Lakeland - Winter Haven Vacations from $284

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Your Lakeland - Winter Haven Vacation

With everything organized before you go, our Lakeland - Winter Haven vacation packages let you focus on having fun. Known for its golfing, walking trails and family-friendly attractions, the only thing left to do is kick back and enjoy every unforgettable moment. Kick off your trip to Lakeland - Winter Haven with a few nights in Lakeland visiting popular sights like RP Funding Center and Lakeside Village. Davenport is another city that draws travelers from far and wide. Reunion Resort Golf Course and Southern Dunes Golf and Country Club are two of the top places to see here. When it's time to stop dreaming and start packing, Expedia will help turn your Lakeland - Winter Haven vacation into a reality.

The Latest Lakeland - Winter Haven vacation packages

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GALAXY HOTEL
voco Sarasota by IHG
Kompose Boutique Hotel
Hibiscus Suites - Gateway to Siesta Key
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Where to stay in Lakeland - Winter Haven

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Lakeland - Winter Haven 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
$179 nightly
The price is $201 total per night from Aug 20 to Aug 21
$201 total
Aug 20 - Aug 21
Total includes taxes and fees
7.8/10 Good! (8,379 reviews)
"Our stay was great. The condo we had was nice, clean and spacious. The Alfresco market was unbelievably expensive so we tried to limit what we had to purchase from there. The area around the pools could be cleaned better. There was trash and wood chips in the pools."

Reviewed on Aug 18, 2025

The Grove Resort & Water Park Orlando
Hilton Vacation Club Mystic Dunes Orlando

Hilton Vacation Club Mystic Dunes Orlando

4 out of 5
7600 Mystic Dunes Lane, Kissimmee, FL
Fully refundableReserve now, pay when you stay
$124 nightly
The price is $141 total per night from Aug 25 to Aug 26
$141 total
Aug 25 - Aug 26
Total includes taxes and fees
9/10 Wonderful! (4,217 reviews)
"First time staying there and loved the amount of space the villa had. With a family of 6 we’ve been disappointed before but this Hilton was perfect!"

Reviewed on Aug 17, 2025

Hilton Vacation Club Mystic Dunes Orlando
Holiday Inn Club Vacations at Orange Lake Resort by IHG

Holiday Inn Club Vacations at Orange Lake Resort by IHG

4 out of 5
8505 W Irlo Bronson Memorial Hwy, Kissimmee, FL
Fully refundable
$148 nightly
The price is $167 total per night from Aug 20 to Aug 21
$167 total
Aug 20 - Aug 21
Total includes taxes and fees
8.6/10 Excellent! (2,329 reviews)
"This place is amazing! We had a great stay. The staff was friendly and responded quickly. The villa was clean and beautifully decorated."

Reviewed on Aug 16, 2025

Holiday Inn Club Vacations at Orange Lake Resort by IHG
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.