Lakeland - Winter Haven Vacation Packages

Book a Stay + Flight or Car to save on your trip

Top Lakeland - Winter Haven vacation package deals

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express Lake Wales N-Winter Haven by IHG
2.5-star property

Holiday Inn Express Lake Wales N-Winter Haven by IHG

9.2/10 Wonderful! (1,002 reviews)

Jun 12 - Jun 19

7 night stay

New York (JFK) to Tampa (TPA)

JetBlue Airways • Roundtrip • Coach
Save 100% on your flight
Price was $976, price is now $696 per person
$696
per person
just found
Room was decent, good variety at breakfast, friendly staff.

Reviewed on Feb 23, 2026

Top rated hotels for your Lakeland - Winter Haven vacation package

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
34.59 mi from city center
$238 nightly
The price is $268 total per night
$268 total
Apr 12 - Apr 13
Total with taxes and fees
Guests of The Grove Resort & Water Park Orlando have access to 6 outdoor pools, a free water park, and a lazy river. Self parking is offered for USD 37.28 per night. Multilingual staff at the 24-hour front desk can assist with luggage storage, securing valuables, and concierge services. Other amenities at this family-friendly resort include a children's pool, a 24-hour gym, and 2 hot tubs.
Pool
Hot Tub
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
33.51 mi from city center
$203 nightly
The price is $231 total per night
$231 total
Apr 12 - Apr 13
Total with taxes and fees
Margaritaville Resort Orlando with H2O Waterpark features a full-service spa, 3 outdoor pools, and a free water park. Valet parking is available for USD 48.38 per night. The front desk is staffed 24/7 to help with access to locker space, concierge services, and luggage storage. Other amenities at this spa resort include a lazy river, a gym, and a steam room.
Pool
Hot Tub
Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
7700 Westgate Blvd. Kissimmee FL
32.79 mi from city center
$120 nightly
The price is $137 total per night
$137 total
May 3 - May 4
Total with taxes and fees
Westgate Town Center Resort features a marina, 14 outdoor pools, and a water park. Free parking is available if you drive. The front desk has multilingual staff standing by 24 hours a day to assist with concierge services and luggage storage. Other amenities at this family-friendly resort include a children's pool, a gym, and 14 hot tubs.
Pool
Hot Tub
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.
All Inclusive Vacations
All Inclusive Vacations
Family Vacation Packages
Family Vacation Packages
Adventure Vacation Packages
Adventure Vacation Packages

Explore More Ways to Travel with Travelocity