Lakeland - Winter Haven Vacations 2026 from CA $433

Lakeland - Winter Haven flight + hotel packages

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

Saddlebrook Resort

Wesley Chapel South

CA $433

per person

Feb 8 - Feb 13

found 9 hours ago

Roundtrip flight included

Detroit (DTW) to Tampa (TPA)

Book a stay at this spa resort in Wesley Chapel. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the pool and the clean rooms in our reviews. Popular attractions Saddlebrook Golf Course and KRATE Shopping Center are located nearby.

Family Home Tampa

Forest Hills

CA $875

per person

Feb 28 - Mar 5

found 11 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Tampa (TPA)

Stay at this guesthouse in Tampa. Enjoy free WiFi, free parking, and a garden. Popular attractions Busch Gardens Tampa Bay and Raymond James Stadium are located nearby.

Zoo House Down Town Tampa

Riverbend

CA $544

per person

Feb 28 - Mar 5

found 11 hours ago

Roundtrip flight included

Toronto (YYZ) to Tampa (TPA)

Stay at this vacation home in Tampa. Enjoy free WiFi and free parking. Popular attractions Raymond James Stadium and Busch Gardens Tampa Bay are located nearby.

Plaza Beach Hotel Beachfront Resort

CA $1,667

per person

Mar 17 - Mar 22

found 4 hours ago

Roundtrip flight included

Detroit (DTW) to Tampa (TPA)

Book a stay at this beach hotel in St. Pete Beach. Enjoy free WiFi, a private beach, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions John's Pass Village & Boardwalk and Fort De Soto Park are located nearby.

The Residences at Siesta Key Beach by Hyatt Vacation Club

South Village

CA $1,828

per person

Apr 4 - Apr 7

found 2 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Tampa (TPA)

Book a stay at this beach aparthotel in Siesta Key. Enjoy free breakfast, free WiFi, and free valet parking. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Siesta Key Beach and Lido 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 $227

CA $331 total

Jan 12 - Jan 13

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

Margaritaville Resort Orlando

8000 Fins Up Circle Kissimmee FL

Free cancellation

Reserve now, pay when you stay

CA $198

CA $300 total

Jan 12 - Jan 13

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.

Pool

Hot tub

Hilton Vacation Club Mystic Dunes Orlando

7600 Mystic Dunes Lane Kissimmee FL

Free cancellation

Reserve now, pay when you stay

CA $138

CA $204 total

Jan 14 - Jan 15

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

Holiday Inn Club Vacations at Orange Lake Resort by IHG

8505 W Irlo Bronson Memorial Hwy Kissimmee FL

CA $157

CA $237 total

Jan 9 - Jan 10

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.

Pool

Hot tub

Destiny Palms Hotel Maingate West

8536 W Irlo Bronson Memorial Hwy Kissimmee FL

CA $94

CA $113 total

Jan 12 - Jan 13

includes taxes & fees

Stay at this hotel in Kissimmee. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Disney's Animal Kingdom® Theme Park and Disney's Hollywood Studios® are located nearby.

Pool

Parking included

Hilton Vacation Club Aqua Sol Orlando West

17777 Bali Blvd Winter Garden FL

Free cancellation

Reserve now, pay when you stay

CA $146

CA $203 total

Jan 13 - Jan 14

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

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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 lively festivals.

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 $433. 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.