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Check availability on Winter Garden Romantic Hotels

Our top choices for Winter Garden romantic hotels

Outdoor pool

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 ￥28,593
￥45,868 total
includes taxes & fees
May 25 - May 26
The Oak View Place..
Interior

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 reviews)
"Great place! Convenient, cozy and clean!"
United States
SHARLA B.
The price is ￥11,925
￥44,083 total
includes taxes & fees
Jun 16 - Jun 17
Upstay - Condo w Pool and More - Near Disney
Fitness facility

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 ￥11,596
￥40,392 total
includes taxes & fees
May 27 - May 28
Condo w Pool, Games Room - Pet Friendly
Exterior

Family-Friendly Condo with Pool & Sauna

Family-Friendly Condo with Pool & Sauna
Winter Garden
The price is ￥12,390
￥41,452 total
includes taxes & fees
Jun 7 - Jun 8
Family-Friendly Condo with Pool & Sauna
TV, table tennis

Beautiful Condo w Outdoor Pool and Sauna

Beautiful Condo w Outdoor Pool and Sauna
Winter Garden
9.0 out of 10, Wonderful, (6 reviews)
"The host of our rental did a fabulous job! We didn’t have washcloths and they made sure to have some delivered. For the amount of time we spent there this place was perfect for our stay. The air condition was freezing!!!! No complaints with the air. "
United States
Tammy M.
The price is ￥9,531
￥41,495 total
includes taxes & fees
May 28 - May 29
Beautiful Condo w Outdoor Pool and Sauna
Interior

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

Upstay: 3BR Condo w Pool, Sauna—Near Disney
Winter Garden
The price is ￥12,390
￥45,534 total
includes taxes & fees
Jun 7 - Jun 8
Upstay: 3BR Condo w Pool, Sauna—Near Disney
Interior

Upstay - Pet-Friendly Family Condo near Disney

Upstay - Pet-Friendly Family Condo near Disney
Winter Garden
The price is ￥11,925
￥44,083 total
includes taxes & fees
Jun 16 - Jun 17
Upstay - Pet-Friendly Family Condo near Disney
Outdoor pool, a heated pool

Mills Cottage by the Little Lake

Mills Cottage by the Little Lake
Lake Weldona
10.0 out of 10, Exceptional, (61 reviews)
"Beautiful grounds and awesome amenities."
United States
Serenity C.
The price is ￥24,923
￥57,494 total
includes taxes & fees
May 25 - May 26
Mills Cottage by the Little Lake
Outdoor pool, a heated pool

Magical Newly Renovated 10 minutes to Disney 2Bed,2Bath

Magical Newly Renovated 10 minutes to Disney 2Bed,2Bath
Champions Gate
9.4 out of 10, Exceptional, (67 reviews)
"Beautiful property to stay at! Property is very clean. There is a pool and restaurant on sight. Not far from Orlando and all the parks. Also close to a Publix. Owners are extremely easy to get in touch with. Will definitely stay here again!!"
United States
Maureen
The price is ￥12,720
￥36,726 total
includes taxes & fees
Jun 2 - Jun 3
Magical Newly Renovated 10 minutes to Disney 2Bed,2Bath
Property grounds

Incredible Private Lakefront Cottage Retreat

Incredible Private Lakefront Cottage Retreat
Altamonte Springs
10.0 out of 10, Exceptional, (36 reviews)
"The host was easy to contact and the cottage was very cozy with all necessary amenities. The lakeside location was both beautiful and peaceful, especially considering it is so close to 436 and I4. We definitely plan to return. "
United States
Carol G.
The price is ￥21,286
￥56,722 total
includes taxes & fees
May 26 - May 27
Incredible Private Lakefront Cottage Retreat
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 Winter Garden Hotel Reviews

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

10/10 Excellent
"This hotel offers excellent amenities and is particularly well-suited for families. We thoroughly enjoyed our stay here."
John 4-night trip
Posted 1 hour ago
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

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 Lake Butler, Orange County National Golf Club, or Lake Louisa State Park. 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 Lake Butler, Orange County National Golf Club, or Lake Louisa State Park.
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.