Winter Garden Holiday Rentals, Florida: Private House Rentals

Our top choices for Winter Garden hotels

The Grove Resort & Water Park Orlando

Winter Garden

Hasam

฿7,279 total

includes taxes & fees

23 Feb - 24 Feb

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

Bay Lake

Christian

฿4,374 total

includes taxes & fees

3 Mar - 4 Mar

TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance

Bay Lake

Luiz

฿3,709 total

includes taxes & fees

1 Mar - 2 Mar

Home2 Suites by Hilton Orlando at Flamingo Crossings

Bay Lake

VIMAL

฿3,989 total

includes taxes & fees

3 Mar - 4 Mar

2 outdoor pools, pool umbrellas, pool loungers

Hilton Vacation Club Aqua Sol Orlando West

Winter Garden

Eduardo

฿4,890 total

includes taxes & fees

10 Mar - 11 Mar

SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance

Bay Lake

Gerardo

฿3,590 total

includes taxes & fees

1 Mar - 2 Mar

Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

Bay Lake

Catalina

฿5,004 total

includes taxes & fees

3 Mar - 4 Mar

Outdoor pool, open 9:00 AM to 10:00 PM, pool loungers

Homewood Suites by Hilton Orlando at Flamingo Crossings

Bay Lake

ALTON

฿4,562 total

includes taxes & fees

4 Mar - 5 Mar

Home2 Suites By Hilton Winter Garden

Winter Garden

Olga

฿5,136 total

includes taxes & fees

15 Mar - 16 Mar

Orange County National Lodge

Horizon West

Cal

฿6,649 total

includes taxes & fees

14 Mar - 15 Mar

Upstay Amazing Disney Condo w Patio Sleeps 6

Winter Garden

฿9,513 total

includes taxes & fees

8 Mar - 9 Mar

Rosen Shingle Creek

Orlando

Steven

฿4,731 total

includes taxes & fees

6 Mar - 7 Mar

Margaritaville Resort Orlando with H2O Waterpark

Kissimmee

Eric Theodore

฿7,588 total

includes taxes & fees

1 Mar - 2 Mar

Summer Bay Orlando MOD Collection by Sonesta

Clermont

Octavio

฿4,765 total

includes taxes & fees

23 Feb - 24 Feb

Vacation Village Orlando, Celebration

Kissimmee

Alicia

฿3,609 total

includes taxes & fees

23 Mar - 24 Mar

Holiday Inn Express Hotel & Suites Ocoee East by IHG

Orlando

Luisa

฿4,171 total

includes taxes & fees

24 Feb - 25 Feb

Alhambra Villas

Solivita

Harry Joseph Lundgren,

฿2,768 total

includes taxes & fees

24 Feb - 25 Feb

4 outdoor pools, pool cabanas (surcharge), pool umbrellas

Hilton Vacation Club Mystic Dunes Orlando

Kissimmee

Terry

฿5,444 total

includes taxes & fees

8 Mar - 9 Mar

Seasons Florida Resort

Kissimmee

David

฿2,224 total

includes taxes & fees

8 Mar - 9 Mar

Kompose Boutique Resort at Theme Parks

Kissimmee

caleb

฿3,249 total

includes taxes & fees

1 Mar - 2 Mar

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Where to stay in Winter Garden

Find the best Winter Garden areas for the activities you enjoy most.

Love this tiny town, just 20 minutes from Walt Disney World. Inside #PlantStreetMarket you’ll find multiple vendors including local food, honey, coffee and desserts, and #crookedcanbrewing #wintergarden #lifeatexpedia

Downtown Winter Garden

Historic City centre Winter Garden charms visitors with its beautifully preserved early 20th century buildings along brick-lined Plant Street. The restored 1935 Garden Theatre anchors this pedestrian-friendly district where wide pavements invite leisurely exploration. Regular street events and a popular farmers market create a lively atmosphere throughout the week. Cyclists will love accessing the scenic West Orange Trail that runs through city centre. History buffs can explore the Central Florida Railway Museum and Heritage Museum to discover local stories. The area's artisanal shops, farm-to-table restaurants, and outdoor dining spots make this walkable district perfect for a relaxed Florida getaway.

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Horizon West

While visiting Horizon West, you might make a stop by sights like Walt Disney World® Resort and Orange County National Golf Club.

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Orange sunset over distant hills on Lake Apopka near Orlando, Florida.

