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
25 Oct - 26 Oct
Tomorrow
26 Oct - 27 Oct
Next weekend
30 Oct - 1 Nov
In two weeks
6 Nov - 8 Nov

Our top choices for Winter Garden romantic hotels

A spacious living area with a dining table, chairs, a sofa, and a kitchen in the background.
A dining area with a wooden table and chairs, a hanging light fixture, and a world map on the wall.
A modern kitchen with white cabinets, a stainless steel range, and a yellow door.
A narrow hallway with a patterned rug, a white door at the end, and a wooden shelf with a picture frame and a box on the right.

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
Ron C.
€368
includes taxes & fees
8 Nov - 9 Nov
House with large deck, walking distance to Historic Downtown Winter Garden
A spacious lobby with leather sofas, a central coffee table, and large windows offering a view of greenery outside.
A bedroom with a bed, a large window, a ceiling fan, and a bathroom with a bathtub and a framed picture on the wall.
A modern living room with a grey sofa, a coffee table, and two armchairs. There is a kitchen area with white cabinets and a bar stool.
A modern living room with a sofa, armchairs, a coffee table, and a TV. There is a balcony with a view of trees and a railing.

2. Upstay | Pet Friendly Condo Near Disney & Pool

Upstay | Pet Friendly Condo Near Disney & Pool
Winter Garden
Upstay | Pet Friendly Condo Near Disney & Pool
A spacious lobby with leather sofas, a central coffee table, and large windows offering a view of greenery outside.
A modern living room with a sofa, armchairs, a coffee table, and a TV. There is a balcony with a view of trees and a railing.
A bedroom with a bed, a large window, a ceiling fan, and a bathroom with a bathtub and a framed picture on the wall.
A multi-story hotel with a brick pathway leading to the entrance, surrounded by palm trees and greenery.

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
A modern living room with a sofa, armchairs, a coffee table, and a TV. There is a balcony with a view of trees and a railing.
A modern living room with a grey sofa, a coffee table, and two armchairs. There is a kitchen area with white cabinets and a bar stool.
A bedroom with a bed, a large window, a ceiling fan, and a bathroom with a bathtub and a framed picture on the wall.
A modern kitchen with white cabinets, stainless steel appliances, and a granite countertop. There are two bar stools under the counter.

4. 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
A spacious living room with a sofa, a coffee table, and a TV. There are large windows with curtains, a balcony, and a ceiling fan.
A modern living room with a grey sofa, a coffee table, and a TV mounted on the wall.
A modern kitchen with a central island, bar stools, and built-in appliances.
A gym with exercise equipment, large windows, and a view of greenery.

5. Condo w Pool, Games Room - Pet Friendly

Condo w Pool, Games Room - Pet Friendly
Winter Garden
United States
Catherine T.
€221
includes taxes & fees
26 Oct - 27 Oct
Condo w Pool, Games Room - Pet Friendly
Resort Amenities
A spacious lobby with leather sofas, a central coffee table, and large windows offering a view of greenery outside.
An aerial view of a resort with a large swimming pool, sun loungers, and palm trees.
A modern living room with a sofa, coffee table, and a dining area with a TV.

6. Pet-friendly Resort Getaway with Patio and Pool

Pet-friendly Resort Getaway with Patio and Pool
Winter Garden
Pet-friendly Resort Getaway with Patio and Pool
A spacious lobby with leather sofas, a central coffee table, and large windows offering a view of greenery outside.
A bedroom with a bed, a large window, a ceiling fan, and a bathroom with a bathtub and a framed picture on the wall.
A multi-story hotel with a brick pathway leading to the entrance, surrounded by palm trees and greenery.
A modern living room with a grey sofa, a coffee table, and two armchairs. There is a kitchen area with white cabinets and a bar stool.

7. 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
A two-story house with a swimming pool, outdoor seating, and a covered patio area.
A stone staircase leading to a pond surrounded by lush greenery and stone railings.
A rustic bar with wooden shelves stocked with bottles, a coffee machine, and bar stools.
A small, rustic building with a metal roof and a red door, surrounded by lush greenery and a pond.

8. Mills Cottage by the Little Lake

Mills Cottage by the Little Lake
Lake Weldona
United States
rick s.
€384
includes taxes & fees
24 Nov - 25 Nov
Mills Cottage by the Little Lake
A residential area with multiple houses, a large central lake, and a swimming pool.
An aerial view of a residential property with a large swimming pool, multiple houses, and a well-maintained garden.
A living room with a grey sofa, a glass coffee table, and a ceiling fan. There are two lamps on the sofa and a bar area with stools.
A beach with a volleyball net, palm trees, and lounge chairs under thatched umbrellas.

9. Tropical Resort Condo Near Disney: Pools, Spa & Family Fun

Tropical Resort Condo Near Disney: Pools, Spa & Family Fun
Bahama Bay
United States
Nathan M.
€282
includes taxes & fees
9 Nov - 10 Nov
Tropical Resort Condo Near Disney: Pools, Spa & Family Fun
A hot tub with a waterfall feature, a covered seating area, and a bar with outdoor seating.
A spacious living area with a large sectional sofa, a dining table with bar stools, a kitchen with dark cabinets, and a ceiling fan.
A kitchen with granite countertops, stainless steel appliances, and wooden cabinets.
A spa area with a hot tub, a wooden door, and a brick patio with lounge chairs.

10. Private Luxury Pool / Swim up bar / Smart-home

Private Luxury Pool / Swim up bar / Smart-home
College Park
United States
Dennis P.
€375
includes taxes & fees
26 Oct - 27 Oct
Private Luxury Pool / Swim up bar / Smart-home
View all properties

Top Winter Garden Hotel Reviews

Hilton Vacation Club Aqua Sol Orlando West

Hilton Vacation Club Aqua Sol Orlando West

10/10 Excellent
"The staff was so friendly and welcoming! The room was cozy and comfortable, and honestly, it felt like we never left home. We really enjoyed our stay and would definitely come back!"
Denzel 3-night trip
Posted less than an hour ago
Hilton Vacation Club Aqua Sol Orlando West
Walt Disney World Dolphin

Walt Disney World Dolphin

10/10 Excellent
"Amazing location, I loved the walking distance to Hollywood Studios"
Jacqueline 1-night trip
Posted 1 hour ago
Walt Disney World Dolphin
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

8/10 Good
"Beautiful, spacious, clean and very friendly"
Anna 2-night trip
Posted 1 hour ago
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

10/10 Excellent
"Good resort, the rooms are clean and comfortable"
Roberto 2-night trip
Posted 2 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
"Very friendly staff. We had a room view where we can see fireworks at night!!"
Inez 5-night trip
Posted 2 hours ago
Drury Plaza Hotel Orlando - Disney Springs Area
Hyatt Regency Orlando International Airport

Hyatt Regency Orlando International Airport

8/10 Good
"This is a nice hotel but the $400+ per night charge is outrageous."
Dale 1-night trip
Posted 2 hours ago
Hyatt Regency Orlando International Airport
Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort

10/10 Excellent
"Nourriture très cher! Mais super hotel"
Guylain 4-night trip
Posted 2 hours ago
Universal's Cabana Bay Beach Resort
DoubleTree by Hilton at the Entrance to Universal Orlando

DoubleTree by Hilton at the Entrance to Universal Orlando

8/10 Good
"Everything was great, but the coffee and breakfast options in the hotel were ridiculously expensive."
Vanessa 3-night trip
Posted 16 hours ago
DoubleTree by Hilton at the Entrance to Universal Orlando

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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