A child riding a bicycle on a wooden boardwalk with a body of water and trees in the background.

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

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Check availability on Winter Garden Romantic Hotels

Tonight
6 Sept - 7 Sept
Tomorrow
7 Sept - 8 Sept
Next weekend
11 Sept - 13 Sept
In two weeks
18 Sept - 20 Sept

Our top choices for Winter Garden romantic hotels

Interior
Private kitchen
Interior
Dining

1. House with large deck, walking distance to Historic Downtown Winter Garden

House with large deck, walking distance to Historic Downtown Winter Garden
Winter Garden
United States
Sam M.
€271
includes taxes & fees
12 Sept - 13 Sept
House with large deck, walking distance to Historic Downtown Winter Garden
Pool
Interior
Point of interest
Point of interest

2. The Oak View Place..

The Oak View Place..
Oakland
United States
Libba F.
€257
includes taxes & fees
7 Sept - 8 Sept
The Oak View Place..
Interior
Room
Living area
Exterior

3. Upstay - Condo w Pool and More - Near Disney

Upstay - Condo w Pool and More - Near Disney
Winter Garden
United States
SHARLA B.
Upstay - Condo w Pool and More - Near Disney
Exterior
Pool
Living area
Living area

4. Pet-friendly Resort Getaway with Patio and Pool

Pet-friendly Resort Getaway with Patio and Pool
Winter Garden
€229
includes taxes & fees
21 Sept - 22 Sept
Pet-friendly Resort Getaway with Patio and Pool
Interior
Living area
Room
Living area

5. Upstay | Disney Area Condo w Pool Pet Friendly

Upstay | Disney Area Condo w Pool Pet Friendly
Winter Garden
Upstay | Disney Area Condo w Pool Pet Friendly
Living area
Living area
Interior
Private kitchen

6. Condo w Pool, Games Room - Pet Friendly

Condo w Pool, Games Room - Pet Friendly
Winter Garden
United States
Catherine T.
Condo w Pool, Games Room - Pet Friendly
Living area
Living area
Pool
Private kitchen

7. Beautiful Condo w Outdoor Pool and Sauna

Beautiful Condo w Outdoor Pool and Sauna
Winter Garden
United States
Tammy M.
Beautiful Condo w Outdoor Pool and Sauna
Interior
Room
Living area
Living area

8. Upstay | Pet Friendly Condo Near Disney & Pool

Upstay | Pet Friendly Condo Near Disney & Pool
Winter Garden
Upstay | Pet Friendly Condo Near Disney & Pool
Pool
Bar (on property)
Property grounds
Outdoor dining

9. Mills Cottage by the Little Lake

Mills Cottage by the Little Lake
Lake Weldona
United States
rick s.
€287
includes taxes & fees
7 Sept - 8 Sept
Mills Cottage by the Little Lake
Pool
Exterior
Exterior
Children’s area

10. Orlando | Lakeside Escape | Pool & Splash Pad

Orlando | Lakeside Escape | Pool & Splash Pad
Orlando
United States
Kristen M.
Orlando | Lakeside Escape | Pool & Splash Pad
View all properties

Top Winter Garden Hotel Reviews

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

10/10 Excellent
"Great location and amenities"
Sheena 4-night trip
Posted 2 hours ago
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
Drury Plaza Hotel Orlando - Disney Springs Area

Drury Plaza Hotel Orlando - Disney Springs Area

10/10 Excellent
"Our stay at the Drury was absolutely wonderful. The staff was amazing. Valencia was a joy. We had 4 rooms for 12 people and nobody complained (except our regular complainer) his only complaint was they wouldn't do an omelet for his breakfast. I will definitely stay at a Drury in the future."
Cecil 1-night trip
Posted 4 hours ago
Drury Plaza Hotel Orlando - Disney Springs Area
Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

8/10 Good
"Muy bueno para ir con niños"
Orestes 2-night trip
Posted 5 hours ago
Westgate Lakes Resort & Spa Universal Studios Area
Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

10/10 Excellent
"If I could give 10 stats I would"
Crystal 3-night trip
Posted 8 hours ago
Sheraton Vistana Villages Resort Villas, I-Drive/Orlando
Rosen Inn Lake Buena Vista

Rosen Inn Lake Buena Vista

10/10 Excellent
"Every thing was great"
Ruben 1-night trip
Posted 10 hours ago
Rosen Inn Lake Buena Vista
Hyatt Regency Orlando International Airport

Hyatt Regency Orlando International Airport

10/10 Excellent
"All was awesome! Great for a long or short layover."
John 1-night trip
Posted 12 hours ago
Hyatt Regency Orlando International Airport

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.

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