Waterfront vacation rentals in Winter Haven

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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

Condo in Orlando

4.97 out of 5 average rating, 72 reviews

Modern Lake view Condo 1 mile from Disney

You will love our updated 1 bedroom, 2 bathrooms, spacious 798 sq ft condo so close to Disney at Blue Heron Beach Resort in wonderful Lake Buena Vista, home to lots of restaurants and shopping! Enjoy spectacular sunrise views from your private balcony overlooking the lake. Resort amenities include large swimming pool, kiddie pool, hot tub, tiki bar, fitness rooms & game room. Located on peaceful Lake Bryan, you have access to water sports like kayaking, boating, jet skis & fishing on the lake.

Guest favorite

Home in Kissimmee

4.91 out of 5 average rating, 103 reviews

#5744 LakeFront Two Master Suites Spa/Pool Disney

Come & Relax in the beautiful Florida sunshine and enjoy all the conveniences this renovated house offers.The private home is located inside the famous Regal Oaks Resort, so you can use all the resort amenities at no extra charge! The best part - Disney World and other attractions are just a short drive away, making it perfect for families and fun lovers alike. 5 Min Walk to Old Town 8 Min Drive to Disney World 20 Min Drive to Universal Studios Experience Kissimmee With Us & Learn More Below!

Superhost

Townhouse in Kissimmee

4.81 out of 5 average rating, 175 reviews

NEW Vacation Home in Storey Lake Resort, Disney!!!

NEW & MODERN HOME with lake view. NEAR DISNEY! Located in the new Storey Lake condominium in Kissimmee, just minutes from the Walt Disney World and within walking distance to shopping, dining, and other local activities. Beautiful townhouse with 5 bedrooms and 4 bathrooms offers great comfort and modern decor with Smart 4k TVs in all bedrooms and living room, private pool, free Wi-Fi, dishwasher, washer and dryer, iron, ironing board, hair dryer and access to the fabulous Storey Lake Clubhouse

Guest favorite

Cottage in Winter Haven

4.83 out of 5 average rating, 141 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 favorite

Villa in Lake Wales

4.98 out of 5 average rating, 192 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

Condo in Orlando

4.86 out of 5 average rating, 147 reviews

Welcome to this Blue Heron Beach Beauty.

Great condo location close to Disney. Recently updated. Shuttles to theme parks. Departure times from Resort: Epcot: 8:20am, 10:50am $10 per person round trip. Sea World: 9:30am, 11:05am, 12:00pm $10 per person round trip. Universal: 9:30am, 11:05am, 12:00 pm $12/PP/USD charge for the shuttle to Universal. SHUTTLE SERVICE IS SUBJECT TO CHANGES. Return times: Epcot: 6:20pm, 8:30pm, 10:30pm Sea World: 5:30pm, 6:30pm Universal: 7:15pm $12/PP/USD charge for the shuttle to Universal.

Superhost

Apartment in Clermont

4.8 out of 5 average rating, 257 reviews

Charming Lakefront Apt. Near Disney

Unique 1,100 sq. ft apartment located in South Clermont, less than 25 minutes to Downtown Orlando, Walt Disney World, and all Central Florida attractions. Lake Sawgrass is available for fishing, kayaking, boating, and other watersports activities. Our location is quiet and peaceful located in the countryside. We are located on the newly paved Schofield Road, with less than 1-mile of dirt road now on Cook Road. The unit is on well water, with water softening and filtration installed.

Guest favorite

Apartment in Kissimmee

4.88 out of 5 average rating, 85 reviews

*NrDisney*BrandNew*LakeFront*APT

Experience lakeside living in this BRAND NEW 5-star luxury apartment, boasting a modern design near Disney and the airport. Perfect for executive stays or Disney vacations, the property is located just 20 minutes from Disney and the airport. Enjoy private outdoor dining on the patio, and unwind in the hammock while soaking up the serene atmosphere. This 5-star apartment offers off-street parking and complimentary Wi-Fi. Step out directly to the lake for stunning sunset and sunrise views

Guest favorite

Home in Kissimmee

4.88 out of 5 average rating, 110 reviews

Peaceful Waterfront Retreat, Close to Everything!

Beautiful 4br peaceful lakefront home in safe, quiet community. Close to major shopping and restaurants! Just a short drive to the Turnpike and 417 highway, close to Disney, Seaworld, Medical City, Lake Nona and the VA Hospital. Comfortable space with smart TVs and central AC. Fully equipped kitchen. Split floor plan perfect for families and friends. The master bedroom faces the rear of the home, large windows allowing natural light to enter the home all while enjoying your waterview!

Guest favorite

Apartment in Auburndale

4.95 out of 5 average rating, 224 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

Superhost

Condo in Orlando

4.86 out of 5 average rating, 128 reviews

SALE! Pool, Lake Views, Disney Fireworks, SALE #5

A newly updated luxurious and spacious condo at Blue Heron Beach Resort for six overlooking beautiful 400+ acre lake Bryan! Guest will have access to first-class amenities available on property which is minutes away from all the Orlando fun and excitement. Gorgeous views from Disney fireworks to true nature along with water sports, several pools, nearby restaurants will complete your experience. Perfect stay for families and people traveling for vacation or work.

Guest favorite

Home in Winter Haven

4.91 out of 5 average rating, 166 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.