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Vacation rentals in Winter Haven

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Top-rated vacation rentals in Winter Haven

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
Home in Winter Haven
4.97 out of 5 average rating, 108 reviews

Adult-Only Getaway w/ Mermaid Pool | 18+, Private

🗝️ Adults only. Ready to turn your vacation into an experience? Explore your fantasies at our romantic getaway, featuring four themed bedroom options* designed to inspire you. Bring your fave toys, experiment with our spicy 🌶️ amenities, or peruse our shop to bring home a little extra to keep the fire going after you leave. You will love our mermaid pool 🧜🏿‍♀️, jetted spa, & stone meditation deck while you soak up the sun or stargaze. 🌟 Your next adventure awaits. (*1 per 2 guests)

Guest favorite
An outdoor patio features a glass-top table surrounded by six black mesh chairs. A small wooden shed is visible in the background, while a stone pathway leads through the well-maintained yard, enclosed by a wooden fence and dotted with greenery.
Cottage in Downtown Winter Haven
4.8 out of 5 average rating, 223 reviews

Sweet Cottage- 5 mi to Legoland & 0.5 mi to dwntwn

This delightful lake-life inspired cottage includes 2 bedrooms and 1 ½ baths, a fooseball table, and easily sleeps 7 guests comfortably. Located just 15 minutes from Legoland and 45 minutes from Tampa & Orlando, this home is perfect for both families and those traveling for work. In fact, this Home is centrally located to dining, shopping, and small town fare. Come stay and enjoy downtown entertainment within walking distance (0.5 miles), or a quick car drive to Legoland (5.2 miles).

Top guest favorite
A charming single-story home is set in a spacious outdoor area, featuring a wide driveway leading to a covered porch. The front yard is framed by lush greenery, with a large tree providing shade to the house and the surrounding landscape.
Home in Winter Haven
4.89 out of 5 average rating, 102 reviews

Newly remodeled House 3BR/2BA

Centrally located in Winter Haven, FL and within minutes to Legoland. Only a 45-60 minute drive to local theme parks Disney and Busch Gardens. West/East Coast Florida Beaches are only a 90 minute drive. This newly remodeled 3/2 is a very spacious and accommodating home to any family wanting to get away on a peaceful vacation or weekend retreat. Quiet neighborhood with no HOA and within walking distance to several downtown restaurants, grocery stores, and shopping establishments.

Top guest favorite
A charming white cottage is framed by a well-kept lawn, with a brick chimney visible on one side. Lush green shrubs and trees provide shade around the property, and a pathway leads to the entrance, suggesting easy access to the home.
Cottage in Davenport
4.99 out of 5 average rating, 113 reviews

Classic Cottage in country setting

Relax with the family in this peaceful setting. Short drive to the parks, shopping, restaurants. 10 minutes from Interstate 4. Walmart and Posner Park Shopping Center nearby. Patio area with fire pit and gas grill and lawn chairs. 2 car carport parking on premise. 2 bedroom w/HDTV's, 2 bath, fully furnished kitchen, dishwasher, breakfast nook, dining room, living room w/HDTV. Washer/dryer. Fully fenced 3/4 acre yard with plenty of room for kids to play. Self check in with keypad.

Guest favorite
A serene lakeside view is observed, featuring gently swaying palm trees on the left and a wooden dock extending into the water. A boat is anchored at the dock, surrounded by lush greenery and a clear blue sky.
Home in Winter Haven
4.95 out of 5 average rating, 109 reviews

Lakefront Home on the Winter Haven Chain O’Lakes!

Completely renovated 2 Bedroom, 1.5 bath home location on beautiful Lake Roy on the Winter Haven Chain O’Lakes. This is a mother-in-law suite that is connected to the main home. One bedroom on the lower level with a queen bed. Second story with king bed and twin bed. Full bath located upstairs). Comfortably sleeps 5. Dog welcome with prior approval and pet fee. Boat parking at dock. Boat rental available at Central Florida Water Sports. Private entry with keyless touchpad.

