Lakeland - Winter Haven Holidays

Photo by Lakeland Convention and Visitors Bureau

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Top Flight + Hotel Deals in Lakeland - Winter Haven

Price found within the past 48 hours. Click for updated prices.
ChartHouse Clearwater Beach Marina Hotel

ChartHouse Clearwater Beach Marina Hotel

2 out of 5
Price was €1,090, price is now €862 per person
€862
per person
4 Aug - 9 Aug
found 20 hours ago
Return flight included
Toronto (YTO) to Tampa (TPA)
9.6/10 Exceptional! (1,179 reviews)
I enjoy the property, the staff were great and the property was clean. The beach was great, clean and beautiful. The hotel pool was ok but not great. The restaurant jimmy wasn’t great. The drink needed to be better.

Reviewed on 3 Jul 2026

CW Hotel

CW Hotel

4 out of 5
Save 100% on your flight
Price was €1,509, price is now €1,018 per person
€1,018
per person
4 Aug - 9 Aug
found 20 hours ago
Return flight included
Toronto (YTO) to Tampa (TPA)
No reviews

The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was €2,030, price is now €1,439 per person
€1,439
per person
4 Aug - 9 Aug
found 20 hours ago
Return flight included
Toronto (YTO) to Tampa (TPA)
9.4/10 Exceptional! (561 reviews)
10/10 would recommend this property. Clean, freindly staff, complimentary coffee bar, and great location are just some of the perks of staying here. The rooftop bar and pool is a nice way the wind down your day that included a comp glass of champagne amd views of awesome sunsets. The property also offered access to free beach chairs and umbrellas for use on the beach which is a huge plus in my book. Numerous stores and restaurants well within walking distance of the hotel. So if your looking for a nice hotel while visiting CWB, look no further. You will not be disappointed. We will definitely be returning on our next beach vacation.

Reviewed on 1 Jul 2026

The Marker

The Marker

2 out of 5
Save 100% on your flight
Price was €1,787, price is now €1,275 per person
€1,275
per person
4 Aug - 9 Aug
found 20 hours ago
Return flight included
Toronto (YTO) to Tampa (TPA)
6/10 (3 reviews)

Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
Price was €1,383, price is now €995 per person
€995
per person
4 Aug - 9 Aug
found 20 hours ago
Return flight included
Toronto (YTO) to Tampa (TPA)
9.4/10 Exceptional! (3,408 reviews)
First of all- Expedia really dropped the ball! They properly DID NOT advise of all the “hidden fees” pertaining to this hotel. Shame on them! What was meant to be a fun and relaxing trip, quickly turned stressful and chaotic. The staff could care less, and not helpful at all. The restaurants were disgusting. Housekeeping took forever to turn the room, good luck getting your towels replaced. No microwave. Sink gets stopped up, toilet was difficult to flush. Ugh.. I could go on!

Reviewed on 3 Jul 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
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

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 €234 per night from 3 Aug to 4 Aug
€234
3 Aug - 4 Aug
includes taxes & fees
8/10 Very good! (10,317 reviews)
"We traveled as a family of 3 with a child to visit Theam park. Resort was amazing location could not be any better. Balcony view at least from our room was amazing. Rooms need some small maintenance nothing crasy, dishwasher was a bit rusty due to detergent they provide, first time in my life I have ..."

Reviewed on 4 Jul 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 €216 per night from 3 Aug to 4 Aug
€216
3 Aug - 4 Aug
includes taxes & fees
8.8/10 Excellent! (3,626 reviews)
"Title: A perfect tropical paradise with world-class service!" The saying First Impression is your Last Impression, "I recently stayed at the Margaritaville Resort Orlando and had an absolutely wonderful experience. From the moment we arrived, the hospitality from the staff was exceptional. Every ..."

Reviewed on 3 Jul 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 €161 per night from 3 Aug to 4 Aug
€161
3 Aug - 4 Aug
includes taxes & fees
8.8/10 Excellent! (3,062 reviews)
"-"

Reviewed on 3 Jul 2026

Holiday Inn Club Vacations at Orange Lake Resort by IHG
See all 43,950 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

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

Walt Disney World® Resort Theme Park Tickets

Walt Disney World® Resort Theme Park Tickets

€158
per adult
88% of travellers recommend
Walt Disney World® Resort Theme Park Tickets
LEGOLAND Florida FasTrack Pass

LEGOLAND Florida FasTrack Pass

€75
per traveller
LEGOLAND Florida FasTrack Pass
Magic Kingdom® Park

Walt Disney World® Theme Park Tickets

€684
per adult
88% of travellers recommend
Walt Disney World® 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 €862. 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.