Lakeland - Winter Haven Vacations 2025 from CA $559

Lakeland - Winter Haven flight + hotel packages

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

Highland Down Town Tampa

Old Seminole Heights

Save 100% on your flight

per person

Jan. 11 - Jan. 18

found 1 day ago

Roundtrip flight included

Detroit (DTW) to Tampa (TPA)

Stay at this 3.5-star vacation home in Tampa. Enjoy free WiFi, free parking, and a garden. Popular attractions Raymond James Stadium and Busch Gardens Tampa Bay are located nearby.

Ocean Club Treasure Island Hotel

per person

Feb. 16 - Feb. 23

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.

Wyndham Grand Clearwater Beach

Save 100% on your flight

per person

Feb. 6 - Feb. 11

found 1 day ago

Roundtrip non-stop flight included

Buffalo (BUF) to Tampa (TPA)

Stay at this 4-star 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 Pier 60 Park and Clearwater Beach are located nearby.

The Don CeSar

Save 100% on your flight

per person

Feb. 6 - Feb. 11

found 1 day ago

Roundtrip non-stop flight included

Buffalo (BUF) to Tampa (TPA)

Book a stay at this beach hotel in St. Pete Beach. Enjoy 2 outdoor pools, a full-service spa, and 2 restaurants. Our guests praise the pool and the helpful staff in our reviews. Popular attractions John's Pass Village & Boardwalk and Fort De Soto Park are located nearby.

BeachTrail Lodging

Save 100% on your flight

per person

Feb. 6 - Feb. 11

found 1 day ago

Roundtrip non-stop flight included

Buffalo (BUF) to Tampa (TPA)

Stay at this 3-star condo in Indian Rocks Beach. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions St. Petersburg - Clearwater Beaches and Sand Key Park 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 $177

CA $269 total

includes taxes & fees

15 Dec - 16 Dec

Stay at this 4-star family-friendly resort in Four Corners. Enjoy free WiFi, 3 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

Free cancellation

Reserve now, pay when you stay

CA $131

CA $197 total

includes taxes & fees

16 Dec - 17 Dec

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 and Disney's Animal Kingdom® Theme Park are located nearby.

Pool

Parking included

Margaritaville Resort Orlando

8000 Fins Up Circle, Kissimmee, FL

CA $166

CA $252 total

includes taxes & fees

15 Dec - 16 Dec

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 Aqua Sol Orlando West

17777 Bali Blvd, Winter Garden, FL

Free cancellation

Reserve now, pay when you stay

CA $131

CA $187 total

includes taxes & fees

8 Dec - 9 Dec

Stay at this 4-star 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

Holiday Inn Club Vacations at Orange Lake Resort, an IHG Hotel

8505 W Irlo Bronson Memorial Hwy, Kissimmee, FL

Free cancellation

CA $127

CA $190 total

includes taxes & fees

19 Dec - 20 Dec

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

Sonder Cirrus

7888 West Irlo Bronson Memorial Highway, Kissimmee, FL

CA $128

CA $145 total

includes taxes & fees

16 Dec - 17 Dec

Stay at this 3.5-star hotel in Kissimmee. Enjoy free parking, a free theme park shuttle, and a fitness center. 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

Parking included

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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

Explore the great outdoors at Bok Tower Gardens, a lovely green space in Lake Wales. Stroll along the lakeside in this family-friendly area, or check out its top-notch restaurants.

Dinosaur World

5/5(1 review)

You can enjoy some culture when you stop by Dinosaur World in Plant City. Discover the area's top-notch restaurants and 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 $559. 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.