Lakeland - Winter Haven Vacations 2026 from CA $1,209

Name: Hilton Vacation Club Mystic Dunes Orlando
Price range: CA $137

Lakeland - Winter Haven flight + hotel packages

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

SkyBeach Resort

Greater Pinellas Point

CA $1,209

per person

May 19 - May 23

found 13 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Tampa (TPA)

Book a stay at this beach hotel in St. Petersburg. Enjoy 2 outdoor pools, 2 restaurants, and a private beach. Popular attractions Salvador Dali Museum and Fort De Soto Park are located nearby.

Plaza Beach Hotel Beachfront Resort

CA $1,552

per person

May 23 - May 30

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) 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 Avalon Club

CA $1,416

per person

May 28 - May 31

found 13 hours ago

Roundtrip flight included

Montreal (YUL) to Tampa (TPA)

Book a stay at this 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.

RumFish Beach at TradeWinds

CA $1,265

per person

May 23 - May 30

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Tampa (TPA)

Book a stay at this beach resort in St. Pete Beach. Enjoy free WiFi, 4 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff in our reviews. Popular attractions John's Pass Village & Boardwalk and Pass-a-Grille Beach are located nearby.

The Sarasota Modern, a Tribute Portfolio Hotel

Central Sarasota

CA $1,592

per person

Jun 6 - Jun 13

found 18 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Tampa (TPA)

Book a stay at this business-friendly hotel in Sarasota. Enjoy free WiFi, 3 outdoor pools, and 2 bars/lounges. Our guests praise the pool and the helpful staff 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 $233

CA $338 total

May 18 - May 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.

Holiday Inn Club Vacations at Orange Lake Resort by IHG

8505 W Irlo Bronson Memorial Hwy Kissimmee FL

Free cancellation

CA $204

CA $290 total

Apr 28 - Apr 29

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.

Margaritaville Resort Orlando with H2O Waterpark

8000 Fins Up Circle Kissimmee FL

Free cancellation

Reserve now, pay when you stay

CA $176

CA $275 total

May 17 - May 18

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.

Westgate Town Center Resort

7700 Westgate Blvd. Kissimmee FL

Free cancellation

Reserve now, pay when you stay

CA $124

CA $187 total

May 3 - May 4

includes taxes & fees

Book a stay at this 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 Complex are located nearby.

Hilton Vacation Club Mystic Dunes Orlando

7600 Mystic Dunes Lane Kissimmee FL

Free cancellation

Reserve now, pay when you stay

CA $137

CA $203 total

Apr 28 - Apr 29

includes taxes & fees

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

Westgate Vacation Villas Resort

7700 Westgate Blvd. Kissimmee FL

Free cancellation

Reserve now, pay when you stay

CA $116

CA $179 total

May 4 - May 5

includes taxes & fees

Book a stay at this family-friendly resort in Kissimmee. Enjoy free parking, 14 outdoor pools, and 2 restaurants. 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 Complex are located nearby.

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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.

A Lockheed XFV plane outside the Sun n Fun Florida Air Museum at Lakeland

Sun N Fun Air Museum

You can spend time browsing the exhibits at Sun N Fun Air Museum during your trip to Lakeland. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

Wooton park on lake Dora in Tavares, Florida

Lakeside Village

You can search for that perfect souvenir at Lakeside Village during your visit to Lakeland. Amble around the area's lakeside or attend a sporting event.

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 $1,209. 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.