Lakeland - Winter Haven Luxury Holidays 2026

Photo by Lakeland Convention and Visitors Bureau

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Top Luxury Lakeland - Winter Haven Hotels

The Terrace Hotel Lakeland, Tapestry Collection by Hilton

329 E Main St Lakeland FL

43 min drive from LEGOLAND® Florida

Stay at this historic hotel in Lakeland. Enjoy free Wi-Fi, breakfast (surcharge) and a 24-hour fitness centre. Our guests praise the helpful staff in their reviews. ...

9.2/10 Wonderful! (454 reviews)

"Worthless it"

Reviewed on 16 Aug 2026

Howard Johnson by Wyndham Winter Haven FL

1300 3rd St Winter Haven FL

7 min drive from LEGOLAND® Florida

Stay at this motel in Winter Haven. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms in their reviews. ...

7.4/10 Good! (1,017 reviews)

"Worst I've been to. No details needed, go elsewhere!"

Reviewed on 15 Aug 2026

Budget Inn

530 South Scenic Highway Lake Wales FL

24 min drive from LEGOLAND® Florida

Stay at this motel in Lake Wales. Enjoy free Wi-Fi, free parking and room service. Our guests praise the helpful staff and the clean rooms in their reviews. ...

See all 44,908 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.