Lakeland - Winter Haven Holidays from £1,062

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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.
The Barrymore Hotel Tampa Riverwalk

The Barrymore Hotel Tampa Riverwalk

3 out of 5
Downtown Tampa
Price was £1,383, price is now £1,062 per person
£1,062
per person
15 Aug - 22 Aug
found 1 day ago
Return direct flight included
London (LHR) to Tampa (TPA)
8.6/10 Excellent! (2,620 reviews)
Amazing stay at the Barrymore Hotel Tampa Riverwalk.Friendly staff, clean rooms with great amenities, a nice kid-friendly pool, excellent food and drinks in the restaurant.Highly recommended ⭐️⭐️⭐️⭐️⭐️

Reviewed on 15 Jun 2026

Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Price was £2,133, price is now £1,489 per person
£1,489
per person
16 Aug - 23 Aug
found 16 hours ago
Return direct flight included
Manchester (MAN) to Tampa (TPA)
9.2/10 Wonderful! (522 reviews)
We had a wonderful stay at Cedar Cove! The beach access was absolutely amazing, and everything throughout the property was very clean and well maintained. The beach itself was beautiful, with clear water and no seaweed, which made the experience even better. The only improvement I would suggest is updating the beds. They felt a bit outdated and were not very stable. Other than that, everything was excellent, and we would definitely stay here again.

Reviewed on 12 Jun 2026

Seaside at Anna Maria Island Inn

Seaside at Anna Maria Island Inn

3 out of 5
Save 100% on your flight
Price was £3,534, price is now £2,529 per person
£2,529
per person
16 Aug - 23 Aug
found 16 hours ago
Return direct flight included
Manchester (MAN) to Tampa (TPA)
9.4/10 Exceptional! (109 reviews)
Would be nice to have a cooler available to bring over to the beach

Reviewed on 8 Jun 2026

Driftwood at Anna Maria Island Inn

Driftwood at Anna Maria Island Inn

3 out of 5
Price was £1,786, price is now £1,354 per person
£1,354
per person
16 Aug - 23 Aug
found 16 hours ago
Return direct flight included
Manchester (MAN) to Tampa (TPA)
8.4/10 Very Good! (119 reviews)
Room was not that clean, little details. Sofa had a few stains and room service was just

Reviewed on 8 Jun 2026

Anna Maria Beach Resort

Anna Maria Beach Resort

3.5 out of 5
Price was £3,000, price is now £2,325 per person
£2,325
per person
16 Aug - 23 Aug
found 16 hours ago
Return direct flight included
Manchester (MAN) to Tampa (TPA)
9.4/10 Exceptional! (351 reviews)
Was a wonderful stay for our anniversary

Reviewed on 10 Jun 2026

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

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 £208 per night from 22 Jun to 23 Jun
£208
22 Jun - 23 Jun
includes taxes & fees
8/10 Very Good! (10,230 reviews)
"La habitación súper limpia"

Reviewed on 14 Jun 2026

The Grove Resort & Water Park Orlando
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 £171 per night from 14 Jul to 15 Jul
£171
14 Jul - 15 Jul
includes taxes & fees
8.8/10 Excellent! (3,667 reviews)
"The lobby was amazing but just after checking in, the timeshare folks wanted to grab your attention and sign you up for a presentation which ruined the vibe. The music wasn’t playing at the pool which was a bummer. The hotel room was okay, nothing spectacular."