Vista del Lago

Vista del Lago offers a peaceful retreat just minutes from Orlando's world-famous attractions. This welcoming Four Corners community features resort-style amenities including sparkling pools and recreation areas. Families appreciate the quiet residential setting after busy theme park days. Wide streets lined with Mediterranean-style holiday homes create a relaxing atmosphere for travellers. Disney's Animal Kingdom and Magic Kingdom are just a short drive away. Most visitors enjoy having kitchen facilities and private spaces while staying close to Orlando's excitement.

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Panoramic view of Lake Apopka and nature Florida.

Oakland

Oakland charms visitors with its well-preserved historic buildings and small-town atmosphere just outside Orlando's bustling tourist zones. Victorian homes line oak-canopied streets while the city centre area offers antique shops and local cafes. The 128-acre Oakland Nature Preserve provides scenic boardwalks through cypress wetlands. Lake Apopka shoreline offers excellent bird watching with over 200 species. History buffs will appreciate the 1889 Healthy House Museum and railway heritage. Most businesses close early, creating a peaceful evening environment. The West Orange Trail connects cyclists to Winter Garden's wider area.

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Killarney

Killarney offers a peaceful retreat from Orlando's tourist bustle while keeping adventure within reach. This family-friendly suburb surrounds you with manicured lawns, palm trees, and quiet residential streets. The nearby West Orange Trail and Lake Apopka provide perfect settings for outdoor recreation. Budget-conscious travellers will appreciate the affordable accommodation and relaxed atmosphere. Take morning strolls along spacious pavements or visit Oakland Nature Preserve just minutes away. A car is essential for exploring Winter Garden's charming city centre and reaching Orlando's famous attractions.

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Stay near popular Winter Garden attractions

Flamingo Crossings Town Center

This convenient retail hub at Disney World's western gateway offers diverse shopping and dining options. Explore Target, Walgreens, and restaurants in a pedestrian-friendly environment perfect for a theme park break.

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Disney's Magnolia Golf Course

4.1/5 (171 reviews)

This championship course stretches through scenic magnolia trees with challenging water hazards on 11 holes. Enjoy Walt Disney-themed hole names and inspiring quotes while navigating the recently reimagined greens.

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Learn more about Winter Garden

Stroll the charming brick-lined streets of historic city centre where the Plant Street Market buzzes with local food vendors and craft beer. Pedal along the West Orange Trail that cuts through town, stopping at the Heritage Museum or to catch a show at the Garden Theatre.

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ARM53A Historic Downtown Area and Clock of Winter Garden Florida

Top Winter Garden Hotel Reviews

Sonesta Essential Orlando Airport

10/10 Excellent

"Goid job"

Westgate Lakes Resort & Spa Universal Studios Area

10/10 Excellent

"The room was absolutely perfect for a family vacation. We didnt spend much time around the resort because we were only in town for one full day, but when we were around the staff we very friendly and helpful and the resort was clean. "

More cheap stays in Winter Garden

Howard Johnson by Wyndham Orlando Lake Buena Vista South

5055 W. Irlo Bronson Memorial Hwy Kissimmee FL

฿1,761

฿2,456 total

24 Feb - 25 Feb

includes taxes & fees

8/10 Very Good! (1,920 reviews)

Frequently asked questions

What's the best place to stay in Winter Garden?

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center is a favourite with Expedia customers. This hotel is a short 1-minute walk from Flamingo Crossings Town Center, and it offers free breakfast and a restaurant. Reviews from our site also recommend Home2 Suites by Hilton Orlando at Flamingo Crossings and Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance as top choices for your stay. See all available top hotels, or vacation rentals in Winter Garden.

What are some of the best holiday rentals that Winter Garden has to offer?

The Berkley, Orlando: This holiday home rental outside of Winter Garden offers a furnished patio, a terrace and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a full-sized fridge, a microwave and a coffee maker. You can relax into your holiday with an arcade/games room and 1 hot tub. See all vacation rentals in Winter Garden.

If I need to cancel my hotel reservation in Winter Garden, will I receive a refund?

Yes, the majority of hotel bookings are fully refundable as long as you cancel before the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of your scheduled arrival. If you have a reservation that's non-refundable, you might still have the option to cancel and get a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Winter Garden.

What's the best budget-friendly accommodation in Winter Garden?

Based on reviews, The Grove Resort & Water Park Orlando is a popular resort for our travellers who want a more economical choice, and features free Wi-Fi and free water-park access. Other good choices for your budget-friendly stay include Home2 Suites by Hilton Orlando at Flamingo Crossings and Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center. View all budget hotels in Winter Garden.

