Book Exclusive Lakeland - Winter Haven Vacation Packages

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Lakeland - Winter Haven flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Price was CA $1,759, price is now CA $1,090 per person
CA $1,090
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
Book a stay at this beach resort in Holmes Beach. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions Bean Point Beach and Anna Maria Beach are located nearby.
ChartHouse Clearwater Beach Marina Hotel

ChartHouse Clearwater Beach Marina Hotel

2 out of 5
Price was CA $1,943, price is now CA $1,136 per person
CA $1,136
per person
Sep 19 - Sep 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
Stay at this hotel in Clearwater Beach. Enjoy free WiFi, a rooftop terrace, and a 24-hour fitness center. Popular attractions Clearwater Beach and Pier 60 Park are located nearby.
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Price was CA $2,516, price is now CA $1,478 per person
CA $1,478
per person
Sep 6 - Sep 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
Book a stay at this beach hotel in Treasure Island. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the pool and the helpful staff in our reviews. Popular attractions John's Pass Village & Boardwalk and St. Petersburg - Clearwater Beaches are located nearby.
CW Hotel

CW Hotel

4 out of 5
Price was CA $2,205, price is now CA $1,367 per person
CA $1,367
per person
Sep 26 - Oct 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
Stay at this hotel in Clearwater Beach. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Popular attractions Clearwater Beach and Pier 60 Park are located nearby.
Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
Price was CA $2,840, price is now CA $1,971 per person
CA $1,971
per person
Aug 28 - Sep 4
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
Book a stay at this beach hotel in Clearwater Beach. Enjoy a full-service spa, 3 restaurants, and a beach locale. Our guests praise the breakfast and the pool in our reviews. Popular attractions Clearwater Beach and Pier 60 Park are located nearby.

Top Lakeland - Winter Haven hotels deals

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

4 out of 5
14501 Grove Resort Avenue Winter Garden FL
Free cancellation
Reserve now, pay when you stay
The price is CA $251 per night
CA $251
CA $360 total
Jul 20 - Jul 21
includes taxes & fees
Book a stay at this family-friendly resort in Four Corners. Enjoy free WiFi, 6 outdoor pools, and 3 restaurants. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Disney's Animal Kingdom® Theme Park and Disney's Hollywood Studios® are located nearby.
Margaritaville Resort Orlando with H2O Waterpark

Margaritaville Resort Orlando with H2O Waterpark

4 out of 5
8000 Fins Up Circle Kissimmee FL
Free cancellation
Reserve now, pay when you stay
The price is CA $190 per night
CA $190
CA $292 total
Aug 19 - Aug 20
includes taxes & fees
Book a stay at this spa resort in Kissimmee. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the restaurant in our reviews. Popular attractions Disney's Animal Kingdom® Theme Park and Disney's Hollywood Studios® are located nearby.
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
Free cancellation
The price is CA $141 per night
CA $141
CA $222 total
Aug 18 - Aug 19
includes taxes & fees
Book a stay at this golf resort in Kissimmee. Enjoy free WiFi, free parking, and 7 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Disney's Animal Kingdom® Theme Park and Disney's Hollywood Studios® are located nearby.
Hilton Vacation Club Mystic Dunes Orlando

Hilton Vacation Club Mystic Dunes Orlando

4 out of 5
7600 Mystic Dunes Lane Kissimmee FL
Free cancellation
Reserve now, pay when you stay
The price is CA $141 per night
CA $141
CA $207 total
Jul 26 - Jul 27
includes taxes & fees
Book a stay at this golf hotel in Kissimmee. Enjoy free WiFi, 4 outdoor pools, and a golf course. Our guests praise the pool and the restaurant in our reviews. Popular attractions ESPN Wide World of Sports Complex and Disney's Animal Kingdom® Theme Park are located nearby.
Embassy Suites By Hilton Orlando Sunset Walk

Embassy Suites By Hilton Orlando Sunset Walk

4 out of 5
3151 Sunset Walk Drive Kissimmee FL
Free cancellation
Reserve now, pay when you stay
The price is CA $194 per night
CA $194
CA $291 total
Aug 3 - Aug 4
includes taxes & fees
Stay at this resort in Kissimmee. Enjoy free breakfast, free WiFi, and room service. Popular attractions Disney's Animal Kingdom® Theme Park and Disney's Hollywood Studios® are located nearby.
Hilton Vacation Club Aqua Sol Orlando West

Hilton Vacation Club Aqua Sol Orlando West

4 out of 5
17777 Bali Blvd Winter Garden FL
Free cancellation
Reserve now, pay when you stay
The price is CA $132 per night
CA $132
CA $188 total
Aug 16 - Aug 17
includes taxes & fees
Book a stay at this family-friendly hotel in Four Corners. Enjoy free WiFi, 2 outdoor pools, and free water park access. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Disney's Animal Kingdom® Theme Park and Disney's Hollywood Studios® are located nearby.
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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)
Have a fun-filled day at LEGOLAND® Florida and find out why this is a popular theme park in Winter Haven. Amble around this family-friendly area's lakeside and enjoy its top-notch restaurants.
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Frequently asked questions

How much are vacation packages to Lakeland - Winter Haven?
Exciting adventures await in Lakeland - Winter Haven, with Travelocity vacation packages starting from as low as CA $1,090. In addition to flights and hotels, these amazing deals make it simple to visit more of our wonderful planet.
Where can I get the best vacation package deals for Lakeland - Winter Haven?
It's simple — look no further than Travelocity. With no less than 400 airlines and 1,000,000 properties worldwide, it's easy to put together a Lakeland - Winter Haven package deal that suits your travel style.
Why should I purchase my Lakeland - Winter Haven vacation package with Travelocity?
Because you'll never roam alone if you book through us, and we offer 24/7 customer support and first-rate service to boot. Add to that our Price Match Guarantee and countless destinations and experiences to select from. We're here to help you have the trip of a lifetime.
Can I save money on my Lakeland - Winter Haven car rental if I combine it with my hotel or flight?
Absolutely. And our Lakeland - Winter Haven vacation packages are the ideal way to do it. With just a few clicks you can save money and time by booking everything in one place. Pick up the keys to your rental car then set your own course. Looking for things to do? Add some tours or experiences to your package and save on those too.
Which airport is best for Lakeland - Winter Haven?
Most visitors come to Lakeland - Winter Haven via Orlando Intl. Airport (MCO) or Tampa Intl. Airport (TPA). St. Petersburg-Clearwater Intl. Airport (PIE) is also popular.
What is there to do in Lakeland - Winter Haven?
Lakeland - Winter Haven is full of fabulous photo-ops, however LEGOLAND® Florida and Publix Field at Joker Marchant Stadium are two favorites.

Photos of local treasures

Browse Lakeland - Winter Haven vacation photos for more inspiration

A baseball player in a white uniform with the number 20, a catcher in an orange uniform, and an umpire standing behind the catcher.
A child lying on the ground with colorful confetti around, in front of a LEGO sign that reads "LEGO LAND FLORIDA".
A vintage airplane and a classic car parked in front of a building with a sign that reads "Fantasy of Flight".
Two swans swimming in a calm body of water surrounded by greenery.
A large dinosaur statue in a park with green grass and trees.