Lakeland - Winter Haven Vacations from $522

Book a Hotel + Flight or Car together to unlock savings

Photo by Lakeland Convention and Visitors Bureau

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

Price found within the past 48 hours. Click for updated prices.
Ocean Club Treasure Island Hotel
voco Sarasota by IHG
The Westin Sarasota
Hibiscus Suites - Gateway to Siesta Key
Wyndham Grand Clearwater Beach
Don't see what you're looking for?
See all available trips from Columbus to Lakeland - Winter Haven
View all trips

Where to stay in Lakeland - Winter Haven

Find the best Lakeland - Winter Haven areas and neighborhoods for the activities you enjoy most. Learn more about Lakeland - Winter Haven

Discover the most popular places to visit in Lakeland - Winter Haven

What to do in Lakeland - Winter Haven

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
$189 nightly
The price is $213 total per night from Aug 11 to Aug 12
$213 total
Aug 11 - Aug 12
Total includes taxes and fees
7.8/10 Good! (8,268 reviews)
"Was an amazing stay definitely would recommend it"

Reviewed on Aug 7, 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 17 to Aug 18
$141 total
Aug 17 - Aug 18
Total includes taxes and fees
9/10 Wonderful! (4,188 reviews)
"This is a very nice resort in a good area"

Reviewed on Aug 6, 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
$143 nightly
The price is $161 total per night from Aug 12 to Aug 13
$161 total
Aug 12 - Aug 13
Total includes taxes and fees
8.6/10 Excellent! (2,271 reviews)
"The amenities are great for a family of diverse ages. The kids had a wonderful time!"

Reviewed on Aug 7, 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.

More vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.