Lakeland - Winter Haven Vacations 2025 from CA $528

Name: Hilton Vacation Club Mystic Dunes Orlando
Price range: CA $139

Lakeland - Winter Haven flight + hotel packages

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

Holiday Inn Express Hotel & Suites Tampa Northwest - Oldsmar by IHG

per person

May 17 - May 21

found 8 hours ago

Roundtrip flight included

Detroit (DTW) to Tampa (TPA)

Book a stay at this business-friendly hotel in Oldsmar. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Oldsmar Historical Society Museum and Oldsmar Flea Market are located nearby.

Saddlebrook Golf Resort & Spa Tampa North - Wesley Chapel

Wesley Chapel South

per person

May 17 - May 21

found 8 hours ago

Roundtrip flight included

Detroit (DTW) to Tampa (TPA)

Book a stay at this golf 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.

Ocean Club Treasure Island Hotel

Save 100% on your flight

per person

May 9 - May 13

found 1 day ago

Roundtrip flight included

Detroit (DTW) to Tampa (TPA)

Stay at this 4-star 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.

The Avalon Club

Save 100% on your flight

per person

Jun. 12 - Jun. 16

found 1 day ago

Roundtrip 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 Pier 60 Park are located nearby.

Legacy Vacation Resorts - Indian Shores

Save 100% on your flight

per person

Jun. 12 - Jun. 16

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Tampa (TPA)

Stay at this 3-star beach aparthotel in Indian Shores. Enjoy free WiFi, free parking, 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 St. Petersburg - Clearwater Beaches are located nearby.

Top Lakeland - Winter Haven hotels deals

The Grove Resort & Water Park Orlando

14501 Grove Resort Avenue, Winter Garden, FL

CA $245

CA $356 total

includes taxes & fees

May 6 - May 7

Stay at this 4-star family-friendly resort in Winter Garden. Enjoy free WiFi, 5 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

Holiday Inn Club Vacations at Orange Lake Resort by IHG

8505 W Irlo Bronson Memorial Hwy, Kissimmee, FL

Free cancellation

CA $210

CA $298 total

includes taxes & fees

Apr 29 - Apr 30

Stay at this 4-star golf resort in Kissimmee. Enjoy free parking, 7 outdoor pools, and 8 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 Aqua Sol Orlando West

17777 Bali Blvd, Winter Garden, FL

Free cancellation

Reserve now, pay when you stay

CA $151

CA $210 total

includes taxes & fees

Apr 28 - Apr 29

Stay at this 4-star family-friendly hotel in Winter Garden. 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

Margaritaville Resort Orlando with H2O Waterpark

8000 Fins Up Circle, Kissimmee, FL

CA $253

CA $358 total

includes taxes & fees

Apr 29 - Apr 30

Stay at this 4-star spa resort in Kissimmee. Enjoy 3 outdoor pools, a full-service spa, and 3 restaurants. 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

Spa

Hilton Vacation Club Mystic Dunes Orlando

7600 Mystic Dunes Lane, Kissimmee, FL

Free cancellation

Reserve now, pay when you stay

CA $139

CA $206 total

includes taxes & fees

May 6 - May 7

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

Westgate Town Center Resort

7700 Westgate Blvd., Kissimmee, FL

CA $125

CA $190 total

includes taxes & fees

Apr 27 - Apr 28

Stay at this 4-star family-friendly resort in Kissimmee. Enjoy free WiFi, free parking, and 14 outdoor pools. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Disney's Animal Kingdom® Theme Park and ESPN Wide World of Sports 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

4.5/5(72 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.

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

5/5(1 review)

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 $528. 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.