Winter Garden Vacations from $484

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The Latest Winter Garden vacation packages

Price found within the past 48 hours. Click for updated prices.
Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
International Drive District
Save 100% on your flight
Price was $842, price is now $484 per person
$484
per person
Jun 11 - Jun 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Orlando (MCO)
8.8/10 Excellent! (1,254 reviews)
Muy limpio bonito y ordenado excelente precio

Reviewed on May 4, 2026

Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Save 100% on your flight
Price was $977, price is now $517 per person
$517
per person
Jun 27 - Jul 4
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Orlando (MCO)
8.2/10 Very Good! (1,854 reviews)
Omg it was amazing better then expected Staff were so kind!!!

Reviewed on May 7, 2026

Westgate Towers Resort

Westgate Towers Resort

3.5 out of 5
Save 100% on your flight
Price was $922, price is now $500 per person
$500
per person
Jun 27 - Jul 4
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Orlando (MCO)
8.6/10 Excellent! (1,007 reviews)
Centrally located in the area that we wanted to be.

Reviewed on May 8, 2026

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Save 100% on your flight
Price was $1,356, price is now $750 per person
$750
per person
Jul 13 - Jul 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8.4/10 Very Good! (6,277 reviews)
The hotel was great and the staff was nice. It’s just that we didn’t know about the trash removal service. Other than that it was great.

Reviewed on May 9, 2026

Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Save 100% on your flight
Price was $846, price is now $493 per person
$493
per person
Jul 13 - Jul 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
9/10 Wonderful! (3,523 reviews)
Nice ambience and location but no options for breakfast and the noise could get inside the rooms from the parking lot.

Reviewed on May 7, 2026

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Where to stay in Winter Garden

Find the best Winter Garden areas and neighborhoods for the activities you enjoy most. Learn more about Winter Garden
Oakland

Oakland

When in Oakland, you can plan a visit to Bella Collina Golf Club and West Orange Trail, some noteworthy sights in the nearby area.

Find hotels in Oakland

Winter Garden Hotel Deals

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

4 out of 5
14501 Grove Resort Avenue Winter Garden FL
Fully refundableReserve now, pay when you stay
$210 nightly
The price is $236 total per night from Jun 9 to Jun 10
$236 total
Jun 9 - Jun 10
Total with taxes and fees
8/10 Very Good! (9,809 reviews)
Muy bonito hotel, y con todas las comodidades para pasar una estancia agradable, y quiero agradecer la atención de Jenifer la chica del front desk, q nos recibio muy atenta y nos aclaro todas nuestras dudas. Asi como nos dio una explicación detallada de las ubicaciones del parque de agua y todas ...

Reviewed on May 9, 2026

The Grove Resort & Water Park Orlando
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

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

3 out of 5
631 FLAGLER AVE Winter Garden FL
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $105 total per night from May 18 to May 19
$105 total
May 18 - May 19
Total with taxes and fees
9.4/10 Exceptional! (4,743 reviews)
Great stay

Reviewed on May 8, 2026

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
Home2 Suites by Hilton Orlando at Flamingo Crossings

Home2 Suites by Hilton Orlando at Flamingo Crossings

3 out of 5
341 Flagler Ave Winter Garden FL
Fully refundableReserve now, pay when you stay
$105 nightly
The price is $118 total per night from Jun 9 to Jun 10
$118 total
Jun 9 - Jun 10
Total with taxes and fees
9.2/10 Wonderful! (5,515 reviews)
What an excellent staff ,everyone was so helpful, friendly and what a clean facility. Plus free full buffet breakfast. This is worth the money to stay here.

Reviewed on May 9, 2026

Home2 Suites by Hilton Orlando at Flamingo Crossings
See all 54,774 properties in Winter Garden
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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