Where to stay in Lakeland - Winter Haven

Downtown Lakeland

If you're spending some time in Downtown Lakeland, RP Funding Center and Lake Mirror are top sights worth seeing.

Lake Hollingsworth

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

South Lake Morton

If you're looking for some top things to see and do in South Lake Morton and surrounding area, you can visit Polk Museum of Art and Lake Mirror.

Lakeland Highlands

When in Lakeland Highlands, you can plan a visit to Family Fun Center and The Club at Eaglebrooke, some noteworthy sights in the nearby area.

Beautiful Florida wooden boardwalk near a body of water

Dixieland

While there might not be top attractions in Dixieland, you can explore the larger area and discover places like RP Funding Center and Polk Museum of Art.

Lakeland, FL, USA - 06 10 2024: Beautiful Hollis botanic garden and lake landscape in Lakeland Florida

Parker Street

Though Parker Street might not have many top sights, you can venture to the surrounding area to see attractions like Lake Mirror and Bryant Stadium.

The Grove Resort & Water Park Orlando

14501 Grove Resort Avenue Winter Garden FL

P10,132

P14,784 total

May 21 - May 22

includes taxes & fees

Book a stay at this family-friendly resort in Four Corners. Enjoy free WiFi, 6 outdoor pools, and 3 restaurants. Our guests praise the pool and the helpful staff ...

8/10 Very Good! (9,852 reviews)

I would have liked a small broom in my room and swiffer for small spills and messes with kids. All the staff was very pleasant and answered any questions.

Reviewed on May 14, 2026

Margaritaville Resort Orlando with H2O Waterpark

8000 Fins Up Circle Kissimmee FL

P9,343

P13,950 total

May 17 - May 18

includes taxes & fees

Book a stay at this spa resort in Kissimmee. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the restaurant in our reviews. ...

8.8/10 Excellent! (3,593 reviews)

Great stay and clean property! Very clean!

Reviewed on May 14, 2026

Holiday Inn Club Vacations at Orange Lake Resort by IHG

8505 W Irlo Bronson Memorial Hwy Kissimmee FL

P9,150

P12,688 total

May 18 - May 19

includes taxes & fees

Book a stay at this golf resort in Kissimmee. Enjoy free WiFi, free parking, and 7 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. ...

8.8/10 Excellent! (2,880 reviews)

This resort is amazing! The only reason we left for one day was to head to the west coast to go to St. Pete's Beach. There is a ton to do. My granddaughters had a blast. Everything went great and we enjoyed every moment. The resort is very clean and well maintained. Minor details were not overlooked. ...

Reviewed on May 13, 2026

See all 45,104 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.

Margaritaville Cottages Orlando by Rentyl with H2O Waterpark

8000 Fins Up Circle Kissimmee FL

Book a stay at this 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 ...

8.8/10 Excellent! (1,966 reviews)

Room was excellent.

Reviewed on May 14, 2026

The Berkley, Orlando

8545 W. Irlo Bronson Highway Kissimmee FL

Book a stay at this family-friendly vacation home in Kissimmee. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff and the ...

9.6/10 Exceptional! (2,218 reviews)

Great place; great staff, easy check in

Reviewed on May 14, 2026

Encantada Resort Vacation Townhomes by IDILIQ

3070-B Secret Lake Drive Kissimmee FL

Book a stay at this family-friendly aparthotel in Kissimmee. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions Disney's Animal Kingdom® ...

8.4/10 Very Good! (1,441 reviews)

The house was roomy. It did look like it needed a deep cleaning. The main master bedroom had a broken bed when we arrived. We had to have some people sleep on the couch. The boards under the bed were broken in half and sticking out the side of the bed. We had to wait until the next day for someone ...

Reviewed on May 12, 2026

See all 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.

Check Lakeland - Winter Haven hotel availability

Popular places to visit

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.

A Lockheed XFV plane outside the Sun n Fun Florida Air Museum at Lakeland

Sun N Fun Air Museum

You can spend time browsing the exhibits at Sun N Fun Air Museum during your trip to Lakeland. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

Wooton park on lake Dora in Tavares, Florida

Lakeside Village

You can search for that perfect souvenir at Lakeside Village during your visit to Lakeland. Amble around the area's lakeside or attend a sporting event.

Dinosaur World

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

Scenic view of Winter Park, Chain of Lakes canal. The Chain of Lakes is a popular tourist destination for residents and visitors to Winter Park, Florida, USA.

Chain of Lakes Park

Catch an event at Chain of Lakes Park during your trip to Winter Haven. Stroll along the lakeside in this family-friendly area, or check out its top-notch restaurants.

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.