Winter Haven Holiday Packages

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It doesn't get any easier than one of our hotel and flight packages.

Winter Haven here we come!

Your savings could reach if you book a package today. Exactly how do you do this? Just mix and match from more than 550 partner airlines and 665,000 worldwide properties.

Wotif has some of the best deals around. So quit fantasising and start creating new experiences.

Winter Haven Accommodation

Booking accommodation is our forte, so you can feel confident knowing you're in the right hands for your next holiday. Wotif currently has 14 accommodations in Winter Haven, so you shouldn’t have any problems grabbing the perfect place to lay your head.

Supposed to have arranged a place to stay by now? Left it to the last minute? Don't panic — we've got you covered. Check out the Hampton Inn Winter Haven (202 Cypress Gardens Blvd) or the Lake Roy Beach Inn (1823 Cypress Gardens Blvd).

Car Hire in Winter Haven

If you're wanting to collect your car in the heart of town, Enterprise (470 Cypress Gardens Blvd.) is only 2 kilometres away. Or, Budget (448 Cypress Gardens Blvd Se) is similarly close by and is sure to have something that suits.

Holidays to Winter Haven

Just like drinking cocktails and scarfing down ice cream, it's never too early to begin learning about your next getaway destination. If you're headed to Winter Haven, here are some basics which will be of help.

Want to visualise where you'll be spending your nights? Winter Haven is 260 kilometres south of the popular city of Jacksonville.

If you've been trying to remember just how many people reside in this area of Lakeland - Winter Haven but your brain's in packing mode, we'll give you a hand. At last count, the population was 34 000.

Top Winter Haven hotels

LEGOLAND Beach Retreat

LEGOLAND Beach Retreat

3 out of 5
100 Legoland Way SE Winter Haven FL
The price is AU$410 per night from 20 Feb to 21 Feb
AU$410
20 Feb - 21 Feb
includes taxes & fees
LEGOLAND Beach Retreat: Hotel with free breakfast and an outdoor pool.
Everything

Reviewed on 12 Feb 2026

Opens in a new windowLEGOLAND Beach Retreat
Legoland Florida Hotel

Legoland Florida Hotel

3 out of 5
1 Legoland Way Winter Haven FL
The price is AU$470 per night from 1 Mar to 2 Mar
AU$470
1 Mar - 2 Mar
includes taxes & fees
Legoland Florida Hotel: Hotel with free breakfast and free WiFi.
We had the absolute best time at the Legoland Pirate Island Hotel with my two little boys (5 and 7). The lobby is so much fun (they loved playing in the castle with other kids and building lego), we enjoyed the PJ Dance Party at night and a little show before that. The decor is perfect for any kid ...

Reviewed on 7 Feb 2026

Opens in a new windowLegoland Florida Hotel
Howard Johnson by Wyndham Winter Haven FL

Howard Johnson by Wyndham Winter Haven FL

2 out of 5
1300 3rd St Winter Haven FL
Fully refundableReserve now, pay when you stay
The price is AU$161 per night from 16 Feb to 17 Feb
AU$161
16 Feb - 17 Feb
includes taxes & fees
Howard Johnson by Wyndham Winter Haven FL: Pet-friendly motel with free breakfast and free WiFi. Located in the business district.
Staff was courteous and helpful

Reviewed on 8 Feb 2026

Opens in a new windowHoward Johnson by Wyndham Winter Haven FL
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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.