Lakeland - Winter Haven Holidays from £886

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Photo by Lakeland Convention and Visitors Bureau

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Your Lakeland - Winter Haven Holiday

Do and see more with an Lakeland - Winter Haven holiday package. Whether you're making your way to Lakeland to enjoy its golfing, walking trails and family-friendly attractions, or someplace else, our package deals make travel planning easy. Start your trip to Lakeland - Winter Haven with a couple of days in Lakeland visiting popular attractions like RP Funding Centre and Lakeside Village. Winter Haven is another city that lures travellers from far and wide. LEGOLAND® Florida and The Circle B Bar Reserve are two of the leading places to see in this destination. If you're ready to stop dreaming and start packing, Expedia will help turn your Lakeland - Winter Haven holiday into a reality.

Top Lakeland - Winter Haven Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Saddlebrook Resort

Saddlebrook Resort

4 out of 5
Wesley Chapel South
Price was £1,195, price is now £886 per person
£886
per person
29 Sept - 6 Oct
found 19 hours ago
Return flight included
London (LHR) to Tampa (TPA)
8/10 Very good! (142 reviews)

SkyBeach Resort

SkyBeach Resort

4 out of 5
Greater Pinellas Point
Price was £1,345, price is now £1,058 per person
£1,058
per person
3 Oct - 10 Oct
found 1 day ago
Return flight included
London (LHR) to Tampa (TPA)
8.6/10 Excellent! (829 reviews)
I did not get a chance to try the breakfast menu. The check-in was fine but they forgot to give the champagne. They offered it but forgot to give it to us. The view from the room was nice.

Reviewed on 29 Jul 2026

Landing Apartments near Sun City Center and Riverview

Landing Apartments near Sun City Center and Riverview

4 out of 5
Price was £1,304, price is now £1,045 per person
£1,045
per person
29 Aug - 5 Sept
found 20 hours ago
Return flight included
London (LHR) to Tampa (TPA)
8.6/10 Excellent! (31 reviews)
The apartment wasn’t completely ready. There was no ice, not enough towels, paper towels or toilet paper. I had to go buy our own supplies.

Reviewed on 15 Jul 2026

The Barrymore Hotel Tampa Riverwalk

The Barrymore Hotel Tampa Riverwalk

3 out of 5
Downtown Tampa
Price was £1,285, price is now £1,045 per person
£1,045
per person
29 Sept - 6 Oct
found 19 hours ago
Return flight included
London (LHR) to Tampa (TPA)
8.6/10 Excellent! (2,722 reviews)
Great spot very close to UT with a shuttle!

Reviewed on 30 Jul 2026

Hilton St. Petersburg Bayfront

Hilton St. Petersburg Bayfront

4 out of 5
Downtown St. Petersburg
Price was £1,198, price is now £978 per person
£978
per person
3 Oct - 10 Oct
found 1 day ago
Return flight included
London (LHR) to Tampa (TPA)
7.8/10 Good! (1,107 reviews)

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

1 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.

Find hotels in Downtown Lakeland

Lakeland - Winter Haven Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Orlando Intl. Airport (MCO)
Population
37,700

Top hotels in Lakeland - Winter Haven

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 £183 per night from 10 Aug to 11 Aug
£183
10 Aug - 11 Aug
includes taxes & fees
8/10 Very good! (10,560 reviews)
"Everything was great. The breakfast buffet was good. Pools and waterparks were great. The bartender at the lobby bar was phenomenal. Parking was a little tight for a big SUV in the parking structure but it was manageable. The housekeeping was my only complaint. We were there for 6 nights and we didn’t ..."

Reviewed on 30 Jul 2026

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 £128 per night from 10 Aug to 11 Aug
£128
10 Aug - 11 Aug
includes taxes & fees
8.8/10 Excellent! (3,154 reviews)
"The pools and lazy river was the biggest hit for our family along with the slides. However the employees that operated the slides needs to understand that people come to your resort for rest and fun so patience and smiles would make all people comfortable being their. What I mean, if your don't like ..."

Reviewed on 30 Jul 2026

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 £159 per night from 19 Aug to 20 Aug
£159
19 Aug - 20 Aug
includes taxes & fees
8.8/10 Excellent! (3,704 reviews)
"Second time staying at this resort and had a wonderful experience. Never disappoints from the staff and the amenities. Thank you for making my stay pleasant"

Reviewed on 30 Jul 2026

Margaritaville Resort Orlando with H2O Waterpark
See all 44,877 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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Stay near popular Lakeland - Winter Haven attractions

A detailed model of a cityscape with various buildings, including a tall skyscraper, a modern building, and a historic building with a red roof.

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.
See properties

What to do in Lakeland - Winter Haven

LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

£29
per traveller
86% of travellers recommend
LEGOLAND® Florida Tickets
LEGOLAND Florida FasTrack Pass

LEGOLAND Florida FasTrack Pass

£65
per traveller
LEGOLAND Florida FasTrack Pass
Swimming manatees in Orlando.

