Lakeland - Winter Haven Vacation Packages

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Photo by Lakeland Convention and Visitors Bureau

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Your Lakeland - Winter Haven Vacation

With everything organized before you go, our Lakeland - Winter Haven vacation packages let you focus on having fun. Known for its golfing, walking trails and family-friendly attractions, the only thing left to do is kick back and enjoy every unforgettable moment. Kick off your trip to Lakeland - Winter Haven with a few nights in Lakeland visiting popular sights like RP Funding Centre and Lakeside Village. Davenport is another city that draws travellers from far and wide. Reunion Resort Golf Course and Southern Dunes Golf and Country Club are two of the top places to see here. When it's time to stop dreaming and start packing, Expedia will help turn your Lakeland - Winter Haven vacation into a reality.

Top Lakeland - Winter Haven Vacation Deals

Price found within the past 48 hours. Click for updated prices.
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Central Sarasota
Price was CA $1,360, price is now CA $940 per person
CA $940
per person
Sep 22 - Sep 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
9/10 Wonderful! (1,002 reviews)

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Price was CA $2,584, price is now CA $1,624 per person
CA $1,624
per person
Sep 18 - Sep 25
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Tampa (TPA)
9.6/10 Exceptional! (1,096 reviews)
This has got to be the Best Deal I have found in a Very Long time. Super clean, like new condition. Huge, sleeps six, full kitchen. Basically a condo. Loved everything about it, we will be Back !!

Reviewed on Jul 29, 2026

St Pete Beach Suites

St Pete Beach Suites

3 out of 5
Price was CA $1,918, price is now CA $1,315 per person
CA $1,315
per person
Oct 5 - Oct 10
found 13 hours ago
Roundtrip flight included
Montreal (YMQ) to Tampa (TPA)
9.2/10 Wonderful! (1,002 reviews)
Excellent property with old world Floridian charm.

Reviewed on Jul 29, 2026

CW Hotel

CW Hotel

4 out of 5
Price was CA $2,010, price is now CA $1,410 per person
CA $1,410
per person
Aug 31 - Sep 6
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Tampa (TPA)
9.8/10 Exceptional! (16 reviews)
New beautiful condo full equiped

Reviewed on Jul 30, 2026

Saddlebrook Resort

Saddlebrook Resort

4 out of 5
Wesley Chapel South
Price was CA $1,397, price is now CA $1,000 per person
CA $1,000
per person
Sep 1 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
8/10 Very good! (142 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

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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 CA $237 per night from Aug 4 to Aug 5
CA $237
CA $344 total
Aug 4 - Aug 5
includes taxes & fees
8/10 Very good! (10,621 reviews)
"I Never ever want to stay at that nasty disgusting place again. On my arrive as I check in and went to my room omg. It’s was so nasty and smelling it was a shame. The bathroom toilet was nasty you can see dirty in the toilet and the place had like hair all On the carpet like some one before had a ..."

Reviewed on Jul 30, 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 CA $149 per night from Aug 30 to Aug 31
CA $149
CA $231 total
Aug 30 - Aug 31
includes taxes & fees
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 CA $195 per night from Aug 17 to Aug 18
CA $195
CA $298 total
Aug 17 - Aug 18
includes taxes & fees
Margaritaville Resort Orlando with H2O Waterpark
See all 44,550 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 Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

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 FasTrack Pass

LEGOLAND Florida FasTrack Pass

CA $123
per traveller
LEGOLAND Florida FasTrack Pass
Scenic One Hour Airboat Tour

Boggy Creek Scenic Everglades Airboat Tour

CA $63
per adult
98% of travellers recommend
Boggy Creek Scenic Everglades Airboat Tour
Swimming manatees in Orlando.

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

CA $228
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

How much does a Lakeland - Winter Haven vacation package cost?
Custom build your Lakeland - Winter Haven package from as little as CA $940. 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.

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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.