Waterfront holiday 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 favourite

Home in Davenport

4.93 out of 5 average rating, 104 reviews

Beautiful Pool Home With Rear Conservation Views

Watersong Resort is a 46 acre paradise set in beautiful conservation, close to tourist attractions. This elegantly designed and beautifully decorated 5-bedroom vacation home boasts enough space to accommodate a large family. Furnished for comfort, it offers three separate living spaces and a modern kitchen, which is perfect for cooking up culinary delights. The large pool deck, with dining for 10, overlooks stunning conservation where you can soak up the sun and appreciate the Florida sunsets.

Guest favourite

Cottage in Winter Haven

4.82 out of 5 average rating, 134 reviews

6 - Just Beachin' Cabin 2bed/2bath - Unit 10

Experience the tranquility of the Sunshine State from this quaint-yet-modern vacation rental home, complete with 2 bedrooms, 2 bathrooms, a private deck, and modern interior finishes. You’ll enjoy direct access to a boat launch and the Chain of Lakes, a fishing and boating paradise complete with 24 canal-connected lakes! Spend your days out on the water, make incredible memories with your family at LEGOLAND Florida, or opt to visit the theme parks in Orlando - from this home, you can do it all!

Guest favourite

Home in Winter Haven

4.99 out of 5 average rating, 113 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 favourite

Villa in Lake Wales

4.98 out of 5 average rating, 190 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 favourite

Guest suite in Winter Haven

4.91 out of 5 average rating, 164 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 favourite

Rental unit in Auburndale

4.95 out of 5 average rating, 223 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 favourite

Cottage in Eagle Lake

4.99 out of 5 average rating, 245 reviews

Lake McLeod, Roe Family House - Close to Legoland

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 favourite

Guest house in Winter Haven

4.87 out of 5 average rating, 254 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 ****

Superhost

Home in Winter Haven

4.84 out of 5 average rating, 206 reviews

💎LakeFront💎ModernCottageTiny-Home☀🎢4milesLEGOLAND🎢

WELCOME! Lake Mariam Tiny Home sits on 3 acres of Lakefront Property. If hospitality & peace is what you want, our space focuses on that & much more. Rejuvenate from a day of Adventure or Business in our Lakefront property home. ONLY 4 miles from LEGOLAND. Famous Orlando attractions (SeaWorld, Disney/Universal, Airport & Downtown) all w/in an hour drive! * Pets considered with prior approval. Please provide pet details before booking. Thank you for understanding!

Guest favourite

Cabin in Davenport

4.93 out of 5 average rating, 201 reviews

$69! Cozy Cabin- Disney 20 Miles Away!

Book with us now and receive access to all of these amenities✨: •Fast Internet •Covered Patio •Safe Gated Location •Keypad Entry Door •Comfortable Queen Sized Bed •Cable TV (Adjustable) •Modernized Brand New Full Bathroom •Nearby All Major Attractions, Theme Parks, and Malls •Outdoor Dining Area •Kitchen, Fridge/Freezer, & Breakfast Nook •Complimentary Coffee & Breakfast •Cooking Equipment •And Much More! Book with us now!

Guest favourite

Guest house in Lakeland

4.98 out of 5 average rating, 229 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 favourite

Home in Lakeland

4.95 out of 5 average rating, 103 reviews

Cozy Lake House Retreat - Amazing Views !

Welcome to our lake house retreat in Lakeland, Florida. You can enjoy a peaceful getaway with beautiful sunset views and tranquil waters during the evenings, and still visit major cities such as Orlando and Tampa during the day which are less than an hour away. Minutes from Southeastern University, Florida Southern, Lake Hollingsworth, and other attractions in the Lakeland area.