From Orlando: Manatees Swim, Snorkel and Boat Day Tour with Hotel Pickup

£121
per adult
98% of travellers recommend
From Orlando: Manatees Swim, Snorkel and Boat Day Tour with Hotel Pickup
See all activities in Lakeland - Winter Haven

Frequently asked questions

Why should I book my Lakeland - Winter Haven holiday with Expedia?
With excellent-value airfares, car hire and accommodation options all in the same place, Expedia makes booking your Lakeland - Winter Haven getaway a cinch. Plus, we can help you bundle your bookings into a package holiday so you can enjoy even more savings. Choose from awesome retreats, add flights and/or a hire car (and maybe even some exciting activities!) and get unbeatable prices. Need to change plans? Expedia offers a flexible cancellation policy for many bookings. To learn more, visit our Customer Service Portal link.
When is the best time of year to holiday in Lakeland - Winter Haven?
If you love the excitement that comes with peak season, head to Lakeland - Winter Haven in January, February and March. If you prefer a more relaxed vibe, June, July and August are better times to visit. To give you an idea of what type of weather you can experience, the average temperature during the day in January, the coolest time of year in Lakeland - Winter Haven, is 16ºC. The warmest month here is June, when temperatures are around 27ºC.
What are the top hotels for my holiday in Lakeland - Winter Haven?
When it comes to properties in Davenport, Hyatt Place Lakeland Centre and Four Corners Area Pool Homes by SVV are two fantastic options. If you're heading to Haines City, Quality Inn Clermont West Kissimmee and Baymont by Wyndham Lakeland look forward to welcoming you.
How do I get a cheap holiday to Lakeland - Winter Haven?
Bundling your hotel and flight with Expedia won't just save you time — it'll save you a tidy sum too. A Lakeland - Winter Haven holiday makes it a cinch to create the perfect trip. With more than 400 airlines all over the world to pick from, finding flights that fit your busy schedule won't be a challenge. Not only that, we've got over 321,000 hotel options globally to choose from. Talk about choice! Whatever your budget, Expedia brings the world within your reach. Learn more about how you can save money on your holiday when you combine your hotel and flight bookings with Expedia.
What should I do on my Lakeland - Winter Haven holiday?
Organise your next holiday in Lakeland - Winter Haven around popular attractions such as LEGOLAND® Florida and Publix Field at Joker Marchant Stadium. Many visitors also highly recommend Chain of Lakes Park and Polk Museum of Art.
What are the best cities to stay in when on holiday in Lakeland - Winter Haven?
To see popular sights like LEGOLAND® Florida and Chain of Lakes Park, Winter Haven is the place to be. Lots of travellers also love spending time in Lakeland, home to Publix Field at Joker Marchant Stadium and Polk Museum of Art. If time isn't an issue, why not visit both cities?
Do I need a visa for my Lakeland - Winter Haven holiday?
Research the latest rules on official government websites. Your nationality and whether you're travelling for leisure, business or study will determine if you'll need a visa for Lakeland - Winter Haven. Find out about the application process, including the required documentation, turnaround times and fees. Start your application well in advance to allow sufficient processing time. Some visas can take weeks or even months to obtain, depending on the country.
What should I wear on my Lakeland - Winter Haven holiday?
Although everyone's style is different, it can be helpful to have some guidelines for what to wear on your holiday in Lakeland - Winter Haven. Consider browsing style blogs before you head off for inspiration on local fashion trends. In Lakeland - Winter Haven, average daytime temperatures reach 27ºC during June, making it the warmest month. January is the coolest time of the year here, with the mercury hovering around 16ºC during the day. Make packing a cinch by checking the forecast for every place you're visiting.
What does an Expedia Lakeland - Winter Haven holiday include?
That depends entirely on you. Simply choose from a variety of Lakeland - Winter Haven packages, such as a hotel, flight and hire car. You can also book a hotel and a flight, or a car hire with a flight. Once you've made your booking, add on the fun stuff like experiences and activities. Whatever your ideal Lakeland - Winter Haven break looks like, get set to save! Explore all sorts of styles on Expedia and discover the perfect fit for you and your travel companions. From the most sought-after property types, like private holiday homes and villas, to many other options, there are plenty of holiday retreats in Lakeland - Winter Haven to choose from so you can plan your stay to suit your needs.
Does Expedia offer Book Now, Pay Later Lakeland - Winter Haven holidays?
Good news! We do. Expedia has partnered with online lender Klarna to help you easily pay for your holiday in manageable instalments. Simply select the payment plan that suits best during checkout and take away the stress of budgeting for your trip. Don't forget to bundle your accommodation, flights and activities with Expedia to get the biggest bang for your travel buck. Take a look at our flexible payment options below:

  • Pay monthly holidays: Realise your holiday dreams sooner with Klarna's convenient payment plans. If paying in multiple transactions sounds right for you, pick this option at checkout.
  • No-deposit holidays: When you spot an incredible deal but don't have the full amount yet, Klarna's no-deposit holiday plan will allow you to Book Now, Pay Later to lock it in.

Can I choose my airline with a Lakeland - Winter Haven Expedia holiday?
Yes, and with over 400 airlines to select from globally, it's all about choice. Take a look at the available options and find out which airline suits your budget and needs.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.