Top guest favorite
A spacious living area features a striking mural of a serene lake scene, complemented by a cozy seating arrangement. Tropical-themed decor and unique ceiling fixtures add to the ambiance. Natural light filters in, highlighting the stone floor and creating a welcoming environment.
Home in Winter Haven
4.99 out of 5 average rating, 146 reviews

Beautiful Lake House Boating Fishing near Legoland

Welcome to The Executive Lake House ten minutes from Lego Land in beautiful Winterhaven, Florida. The brand new rental home sits on a lake and offers a dock, with boats, fishing gear and beautiful views of the lake. The home offers one bedroom a full kitchen and laundry and one full bathroom The backyard has a playground and pool area that is ( not) included at this price point. If wanting an additional charge of 20 dollars per night Will be charged. Let me know at booking.

Top guest favorite
A view of the blue lake house is presented with a well-manicured lawn leading up to it. The house is framed by mature trees, providing shade. A wooden walkway extends toward the entrance, while the serene lake is visible in the background.
Cottage in Eagle Lake
4.99 out of 5 average rating, 289 reviews

Roe Family Lake House (Lake Mcleod)

We can't wait for you to enjoy our fully renovated, family friendly lake house. It's a happy home that provides a wonderful backdrop to any vacation. Centrally located to many Florida destinations- Legoland is only 7 miles away, Disney World is 35 miles away, and you are less than 50 miles from Tampa. The house is located on over an acre of lakefront property. The lake has a public boat launch if your family enjoys water sports or fishing or use the kayaks we provide on site!

Superhost
An open-plan living area features a blue couch set against a light wall, complemented by a patterned area rug. A dining table and four chairs are situated nearby, with a glimpse of the kitchen visible in the background.
Home in Downtown Winter Haven
4.94 out of 5 average rating, 348 reviews

Spacious 3 Bed, 2 Bath Home Near Legoland

Enjoy family vacation in this fresh, clean 3-bedroom, 2-bathroom home. With keyless entry and a private fenced backyard, you'll have everything you need for a comfortable stay. 4 miles from Legoland 1 mile from downtown Locally owned & operated As residents of Winter Haven, we're passionate about sharing our community with you. We're always ready to assist you with any questions or requests during your stay. Book your stay today and discover the charm of Winter Haven!

Guest favorite
A spacious room features a queen size bed with a neatly arranged white blanket. Light tiles enhance the bright atmosphere, while a barn-style door leads to a private bathroom. A small kitchenette area with dark cabinetry and a modern sink is visible in the background.
Guesthouse in Winter Haven
4.82 out of 5 average rating, 268 reviews

Adorable 1 bedroom Guesthouse near Lego Land

This is a beautiful and private place offers a queen size bed, newly renovated with private access and parking. It’s a great place to get away and relax with a large and beautiful backyard! We are located less than 8.6 miles from Legoland & under 6.2 miles from the Lake Myrtle Sports complex. Winter Haven is halfway between Orlando and Tampa. Around 29 miles to Disney World, Universal and Sea World. Around 38 miles to Bush Gardens, Dali museum, Aquarium and much more!

Guest favorite
A serene pool area is enclosed by a protective screen, featuring a clear swimming pool surrounded by a tiled patio. A comfortable seating area is visible in the background, with a stylish egg chair. Lush greenery enhances the tranquil setting.
Guesthouse in Auburndale
4.97 out of 5 average rating, 246 reviews

Private Poolside Villa

Lovely, private, poolside villa. The apartment is inside a completely enclosed, block walled pool deck. It provides privacy & your own personal oasis! Due to the proximity to the pool, my place is best suited for adults. I will only host young ones 13 & older that are proficient swimmers. The apartment is behind my personal home with no connecting doors. I live in a centralized location. I am within walking distance to restaurants, park, arcade, gym & library.

