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

Our top choices for Winter Garden hotels with a 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

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
2.5 star property
Bay Lake
9.4 out of 10, Exceptional, (4,416 reviews)
"Amazing room and great breakfasts for the price "
United States
Christian
The price is €112
includes taxes & fees
26 Jan - 27 Jan
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
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

Home2 Suites by Hilton Orlando at Flamingo Crossings
3.0 star property
Bay Lake
9.2 out of 10, Wonderful, (5,174 reviews)
"Great stay"
United States
Monica
The price is €104
includes taxes & fees
10 Feb - 11 Feb
Home2 Suites by Hilton Orlando at Flamingo Crossings
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

SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
3.5 star property
Bay Lake
9.0 out of 10, Wonderful, (2,260 reviews)
"Check in staff was friendly, good breakfast selections, close to Disney "
United States
Allison
The price is €86
includes taxes & fees
21 Jan - 22 Jan
SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
2 outdoor pools, pool umbrellas, pool loungers
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, (4,099 reviews)
"The stay was nice & very clean everywhere. "
United States
Kristina
The price is €127
includes taxes & fees
19 Jan - 20 Jan
Hilton Vacation Club Aqua Sol Orlando West
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

TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
3.5 star property
Bay Lake
9.0 out of 10, Wonderful, (1,663 reviews)
"Breakfast was amazing, room was wonderful experience, very quiet and comfortable"
United States
Igor
The price is €92
includes taxes & fees
21 Jan - 22 Jan
TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
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

Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance
3.0 star property
Bay Lake
9.6 out of 10, Exceptional, (1,990 reviews)
"Great stay, easy and convenient! "
United States
Maria Fernanda
The price is €138
includes taxes & fees
20 Jan - 21 Jan
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

Homewood Suites by Hilton Orlando at Flamingo Crossings
3.0 star property
Bay Lake
9.4 out of 10, Exceptional, (2,192 reviews)
"Clean and spacious room, comfortable beds, very quiet, close to shops and Disney attractions, lovely staff and great service! "
United States
Faina
The price is €126
includes taxes & fees
26 Jan - 27 Jan
Homewood Suites by Hilton Orlando at Flamingo Crossings
Aerial view
The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando
4.0 star property
Winter Garden
8.0 out of 10, Very good, (8,949 reviews)
"Great place to stay with the family. "
United States
Nabeel
The price is €211
includes taxes & fees
12 Jan - 13 Jan
The Grove Resort & Water Park Orlando
Outdoor pool
Home2 Suites By Hilton Winter Garden

Home2 Suites By Hilton Winter Garden

Home2 Suites By Hilton Winter Garden
3.0 star property
Winter Garden
9.4 out of 10, Exceptional, (368 reviews)
"Friendly staff, clean rooms , and great breakfast "
United States
Julee
The price is €126
includes taxes & fees
18 Jan - 19 Jan
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

Monarch Apartments 15m to Parks, Pet Friendly, Free Parking by Heavenly Homes
3.5 star property
Winter Garden
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful apartment, clean, quiet, and beautiful location. Host was very helpful. I would recommend this beautiful apartment for anyone wanting a home away from home."
United States
Kowanda
The price is €189
includes taxes & fees
12 Jan - 13 Jan
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

Wyndham I-Drive Avanti Resort & Conference Center

Wyndham I-Drive Avanti Resort & Conference Center

10/10 Excellent
"Ms Nina was Very efficient and friendly"
James 1-night trip
Posted 19 hours ago
Wyndham I-Drive Avanti Resort & Conference Center

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 23 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, 4-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 23 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 Butler 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.