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

While visiting Lake Hollingsworth, you might make a stop by sights like Lake Hollingsworth and Veterans Park.

Lakeland Highlands

While there might not be top attractions in Lakeland Highlands, you can explore the larger area and discover places like Family Fun Center and The Club at Eaglebrooke.

South Lake Morton

South Lake Morton might not have many top sights, but Lake Mirror and RP Funding Center are two attractions nearby that you can check out.

Beautiful Florida wooden boardwalk near a body of water

Dixieland

Though Dixieland may not have many top sights, you can venture to the surrounding area to see attractions 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

Parker Street might not have many top sights, but Lake Mirror and Bryant Stadium are two attractions nearby that you can check out.

The Grove Resort & Water Park Orlando

14501 Grove Resort Avenue Winter Garden FL

฿5,317

฿7,757 total

14 May - 15 May

includes taxes & fees

Stay at this family-friendly resort in Four Corners. Enjoy free Wi-Fi, 6 outdoor pools and 3 restaurants. Our guests praise the pool and the helpful staff in ...

8/10 Very Good! (9,785 reviews)

Love it! Great stay for families

Reviewed on 7 May 2026

Margaritaville Resort Orlando with H2O Waterpark

8000 Fins Up Circle Kissimmee FL

฿3,966

฿6,271 total

13 May - 14 May

includes taxes & fees

Stay at this spa resort in Kissimmee. Enjoy free Wi-Fi, 3 outdoor pools and a full-service spa. Our guests praise the pool and the restaurant in their reviews. ...

8.8/10 Excellent! (3,606 reviews)

Awesome!

Reviewed on 6 May 2026

Holiday Inn Club Vacations at Orange Lake Resort by IHG

8505 W Irlo Bronson Memorial Hwy Kissimmee FL

฿4,801

฿6,658 total

12 May - 13 May

includes taxes & fees

Stay at this golf resort in Kissimmee. Enjoy free Wi-Fi, free parking and 7 outdoor pools. Our guests praise the pool and the helpful staff in their reviews. ...

8.8/10 Excellent! (2,871 reviews)

👍👍👍👍👍

Reviewed on 7 May 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

Stay at this spa aparthotel in Kissimmee. Enjoy free Wi-Fi, free parking and a full-service spa. Our guests praise the pool and the helpful staff in their reviews. ...

The Berkley, Orlando

8545 W. Irlo Bronson Highway Kissimmee FL

Stay at this family-friendly holiday home in Kissimmee. Enjoy free Wi-Fi, free parking and 2 outdoor pools. Our guests praise the helpful staff and the clean ...

9.6/10 Exceptional! (2,210 reviews)

Our first time staying here after about 25 visits to Orlando. We will be back, and here is why: Easy check in, free parking, well lit areas, very clean grounds. Three bedroom,(one room handicap accessible) three bath, full kitchen, comfortable space. First floor access for us. Comfy bed, loved the ...

Reviewed on 7 May 2026

Encantada Resort Vacation Townhomes by IDILIQ

3070-B Secret Lake Drive Kissimmee FL

Stay at this family-friendly aparthotel in Kissimmee. Enjoy free Wi-Fi, free parking and 2 outdoor pools. Popular attractions Disney's Animal Kingdom® Theme ...

8.4/10 Very Good! (1,439 reviews)

The pool was gross and didn’t step foot in it. The place was not cleaned, couch and carpet looked like it had not been cleaned in years. Place had roaches and ants on lower floors. Bed sheeting had some sort of mites/tiny bugs . The pool and onsite cabana and clubhouse close too early sunset and ...

Reviewed on 26 Apr 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.

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 exploring the galleries in Sun N Fun Air Museum in 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 find the perfect gifts to bring home 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 visit 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 visit its top-notch restaurants.