Guest favorite
The entrance features wooden steps leading up to a covered porch, flanked by tropical foliage. Two chairs are positioned on the porch, offering a place to relax. The home’s exterior is painted in soft green, complemented by light-colored trim.
Cottage in Winter Haven
4.84 out of 5 average rating, 158 reviews

5 - Life's a Beach Retreat 1bed/1bath - Unit 13

The 1-bedroom, 1-bathroom home features a fully equipped kitchen and covered front porch, making it the perfect spot to reel in a relaxing getaway. A cozy one-bedroom unit on the property of Cypress Inlet. Less than 10 minutes from LegoLand and Peppa Pig theme park. The property is on a canal that leads to Lake Eloise and the WH Chain of Lakes, and has boat ramp access and docks available; this vacation rental is an angler's paradise!

Guest favorite
An inviting sleeping area features a spacious bed adorned with decorative pillows and a quilt. A window allows natural light to fill the room, complemented by soft curtains. A ceiling fan circulates air, while a chair and mirror provide additional functional touches.
Guesthouse in Winter Haven
4.87 out of 5 average rating, 208 reviews

Brutus Way Cottage, a cosy hide away

Enjoy a quick get away at Brutus Way Cottage. It is located to the rear of Lili Haven Bed N Breakfast. On your picturesque drive around Lake Howard, with its walking trail, you will take a right onto a quaint curvy lane known as S. Lake Cannon Drive NW . Be my guest at the cottage surrounded by flowers ; the cottage is nestled in the trees to the back past the Iron gates. Use of the Laundry room available upon request.

Popular amenities for Winter Haven vacation rentals

Self check-inGymBBQ grillLaptop-friendly workspaceWifi

Stay near Winter Haven's top sights

LEGOLAND Florida Resort

990 locals recommend

LEGOLAND Florida Water Park

247 locals recommend

Winter Haven Hospital

9 locals recommend

Winter Haven home rentals

Top guest favorite
The private pool is enclosed by a screened lanai, featuring a generous seating area around the water. Lush greenery and manicured landscaping frame the pool, while a golf course vista is visible beyond the enclosure. Bright blue skies and scattered clouds enhance the sunny ambiance.
Home in Haines City
5 out of 5 average rating, 10 reviews

8th Fairway, Private Pool Villa, Southern Dunes

Guest favorite
A serene waterfront view captures a vibrant sunset reflected on the lake's surface. Silhouetted palm fronds frame the scene, while a wooden dock extends into the water, creating a peaceful atmosphere for relaxation and contemplation.
Home in Eagle Lake
4.94 out of 5 average rating, 18 reviews

30 minutes to Disney and Universal Studios

Top guest favorite
Home in Auburndale
4.97 out of 5 average rating, 31 reviews

King Bed Suite, Fireside Hot Tub, Gameroom

Top guest favorite
Home in Winter Haven
5 out of 5 average rating, 29 reviews

Luxury 3BR 2Bath•Pool• Game Room• Legoland 4 Min

Top guest favorite
A private backyard features a clean in-ground pool surrounded by a paved patio. Two lounge chairs are positioned beside the pool, and a dining set with four chairs sits nearby. Lush greenery and a white privacy fence enhance the serene outdoor setting.
Home in Winter Haven
4.98 out of 5 average rating, 126 reviews

The Dalt Retreat

Superhost
A cottage home is nestled among trees, featuring a welcoming front porch with large windows. The surrounding yard is spacious and marked by a gravel path, providing a sense of openness, while a wooden fence outlines the property.
Home in Eagle Lake
4.7 out of 5 average rating, 60 reviews

Quaint Cottage, 6 miles to Legoland, Pet friendly!

