A LEGO-themed welcome sign with 'LEGO FLORIDA' and 'WELCOME' in large letters, surrounded by greenery.

Cottages in Winter Haven

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Cottages in Winter Haven

A small, single-story house with a gray roof and white siding, featuring two white plastic chairs outside.

A dock extending into a body of water with a grassy area in the foreground.

A swimming pool with a fence, lounge chairs, and a palm tree.

A compact room with wooden walls, a sofa, a television, a small table, and a stove.

1. Lake Ida Beach Resort

Winter Haven

$71

$80 total

includes taxes & fees

Oct 9 - Oct 10

A two-story house with a front porch, a garage, and a well-maintained lawn.

A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

A dining area with a round table, two chairs, a view of a lake, and a decorative wall piece.

A house with a covered porch, a view of a lake, and a grassy yard.

2. Lakefront Vibes w/ Lanai Bird Watching Paradise

Florence Villa

$165

$404 total

includes taxes & fees

Oct 7 - Oct 8

A covered porch with two wooden chairs and a bench, overlooking a road and a body of water.

A bathroom with a toilet, a sink, and a bathtub.

A dining area with a wooden table, chairs, a chandelier, and a window with blinds.

A single-story house with a light green exterior, a dark roof, and a front porch with two wooden chairs.

3. Lakefront Retreat on Lake Ariana w/ EV Charger

Auburndale

$115

$334 total

includes taxes & fees

Oct 13 - Oct 14

A two-story house with a garage, surrounded by well-maintained lawns and palm trees.

A spacious living room with a dining area, featuring a wooden dining table, chairs, and a sofa set.

An aerial view of a resort with a central swimming pool, palm trees, and red umbrellas.

A living room with a TV, sofa, coffee table, and plants.

4. Family Resort Home w Pool, BBQ & Game Room

Solana

$109

$334 total

includes taxes & fees

Oct 20 - Oct 21

A modern hotel with a curved driveway, large windows, and palm trees.

A restaurant with round tables set with blue glassware, white plates, and silverware. There are chairs around the tables, and a potted plant on one table. The walls are green with a leafy pattern, and there is a large window in the background.

An outdoor patio with a dining table, chairs, a grill, and a sofa.

A bedroom with a large bed, a bedside table with a lamp, a window with curtains, and a view of the outside.

5. Mvv7482 - 3BR House Near Disney at Magic Village

Kissimmee

$226

$488 total

includes taxes & fees

Oct 27 - Oct 28

A multi-story building with a 'STUDIO MOVIE GRILL' sign, parking lot, and surrounding greenery.

A kitchen with wooden cabinets, a stainless steel refrigerator, a microwave, and a stove. There is a dining table with chairs and a kitchen island with stools.

An aerial view of a water park with multiple pools, slides, and a large parking area.

A living room with a leather sofa, a wooden coffee table, a TV, and a ceiling fan.

6. Serenity - Family & Pet Friendly, Amazing Location

Crestwynd Bay

$91

$395 total

includes taxes & fees

Oct 7 - Oct 8

A residential neighborhood with two houses, a driveway, and a lawn.

A modern kitchen with granite countertops, stainless steel appliances, and pendant lighting.

A living room with a Christmas tree, a dining table with chairs, and a sofa with a decorative pillow.

A dining area with a long table, chairs, a decorative runner, a mirror, and a door with a window view.

7. Walkable Dixieland District Gem With Yard

Dixieland

$126

$278 total

includes taxes & fees

Oct 13 - Oct 14

A single-story house with a covered patio area, a lawn, and a clear sky.

A modern kitchen with a refrigerator, stove, microwave, and dishwasher.

A pool area with a water feature, lounge chairs, and a pergola.

A bedroom with a bed, bedside table, lamp, and a dresser.

8. Pond Access & Grill! Group Escape, 19 Mi to WDW

Kissimmee

$147

$202 total

includes taxes & fees

Oct 12 - Oct 13

A modern two-story house with a brick foundation, large windows, and a covered porch.

A modern bathroom with a glass shower enclosure, a toilet, and a sink.

A modern kitchen with a central island, built-in appliances, and a sleek design.

A modern living room with a black leather sofa, a wooden coffee table, and a black armchair.

9. Modern Lakeland Golf Retreat w/ Putting Green

Lake Hollingsworth

$180

$419 total

includes taxes & fees

Oct 13 - Oct 14

A modern hotel with a central courtyard, palm trees, and a parking area.

A poolside area with lounge chairs and palm trees, a clear blue sky, and a building with a modern design.

A patio with a glass table and wicker chairs, a barbecue grill, and a hot tub.

A gym with brick walls, treadmills, weight machines, and a door leading to another room.

10. Mvy7664 - 3BR House Near Disney With Hot Tub

Kissimmee

$193

$449 total

includes taxes & fees

Oct 15 - Oct 16

A modern building with large windows and a parking lot.

A high-ceiling living room with a fireplace, a TV, and a view of a balcony with a pool.

A modern kitchen with wooden cabinetry, a central island, bar stools, and a view of the outdoors.

