
Waterfront holiday 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.

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

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.

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!

Lakefront Home on the Winter Haven Chain O’Lakes!
Completely renovated 2 Bedroom, 1.5 bath home location on beautiful Lake Roy on the Winter Haven Chain O’Lakes. One bedroom on the lower level with a queen bed. Second story with king bed and twin bed. Full bath located upstairs). Comfortably sleeps 5. (Additional guests must be pre-approved). Free boat parking and boat rental available. House is connected to the main home with a private keyless touchpad for contactless entry. Pet friendly with prior approval and pet deposit.

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 , full kitchen and laundry and one full bathroom The backyard has a playground and pool area that is ( not) included at this price point. If wanting an additional charge of 20 dollars per night Will be charged. Let me know at booking.

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

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!

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 ****

Legoland Lakeside Splash 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!

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.
Popular amenities for waterfront rentals in Winter Haven
Waterfront apartment rentals

Magical Holiday+Relax+FreeParking

Lovely one bedroom apartment.

WATER View 4BR/Elevator/DISNEY Area

Renovated Studio-Near INT'L Drive and Parks!

Amazing Apartment in Orlando - Kissimmee

*NrDisney*BrandNew*LakeFront*APT

Serenity Lake: Spacious & comfy 3BR/2BA Apartment

★BRAND NEW APT with LAKEVIEW - Close to Disney★
Waterfront house rentals

Lake Whistler Beach House with lakefront pool

Private Ranch Style Home on Lake

Spacious 3BR Home | Peaceful Stay Near I-4

Cozy Lakefront Home w/ Pool -7 mins from Legoland

*Luxurious Paradise Mansion: Pool, Spa & Cinema

Luxury Tropical Themed Villa With Lake View!

Southern Dunes Lakeview Poolhome

LARNE LODGE House with Hot Tub 3 miles to Disney!
Waterfront apartment rentals

3161-305 Resort Lake View Disney Universal Orlando

303_To Infinity & the Ocean Breeze Apartment

Chic Disney Resort Condo • Pool Access Near Parks

A Resort Getaway with many amenities

*NEW* Adventureland Stay / Sleeps 6 / Near Disney

Universal Studios Getaway – Prime Location!

Marvelous apartment near Disney first floor

[Lake View, Modern Decor, 1 Mile to Disney!]
When is the best time to visit Winter Haven?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | € 126 | € 142 | € 144 | € 141 | € 124 | € 116 | € 116 | € 120 | € 116 | € 131 | € 131 | € 129 |
| Avg. temp | 16°C | 18°C | 20°C | 22°C | 25°C | 27°C | 28°C | 28°C | 27°C | 24°C | 20°C | 17°C |
Quick stats about waterfront rentals in Winter Haven

Total holiday rentals
Explore 90 holiday rentals in Winter Haven

Nightly prices starting at
Winter Haven holiday rentals start at € 34 per night before taxes and fees

Verified guest reviews
Over 6,240 verified reviews to help you choose

Family-friendly holiday rentals
70 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 40 rentals that welcome pets

Holiday rentals with a pool
30 properties feature pools

Rentals with dedicated workspaces
70 properties have a dedicated workspace

Wifi availability
90 of Winter Haven holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Winter Haven rentals

4.9 Average rating
Winter Haven stays are highly rated by guests – averaging 4.9 out of 5!
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- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Disney Springs
- SeaWorld Orlando
- Busch Gardens Tampa Bay
- Magic Kingdom Park
- Disney's Animal Kingdom Theme Park
- Raymond James Stadium
- Old Town Kissimmee
- Walt Disney World Resort Golf
- Epcot
- ESPN Wide World of Sports
- Amway Center
- Reunion Resort Golf Courses - Palmer & Watson
- Universal's Volcano Bay
- Discovery Cove
- Aquatica
- Amalie Arena
- Island H2O Water Park
- Disney's Hollywood Studios
- ICON Park
- Southern Dunes Golf and Country Club
- ZooTampa at Lowry Park




