Lakeland - Winter Haven Vacations 2025/2026 from CA $936

Lakeland - Winter Haven flight + hotel packages

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

Mar Bay Motel &Suites

CA $936

per person

Dec 6 - Dec 13

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Tampa (TPA)

Stay at this hotel in Safety Harbor. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Philippe Park and Chi Chi Rodriguez Golf Club are located nearby.

FUSION Resort Waterfront Suites

CA $1,483

per person

Dec 16 - Dec 23

found 5 hours ago

Roundtrip flight included

Montreal (YUL) to Tampa (TPA)

Stay at this 3.5-star aparthotel in Treasure Island. Enjoy free WiFi, free parking, and a rooftop terrace. 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.

voco Sarasota by IHG

Central Sarasota

CA $1,379

per person

Nov 30 - Dec 7

found 21 hours ago

Roundtrip flight included

Toronto (YYZ) to Tampa (TPA)

Stay at this 3.5-star 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.

The Westin Sarasota

Central Sarasota

CA $1,425

per person

Nov 30 - Dec 7

found 21 hours ago

Roundtrip flight included

Toronto (YYZ) to Tampa (TPA)

Stay at this 4-star spa hotel in Sarasota. Enjoy a full-service spa, 2 restaurants, and a rooftop terrace. Our guests praise the breakfast and the pool in our reviews. Popular attractions Lido Beach and Siesta Key Beach are located nearby.

Voyager Beach Club

Sunshine Beach

CA $1,029

per person

Nov 8 - Nov 15

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Tampa (TPA)

Book a stay at this beach condo in Treasure Island. Enjoy free WiFi, free parking, and a beach locale. 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

Free cancellation

Reserve now, pay when you stay

CA $235

CA $328 total

Sep 30 - Oct 1

includes taxes & fees

Stay at this 4-star 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

Free cancellation

Reserve now, pay when you stay

CA $153

CA $221 total

Oct 5 - Oct 6

includes taxes & fees

Stay at this 4-star 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 Disney's Animal Kingdom® Theme Park and Disney's Hollywood Studios® 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 $164

CA $256 total

Oct 6 - Oct 7

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

Free cancellation

CA $152

CA $232 total

Sep 30 - Oct 1

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

Free cancellation

Reserve now, pay when you stay

CA $157

CA $216 total

Oct 6 - Oct 7

includes taxes & fees

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

voco Kissimmee Orlando by IHG

7888 W Irlo Bronson Hwy, Kissimmee, FL

Free cancellation

CA $92

CA $104 total

Oct 2 - Oct 3

includes taxes & fees

Stay at this 3.5-star family-friendly aparthotel in Kissimmee. Enjoy free WiFi, a free theme park shuttle, and a fitness center. Popular attractions Disney's Animal Kingdom® Theme Park and Disney's Hollywood Studios® are located nearby.

Pool

Free WiFi

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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.

The Circle B Bar Reserve

Explore the great outdoors at The Circle B Bar Reserve, a lovely green space in Lakeland. Check out the shops and top-notch restaurants in this family-friendly area.

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 $936. 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.