Reviewed on 15 Jun 2026

Margaritaville Resort Orlando with H2O Waterpark
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 £143 per night from 22 Jun to 23 Jun
£143
22 Jun - 23 Jun
includes taxes & fees
8.8/10 Excellent! (3,009 reviews)
"Rooms were beautiful but the pools could use some love… also wish the amenities were open alittle bit later"

Reviewed on 15 Jun 2026

Holiday Inn Club Vacations at Orange Lake Resort by IHG
See all 43,890 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
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Beach Holidays
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Family Friendly Holidays

Stay near popular Lakeland - Winter Haven attractions

LEGOLAND® Florida

4.5/5 (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

Frequently asked questions

Can I cancel my flight booking to Lakeland - Winter Haven due to COVID-19?
Our handy Customer Service Portal is your one-stop shop for most travel questions, including about flight changes due to COVID-19. For extra peace of mind, we suggest looking over the terms and conditions of your preferred carrier before reserving your tickets.
What's the best way to find cheap flights to Lakeland - Winter Haven that have flexible change policies?
It's as easy as counting 1-2-3 with Expedia. Firstly, enter your preferred dates and destination and click on "Search." Next step? Check "No change fee" just below the "Flexible change policies" subheading on the left-hand side of your screen. Step 3. Book a cheap and flexible ticket to Lakeland - Winter Haven.
What are some of the general tips for travellers to Lakeland - Winter Haven during the COVID-19 outbreak?
The COVID-19 pandemic has brought about substantial changes to how we travel. If you're planning a holiday in Lakeland - Winter Haven, the following tips will help you navigate this new travelling reality:
  • Understand the rules and restrictions in both your destination and origin. You may not be able to travel depending on local circumstances, so don't forget to check before you book your flight.
  • You must wear a face mask at the airport, including at screening checkpoints. Be prepared to lower your mask for ID verification when asked by a TSA officer.
  • Instead of handing a TSA employee your boarding pass, place it directly on the scanner yourself. When that's done, hold it up for inspection.
  • One container of liquid hand sanitizer is now allowed in your carry-on baggage. It must not be larger than 12 oz (350 ml), and you'll have to take it out of your bag for X-ray screening.
  • Put any personal items (keys, wallet and phone) in your carry-on instead of a bin to reduce handling during the screening process.
  • Transport any food items in a clear plastic bag and also put them in a screening bin. Separating food from your carry-on means it's less likely a TSA agent will need to open your bag for inspection.

Which airlines fly to Lakeland - Winter Haven?
Lock in your fare with Delta and then start organising your Lakeland - Winter Haven to-do list. This popular airline has 1472 flights each month to Orlando Intl. Airport (MCO), a central gateway.
How can I find cheap tickets to Lakeland - Winter Haven?
For an unbeatable deal to Lakeland - Winter Haven, book well ahead. Also take advantage of Expedia's handy "flexible dates" feature above your search results. This will compare the cheapest prices for similar time frames. In the last seven days, was the best price for a flight to Lakeland - Winter Haven.
How much is a flight to Lakeland - Winter Haven?
There were plenty of bargain fares up for grabs in the last seven days, with the price of a return ticket to Lakeland - Winter Haven ranging between and . Many lucky holiday makers nabbed one-way seats from () for just .
What are the most popular airports to fly into in Lakeland - Winter Haven?
Zip up your suitcase and jet into Orlando Intl. Airport (MCO), Lakeland - Winter Haven's major flight hub. Book a seat on one of the 13460 flights that land at this awesome destination each month.
When is the cheapest time to fly to Lakeland - Winter Haven?
Flying on a Tuesday, followed by a Monday, is generally the best way to get the cheapest fare. Steer clear of weekends if possible, because Saturday is typically the most expensive day. Spend the dollars you saved having a ball in Lakeland - Winter Haven instead!
How much is a plane ticket to Lakeland - Winter Haven?
Flights to Lakeland - Winter Haven ranged from to in the last seven days. Normally, the sooner you book the bigger the bargain.
Which airlines with flights to Lakeland - Winter Haven employ COVID-19 cleanliness policies?
As passengers take to the skies once again, most commercial airlines have implemented physical distancing and other important actions to help lessen the spread of COVID-19. Here are some great examples:
  • Southwest Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • Spirit Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • American Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.

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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. Flight-inclusive packages are ATOL protected.