What's the best family accommodation in Winter Garden?

The Grove Resort & Water Park Orlando is a resort with free water park access and a lazy river, and it's a top choice on Expedia for families. Other good options for your stay with the children include Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center and Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance. Also, attractions such as Surfari Water Park and Central Florida Railroad Museum are fun for children of all ages. Find more child-friendly accommodations in Winter Garden.

What's the best LGBTQ-friendly hotel in Winter Garden?

Home2 Suites by Hilton Orlando at Flamingo Crossings is a top LGBTQ-friendly hotel that features free breakfast and a 24-hour fitness centre. The Grove Resort & Water Park Orlando and Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center are two other good choices for your trip. See all available hotels listed as LGBTQ-friendly in Winter Garden.

What's the best dog-friendly accommodation option in Winter Garden?

Home2 Suites by Hilton Orlando at Flamingo Crossings is a top hotel for people travelling with their pets, and offers a restaurant and in-room kitchenettes for its human guests. Two other good options for you and your pet's trip include Homewood Suites by Hilton Orlando at Flamingo Crossings and TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance. See more pet-friendly hotel accommodations in Winter Garden.

What's the best accommodation for a golf trip to Winter Garden?

Orange County National Lodge is a top lodge that has a golf course and features free WiFi. Another good choice is Oakland Manor House if you'd like to stay near a golf course while in town. You can tee off at Orange County National Golf Club, Disney's Magnolia Golf Course or Disney's Palm Golf Course while you're in town. See more golf hotels in Winter Garden.

What are some accommodation options with pools in Winter Garden?

The Grove Resort & Water Park Orlando is a top resort with 6 outdoor swimming pools, a children's pool and free water park access. A couple of other options with an on-site pool include Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center and Hilton Vacation Club Aqua Sol Orlando West. View all hotels with pools in Winter Garden.

What's the most popular hotel in Winter Garden with an on-site water park or a water park nearby?

The Grove Resort & Water Park Orlando is a popular resort, featuring free water park access, 6 outdoor pools and a children's club. It's located within a short walk of Surfari Water Park. Hilton Vacation Club Aqua Sol Orlando West and The Palisades Resort Orlando are two other water park hotels you can choose from. Take a look at all hotels with or near waterparks in Winter Garden.

How is it staying in Winter Garden?

Families will find child-friendly activities in Winter Garden, and visitors give high marks for the theme park, shopping and water parks. Welcoming and relaxing, this city attracts tourists with its restaurants and golf courses. Top sights around the area include Universal Studios Florida, Universal Orlando Resort and Magic Kingdom® Park. In Winter Garden, there are 322 hotels and other accommodation options to choose from. Find out more about Winter Garden.

What should I do while I'm visiting Winter Garden?

Cultural venues include Central Florida Railroad Museum, Garden Theatre and Winter Garden Art Association. Families come for the theme park and water parks, specifically attractions such as Surfari Water Park and Carter Family Bowl. Landmarks like Plant Street Market and Newton Park might be worth a visit. Take a look at what more there is to see and do in Expedia's Winter Garden guide.

What's the weather like 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.

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Our top choices for Winter Garden hotels

The Grove Resort & Water Park Orlando

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance

Home2 Suites by Hilton Orlando at Flamingo Crossings

Hilton Vacation Club Aqua Sol Orlando West

SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance

Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

Homewood Suites by Hilton Orlando at Flamingo Crossings

Home2 Suites By Hilton Winter Garden

Orange County National Lodge

Upstay Amazing Disney Condo w Patio Sleeps 6

Rosen Shingle Creek

Margaritaville Resort Orlando with H2O Waterpark

Summer Bay Orlando MOD Collection by Sonesta

Vacation Village Orlando, Celebration

Holiday Inn Express Hotel & Suites Ocoee East by IHG

Alhambra Villas

Hilton Vacation Club Mystic Dunes Orlando

Seasons Florida Resort

Kompose Boutique Resort at Theme Parks

Where to stay in Winter Garden

Downtown Winter Garden

Horizon West

Vista del Lago

Oakland

Killarney

Stay near popular Winter Garden attractions

Flamingo Crossings Town Center

Disney's Magnolia Golf Course

Learn more about Winter Garden

Top Winter Garden Hotel Reviews

Sonesta Essential Orlando Airport

More cheap stays in Winter Garden

Howard Johnson by Wyndham Orlando Lake Buena Vista South

Frequently asked questions

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