Lakeland - Winter Haven Vacations 2026 from CA $1,510

Name: Hilton Vacation Club Aqua Sol Orlando West
Price range: CA $147

Lakeland - Winter Haven flight + hotel packages

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

Treasure Island Hotel and Marina

CA $1,510

per person

May 16 - May 23

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Tampa (TPA)

Book a stay at this business-friendly hotel in Treasure Island. Enjoy free WiFi, a marina, and a rooftop terrace. 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.

Anna Maria Island Surfside Bungalow

CA $31,961

per person

May 27 - Jun 3

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Tampa (TPA)

Stay at this vacation home in Holmes Beach. Enjoy free parking, a beach bar, and an outdoor pool. Popular attractions Bradenton Beach and Anna Maria Beach are located nearby.

Anna Maria Island Edgewater Bungalow

CA $23,545

per person

May 27 - Jun 3

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Tampa (TPA)

Stay at this vacation home in Holmes Beach. Enjoy free parking, a beach bar, and an outdoor pool. Popular attractions Bradenton Beach and Anna Maria Beach are located nearby.

Bilmar Beach Resort

CA $1,633

per person

May 16 - May 23

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Tampa (TPA)

Book a stay at this beach resort in Treasure Island. Enjoy free WiFi, free parking, and 2 outdoor pools. 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.

Wyndham Grand Clearwater Beach

CA $1,788

per person

Jul 5 - Jul 11

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Tampa (TPA)

Book a stay at this 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 Clearwater Beach and Beach Walk 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 $247

CA $354 total

May 12 - May 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

Westgate Town Center Resort

7700 Westgate Blvd. Kissimmee FL

CA $125

CA $189 total

May 12 - May 13

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.

Pool

Hot tub

Margaritaville Resort Orlando with H2O Waterpark

8000 Fins Up Circle Kissimmee FL

CA $187

CA $288 total

May 13 - May 14

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

CA $138

CA $204 total

Apr 20 - Apr 21

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.

Pool

Free WiFi

Westgate Vacation Villas Resort

7700 Westgate Blvd. Kissimmee FL

CA $117

CA $180 total

May 12 - May 13

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.

Pool

Hot tub

Hilton Vacation Club Aqua Sol Orlando West

17777 Bali Blvd Winter Garden FL

CA $147

CA $204 total

Apr 20 - Apr 21

includes taxes & fees

Book a stay at this family-friendly hotel in Four Corners. Enjoy free WiFi, 2 outdoor pools, and free water park access. 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

4.5/5(73 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.

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 $1,510. 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.