Winter Garden Hotel Guide - Romantic Hotels in Winter Garden, Florida

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

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

    Search almost a million properties worldwide

Check availability on Winter Garden Romantic Hotels

This weekend
Next weekend

Our top choices for Winter Garden romantic hotels

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, (8,980 reviews)
"Great place to stay with the family. "
United States
Nabeel
The price is €181
includes taxes & fees
9 Feb - 10 Feb
The Grove Resort & Water Park Orlando

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

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

The Oak View Place..

The Oak View Place..
Oakland
9.2 out of 10, Wonderful, (10 reviews)
"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 €246
includes taxes & fees
9 Feb - 10 Feb
The Oak View Place..

Upstay - Pet-Friendly Family Condo near Disney

Upstay - Pet-Friendly Family Condo near Disney
Winter Garden
The price is €231
includes taxes & fees
3 Feb - 4 Feb
Upstay - Pet-Friendly Family Condo near Disney

Family-Friendly Condo with Pool & Sauna

Family-Friendly Condo with Pool & Sauna
Winter Garden
The price is €212
includes taxes & fees
2 Feb - 3 Feb
Family-Friendly Condo with Pool & Sauna

Upstay Condo with Outdoor Pool & Sauna

Upstay Condo with Outdoor Pool & Sauna
Winter Garden
10.0 out of 10, Exceptional, (1 review)
"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 €216
includes taxes & fees
3 Feb - 4 Feb
Upstay Condo with Outdoor Pool & Sauna

Condo w Pool, Games Room - Pet Friendly

Condo w Pool, Games Room - Pet Friendly
Winter Garden
8.0 out of 10, Very good, (3 reviews)
"Property is very clean, with easy access and parking. Property management team is responsive and helpful."
United States
Catherine T.
The price is €211
includes taxes & fees
2 Feb - 3 Feb
Condo w Pool, Games Room - Pet Friendly

Beautiful Condo w Outdoor Pool and Sauna

Beautiful Condo w Outdoor Pool and Sauna
Winter Garden
8.8 out of 10, Excellent, (5 reviews)
"I loved it!!"
United States
Telicia D.
Beautiful Condo w Outdoor Pool and Sauna

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, (1,135 reviews)
"Room was clean and comfortable."
United States
Allan
The price is €89
includes taxes & fees
8 Feb - 9 Feb
Holiday Inn Express & Suites Clermont Se West Orlando by IHG

Rosen Shingle Creek

Rosen Shingle Creek
4.5 star property
Orlando
9.4 out of 10, Exceptional, (4,471 reviews)
"Very nice place to stay with family. "
United States
Anick
The price is €127
includes taxes & fees
2 Mar - 3 Mar
Rosen Shingle Creek
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.

Top Winter Garden Hotel Reviews

Frequently asked questions

Searching for romantic hotels in Winter Garden?
Are you looking for a romantic getaway? 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 particular destination, you can sort properties by neighbourhood or distance to top landmarks, 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, take a look at these details about year-round temperatures in Winter Garden: 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.
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 trip get off to a smooth start: To get to Winter Garden, book a flight to Orlando International Airport (MCO), which is the closest major airport, located 19.3 mi (31 km) from the city centre. If you'd like to venture out around the area, you may want to rent a car for your trip.

Explore a world of travel with Expedia