor pool featuring an exciting waterslide and sun loungers for post-swim relaxation. Families appreciate the nearby theme park shuttle, on-site dining, and spacious suites with full kitchenettes.
The price is €109
includes taxes & fees
18 Dec - 19 Dec
Homewood Suites by Hilton Orlando at Flamingo Crossings
Aerial view
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
8.0 out of 10, Very good, (8769)
Flowing waters beckon from six outdoor pools, including a free water park with waterslide and lazy river. Cabanas provide shade while three poolside bars serve refreshing drinks between fishing excursions and arcade games.
The price is €193
includes taxes & fees
2 Dec - 3 Dec
The Grove Resort & Water Park Orlando
Outdoor pool
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, (351)
Fitness enthusiasts appreciate this hotel's well-maintained outdoor pool and fully equipped fitness centre. Spotlessly clean rooms with designer toiletries offer a peaceful retreat after enjoying the complimentary breakfast praised by travellers.
The price is €111
includes taxes & fees
18 Dec - 19 Dec
Home2 Suites By Hilton Winter Garden
Outdoor pool
Monarch Apartments 15m to Parks, Pet Friendly, Free Parking by Heavenly Homes

Monarch Apartments 15m to Parks, Pet Friendly, Free Parking by Heavenly Homes

3.5 star property
Winter Garden
  • Outdoor pool
The price is €199
includes taxes & fees
23 Nov - 24 Nov
Monarch Apartments 15m to Parks, Pet Friendly, Free Parking by Heavenly Homes
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.
View all properties

Top Winter Garden Hotel Reviews

Hyatt Regency Orlando

Hyatt Regency Orlando

10/10 Excellent
"Room was spotless. Great cotton sheets and an assortment of pillows by firmness. "
Christine 1-night trip
Posted 1 day ago
Hyatt Regency Orlando

Explore a world of travel with Expedia

Frequently asked questions

What's it like visiting Winter Garden?
If lounging by a pool is your idea of the perfect getaway, you may want to consider family-friendly Winter Garden, which has 25 places to stay with pools. During your trip, you can explore sights such as Universal Studios Florida and Universal Orlando Resort, and then unwind poolside at one of the accommodation options in Winter Garden that guests like for their pools.
What are some accommodation options with pools in Winter Garden?
The Grove Resort & Water Park Orlando: Resort located near Flamingo Crossings Town Center. Features 6 outdoor swimming pools, a children's pool and free water park access. Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center: Hotel steps from Flamingo Crossings Town Center. Offers buffet, an outdoor pool and complimentary wireless Internet access. Hilton Vacation Club Aqua Sol Orlando West: Hotel located near Flamingo Crossings Town Center. Provides 2 outdoor swimming pools, a children's pool and free water park access. TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance: Hotel, 1-minute walk from Flamingo Crossings Town Center. Features a snack bar/deli, a pool and buffet. Orange Lake Holiday Inn Resort 2 Bedroom Villa In Beautiful Orlando/Kissimmee: Resort located near Walt Disney World® Resort. Offers complimentary wireless Internet access, a pool and kitchens.
How many pool hotels will I find in Winter Garden?
Expedia's 25 hotels in Winter Garden give you a great choice for your poolside getaway.
What is there to see and do in Winter Garden?
Explore places such as Universal Studios Florida, Universal Orlando Resort and Magic Kingdom® Park while you're in the area. Make a point to visit attractions such as Lake Louisa State Park and Surfari Water Park. Winter Garden appeals to visitors with its array of dining options, fun-filled attractions and major shopping area.
When is the best time to book a hotel with a pool in Winter Garden?
Taking the local weather in Winter Garden into account can help you maximise your time at the pool during your trip. The hottest months are usually August and July, with an average temperature of 28°C, while the coldest months are January and February, with an average of 18°C. The rainiest months in Winter Garden are August, July, September and June, with each month seeing an average of 217 mm of rainfall.