Lakeland - Winter Haven Vacation Packages
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Top Lakeland - Winter Haven vacation package deals
Price found within the past 48 hours. Click for updated prices.
4.0-star property
Ocean Club Treasure Island Hotel
Sunshine Beach
9.6/10 Exceptional! (1,236 reviews)
Nov 5 - Nov 9
4 night stay
Chicago (CHI) to Tampa (TPA)
Frontier Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $944, price is now $648 per person
$648
per person
found 1 day ago
Had a wonderful stay, everything was very clean and well maintained, staff was very friendly, convenient parking at the property, dog friendly and walking path right of the property,
Reviewed on Sep 27, 2026
3.0-star property
Cedar Cove Resort and Cottages
9.2/10 Wonderful! (591 reviews)
Oct 28 - Nov 4
7 night stay
Chicago (CHI) to Tampa (TPA)
Southwest Airlines • Coach
Tampa (TPA) to Chicago (CHI)
Frontier Airlines • Coach
Save 100% on your flight
Price was $2,170, price is now $1,378 per person
$1,378
per person
found 6 hours ago
4.0-star property
The Avalon Club
9.4/10 Exceptional! (595 reviews)
Nov 29 - Dec 5
6 night stay
Chicago (CHI) to Tampa (TPA)
Frontier Airlines • Coach
Tampa (TPA) to Chicago (CHI)
American Airlines • Coach
Save 100% on your flight
Price was $1,435, price is now $967 per person
$967
per person
found 5 hours ago
Hotel was great, front desk was very helpful. Rooms were spotless. Convenient to everything. The only thing we were upset about is extra $250 charge besides what Expedia charged us.
Reviewed on Sep 26, 2026
3.0-star property
Luxury Pool Retreat near Siesta Key
9/10 Wonderful! (4 reviews)
Nov 3 - Nov 10
7 night stay
Chicago (CHI) to Tampa (TPA)
American Airlines • Coach
Tampa (TPA) to Chicago (CHI)
Frontier Airlines • Coach
Save 100% on your flight
Price was $1,519, price is now $1,027 per person
$1,027
per person
found 11 hours ago
The house was super clean and well organized, with all the furniture and appliances ready to use. My family was extremely happy with our stay. The outdoor area was spotless, and the pool was clean and heated. Without a doubt, we will be coming back! Highly recommended!
Reviewed on Aug 9, 2026
Top rated hotels for your Lakeland - Winter Haven vacation package
The Grove Resort & Water Park Orlando
14501 Grove Resort Avenue Winter Garden FL
Free Cancellation
Reserve now, pay when you stay
34.59 mi from city center
$219 nightly
The price is $246 total per night
$246 total
Oct 27 - Oct 28
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 securing valuables, concierge services, and luggage storage. 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
8000 Fins Up Circle Kissimmee FL
Free Cancellation
Reserve now, pay when you stay
33.51 mi from city center
$163 nightly
The price is $185 total per night
$185 total
Oct 4 - Oct 5
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 tours or tickets, access to locker space, and luggage storage. Other amenities at this spa resort include a lazy river, a gym, and a steam room.
Pool
Hot Tub
Holiday Inn Winter Haven by IHG
200 Cypress Gardens Boulevard Winter Haven FL
Free Cancellation
9.99 mi from city center
$110 nightly
The price is $123 total per night
$123 total
Oct 4 - Oct 5
Total with taxes and fees
At Holiday Inn Winter Haven by IHG, guests enjoy an outdoor pool, a 24-hour gym, and free WiFi in public areas. If you plan to drive, free parking is available. The 24-hour front desk has staff standing by to help with luggage storage, dry cleaning/laundry, and securing valuables. Additional amenities include conference space, a 24-hour business center, and coffee/tea in a common area.
Pool
Parking included
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See all available properties in Lakeland - Winter Haven
View all propertiesLowest 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.
Things to do
Orlando Tree Trek Adventure Park
$65
per adult
96% of travellers recommend
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