Lakeland - Winter Haven Holidays

Photo by Lakeland Convention and Visitors Bureau

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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
A calm lake with lily pads, surrounded by a park with palm trees and buildings.

Downtown Lakeland

2 out of top 10 points of interest in this area

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

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A garden with a central fountain, surrounded by white columns and covered walkways.

Lake Hollingsworth

While visiting Lake Hollingsworth, you might make a stop by sights like Lake Hollingsworth and Veterans Park.

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A circular fountain with a statue in the center, surrounded by palm trees and a building with a red roof in the background.

South Lake Morton

South Lake Morton might not have many top sights, but Lake Mirror and Polk Theatre are two attractions nearby that you can check out.

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A crocodile resting on a log near a body of water with greenery around.

Lakeland Highlands

While there might not be top attractions in Lakeland Highlands, you can explore the larger area and discover places like The Club at Eaglebrooke and Family Fun Center.

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Downtown

When in Downtown, you can plan a visit to Robert W. Willaford Railroad Museum and Otis M. Andrews Sports Complex, some noteworthy sights in the nearby area.

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Top hotels in Lakeland - Winter Haven

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

14501 Grove Resort Avenue Winter Garden FL
Fully refundableReserve now, pay when you stay
S$341
20 Sept - 21 Sept
includes taxes & fees
8/10 Very good! (10,831 reviews)
"The checkin process was a little crazy (crowded, holiday weekend) but easy still. Room was super convenient to parking and was huge! We had only one minor issue with the blinds but was fixed that same evening. I did have family come the next day and had a room booked and it took 2 hours to get their ..."

Reviewed on 17 Sept, 2026

The Grove Resort & Water Park Orlando
Margaritaville Resort Orlando with H2O Waterpark

Margaritaville Resort Orlando with H2O Waterpark

8000 Fins Up Circle Kissimmee FL
Fully refundableReserve now, pay when you stay
S$271
28 Sept - 29 Sept
includes taxes & fees
Margaritaville Resort Orlando with H2O Waterpark
Holiday Inn Winter Haven by IHG

Holiday Inn Winter Haven by IHG

200 Cypress Gardens Boulevard Winter Haven FL
Fully refundable
S$150
20 Sept - 21 Sept
includes taxes & fees
Holiday Inn Winter Haven by IHG
See all 44,760 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.

Stay near popular Lakeland - Winter Haven attractions

The entrance to LEGO Florida with colorful LEGO structures and a large LEGO sign.

LEGOLAND® Florida

9.0/10 (2,150 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.
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A lakeside park with a walking path, palm trees, and a dock extending into the water.

Lakeside Village

7.8/10 (443 reviews)
You can find the perfect gifts to bring home at Lakeside Village during your visit to Lakeland. Amble around the area's lakeside or attend a sporting event.
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A wooden boardwalk leading to a sign that reads "Deinonychus Island."

Dinosaur World

8.6/10 (65 reviews)
With more than 200 life-size dinosaur models and many interactive games and activities, this educational theme park is great for families.
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A historic tower with intricate designs, surrounded by lush greenery and a clear blue sky.
Photo by throwingsofas

Bok Tower Gardens

9.0/10 (158 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 visit its top-notch restaurants.
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A large aircraft with a red nose and four propellers, mounted on a white structure.

Sun N Fun Air Museum

7.6/10 (272 reviews)
You can spend time exploring the galleries in Sun N Fun Air Museum in Lakeland. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.
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RP Funding Center

7.6/10 (545 reviews)
You can enjoy a show at RP Funding Center during your stay in Lakeland. Amble around the area's lakeside or attend a sporting event.
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Publix Field at Joker Marchant Stadium

7.8/10 (448 reviews)
Catch an event at Publix Field at Joker Marchant Stadium during your trip to Lakeland. Stroll along the lakeside or attend a sporting event in this family-friendly area.
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Southern Dunes Golf and Country Club

7.8/10 (15 reviews)
Enjoy a round of golf in Haines City at Southern Dunes Golf and Country Club. Stroll along the lakeside in this family-friendly area or visit its top-notch restaurants.
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What to do in Lakeland - Winter Haven

LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

S$42
per traveller
86% of travellers recommend
LEGOLAND® Florida Tickets
LEGOLAND Florida FasTrack Pass

LEGOLAND Florida FasTrack Pass

S$139
per traveller
LEGOLAND Florida FasTrack Pass
Walt Disney World® Resort Theme Park Tickets

Walt Disney World® Resort Theme Park Tickets

S$170
per adult
Walt Disney World® Resort Theme Park Tickets
See all activities in Lakeland - Winter Haven

Frequently asked questions

How much does a Lakeland - Winter Haven holiday package cost?
Custom build your Lakeland - Winter Haven package from as little as . Pick from any combination of rental cars, flights and hotels to craft the getaway of your dreams. Don't forget to add on a few experiences or tours!
How do I get a cheap travel package to Lakeland - Winter Haven?
Bundle your hotels and flights with Expedia to save big on your next getaway. With more than 550 airlines and 1,000,000 hotel options worldwide, your Lakeland - Winter Haven holiday package can be tailored exactly to suit your travel style. With all that extra money, why not include a few exciting activities and tours? It's an easy way to unlock even more discounts. That holiday you've always dreamed of in Lakeland - Winter Haven is much closer than you thought!
Where should I stay in Lakeland - Winter Haven?
There's an abundance of excellent places to stay in Lakeland - Winter Haven, including Lakeland. This destination is home to many much-loved attractions including Publix Field at Joker Marchant Stadium and Polk Museum of Art. Another option is to head to Winter Haven, where you'll find LEGOLAND® Florida and Chain of Lakes Park. If you're here for a while, journey to both vibrant cities!
What are the top hotels in Lakeland - Winter Haven?
Days Inn & Suites by Wyndham Lakeland and Hyatt Place Lakeland Centre know how to make their guests feel welcome in Davenport. If you also plan to get to Haines City, have a look at Comfort Inn & Suites Maingate South and Winter Haven Gardens Inn. Both are popular with travellers.
How far in advance should I book my Lakeland - Winter Haven holiday?
Your best bet is to book early. Airlines typically advertise flight tickets nearly 12 months ahead of departure, and this is a great opportunity to pick up some of the cheapest prices. Just been told you need to take some holiday time next month? No sweat. Expedia are never short on fantastic deals to help you have the getaway of your dreams, at an affordable price.
What does an Expedia Lakeland - Winter Haven travel package include?
Rental cars, flights and hotels — we've got them covered. With Expedia, you can shape your Lakeland - Winter Haven package just the way you want. All you have to do is decide what you need. Once you've made your booking, you can add on fun things like experiences and activities. The more you bundle, the more you save!
What should I know before booking a Lakeland - Winter Haven travel package?
An Expedia travel package can be customized for your budget and is an easy way to stretch your dollars further. How much you include is totally up to you. Hotels, rental cars and flights — decide on a combination that suits your style.
Can I choose my airline with a Lakeland - Winter Haven Expedia holiday package?
Yes — and it's simple too. Expedia has access to more than 550 partner airlines around the world. Our packages give you the flexibility to pick from available flights, hotels and activities that fit your needs.
If I'm not able to travel, can I cancel my Lakeland - Winter Haven holiday package?
Whether it's your hotel or flight, you can cancel or alter it. Booked your Lakeland - Winter Haven holiday package in the last 24 hours? You may be able to make changes at no cost. If it's been longer than that, you may be charged a fee by your airline, hotel or car rental company. For further information, head to our Customer Service Portal. We'll help you each step of the way.

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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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.