Waterfront holiday rentals in Lakeland

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!

Lakefront Cottage in the Trees. Near SEU and FSC

This 1920’s 1 bedroom 1 bath lakefront historic cottage is separate from the main house with its own parking, fire pit, outdoor grill / picnic area, dock & beach. The queen bed and large couch sleeps 3 adults. Only a half mile from Southeastern University and 2 miles to Florida Southern College. Kayaks, stand up paddle board, 4 seater pedal boat, fishing poles and basic tackle are provided for your enjoyment. Come unwind and enjoy the lake and views from the hammock and your private beach!

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!

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!

Extra large home! Bring Your Boat & all the Toys!

Bring your boat, skis, fishin’ pole, or any other water toys! We supply ping pong, corn hole, bicycles and other toys! Directly across from Lake Howard boat ramp and 10 minutes from LegoLand! Enjoy this spacious, well-equipped 2300 sf home that has everything you need to enjoy your stay in Winter Haven, aka Chain of Lakes City, a quaint downtown with free parking-- and just a skip away from Disney and Universal. This getaway is an above-average accommodation both in style and comfort!

3 Bedroom House | 2 Blocks from Lake Hollingsworth

Enjoy the convenience of this beautiful home located around the most sought-after area, Lake Hollingsworth. Located just two blocks from the lake, one block from Cleveland Heights country club, and directly across from Common Ground park, this property boasts an unbeatable location. Comfortably sleeping 6 guests, this 3 bedroom, 2 bathroom home is the perfect place to stay when visiting Lakeland if you want to experience all of the city's beauty, restaurants, shopping, and things to do.

Brand New! Florida Riverfront Getaway

Take it easy at this unique and tranquil getaway. Beautiful cabin in the woods with modern amenities right on the Alafia River, just 20 minutes canoe/kayak ride to Lithia Springs! No need to rent or haul any equipment, Kayaks and Canoe are ready for use on the property! Enjoy Florida's best kept secret from the oversized deck overlooking the river and conservation area or from the hammocks under the palm trees; light up the fire pit or the grill and enjoy all that nature has to offer!

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!

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.

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!

Beautiful Lake House Boating Fishing near Legoland

Welcome to The Executive Lake House 15 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 2 bedrooms and a kids loft. A full kitchen and laundry and one full bathroom The backyard has a playground and pool area that is on the property in backyard and is shared with other guests who may be staying here.

Cozy 2-bedroom guesthouse on the lake

Enjoy a relaxing getaway on the beautiful Lake Ariana. Two bedrooms with queen beds comfortably accommodating four adults. Fully equipped kitchen and full bathroom with tub. Laundry room with washer and dryer. Private parking with plenty of room for boat or jet skis. Private entry with hosts on premises. Camera at exterior door for security. The guesthouse is behind the main home. There is not a view of the lake from inside the guesthouse.