Guest favorite
A serene backyard features a clear swimming pool surrounded by a tiled deck. Sun loungers are positioned around the pool, with a shaded dining area beneath a striped umbrella. Lush greenery and tall trees provide a natural backdrop, enhancing the outdoor space.
Home in Winter Haven
4.78 out of 5 average rating, 337 reviews

Florida Oasis w/ Pool near LEGOLAND

Guest favorite
A screened-in pool area features a spacious pool with clear blue water, surrounded by a concrete deck. A hot tub is adjacent, and a view of the lake is visible beyond. Lush greenery and a few lounge chairs complement the outdoor ambiance.
Home in Winter Haven
4.93 out of 5 average rating, 121 reviews

Fantastic Water Front Home on the Chain of Lakes

Other great vacation rentals in Winter Haven

Guest favorite
Home in Downtown Winter Haven
5 out of 5 average rating, 6 reviews

Million-Dollar Sunsets Included

Guest favorite
A cozy loft bedroom features a spacious bed with soft linens and decorative pillows. A Roku screen projector casts images onto the slanted ceiling. Light from recessed fixtures brightens the room, while minimalist decor includes two small plants and a white dresser against the wall.
Home in Downtown Winter Haven
4.92 out of 5 average rating, 51 reviews

Lake House by Legoland + Loft & Private Dock

Guest favorite
A well-appointed bedroom features a spacious bed with a decorative quilt draped across it. Elegant wood finishes are highlighted on the bed frame, complemented by a bedside lamp and floral-patterned curtains that frame a window. Soft lighting enhances the room's calmness.
Home in Winter Haven
4.72 out of 5 average rating, 69 reviews

4 Bedroom in Quiet Neighborhood

Top guest favorite
A private outdoor area is depicted, featuring a stone path with a small table and chairs shaded by a striped umbrella. A wooden fence encloses the space, enhancing privacy, while decorative items, including a fishing net, add a touch of charm.
Tiny home in Winter Haven
4.91 out of 5 average rating, 98 reviews

Tiny Paradise

Top guest favorite
A wooden dock extends over the calm waters of Lake Howard, bordered by lush grass on either side. A sign indicating 'Private Property' stands at the dock's entrance, while the clear blue sky is dotted with fluffy white clouds in the background.
Guesthouse in Winter Haven
5 out of 5 average rating, 97 reviews

Charming Lakeside Cottage

Top guest favorite
A large outdoor space features a private pool surrounded by loungers in blue and a shaded dining area. A patio table with chairs is placed in the foreground, while a safety fence encloses the pool area, providing a secure environment.
Home in Winter Haven
4.98 out of 5 average rating, 100 reviews

Kid-friendly Home w/ Pool & BBQ

Top guest favorite
A modern living area features a sectional sofa adorned with blue and white decorative pillows. A round coffee table with a marble top sits on a textured area rug. Natural light fills the space through sheer curtains, complemented by a stylish console table and a round mirror.
Home in Downtown Winter Haven
4.99 out of 5 average rating, 72 reviews

Cozy 3 bedrooms 2 bathrooms

Guest favorite
Guesthouse in Winter Haven
4.89 out of 5 average rating, 45 reviews

2 King Beds + Fireplace + Fenced Yard Retreat

When is the best time to visit Winter Haven?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceR1,844 ZARR1,928 ZARR1,945 ZARR1,911 ZARR1,878 ZARR1,810 ZARR1,727 ZARR1,693 ZARR1,609 ZARR1,660 ZARR1,810 ZARR1,928 ZAR
Avg. temp16°C18°C20°C22°C25°C27°C28°C28°C27°C24°C20°C17°C

Frequently Asked Questions

  • What are the best places to stay in Winter Haven?

    Many visitors look for vacation rentals in areas near the lakes, downtown, or residential neighborhoods known for walkability. Rentals with family amenities, lake access, or outdoor spaces are often appreciated.

  • What are the best things to do in Winter Haven with kids?

    Families with kids often visit LEGOLAND Florida Resort for rides and creative spaces, or enjoy hands-on learning at local museums. Lakeside parks with playgrounds provide plenty of room for play.

  • What are some of the best things to do in Winter Haven?

    Explore LEGOLAND Florida Resort, relax along the Chain of Lakes, and experience performances at the local theatre. Art galleries and waterfront dining are also frequently suggested.

  • How is the weather in Winter Haven?

    Winter Haven has mild winters with temperatures typically ranging 49–72°F (10–22°C) and hot, humid summers near 92°F (33°C). Rain is more common from late spring through summer, so packing for brief showers is a good idea.

