Top Chalets in Lakeland - Winter Haven in 2026

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Recommended hotels in Lakeland - Winter Haven

A Holiday Inn Express hotel with a covered entrance, large columns, and a well-lit facade.

1. Holiday Inn Express Bartow by IHG

Bartow

STEVE

Rp2.147.052 total

includes taxes & fees

6 Dec - 7 Dec

A resort pool area with a winding pool design, lounge chairs, and palm trees.

2. Kompose Boutique Resort at Theme Parks

Kissimmee

ivan

Rp1.267.305 total

includes taxes & fees

17 Nov - 18 Nov

A modern hotel with a prominent entrance, multiple floors, and a parking lot.

3. Best Western Plus Winter Haven Inn & Suites

Winter Haven

DeCheryl

Rp2.474.780 total

includes taxes & fees

17 Nov - 18 Nov

A hotel entrance with a sign reading "Days Inn Suites 4502," featuring a covered entrance, a parking lot, and a landscaped area with small plants and a palm tree.

4. Days Inn & Suites by Wyndham Lakeland

Lakeland

Jesica

Rp1.337.139 total

includes taxes & fees

6 Dec - 7 Dec

5. Best Western Plus Lakeland

Lakeland

Alison

Rp1.942.879 total

includes taxes & fees

11 Nov - 12 Nov

A Marriott Fairfield hotel sign with a landscaped garden in front.

6. Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

Bay Lake

Robert

Rp1.608.678 total

includes taxes & fees

8 Dec - 9 Dec

A Holiday Inn hotel with a covered entrance and a clear sky.

7. Holiday Inn Winter Haven by IHG

Winter Haven

Jova Jane

Rp2.390.114 total

includes taxes & fees

24 Nov - 25 Nov

A hotel entrance with a covered walkway, columns, and arched windows.

8. Comfort Inn & Suites Lakeland North I-4

Lakeland

Amber

Rp1.738.909 total

includes taxes & fees

7 Dec - 8 Dec

A row of colorful, single-story buildings with a uniform roof design, white picket fences, and a clear pathway leading to the entrance.

9. LEGOLAND Beach Retreat

Winter Haven

Efrayn

Rp4.739.717 total

includes taxes & fees

13 Nov - 14 Nov

A large hotel with multiple floors, a central courtyard, and a reflective water feature.

10. Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

Bay Lake

Michael

Rp1.816.250 total

includes taxes & fees

29 Nov - 30 Nov

A hotel entrance with a stone facade, a double entrance, and a welcoming reception area.

11. Holiday Inn Express Lake Wales N-Winter Haven by IHG

Lake Wales

Jessica

Rp2.734.452 total

includes taxes & fees

22 Nov - 23 Nov

A Travelodge building with a registration area, palm trees, and a well-maintained lawn.

12. Travelodge by Wyndham Lakeland

Lakeland

John

Rp1.252.987 total

includes taxes & fees

11 Nov - 12 Nov

An outdoor patio with a sofa set, chairs, and a fire pit.

13. SpringHill Suites by Marriott Lakeland

Downtown Lakeland

Louis

Rp2.533.927 total

includes taxes & fees

22 Nov - 23 Nov

An outdoor patio with a barbecue grill, a fire pit, and a seating area with a sofa and a side table.

14. Staybridge Suites Winter Haven Auburndale by IHG

Winter Haven

Jacqueline

Rp2.714.197 total

includes taxes & fees

29 Nov - 30 Nov

A hotel with a pool, outdoor seating, and a sign for 'Galleria'.

15. Galleria Palms Hotel

Kissimmee

Joshua

Rp1.525.115 total

includes taxes & fees

17 Nov - 18 Nov

A modern hotel with a white facade, large windows, and a landscaped entrance.

16. Hyatt Place Lakeland Center

Downtown Lakeland

John Thomas Spencer

Rp2.309.093 total

includes taxes & fees

23 Nov - 24 Nov

A Hampton Inn hotel with a parking lot and landscaping.

17. Hampton Inn by Hilton Plant City

Plant City

Duane

Rp2.076.254 total

includes taxes & fees

29 Nov - 30 Nov

An outdoor patio with yellow chairs and tables, a grill station, and a red umbrella.

18. Home2 Suites By Hilton Winter Haven

Winter Haven

Joseph

Rp2.875.227 total

includes taxes & fees

25 Nov - 26 Nov

A hotel entrance with a landscaped area, a fountain, and a view of fireworks in the background.

19. Holiday Inn Resort Kissimmee by the Parks by IHG

Kissimmee

Kimberly

Rp1.652.336 total

includes taxes & fees

8 Dec - 9 Dec

A spacious lobby with a high ceiling, wooden beams, and a central fountain.

20. Margaritaville Resort Orlando with H2O Waterpark

Kissimmee

Samuel

Rp3.633.991 total

includes taxes & fees

29 Nov - 30 Nov

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Lakeland - Winter Haven and related destinations

Discover the family-friendly area of Lakeland - Winter Haven—lake views, baseball and top sights like LEGOLAND® Florida.

See all hotels in Lakeland - Winter Haven

A child lying on the ground with colorful confetti around, in front of a LEGO sign that reads "LEGO LAND FLORIDA".

Top reviews in Lakeland - Winter Haven

Staybridge Suites Winter Haven Auburndale by IHG

Winter Haven

10/10 Excellent

Julie Anne

Best Western Plus Winter Haven Inn & Suites

Winter Haven

10/10 Excellent

This was the first time my family travelled outside of Orlando during our vacation to Disney. We were visiting Legoland and so pre booked one nights stay before heading down to Clearwater the following evening. I will certainly be coming back for more then one night next fime and would recommend to others without hesitation. Luxury hotel for the price paid. Well worth the money. The hotel was located in an easy location to find when driving. Ample parking outside with no issues going out and...

Vishal

Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

Bay Lake

10/10 Excellent

Sanjay

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

Bay Lake

10/10 Excellent

Dileep

A spacious lobby with a high ceiling, wooden beams, and a central round table surrounded by chairs. There are potted plants, a reception desk, and a wall with a welcome sign.

Hilton Vacation Club Polynesian Isles Kissimmee

Kissimmee

10/10 Excellent

Josephine

SpringHill Suites by Marriott Lakeland

Downtown Lakeland

10/10 Excellent

Elizabeth

Home2 Suites By Hilton Winter Haven

Winter Haven

10/10 Excellent

Victoria

An aerial view of a resort with a central swimming pool, a covered deck area, and a landscaped garden.

The Berkley, Orlando

Kissimmee

10/10 Excellent

We really cannot fault the hotel and staff during our two week stay. We went October/November so at then end of the season, therefore the hotel was only at 25% capacity, however the style and standard of the accomodation was excellent, we would definitely reccomend it and would stay there again without reservation. Our only tiny gripe (and this is pedantic) is that it is placed a little out of the main area. However, everything is within 20 to 25 minutes drive. We also felt that the security...

Fiona