Waterfront vacation rentals in Winter Haven

Find and book unique waterfront rentals on Airbnb

Top-rated waterfront rentals in Winter Haven

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

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Guest favorite

Guest suite in Haines City

4.92 out of 5 average rating, 87 reviews

1 BR 1BA Lake Apt. Boat slip, Deck, Pets, Laundry

Come wake up to birds singing, looking out your windows to a nice deep water canal view. The canal leads to Lake Hatchineha (great fishing). TVs in every room. Fully loaded kitchen; private entrance. There is a porch, laundry and deck area shared with one other apt. Free laundry . We are 45 min from MCO(airport) 45 min from Disney and 15 minutes to Legoland. Bok Towers is a unique park that is 18 miles away. Star gazing and bicycling or fishing. Pets $35 per trip with a fenced in area for them.

Guest favorite

Home in Davenport

4.91 out of 5 average rating, 114 reviews

No Airbnb Fees! Theater/Pool/ Spa/Game Room 278491

Unable to book this house? Don't worry! Check my profile for similar homes that might suit your needs WE HAVE 24/7 CUSTOMER SERVICE! Tired of visiting the parks every day? Step inside of this beautiful 3117 sqft house and discover private pool, BBQ, cinema and a game room specially designed to entertain your family and keep the fun going. Enjoy the resort's clubhouse with a restaurant, pool with water slide, lazy river, gym, playground and a tennis court. Experience the vacation of a lifetime!

Top guest favorite

Home in Winter Haven

4.98 out of 5 average rating, 133 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 two bedrooms, a loft , full kitchen and laundry and one full bathroom. The 1100 square foot space which offers 12 foot ceilings and unique interior design will leave you amazed. If your looking for more than a space to sleep but a place to vacation than this is It.

Guest favorite

Guest suite in Winter Haven

4.89 out of 5 average rating, 190 reviews

2 Bedroom Winter Haven Guest Suite

Private lock-off unit. Only shared between your party. Attached to main home , no shared spaces inside. 1st bedroom -Queen bed and sitting area bathroom attached. 2nd bedroom- two twin sized beds Kitchen and living room included and not shared outside of your party. 3 minutes from Winter Haven hospital. Self check in and out. 20 minutes from Legoland. 45 minutes from Disney and Universal This is an older florida neighborhood with a diverse and working class vibe. Located on Lake Maude

Guest favorite

Home in Haines City

4.89 out of 5 average rating, 112 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 (extra fee), arcade, gym, volleyball court, soccer & football fields, & event center for parties & weddings. (Pet free home) 12 mi Legoland/19 mi Disney/26 mi SeaWorld & International Drive/29 mi Universal Studios.

Top guest favorite

Home in Winter Haven

4.98 out of 5 average rating, 119 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

Apartment in Auburndale

4.95 out of 5 average rating, 237 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

Guest favorite

Cottage in Eagle Lake

4.99 out of 5 average rating, 270 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

Guesthouse in Winter Haven

4.88 out of 5 average rating, 273 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

Home in Winter Haven

4.91 out of 5 average rating, 175 reviews

Hidden Haven Lakehouse Pool by Legoland

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

Guesthouse in Lakeland

4.98 out of 5 average rating, 247 reviews

Modern lakeside retreat by SEU and FSC

This 1/1 lakefront historic cottage, built in 1920, is separate from the main house with its own entrance, parking, front porch & beach. The queen bed and large couch sleeps 3 adults. Only 1 mile from Southeastern University and 3 miles to Florida Southern College. Kayaks and fishing poles are provided for your enjoyment during your stay. Come unwind and enjoy the lake views from the hammock and private beach!

Guest favorite

Cottage in Winter Haven

4.89 out of 5 average rating, 135 reviews

3 - Lake Life House 1 bed/1bath - Unit 15

Whether you’re planning to try your hand at fishing in the region’s world-famous Chain of Lakes or scheming up a surprise family retreat to Legoland with the kiddos, this Winter Haven home is ideally located for your getaway! With 1 bedroom, 1 bathroom and access to a boat ramp on a private canal to Lake Eloise. This vacation rental makes it easy to experience the Florida lake life.