  • When is the best time to visit Winter Haven?

    Late fall through early spring is often recommended, thanks to comfortable temperatures from about 50°F to 80°F (10°C to 27°C) and fewer rainy days. This season aligns with many outdoor events and milder weather.

  • What are the best places to visit in Winter Haven?

    Popular destinations in Winter Haven include LEGOLAND Florida Resort, the Chain of Lakes Park, and downtown’s shops and art spaces. Many visitors also explore waterfront areas and gardens around the city.

  • What are some hiking trails in Winter Haven?

    Winter Haven has nature trails around local lakes and within city parks, often recommended for walking, birding, or gentle hikes. Many trails wind through scenic wetland or forest settings.

  • What are some family activities we can do in Winter Haven?

    Families often enjoy time at theme parks, nature centers, or on guided boat tours across the city’s lakes. Seasonal community events and interactive museums provide engaging activities for all ages.

  • What are some of the best day trip ideas from Winter Haven?

    Visitors often explore nearby botanical gardens, wildlife preserves, and local state parks. Beaches, historic towns, and cultural attractions located around the region also make for memorable day trips.

  • Are there any pet friendly accommodations available in Winter Haven?

    Many vacation rentals in Winter Haven welcome pets, especially in residential neighborhoods with easy access to parks and walking areas. Some hosts provide yards or pet-friendly amenities to make stays more comfortable.

  • What are some local tips for visiting Winter Haven?

    Arrive early for popular lake activities and consider exploring local walking trails or farmers markets for a relaxed pace. Sun protection, like hats and sunscreen, is advised year-round, as the Florida sun can be strong even in cooler seasons.

  • What is Winter Haven known for?

    Winter Haven is known for its historic chain of lakes, water sports, and a theme park that attracts families. The city’s roots in citrus agriculture are also reflected in its local culture.

  • What are the best hidden gems to explore in Winter Haven?

    Winter Haven has tucked-away lakeside parks, independent coffee shops, and small art galleries that are often recommended among locals. Early mornings on less crowded walking paths provide a tranquil city experience.

  • What are the best foods to try in Winter Haven?

    Locally inspired dishes often feature fresh citrus, southern barbecue, and seafood. Winter Haven is also known for its dessert shops and traditional American diners.

  • What should I bring for a trip to Winter Haven?

    Bring lightweight, breathable clothing for warm days, along with a light jacket for cooler evenings. Sunscreen, swimwear, and comfortable shoes are handy for lakeside activities or exploring city parks.

  • What is the nightlife in Winter Haven like?

    Winter Haven’s nightlife centers around casual bars, live music venues, and locally owned restaurants. Visitors can explore spaces with outdoor patios, craft beer selections, and venues occasionally hosting local musicians.

  • What are the most popular events or festivals in Winter Haven?

    Winter Haven has well-attended community events in spring and summer, as well as celebrations connected to holidays like Labor Day weekend. Festivals often highlight local music, food, and lake-centered activities.

  • Are there family friendly vacation rentals in Winter Haven?

    Winter Haven has many family-friendly vacation rentals, including homes with multiple bedrooms, kitchens, and outdoor spaces. Areas near parks, lakes, and family attractions are often suggested for those traveling with children.

Quick stats about vacation rentals in Winter Haven

  • Total vacation rentals

    Explore 460 vacation rentals in Winter Haven

  • Nightly prices starting at

    Winter Haven vacation rentals start at R335 ZAR per night before taxes and fees

  • Verified guest reviews

    Over 18,410 verified reviews to help you choose

  • Family-friendly vacation rentals

    260 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 160 rentals that welcome pets

  • Vacation rentals with a pool

    150 properties feature pools

  • Rentals with dedicated workspaces

    270 properties have a dedicated workspace

  • Wi-Fi availability

    460 of Winter Haven vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Self check-in, Gym, and BBQ grill across Winter Haven rentals

  • 4.8 Average rating

    Winter Haven stays are highly rated by guests—averaging 4.8 out of 5!

Destinations to explore

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