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Waterfront vacation rentals in Winter Haven

Find and book unique waterfront rentals on Airbnb

Quick stats about waterfront rentals in Winter Haven

  • Total vacation rentals

    Explore 100 vacation rentals in Winter Haven

  • Nightly prices starting at

    Winter Haven vacation rentals start at G$8,359 GYD per night before taxes and fees

  • Verified guest reviews

    Over 6,340 verified reviews to help you choose

  • Family-friendly vacation rentals

    70 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 50 rentals that welcome pets

  • Vacation rentals with a pool

    30 properties feature pools

  • Rentals with dedicated workspaces

    70 properties have a dedicated workspace

  • Wi-Fi availability

    100 of Winter Haven vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Winter Haven rentals

  • 4.9 Average rating

    Winter Haven stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated waterfront rentals in Winter Haven

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

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Superhost
A comfortable living area features a spacious sectional sofa adorned with neutral-toned cushions. A patterned area rug lies beneath, and a wall-mounted television is positioned above a wooden shelf. Natural light enters through the large window covered with light curtains.
Home in Wahneta
4.92 out of 5 average rating, 105 reviews

Hidden 💎 Minimalist Design | Lego+Disney

Brand new, single family home with free parking. 4 Bed/2 Bath updated home with a large screened sun room. We made this home family-friendly because as parents ourselves, we know how nice that is! We even provided a baby crib. This home is light, breezy, comfortable, newly furnished and decorated; centered around a minimalistic vibe. Fully equipped, washer and dryer. Internet WiFi included. Close to Legoland (9 mi.), Disney (29 mi.), Golfing (6 mi.), and surrounded by beautiful lakes.

Top guest favorite
The living area features a modern sectional sofa with colorful throw pillows in vibrant red and yellow. A matching ottoman sits in front, accompanied by stylish side tables with lamps. Bright blue walls create a lively backdrop, enhanced by a large abstract painting and adjacent dining space.
Villa in Lake Wales
4.98 out of 5 average rating, 207 reviews

Lakefront, Dock, 2 Kayaks, near Bok & Legoland

** New Construction ** Breathtaking view of lake, private dock (2 kayaks for guests included), beach/swim area, outdoor shower, large private balcony w/gas grill and gorgeous sunsets! 2 Bedrooms each w/walk in closet, two full baths, full kitchen w/all amenities. All new furnishings, (3) 4K Smart TV's, FAST free wifi. Gorgeous location, quiet street, private free parking, 2 private entrances. Villa is detached from main house. Near Disney, LegoLand, Bok Tower. WEEKLY & MONTLY DISCOUNTS

Guest favorite
The exterior of a spacious home is presented, featuring a blue façade and a welcoming entrance. Lush tropical foliage surrounds the property, which is highlighted by palm trees and manicured lawns. A vibrant sunset casts colorful hues in the sky, enhancing the serene atmosphere.
Home in Winter Haven
4.98 out of 5 average rating, 133 reviews

Spectacular Waterfront Home in Winter Haven

Enjoy a wonderful family get away at this premier waterfront home on the famous Chain of (19) Lakes! Separate yourself from the crowd at this beautiful Cypress Gardens home set on an acre with lush tropical foliage and surrounded by 3 sides of water. Featuring a chef's kitchen, 2 private docks, the "New Florida Pool," 2 hot tubs, fire pit and many more amenities. Enjoy relaxed luxury at its finest. We are just a few minutes to Legoland, restaurants and shopping, but miles from ordinary!

Top guest favorite
A bright workspace is showcased with large windows offering views of the lake. Two yellow armchairs sit beside a glass-top table. A desk with a lamp is positioned against the wall, with a potted plant adding a touch of greenery.
Apartment in Lakeland
5 out of 5 average rating, 140 reviews

Romantic Lakefront – Feed Swans – Walkable Dining

Discover SWAN LAKE VACATIONS. Swan elegance meets city charm steps away. Highlights: • Lake Views • Downtown Stroll • King-sized bed • Modern Comfort • Full Kitchen • Semiprivate Patio • Between Tampa & Orlando Why Swan Lake Vacations? • Central Hub • Safety Assurance • Easy drive to beaches and Walt Disney World • Experienced Hosts Escape to Swan Lake Vacations—a place where swans grace the surroundings next to quaint downtown life. Book for a perfect blend of nature and urban comfort!

Guest favorite
A two-story, tropical style home is showcased, featuring a vibrant exterior in warm shades. A Tesla is parked prominently in the driveway, with lush palm trees and greenery flanking the entrance. The garage is accessible, contributing to the property's inviting curb appeal.
Home in Haines City
4.92 out of 5 average rating, 106 reviews

Luxury Tropical Themed Villa With Lake View!

