Winter Haven

Travel Guide

Winter Haven featuring rides
Winter Haven
Legoland Florida featuring signage and rides
Winter Haven
Legoland Florida featuring a statue or sculpture, rides and outdoor art

Whether you explore the Chain of Lakes or revisit your childhood at LEGOLAND®, this Central Florida city is an oasis every month of the year.

As the name suggests, Winter Haven first became a popular destination for people seeking sun during winter. Today you can enjoy a variety of indoor and outdoor attractions in this Central Florida city at any time of year.

Immerse yourself in all things LEGO® at LEGOLAND® Florida. This massive park delights kids of all ages. Go on themed rides, play games and tour exhibits all centred on one of America’s favourite plastic toys. Climb to the top of the Island in the Sky platform for a 360-degree view of Central Florida. 

No visit to Winter Haven would be complete without touring the Chain of Lakes. The city is surrounded by several dozen lakes 16 are connected by canals to form a chain. The area has prime fishing conditions and attracts fishermen from all over the world for leisure or competitions. Try a water sport spend a day tubing, Jet-Skiing or water skiing.

Many consider Winter Haven to be the home of water skiing. The sport was used to promote Cypress Gardens, Florida’s first theme park, in the 1930s. Eventually the water shows there became the city’s main attraction. LEGOLAND® Florida now stands on the original Cypress Gardens site and continues the traditions of water performances. Today, watch amazing water ski tricks, such as the human pyramid or barefoot skiing, at the park’s daily water shows.

See the beautiful Central Florida wilderness at the Street Audubon Centre. Explore miles of nature trails and grab your binoculars for wonderful birding opportunities. Golf is a major leisure activity in the state Winter Haven has several world-class courses. Grab your equipment and head to Cypresswood Golf and Country Club’s 18-hole course or take a lesson at Willowbrook Golf Course.

See a performance at Theatre Winter Haven, a small theatre with a big reputation. Throughout the year, “Florida’s Most-Honored Community Theatre” puts on several plays that span across every genre and style.

Reach Winter Haven in less than an hour from Tampa or Orlando airports. 

Best Western Plus Winter Haven Inn & Suites 
Best Western Plus Winter Haven Inn & Suites 
3.5 out of 5
5801 Roosevelt Dr, Winter Haven, FL
The price is S$177 per night from 13 Jul to 14 Jul
S$177
13 Jul - 14 Jul
includes taxes & fees
Stay at this 3.5-star business-friendly hotel in Winter Haven. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
9.4/10 Exceptional! (867 reviews)
"Me encantó ver mi nombre en la pantalla cuando encendí la TV."

Reviewed on 4 Jul, 2025

Best Western Plus Winter Haven Inn & Suites 
Staybridge Suites Winter Haven Auburndale by IHG
Staybridge Suites Winter Haven Auburndale by IHG
3 out of 5
305 5th St NW and Avenue D NW, Winter Haven, FL
The price is S$197 per night from 13 Jul to 14 Jul
S$197
13 Jul - 14 Jul
includes taxes & fees
Stay at this 3-star hotel in Winter Haven. Enjoy free breakfast, free WiFi, and a 24-hour front desk. Our guests praise the breakfast and the helpful staff in ...
9.6/10 Exceptional! (400 reviews)
"Great experience. No complaints. Small pool, good for young children. Very clean building and room."

Reviewed on 4 Jul, 2025

Staybridge Suites Winter Haven Auburndale by IHG
Kompose Boutique Resort at Theme Parks
Kompose Boutique Resort at Theme Parks
4 out of 5
7491 W Irlo Bronson Memorial Hwy, Kissimmee, FL
The price is S$129 per night from 7 Aug to 8 Aug
S$129
7 Aug - 8 Aug
includes taxes & fees
Stay at this 4-star business-friendly resort in Kissimmee. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Disney's Animal Kingdom® Theme ...
9.4/10 Exceptional! (527 reviews)
"Property is well located, everything close. The hotel was super clean with all the amenities you need to have an amazing stay. Staff was very friendly."

Reviewed on 7 Jul, 2025

Kompose Boutique Resort at Theme Parks
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.
Vacation Village at Parkway
Vacation Village at Parkway
3 out of 5
2975 Arabian Nights Blvd, Kissimmee, FL
Stay at this 3-star family-friendly condo in Kissimmee. Enjoy free WiFi, 7 outdoor pools, and 7 hot tubs. Our guests praise the helpful staff and the clean rooms ...
8.4/10 Very Good! (2,406 reviews)
"The room was massive! The kitchen was perfect for our needs. Will be coming back!"

Reviewed on 7 Jul, 2025

Vacation Village at Parkway
Margaritaville Cottages Orlando with H2O Waterpark by Rentyl
Margaritaville Cottages Orlando with H2O Waterpark by Rentyl
4 out of 5
8000 Fins Up Circle, Kissimmee, FL
Stay at this 4-star spa aparthotel in Kissimmee. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
8.6/10 Excellent! (1,469 reviews)
"Stayed in the cottages and it was great except we needed extra pillows and blankets for 2 people and only got one of each and it took hours to come we were already asleep when they set the items in our door. It sucked that the pool bar and grill closed at 6/7 everyday when it’s the summer and you. ..."

Reviewed on 4 Jul, 2025

Margaritaville Cottages Orlando with H2O Waterpark by Rentyl
Summer Bay Orlando by Exploria Resorts
Summer Bay Orlando by Exploria Resorts
3.5 out of 5
17805 US Highway 192, Clermont, FL
Stay at this 3.5-star family-friendly condo in Four Corners. Enjoy free parking, 5 outdoor pools, and 4 hot tubs. Our guests praise the pool and the helpful ...
8.4/10 Very Good! (5,508 reviews)
"I like that it wasn’t crowded it was just right! Slept great, lots of restaurants close by. Not to far from the parks Just what I needed!"

Reviewed on 5 Jul, 2025

Summer Bay Orlando by Exploria Resorts
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.

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