Name: Margaritaville Resort Orlando
Price range: $179 total
Rating: 8.8

Your Lakeland - Winter Haven Vacation

With everything organized before you go, our Lakeland - Winter Haven vacation packages let you focus on having fun. Known for its golfing, walking trails and family-friendly attractions, the only thing left to do is kick back and enjoy every unforgettable moment. Kick off your trip to Lakeland - Winter Haven with a few nights in Lakeland visiting popular sights like RP Funding Center and Lakeside Village. Davenport is another city that draws travelers from far and wide. Reunion Resort Golf Course and Southern Dunes Golf and Country Club are two of the top places to see here. When it's time to stop dreaming and start packing, Expedia will help turn your Lakeland - Winter Haven vacation into a reality.

The Latest Lakeland - Winter Haven vacation packages

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

Coral Reef Beach Resort

Save 100% on your flight

$365

per person

Jan 19 - Jan 23

found 10 hours ago

Roundtrip flight included

Philadelphia (PHL) to Tampa (TPA)

8.8/10 Excellent! (251 reviews)

Kompose Boutique Hotel

Save 100% on your flight

$748

per person

Feb 1 - Feb 8

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

18.4/10 Exceptional! (4,624 reviews)

I booked for my Grandmas Funeral and I couldn’t have asked for a better experience. The staff are warm and welcoming. The ambience is beautiful and the hotel feels and looks luxurious for a great price. I will definitely book again thank you Julio and Valeria for your service.

Reviewed on Nov 18, 2025

Hibiscus Suites - Gateway to Siesta Key

Save 100% on your flight

$881

per person

Feb 1 - Feb 8

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

17.2/10 Exceptional! (2,191 reviews)

Close enough to the village!

Reviewed on Nov 17, 2025

voco Sarasota by IHG

Central Sarasota

Save 100% on your flight

$965

per person

Feb 1 - Feb 8

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

18.4/10 Exceptional! (1,001 reviews)

Great front desk staff ! Very kind and helpful

Reviewed on Oct 27, 2025

Innisbrook Resort

Save 100% on your flight

$667

per person

Jan 24 - Jan 31

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

16.8/10 Exceptional! (1,001 reviews)

The room was perfect and very clean. We spent 3 days by the pool which was the highlight of our weekend. All of the staff were very courteous and friendly. The resort is so huge and it was our first time there so we were a bit overwhelmed the first day. However, the staff helped us situate and made several recommendations to help us enjoy our stay. I am old and i forget his name, but the gentleman at the pool (Bill?) who has been at Innisbrook since 1990 was especially helpful. We are planning an annual trip at Innisbrook. Thank you!

Reviewed on Nov 15, 2025

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Where to stay in Lakeland - Winter Haven

Find the best Lakeland - Winter Haven areas and neighborhoods for the activities you enjoy most. Learn more about Lakeland - Winter Haven

Lake Hollingsworth

If you're spending some time in Lake Hollingsworth, Lake Hollingsworth and Veterans Park are top sights worth seeing.

Discover the most popular places to visit in Lakeland - Winter Haven

LEGOLAND® Florida

Take the kids to this dynamic theme park for a day full of exciting rides, LEGO® brick creations and the chance to build your own LEGO®robots.

The 205 foot Neo-gothic 'singing tower' houses a 60-bell carillon – one of
about 185 carillons in North America.

Designed by Milton B. Medary, he was awarded in 1929 the American Institute of
Architects gold medal for this design.

#Trovember

Bok Tower Gardens

Bok Tower Gardens is just one of the places to see in Lake Wales, so why not enjoy the other things to explore during your travels? Stroll along the lakeside in this family-friendly area, or check out its top-notch restaurants.

Dinosaur World

With more than 200 life-size dinosaur models and many interactive games and activities, this educational theme park is great for families.

What to do in Lakeland - Winter Haven

LEGOLAND® Florida Tickets

$58

per traveler

84% of travellers recommend

Wild Dolphin Exploration Boat Ride and Clearwater Beach Day

$125

per adult

88% of travellers recommend

See all activities in Lakeland - Winter Haven

Lakeland - Winter Haven Hotel Deals

The Grove Resort & Water Park Orlando

14501 Grove Resort Avenue Winter Garden FL

Fully refundableReserve now, pay when you stay

$159 nightly

$179 total

Nov 19 - Nov 20

Total with taxes and fees

7.8/10 Good! (8,748 reviews)

Two bedroom was great! Clean and big. Pool is amazing!

Reviewed on Nov 17, 2025

Hilton Vacation Club Mystic Dunes Orlando

7600 Mystic Dunes Lane Kissimmee FL

$128 nightly

$145 total

Nov 30 - Dec 1

Total with taxes and fees

9/10 Wonderful! (4,422 reviews)

The best universal hotel

Reviewed on Nov 14, 2025

Margaritaville Resort Orlando

8000 Fins Up Circle Kissimmee FL

Fully refundableReserve now, pay when you stay

$157 nightly

$179 total

Dec 16 - Dec 17

Total with taxes and fees

8.8/10 Excellent! (3,656 reviews)

Clean room

Reviewed on Nov 13, 2025

See all 45,132 properties in Lakeland - Winter Haven

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.