Lakeland - Winter Haven Vacations from ￥258,889

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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

EVEN Hotel Sarasota-Lakewood Ranch by IHG

3.5 out of 5
per person
Aug 21 - Aug 27
found 8 hours ago
Roundtrip flight included
Tokyo (TYO) to Tampa (TPA)
8.4/10 Very Good! (994 reviews)
Hidden gem! Excellent service

Reviewed on Jul 2, 2025

Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key

2.5 out of 5
per person
Aug 21 - Aug 27
found 8 hours ago
Roundtrip flight included
Tokyo (TYO) to Tampa (TPA)
8.6/10 Excellent! (2,137 reviews)
Adorable property!! A block away from the bridge to cross over to Siesta Key beach. 7-Eleven 4 minutes away to get ice, beach necessities. Didn't use the pool, but there is parking in front of the rooms. The room itself very comfortable, full kitchen you can cook and it has all items needed to make and serve a meal, full size fridge, good hvac unit to cool the room. Sleeper couch in living room and queen size bed. Super cozy, cute and very comfortable. Would love to return next time we are visiting Siesta Key.

Reviewed on Jun 23, 2025

voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Central Sarasota
per person
Aug 21 - Aug 27
found 8 hours ago
Roundtrip flight included
Tokyo (TYO) to Tampa (TPA)
9.2/10 Wonderful! (1,008 reviews)
The staff were very helpful and friendly.

Reviewed on Jul 4, 2025

The Westin Sarasota

The Westin Sarasota

4 out of 5
Central Sarasota
per person
Aug 21 - Aug 27
found 8 hours ago
Roundtrip flight included
Tokyo (TYO) to Tampa (TPA)
9/10 Wonderful! (1,013 reviews)
From the valet team to María and Valeria at the front desk, and the rooftop bartenders — amazing service all around! It’s a perfect spot to relax and enjoy a bit of a party. Breakfast with Richard and drinks with Jack at the rooftop were a highlight. This is a great place to unwind and soak in the Sarasota weather. I’d love to come back and stay longer next time.

Reviewed on Jul 6, 2025

Carlisle Inn

Carlisle Inn

3.5 out of 5
Pinecraft
per person
Aug 21 - Aug 27
found 8 hours ago
Roundtrip flight included
Tokyo (TYO) to Tampa (TPA)
10/10 Exceptional! (1,868 reviews)
We had such an amazing experience here. We will definitely be back again.

Reviewed on Jul 6, 2025

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
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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, Polk Theatre and RP Funding Center are top sights worth seeing.

Find hotels in Downtown Lakeland

Find the Best Lakeland - Winter Haven Vacation Packages

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
The price is ￥24,415 per night from Jul 7 to Jul 8
￥24,415
￥33,969 total
Jul 7 - Jul 8
includes taxes & fees
7.8/10 Good! (8,022 reviews)
"Clean and water park"

Reviewed on Jul 6, 2025

The Grove Resort & Water Park 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
The price is ￥17,069 per night from Jul 9 to Jul 10
￥17,069
￥25,559 total
Jul 9 - Jul 10
includes taxes & fees
8.6/10 Excellent! (2,112 reviews)
"It was superb!"

Reviewed on Jul 1, 2025

Holiday Inn Club Vacations at Orange Lake Resort by IHG
Margaritaville Resort Orlando with H2O Waterpark
Margaritaville Resort Orlando with H2O Waterpark
4 out of 5
8000 Fins Up Circle, Kissimmee, FL
Fully refundableReserve now, pay when you stay
The price is ￥19,660 per night from Aug 6 to Aug 7
￥19,660
￥29,530 total
Aug 6 - Aug 7
includes taxes & fees
8.8/10 Excellent! (3,419 reviews)
"The resort has nice pools/parking/rooms, clean resort. Nearby activities were great. service needs some improvement. On several occasions I had to go get items from front desk that should have been provided by room service, for example shower caps, sugar, coffee. I requested these items be delivered ..."

Reviewed on Jul 6, 2025

Margaritaville Resort Orlando with H2O Waterpark
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.

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

Legoland Florida which includes a pond, a river or creek and rides

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.

LEGOLAND® Florida
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.

Bok Tower Gardens

What to do in Lakeland - Winter Haven

LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

￥12,221
per traveler
84% of travellers recommend
LEGOLAND® Florida Tickets
Orlando Paintball Experience

Orlando Paintball Experience

￥3,615
per adult
Orlando Paintball Experience
Playground

Dinosaur World Theme Park

￥3,880
per adult
Dinosaur World Theme Park
See all activities in Lakeland - Winter Haven

Frequently asked questions

How much does a Lakeland - Winter Haven vacation package cost?
Custom build your Lakeland - Winter Haven package from as little as ￥258,889. 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 vacation 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 vacation 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 Center 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 travelers.
How far in advance should I book my Lakeland - Winter Haven vacation?
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 vacation 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 vacation 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 vacation package?
Whether it's your hotel or flight, you can cancel or alter it. Booked your Lakeland - Winter Haven vacation 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.