Just a half-hour from Disney and other major theme parks, this beautiful Tropical style home has a sunset lake view and was recently renovated with brand new furniture! The house resides comfortably in a gated community with 4 bedrooms and 3 bathrooms in a 2-story, 1700 square foot tropical setting! A private heated pool and Tesla charging is also accessible at the home. The Southern Dunes community boasts a large public golf course within a few minutes walk through the neighborhood!

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 Cypress Gardens
4.96 out of 5 average rating, 115 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 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, 303 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!

Guest favorite
Home in Haines City
4.88 out of 5 average rating, 129 reviews

Breathtaking Home

New two story home with private pool, patio, barbecue area & game room. Surrounded by parks, gardens, tranquil lakes & walkways with breathtaking views. Resort amenities located right across the street with an amazing clubhouse (private owned), Bar & Grill restaurant, water park, arcade and gym (extra fee), soccer & football field, & event center for parties & weddings. (Pet free home) 12 mi Legoland/19 mi Disney/26 mi SeaWorld & International Drive/29 mi Universal Studios.

Guest favorite
A serene lakefront scene captures a sparkling pool surrounded by palm trees at sunset. The sky features vibrant hues of orange and purple, reflecting in the calm water. Two lounge chairs are positioned beside the pool, creating a peaceful retreat.
Guesthouse in Winter Haven
4.87 out of 5 average rating, 283 reviews

The Russell Lake House

This is a Cabana. It has 2 sets of bunk beds (4 total beds). Approx 400 sq. Ft. . Includes a bathroom with sink, toilet, and walk-in shower. AC and heat are available. The property has a pool that can be used while onsite. The entire property's back yard is on a lake (lakefront) with a dock. Ample off street parking, quiet neighborhood with a private entrance for guests. **** we are in the process of rebuilding the dock so it will be unavailable until further notice ****

Guest favorite
An outdoor dining area is shown under a shaded pergola, featuring a large table surrounded by comfortable chairs. The spacious pool is visible in the background, with a patio area adorned with colorful tiles. Lush greenery frames the scene, adding a tranquil vibe.
Home in Cypress Gardens
4.95 out of 5 average rating, 106 reviews

4/2 House near Legoland w Optional Heated Pool

Relax with the whole family at this peaceful home in Winter Haven 5mins to Legoland and the new Peppa Pig theme park, perfect for your next family vacation! Right across the street from lake Ned park with lake View from the front porch and office, bring your small water toys as there is a public boat ramp across the street. There are many restaurants as well as a Publix grocery store all within 2 miles from the home! Downtown winter haven is a short 10 minute commute.

Top guest favorite
An inviting swimming pool is surrounded by a spacious patio area, featuring lounge chairs and a shaded table with an umbrella. The serene view of Little Lake Otis and lush greenery is visible in the background under a partly cloudy sky.
Home in Winter Haven
4.92 out of 5 average rating, 214 reviews

Legoland Lakehouse Canoe & Kayak Retreat

Relax in style in this 100 year old custom built home.Tall ceilings,large rooms and wood floors throughout.With an extra large swimming pool overlooking Little Lake Otis this outdoor area is second to none.Less than 2 miles from Legoland,Chain of Lakes Fieldhouse,and Downtown Winter Haven. It is possible that days may be available and not listed on the calendar. This is to give ample time for cleaning. Feel free to ask for additional availability and shorter stays.

Top guest favorite
A charming lake home is showcased with a light-coloured façade and blue shutters. A welcoming entrance is flanked by decorative chairs, with well-maintained landscaping featuring green grass and flower beds enhancing the outdoor appeal.
Home in Winter Haven
4.98 out of 5 average rating, 123 reviews

Lake View, Game Room, 10 min Legoland

Welcome to The Elby, a fully renovated 1940's lake home with spacious rooms, modern amenities, and indoor and outdoor games designed w/ family fun in mind! Only 3 min to charming downtown Winter Haven shopping & restaurants, 10 min to Legoland, 30 min to historic downtown Lakeland, & conveniently located between Tampa & Orlando (45 min to Disney & just 60 min to Tampa). We can't wait for you to enjoy the beautiful lakes of Winter Haven at The Elby!

Popular amenities for Winter Haven waterfront rentals

When is the best time to visit Winter Haven?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$35,110 GYDG$36,991 GYDG$37,409 GYDG$34,274 GYDG$30,094 GYDG$28,213 GYDG$28,213 GYDG$29,258 GYDG$28,213 GYDG$31,139 GYDG$32,602 GYDG$33,229 GYD
Avg. temp16°C18°C20°C22°C25°C27°C28°C28°C27°C24°C20°C17°C

Destinations to explore

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  4. Polk County
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