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Waterfront holiday rentals in Lakeland

Find and book unique waterfront rentals on Airbnb

Top-rated waterfront rentals in Lakeland

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

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Top guest favourite
A serene lakeside view showcases the tranquil waters of Lake Hollingsworth, surrounded by lush greenery and walking paths. Patterns of vegetation are visible along the shoreline, while distant trees line the horizon, creating a peaceful natural landscape.
Home in Lakeland
4.98 out of 5 average rating, 108 reviews

Lakeland LakeFront 4BD | 3BA FSC SEU Sun & Fun Tigers

Welcome to Laketitude—your spacious lakefront escape on Lake Hollingsworth! Just steps from Florida Southern College and Frank Lloyd Wright gems, minutes to downtown Lakeland, Sun ’n Fun, and Tiger Town, with Tampa and Orlando only 40 mins away. This 4BR/3BA retreat sleeps 10 and features a large backyard, 65” Smart TV, Xbox, coffee bar, and full kitchen—perfect for families, college visits, and getaways. Don’t miss out on our deep connection with FSC’s rich history- message us to learn more!

Guest favourite
A dining area features a wooden table surrounded by beige chairs and a bench. Two decorative blue vases are placed at the center. A stone fireplace serves as a backdrop, with a modern light fixture above. A mirror reflects the room's light blue walls.
Home in Lakeland
4.8 out of 5 average rating, 132 reviews

Spacious 3BR Home | Peaceful Stay Near I-4

Located in a safe and quiet neighborhood, this stylish home offers the perfect mix of comfort, convenience, and privacy, ideal for families, work trips, or weekend getaways. 🌿 Enjoy peaceful mornings or golden sunsets from the backyard with relaxing views of the pond. You might spot birds like cranes, ducks, or even herons. 📍Whether you're in town for work, visiting family, or just passing through, this home is your cozy home base in Central Florida. ✨ Weekly & Monthly Discounts Available

Top guest favourite
An outdoor porch features a two-person Jacuzzi, inviting relaxation while overlooking a lake. Warm lighting is provided by lanterns, creating an ambient atmosphere against the backdrop of a colorful sunset and silhouettes of trees.
Tiny home in Dade City
4.98 out of 5 average rating, 217 reviews

Eco-Luxurious Lakefront haven (Fire pit & Hot Tub)

Experience the perfect blend of an eco-friendly retreat and modern luxury of our lakefront container home. Nestled in the heart of nature, this stylish oasis promises an unforgettable experience where you can immerse yourself amidst the beauty of the countryside without sacrificing comfort. Plus, enjoy the opportunity to interact with our farm animals, adding a touch of rural charm to your agritourism escape. Also, feel free to check out my other listing, Casa de Elvira on my host profile.

Top guest favourite
Three thoroughbred horses graze peacefully on a lush green pasture. The area is surrounded by tall trees, providing shade and a natural backdrop. A glimpse of a trailer can be seen in the background, indicating the farm's working environment.
Guest suite in Winter Haven
4.96 out of 5 average rating, 307 reviews

Horse Farm on a Beautiful Lake

Small Thoroughbred Race Horse Farm on a beautiful lake. The dock has plenty of benches for fishing, picnicking, or just dreaming. There is a Swimming pool right out your door. Please note there is no barrier around pool and all children (anyone under age of 18)must be supervised at all times. Guests must swim at their own risk. You may see horses in the paddocks. The pool deck overlooks the lake for hanging out or quiet time. Please note price is for studio (sleeps 3 or more with sofa beds)

Top guest favourite
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 favourite
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.
Flat in Lakeland
5 out of 5 average rating, 136 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 favourite
A modern living area features a light gray sectional sofa and a round coffee table set atop a soft area rug. The open design allows visibility into a fully equipped kitchen with white cabinetry and stainless steel appliances. Natural light brightens the space from nearby windows.
Home in Lakeland
4.77 out of 5 average rating, 172 reviews

Gorgeous Private Lakeland Home

Guests love our spacious and charming fully updated and renovated home, just a short drive from Disney and Universal Orlando, Busch Gardens, and the beaches of Tampa Bay! Take an evening stroll to one of the serene surrounding lakes. Adjacent to famous Lake Hollingsworth and within close proximity of downtown Lakeland and the RP Funding Center. Perfect for your next getaway including High speed Wifi, Two 4K 55” and One 4K 65" TV with Netflix and everything you need for your vacation!

Top guest favourite
A wooden deck overlooks the calm waters of Lake Ariana, framed by greenery. A small table with two chairs is positioned to enjoy the view, while a potted plant adds a touch of nature to the space. Spanish moss drapes gracefully from nearby branches.
Flat in Auburndale
4.96 out of 5 average rating, 258 reviews

Ariana Place - Tree House Like Lakefront Views

An Upstairs Sumptuous Tree house (like) Apt on Lake Ariana Waterfront. Upper Outside Deck with chairs & table. Quiet and tranquil with Hi-Speed Wifi for Business Travelers, Smart Antenna TV and Incredible Views for Romantic Get-Aways. Located near Disney, Legoland & Busch Gardens in Central Florida. Luxurious Bedding, Full Kitchen with Coffee & Wine Bar. One Complimentary Bottle of Cabernet per Stay. Sorry, No Pets. No Smoking inside Apt but allowed on property. Save 5% monthly

Top guest favourite
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, 301 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!

Top guest favourite
The quaint lakefront cottage is framed by large, leafy trees and draped with Spanish moss. A gravel entrance leads to a welcoming porch, featuring large screened windows. Lush greenery surrounds the property, creating a natural, serene setting.
Guest house in Crystal Lake
4.98 out of 5 average rating, 275 reviews

Modern lakeside retreat by SEU and FSC

This 1920’s 1 bedroom 1 bath lakefront historic cottage is separate from the main house with its own entrance, parking, screened front porch, fire pit dock & beach. The queen bed and large couch sleeps 3 adults. Only 1 mile from Southeastern University and 3 miles to Florida Southern College. Kayaks, stand up paddle board, 4 seater pedal boat, and fishing poles and tackle are provided for your enjoyment. Come unwind and enjoy the lake views from the hammock and private beach!

Guest favourite
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, 104 reviews

3/2 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 favourite
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
4.91 out of 5 average rating, 210 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.

Popular amenities for waterfront rentals in Lakeland

When is the best time to visit Lakeland?

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Avg. price$137 SGD$142 SGD$143 SGD$143 SGD$143 SGD$135 SGD$130 SGD$133 SGD$124 SGD$125 SGD$129 SGD$135 SGD
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Quick stats about waterfront rentals in Lakeland

  • Total holiday rentals

    Explore 30 holiday rentals in Lakeland

  • Nightly prices starting at

    Lakeland holiday rentals start at $64 SGD per night before taxes and fees

  • Verified guest reviews

    Over 2,450 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Holiday rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    30 of Lakeland holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Lakeland rentals

  • 4.8 Average rating

    Lakeland stays are highly rated by guests – averaging 4.8 out of 5!

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