A two-story house with a balcony, surrounded by lush greenery and trees.

Find Romantic Hotels in Winter Park, FL

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Check availability on Winter Park Romantic Hotels

Tonight
Sep 10 - Sep 11
Tomorrow
Sep 11 - Sep 12
This weekend
Sep 11 - Sep 13
Next weekend
Sep 18 - Sep 20

Top Winter Park Hotel Reviews

Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort

10/10 Excellent
"This hotel was amazing. The staff was so very helpful. I have recommended to all my friends. Will definitely stay here again."
Kimberley 3-night trip
Posted 4 hours ago
Universal's Cabana Bay Beach Resort
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

8/10 Good
"The unit was very spacious! The bad part was the units are very dated so the bathrooms were not as clean and the screen doors kept coming off track. The closet doors were not on track either so they were hard to open. Again, its an okay resort because of the space but unit itself is dated and kind of dingy. I called the front desk to let them know about the doors but we just ended up leaving them open so we didn't have to fight with them."
Territa 3-night trip
Posted 4 hours ago
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
Marriott's Grande Vista

Marriott's Grande Vista

10/10 Excellent
"Thanks to Caya checking me in i’ll be back soon"
Michael 3-night trip
Posted 6 hours ago
Marriott's Grande Vista
Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

10/10 Excellent
"Beautiful villas and amenities! Family friendly and close to all the Orlando attractions."
Q 2-night trip
Posted 7 hours ago
Sheraton Vistana Villages Resort Villas, I-Drive/Orlando
Holiday Inn Resort Orlando Suites - Waterpark by IHG

Holiday Inn Resort Orlando Suites - Waterpark by IHG

10/10 Excellent
"A mis hijos le encantó la estancia en este lugar, el parque de agua divertido para los niños, la actividad al medio día con la participación de los niños, definitivamente regresaremos en octubre."
yara 2-night trip
Posted 8 hours ago
Holiday Inn Resort Orlando Suites - Waterpark by IHG
Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

10/10 Excellent
"Staff excellent"
cary 3-night trip
Posted 11 hours ago
Westgate Lakes Resort & Spa Universal Studios Area
Drury Plaza Hotel Orlando - Disney Springs Area

Drury Plaza Hotel Orlando - Disney Springs Area

10/10 Excellent
"Everything!!!"
Emmanuel 4-night trip
Posted 15 hours ago
Drury Plaza Hotel Orlando - Disney Springs Area
Caribe Royale Orlando, WorldHotels Elite

Caribe Royale Orlando, WorldHotels Elite

10/10 Excellent
"Todo bien"
Liscelys 3-night trip
Posted 1 day ago
Caribe Royale Orlando, WorldHotels Elite
Coco Key Hotel & Water Park Resort

Coco Key Hotel & Water Park Resort

8/10 Good
"."
meixiang 1-night trip
Posted 1 day ago
Coco Key Hotel & Water Park Resort

Frequently asked questions

Searching for romantic hotels in Winter Park?
Are you looking for a romantic escape? Our guests also enjoy Winter Park for its restaurants and shopping. You might consider checking out some of the nearby sights and attractions such as Winter Park Village, Lee Road Shopping Center, or Albin Polasek Museum and Sculpture Gardens. If you're interested in staying near a certain attraction, you can sort properties by neighborhood or distance 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 Park?
If you're hoping to get lost in the rain on your romantic getaway, check out these details about year-round temperatures in Winter Park: The hottest months are usually July and August 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 Park are August, September, July, and June, with each month seeing an average of 7 inches of rainfall.
What is there to do in Winter Park?
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 Park. If you and your partner are interested in sampling the area's cuisine, you'll love Winter Park for its array of dining options. If you want to spend a day exploring, you might consider a stop at Winter Park Village, Lee Road Shopping Center, or Albin Polasek Museum and Sculpture Gardens.
What's the best way to get to Winter Park and around town during my romantic getaway?
This information about transportation options in Winter Park might help your romantic getaway go off without a hitch: If you're looking to fly to Winter Park, the closest major airport is Orlando Intl. Airport (MCO), located 11.8 mi (19 km) from the city center. To see more of the larger area, hop aboard a train at Winter Park Station.

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