Lakeland - Winter Haven Vacation Packages 2025

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.

EVEN Hotel Sarasota-Lakewood Ranch by IHG

Save 100% on your flight

per person

Sep 18 - Sep 23

found 1 day ago

Roundtrip flight included

New York (JFK) to Tampa (TPA)

8.4/10 Very Good! (994 reviews)

Hidden gem! Excellent service

Reviewed on Jul 2, 2025

voco Sarasota by IHG

Central Sarasota

Save 100% on your flight

per person

Sep 7 - Sep 14

found 4 hours ago

Roundtrip flight included

New York (JFK) to Tampa (TPA)

9.2/10 Wonderful! (1,008 reviews)

The staff were very helpful and friendly.

Reviewed on Jul 4, 2025

Ocean Club Treasure Island Hotel

Save 100% on your flight

per person

Sep 17 - Sep 20

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Tampa (TPA)

9.6/10 Exceptional! (499 reviews)

Staff was very friendly. Property was clean and well taken care . Right on the beach, volleyball court and a nice bar near pool.

Reviewed on Jul 2, 2025

The Westin Sarasota

Central Sarasota

Save 100% on your flight

per person

Sep 18 - Sep 23

found 1 day ago

Roundtrip flight included

New York (JFK) to Tampa (TPA)

9/10 Wonderful! (1,013 reviews)

Beautiful property! We had a great stay. It felt very clean, & staff were very accommodating to our needs & requests. The only thing is that no where on the site does it list that they will charge $50 overnight for parking. This would have been nice to know prior as we probably wouldn’t have rented a car, and Uber-Ed everywhere instead. However for future guests that are capable of walking; we found a parking garage that was within walking distance & only $1/an hour .. make sure you check it out

Reviewed on Jul 3, 2025

The Fold Hotels Indian Shores

Save 100% on your flight

per person

Sep 22 - Sep 27

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Tampa (TPA)

9.2/10 Wonderful! (901 reviews)

There was a small glitch when I checked in, but the overnight security guard who checked me in handled it like a champ. The staff was friendly and being across the street from the beach was nice as well.

Reviewed on Jul 4, 2025

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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

Downtown Lakeland

2 out of top 10 points of interest in this area

4.5/5(101 area reviews)

If you're spending some time in Downtown Lakeland, RP Funding Center and Lake Mirror are top sights worth seeing.

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

LEGOLAND® Florida

4.5/5(1,082 reviews)

Take the kids to this dynamic theme park for a day full of exciting rides, LEGO® brick creations and the chance to build your own LEGO®robots.

The 205 foot Neo-gothic 'singing tower' houses a 60-bell carillon – one of
about 185 carillons in North America.

Designed by Milton B. Medary, he was awarded in 1929 the American Institute of
Architects gold medal for this design.

#Trovember

Bok Tower Gardens

4.5/5(64 reviews)

Bok Tower Gardens is just one of the places to see in Lake Wales, so why not enjoy the other things to explore during your travels? Stroll along the lakeside in this family-friendly area, or check out its top-notch restaurants.

Dinosaur World

4.5/5(26 reviews)

With more than 200 life-size dinosaur models and many interactive games and activities, this educational theme park is great for families.

What to do in Lakeland - Winter Haven

LEGOLAND® Florida Tickets

$76

per traveler

84% of travellers recommend

Ladies Luncheon Pontoon Tour (Gentleman welcome)

$100

per adult

Day Trip to Clearwater Beach with Sea Screamer Ride

$125

per adult

90% of travellers recommend

See all activities in Lakeland - Winter Haven

Lakeland - Winter Haven Hotel Deals

The Grove Resort & Water Park Orlando

14501 Grove Resort Avenue, Winter Garden, FL

Fully refundableReserve now, pay when you stay

$209 nightly

$235 total

Jul 7 - Jul 8

Total includes taxes and fees

7.8/10 Good! (8,011 reviews)

"Great resort but you could tell they were short staffed....we had to pretty much do our own room service.Lawns were over grown....I guess they were missing our hard working migrants"

Reviewed on Jul 5, 2025

Holiday Inn Club Vacations at Orange Lake Resort by IHG

8505 W Irlo Bronson Memorial Hwy, Kissimmee, FL

Fully refundable

$157 nightly

$177 total

Jul 8 - Jul 9

Total includes taxes and fees

8.6/10 Excellent! (2,112 reviews)

"It was superb!"

Reviewed on Jul 1, 2025

Margaritaville Resort Orlando with H2O Waterpark

8000 Fins Up Circle, Kissimmee, FL

Fully refundableReserve now, pay when you stay

$180 nightly

$204 total

Aug 6 - Aug 7

Total includes taxes and fees

8.8/10 Excellent! (3,403 reviews)

"Our room was very quiet. We had house keeping replace our towels and when they took the garbages they didnt replace any of the bags. Wouldn't find any ice machines, we ended up having to get ice from the store within the resort"

Reviewed on Jul 3, 2025

See all 44,324 properties in Lakeland - Winter Haven

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.