Book Exclusive Lakeland - Winter Haven Vacation Packages

Choose one or more items to build your trip:

Lakeland - Winter Haven flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key

2.5 out of 5
Price was CA $1,685, price is now CA $1,109 per person
CA $1,109
per person
Nov 7 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
Book a stay at this business-friendly aparthotel in Sarasota. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Siesta Key Beach and Lido Beach are located nearby.
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Price was CA $3,598, price is now CA $2,012 per person
CA $2,012
per person
Nov 7 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
Book a stay at this beach resort in Holmes Beach. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions Bradenton Beach and Coquina Beach are located nearby.
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Central Sarasota
Price was CA $2,382, price is now CA $1,522 per person
CA $1,522
per person
Nov 7 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
Book a stay at this 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

The Westin Sarasota

4 out of 5
Central Sarasota
Price was CA $2,265, price is now CA $1,525 per person
CA $1,525
per person
Nov 7 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
Book a stay at this 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.
Captiva Beach Resort

Captiva Beach Resort

3 out of 5
South Village
Price was CA $1,998, price is now CA $1,358 per person
CA $1,358
per person
Nov 7 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
Book a stay at this beach condo in Siesta Key. Enjoy free WiFi, free parking, and a private beach. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Siesta Key Beach and Lido Beach are located nearby.

Top Lakeland - Winter Haven hotels deals

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

4 out of 5
14501 Grove Resort Avenue Winter Garden FL
Free cancellation
Reserve now, pay when you stay
The price is CA $238 per night
CA $238
CA $345 total
Oct 20 - Oct 21
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.
Margaritaville Resort Orlando with H2O Waterpark

Margaritaville Resort Orlando with H2O Waterpark

4 out of 5
8000 Fins Up Circle Kissimmee FL
Free cancellation
Reserve now, pay when you stay
The price is CA $180 per night
CA $180
CA $281 total
Sep 27 - Sep 28
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.
Holiday Inn Winter Haven by IHG

Holiday Inn Winter Haven by IHG

3 out of 5
200 Cypress Gardens Boulevard Winter Haven FL
Free cancellation
The price is CA $154 per night
CA $154
CA $172 total
Sep 27 - Sep 28
includes taxes & fees
Book a stay at this business-friendly hotel in Winter Haven. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions LEGOLAND® Florida and Theatre Winter Haven are located nearby.
Holiday Inn Club Vacations at Orange Lake Resort by IHG

Holiday Inn Club Vacations at Orange Lake Resort by IHG

4 out of 5
8505 W Irlo Bronson Memorial Hwy Kissimmee FL
Free cancellation
The price is CA $143 per night
CA $143
CA $231 total
Sep 20 - Sep 21
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.
Hilton Vacation Club Mystic Dunes Orlando

Hilton Vacation Club Mystic Dunes Orlando

4 out of 5
7600 Mystic Dunes Lane Kissimmee FL
Free cancellation
Reserve now, pay when you stay
The price is CA $121 per night
CA $121
CA $185 total
Sep 27 - Sep 28
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.
Omni Orlando Resort at ChampionsGate

Omni Orlando Resort at ChampionsGate

4 out of 5
1500 Masters Blvd Davenport FL
Free cancellation
Reserve now, pay when you stay
The price is CA $234 per night
CA $234
CA $345 total
Oct 2 - Oct 3
includes taxes & fees
Book a stay at this spa hotel in Four Corners. Enjoy free WiFi, 5 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions ChampionsGate Golf Club and Reunion Resort Golf Course are located nearby.
Don't see what you're looking for?
See all available properties in Lakeland - Winter Haven
View all properties
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.

Stay near popular Lakeland - Winter Haven attractions

The entrance to LEGO Florida with colorful LEGO structures and a large LEGO sign.

LEGOLAND® Florida

9.0/10 (2,150 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.
See properties

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 $1,109. 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.

Photos of local treasures

Browse Lakeland - Winter Haven vacation photos for more inspiration

A baseball player in a white uniform with the number 20, a catcher in an orange uniform, and an umpire standing behind the catcher.
A child lying on the ground with colorful confetti around, in front of a LEGO sign that reads "LEGO LAND FLORIDA".
A vintage airplane and a classic car parked in front of a building with a sign that reads "Fantasy of Flight".
Two swans swimming in a calm body of water surrounded by greenery.
A large dinosaur statue in a park with green grass and trees.