Find Romantic Hotels in Winter Garden, FL

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Check availability on Winter Garden Romantic Hotels

Tonight
Dec 29 - Dec 30
Tomorrow
Dec 30 - Dec 31
This weekend
Jan 2 - Jan 4
Next weekend
Jan 9 - Jan 11

Our top choices for Winter Garden romantic hotels

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, (8853)
"Excellent Resort! "
United States
Chelsea
The price is ￥26,460
￥38,399 total
includes taxes & fees
Jan 5 - Jan 6, 2026
The Grove Resort & Water Park Orlando
Pool
Upstay: 3BR Condo w Pool, Sauna—Near Disney

Upstay: 3BR Condo w Pool, Sauna—Near Disney

Upstay: 3BR Condo w Pool, Sauna—Near Disney
Winter Garden
The price is ￥11,899
￥44,212 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Upstay: 3BR Condo w Pool, Sauna—Near Disney
Outdoor pool
The Oak View Place..

The Oak View Place..

The Oak View Place..
Oakland
9.2 out of 10, Wonderful, (10)
"The VRBO looked brand new and I only knew it was not because of the reviews from previous years. The live oak trees on the property added to the beauty of the surroundings."
United States
Libba F.
The price is ￥28,183
￥44,427 total
includes taxes & fees
Jan 8 - Jan 9, 2026
The Oak View Place..
Pool
Family-Friendly Condo with Pool & Sauna

Family-Friendly Condo with Pool & Sauna

Family-Friendly Condo with Pool & Sauna
Winter Garden
The price is ￥14,874
￥44,035 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Family-Friendly Condo with Pool & Sauna
Pool
Upstay - Pet-Friendly Family Condo near Disney

Upstay - Pet-Friendly Family Condo near Disney

Upstay - Pet-Friendly Family Condo near Disney
Winter Garden
Upstay - Pet-Friendly Family Condo near Disney
Pool
Upstay - Condo w Pool and More - Near Disney

Upstay - Condo w Pool and More - Near Disney

Upstay - Condo w Pool and More - Near Disney
Winter Garden
9.0 out of 10, Wonderful, (22)
"Great place! Convenient, cozy and clean!"
United States
SHARLA B.
Upstay - Condo w Pool and More - Near Disney
Pool
Upstay Condo with Outdoor Pool & Sauna

Upstay Condo with Outdoor Pool & Sauna

Upstay Condo with Outdoor Pool & Sauna
Winter Garden
10.0 out of 10, Exceptional, (1)
"The check in process was easy and quick. We had self check in and 2 balconies the view was amazing! We loved everything about this property"
United States
Trennecia B.
The price is ￥14,091
￥43,302 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Upstay Condo with Outdoor Pool & Sauna
Interior
Beautiful Condo w Outdoor Pool and Sauna

Beautiful Condo w Outdoor Pool and Sauna

Beautiful Condo w Outdoor Pool and Sauna
Winter Garden
8.8 out of 10, Excellent, (5)
"I loved it!!"
United States
Telicia D.
The price is ￥13,152
￥46,104 total
includes taxes & fees
Jan 20 - Jan 21, 2026
Beautiful Condo w Outdoor Pool and Sauna
Dining
Condo w Pool, Games Room - Pet Friendly

Condo w Pool, Games Room - Pet Friendly

Condo w Pool, Games Room - Pet Friendly
Winter Garden
8.0 out of 10, Very Good, (3)
"Property is very clean, with easy access and parking. Property management team is responsive and helpful."
United States
Catherine T.
The price is ￥14,091
￥43,302 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Condo w Pool, Games Room - Pet Friendly
Property amenity
Holiday Inn Express & Suites Clermont Se West Orlando by IHG

Holiday Inn Express & Suites Clermont Se West Orlando by IHG

Holiday Inn Express & Suites Clermont Se West Orlando by IHG
2.5 star property
Clermont
8.4 out of 10, Very Good, (1083)
"Friendly staff, clean property, appreciate transportation to WDW and light breakfast included. "
United States
Janet
The price is ￥17,157
￥19,045 total
includes taxes & fees
Jan 29 - Jan 30, 2026
Holiday Inn Express & Suites Clermont Se West Orlando by IHG
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

Lake Buena Vista Resort Village & Spa

Lake Buena Vista Resort Village & Spa

10/10 Excellent
"Thre room was spacious and spotless. the tub was wonderful. multiple baths helps get the family ready to go early. Pool is freat for down days. Helpful store on site for quick needs.Location is beautiful and safe. Stayed 2 times and would stay again. "
Cynthia 4-night trip
Posted 14 hours ago
Lake Buena Vista Resort Village & Spa

Frequently asked questions

Searching for romantic hotels in Winter Garden?
Are you in need of a romantic vacation? Our guests also love Winter Garden for its fun-filled attractions, major shopping area, and array of dining options. You might consider checking out some of the nearby sights and attractions such as Orange County National Golf Club, Lake Louisa State Park, or Disney's Magnolia Golf Course. If you're interested in staying close to a certain attraction, you can sort properties by neighborhood and proximity to top sights, so you'll be able to see everything on your list.
When is the best time of year for a romantic getaway to Winter Garden?
If you're hoping to get lost in the rain on your romantic getaway, check out these details about year-round temperatures in Winter Garden: The hottest months are usually August and July with an average temp of 82°F, while the coldest months are January and February with an average of 64°F. The rainiest months in Winter Garden are August, July, September, and June, with each month seeing an average of 9 inches of rainfall.
What is there to do in Winter Garden?
There's nothing better than experiencing a new place with your sweetheart, so consider taking time to discover all there is to see and do in Winter Garden. If you're hoping to see some of the area's cultural attractions, you and your partner will love Winter Garden for its fun-filled attractions and major shopping area. You might think about visiting Orange County National Golf Club, Lake Louisa State Park, or Disney's Magnolia Golf Course.
What's the best way to get to Winter Garden and around town during my romantic getaway?
This information about transportation options in Winter Garden might help your romantic getaway go off without a hitch: To get to Winter Garden, book a flight to Orlando Intl. Airport (MCO), which is the closest major airport, located 19.3 mi (31 km) from the city center. If you'd like to venture out around the area, you may want a rental car for your journey.