Lakeland - Winter Haven Vacations from $355

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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

Price found within the past 48 hours. Click for updated prices.
Clearwater Suites
voco Sarasota by IHG
FUSION Resort Waterfront Suites
Ocean Club Treasure Island Hotel
Wyndham Grand Clearwater Beach
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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
$189 nightly
The price is $213 total per night from Aug 24 to Aug 25
$213 total
Aug 24 - Aug 25
Total with taxes and fees
7.8/10 Good! (8,389 reviews)
"The water park is a bonus."

Reviewed on Aug 23, 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 Sep 17 to Sep 18
$141 total
Sep 17 - Sep 18
Total with taxes and fees
9/10 Wonderful! (4,247 reviews)
"This was probably one of my favorite Florida vacation locations. They did great at when we needed to extend our vacation. They added the day so we didn’t have to switch around rooms. The staff was very nice. Very kind. The facilities were clean. The beds were clean. We really enjoyed it and will ..."

Reviewed on Aug 20, 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
$124 nightly
The price is $140 total per night from Aug 26 to Aug 27
$140 total
Aug 26 - Aug 27
Total with taxes and fees
8.6/10 Excellent! (2,354 reviews)
"Place was really nice, you do have to drive everywhere to do anything cause the property is so big. The only thing that I didn’t like was everything closed early."

Reviewed on Aug 20, 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.