A restaurant interior with wooden walls, multiple tables and chairs, a computer desk, and a television.

11. Mvv7460 - 3BR House Near Disney w/ Hot tub

Kissimmee

$228

$490 total

includes taxes & fees

Oct 13 - Oct 14

An outdoor patio area with a long table and chairs, a sofa, and a stone wall.

A laundry room with two front-loading washing machines, a window, and a built-in shelf above the machines.

A hotel room with two beds, wooden panel walls, a clock, and a window with curtains.

12. Mvv7485 - 3BR House Near Disney With Hot Tub

Kissimmee

$224

$485 total

includes taxes & fees

Oct 13 - Oct 14

A resort with a central swimming pool, sun loungers, and palm trees.

A modern reception area with a long counter, four chairs, and a sign reading "MAGIC VILLAGE Resort".

A hotel pool area with a hot tub, lounge chairs, and palm trees.

A multi-story residential building with a parking lot in front.

13. Mvy7632 - 4BR House Near Disney

Kissimmee

A single-story house with a brick facade, a garage, and a well-maintained lawn.

A living room with floral-patterned sofas, a glass coffee table, and a ceiling fan. There are two wall-mounted lamps and a framed picture on the wall.

A covered outdoor swimming pool with a patio area, lounge chairs, and a hot tub.

A living room with a glass coffee table, floral sofas, a TV, and a ceiling fan.

14. ~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool

Indian Ridge

$144

$476 total

includes taxes & fees

Oct 7 - Oct 8

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Top neighborhoods in Winter Haven

A circular fountain with a statue in the center, surrounded by palm trees and a building with a red roof in the background.

Florence Villa

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Lucerne Park

Winter Haven's Lucerne Park neighborhood offers attractions including Lake Henry.

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Top landmarks in Winter Haven

The entrance to LEGO Florida with colorful LEGO structures and a large LEGO sign.

LEGOLAND® Florida

9.0/10 (2,150 reviews)

Why not give yourself a treat with a trip to LEGOLAND® Florida, one of the most popular family attractions located 3.2 mi (5.2 km) from central Winter Haven. If you have fun at LEGOLAND® Florida, you'll love Peppa Pig Theme Park Florida, just a short walk away.

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A narrow water channel surrounded by lush greenery and tall trees.

Chain of Lakes Park

8.2/10 (185 reviews)

You can catch an event at Chain of Lakes Park, located 1.6 mi (2.5 km) from central Winter Haven. If you think Chain of Lakes Park is cool, you also might like Winter Haven City Tennis Center, located nearby.

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Peppa Pig Theme Park Florida

If thrills are what you're after, head to Peppa Pig Theme Park Florida, located 3.6 mi (5.8 km) from central Winter Haven. If you have fun at Peppa Pig Theme Park Florida, you'll love LEGOLAND® Florida, just a short walk away.

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Theatre Winter Haven

7.4/10 (56 reviews)

Theatre Winter Haven is 1.3 mi (2.2 km) from central Winter Haven, why not stop by during your stay. If you want to experience more of the culture Winter Haven has to offer, head to LEGOLAND® Florida, Chain of Lakes Park, and Indigo's Family Fun Center.

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Cypresswood Golf and Country Club

6.4/10 (25 reviews)

You might want to practice your swing at Cypresswood Golf and Country Club, a golf course located 5.2 mi (8.4 km) from central Winter Haven. If Cypresswood Golf and Country Club doesn't quite scratch your golfing itch, Winter Pines Golf Course, and Lake Region Golf Club are also nearby.

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Sertoma Park

6.6/10 (28 reviews)

Sertoma Park is worth a visit, located 1.7 mi (2.7 km) from central Winter Haven.

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Inman Park

7.4/10 (14 reviews)

Inman Park is worth a visit, located 1.4 mi (2.3 km) from central Winter Haven.

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Winter Haven City Tennis Center

You can catch an event at Winter Haven City Tennis Center, located 0.5 mi (0.7 km) from central Winter Haven. If you think Winter Haven City Tennis Center is cool, you also might like Chain of Lakes Park and Cindy Hummed Tennis Center, both located nearby.

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Learn more about Winter Haven

Beyond the splash and color of LEGOLAND Florida, Winter Haven reveals itself as a watery playground across its famed Chain of Lakes. Rent a pontoon boat and discover why locals treasure these interconnected waterways above all else. The recently added Peppa Pig Theme Park offers gentler thrills for the smallest travelers. Theatre Winter Haven stages surprisingly professional productions in this modest-sized community. Between adventures, duck into Andy's Igloo for old-Florida milkshakes that haven't changed their recipe since your grandparents' era. The Circle B Bar Reserve rewards early risers with boardwalk trails where alligators and wading birds seem utterly unimpressed by human visitors. Come evening, lakeside restaurants offer sunset views that explain why snowbirds refuse to leave.

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About the destination

Winter Haven is a family-friendly place known for its restaurants. Top attractions include LEGOLAND® Florida. There's plenty more to see, including sights like Theatre Winter Haven and Chain of Lakes Park.