Lakeland - Winter Haven Vacations 2025/2026 from CA $1,048

Lakeland - Winter Haven flight + hotel packages

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

Kompose Boutique Hotel

CA $1,048

per person

Jan 26 - Feb 2

found 4 hours ago

Roundtrip non-stop flight included

Halifax (YHZ) to Tampa (TPA)

Book a stay at this business-friendly hotel in Sarasota. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the breakfast and the pool in our reviews. Popular attractions Lido Beach and St. Armands Circle are located nearby.

The Avalon Club

CA $2,660

per person

Dec 28 - Jan 2

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Tampa (TPA)

Stay at this 4-star beach aparthotel in Clearwater Beach. Enjoy a beach locale, a fitness center, and parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Clearwater Beach and Sand Key Park are located nearby.

Crystal Palms Beach Resort

Sunshine Beach

CA $2,081

per person

Dec 27 - Jan 3

found 2 days ago

Roundtrip non-stop flight included

Toronto (YYZ) to Tampa (TPA)

Stay at this 3.5-star aparthotel in Treasure Island. Enjoy a 24-hour front desk, dry cleaning or laundry services, and laundry facilities. Our guests praise the helpful staff in our reviews. Popular attractions John's Pass Village & Boardwalk and St. Petersburg Municipal Beach are located nearby.

Provident Oceana Beachfront Suites

CA $1,285

per person

Jan 10 - Jan 17

found 16 hours ago

Roundtrip flight included

Toronto (YYZ) to Tampa (TPA)

Book a stay at this beach condo in Treasure Island. Enjoy 2 outdoor pools, a beach locale, and 2 hot tubs. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions John's Pass Village & Boardwalk and St. Petersburg - Clearwater Beaches are located nearby.

voco Sarasota by IHG

Central Sarasota

CA $1,699

per person

Feb 7 - Feb 14

found 10 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Tampa (TPA)

Book a stay at this business-friendly hotel in Sarasota. Enjoy breakfast (surcharge), 24-hour room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Lido Beach and Siesta Key Beach are located nearby.

Top Lakeland - Winter Haven hotels deals

The Grove Resort & Water Park Orlando

14501 Grove Resort Avenue Winter Garden FL

Free cancellation

Reserve now, pay when you stay

CA $209

CA $298 total

Nov 18 - Nov 19

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.

Pool

Hot tub

Hilton Vacation Club Mystic Dunes Orlando

7600 Mystic Dunes Lane Kissimmee FL

CA $137

CA $203 total

Nov 24 - Nov 25

includes taxes & fees

Book a stay at this golf property in Kissimmee. Enjoy free WiFi, free parking, and 4 outdoor pools. 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.

Pool

Parking included

Margaritaville Resort Orlando with H2O Waterpark

8000 Fins Up Circle, Kissimmee, FL

Free cancellation

Reserve now, pay when you stay

CA $172

CA $265 total

Nov 24 - Nov 25

includes taxes & fees

Stay at this 4-star 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.

Pool

Hot tub

Holiday Inn Club Vacations at Orange Lake Resort by IHG

8505 W Irlo Bronson Memorial Hwy, Kissimmee, FL

CA $149

CA $229 total

Nov 20 - Nov 21

includes taxes & fees

Stay at this 4-star 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.

Pool

Hot tub

Hilton Vacation Club Aqua Sol Orlando West

17777 Bali Blvd Winter Garden FL

CA $149

CA $207 total

Dec 8 - Dec 9

includes taxes & fees

Book a stay at this family-friendly hotel in Four Corners. Enjoy free WiFi, free parking, and 2 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.

Pool

Hot tub

Omni Orlando Resort at ChampionsGate

1500 Masters Blvd Davenport FL

Free cancellation

Reserve now, pay when you stay

CA $201

CA $307 total

Dec 15 - Dec 16

includes taxes & fees

Stay at this 4-star spa hotel in Four Corners. Enjoy free WiFi, 6 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Reunion Resort Golf Course and Mystic Dunes Golf Club are located nearby.

Pool

Spa

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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.

Popular places to visit

LEGOLAND® Florida

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.

Bok Tower Gardens

Bok Tower Gardens is just one of the places to see in Lake Wales, so why not enjoy the other things to explore during your travels? Stroll along the lakeside in this family-friendly area, or check out its top-notch restaurants.

Dinosaur World

You can spend time exploring the galleries in Dinosaur World in Plant City. Wander around the area's picturesque gardens or experience its acclaimed theater scene.

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 $1,048. 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.