Top-Rated Winter Haven Holiday homes for Every Budget and Style!
Looking for a holiday home in Winter Haven (Florida)? Browse a wide range of vacation rentals – from cozy retreats to spacious family homes – starting at just $50.00 per night. Whether you are planning a weekend getaway or a longer stay, you will find the perfect home away from home in the heart of Winter Haven.
We found 45 Holiday-homes in Winter Haven and the surrounding area (within 20 miles)
Villa in Winter Haven, Florida , 2511 Cypress Gardens Boulevard
Walk to LEGOLAND Heated Pool Putting Green Beach Sunsets Boat Dock offers accommodations in Winter Haven, 0.9 miles from Legoland Florida and 12 miles...
Villa in Winter Haven, Florida , 144 Avenue East Southeast
Getaway Clubhouse 5 mil Legoland &.5 mil Downtown offers accommodations in Winter Haven, 4.1 miles from Legoland Florida and 11 miles from Dearborn Ra...
Family-Friendly Eagle Lake Home, 7 Mi to Legoland! is located in Winter Haven, just 6 miles from Legoland Florida and 8.5 miles from Dearborn Railroad...
Holiday home in Winter Haven, Florida , 146 Brad Circle
146 Florida 3BR Home close to Legoland Park 12ppl is located in Winter Haven, just 7.7 miles from Legoland Florida and 9.3 miles from Morris Mine Rail...
Family-Friendly Winter Haven Home with Pool! is located in Winter Haven, just 7.9 miles from Dearborn Railroad Station and 9.1 miles from Legoland Flo...
Winter Haven Retreat with Private Pool! offers accommodations in Winter Haven, 1.8 miles from Legoland Florida and 12 miles from Dearborn Railroad Sta...
Holiday home in Winter Haven, Florida , 806 Wakulla Drive
Stylish-N-Private 1BR Retreat 2 Miles to LegoLand offers accommodations in Winter Haven, 15 miles from Morris Mine Railroad Station and 15 miles from ...
Holiday home in Cypress Gardens near Winter Haven, Florida
Bright Cypress Gardens Home Near Legoland! offers accommodations in Cypress Gardens, 12 miles from Dearborn Railroad Station and 17 miles from Elmer R...
Holiday home in Winter Haven, Florida , 3357 Timberline Road West
Groovy Funhouse Getaway - 4 bdrm near Legoland is a recently renovated vacation home in Winter Haven where guests can make the most of its outdoor swi...
Holiday home in Winter Haven, Florida , 104 Lake Ring Drive
Cozy Lakefront Home w/ Pool -7 mins from Legoland is located in Winter Haven, just 2 miles from Legoland Florida and 12 miles from Dearborn Railroad S...
Holiday home in Winter Haven, Florida , 120 Lake Ring Drive
Stylish Lake home with HEATED POOL, Arcade with PS5, and Theater Just 5 min from Legoland offers accommodations in Winter Haven, 2 miles from Legoland...
Holiday home in Winter Haven, Florida , 677 Ave F SE
Large 3Bedrooms 1 Bath Near DownTown Dining is located in Winter Haven, just 3.5 miles from Legoland Florida and 11 miles from Dearborn Railroad Stati...
Holiday home in Winter Haven, Florida , 138 Avenue East Southeast
Cozy Bungalow 5 mi Legoland and 0.5 mi Dwntwn offers accommodations in Winter Haven, 11 miles from Dearborn Railroad Station and 13 miles from Elmer R...
Holiday home in Winter Haven, Florida , 144 Avenue East Southeast
Getaway Clubhouse 5 mil Legoland.5 mil Downtown is located in Winter Haven, just 11 miles from Dearborn Railroad Station and 13 miles from Elmer Railr...
Winter Haven Vacation Rental about 1 Mi to Downtown! is located in Winter Haven, just 12 miles from Dearborn Railroad Station and 13 miles from Elmer ...
Holiday home in Winter Haven, Florida , 718 Carroll Avenue Southwest
The Old Haven - An Enduring Piece of Nostalgia is located in Winter Haven, just 4.6 miles from Legoland Florida and 11 miles from Tanco Railroad Stati...
Winter Haven Abode Near Lakes and Attractions offers accommodations in Winter Haven, 12 miles from Dearborn Railroad Station and 13 miles from Elmer R...
Holiday home in Winter Haven, Florida , 1724 Lake Mariam Drive
3Bed 2 Bath Spacious Lake Home Ace Location4Miles2 Legoland is located in Winter Haven, just 13 miles from Dearborn Railroad Station and 14 miles from...
Holiday home in Cypress Gardens near Winter Haven, Florida , 1722 Lake Mariam Drive
Modern Cottage Tiny-Home 4miles to LEGOLAND offers accommodations in Cypress Gardens, 13 miles from Dearborn Railroad Station and 14 miles from Elmer ...
Providing a garden, Peaceful Lakeside Retreat provides accommodations in Winter Haven. This vacation home feat...
Parking
Family rooms
from $261.68
Holiday homes in Winter Haven (Florida), comfortable and familiar
Staying in a holiday or vacation home in Winter Haven can be a great alternative to a hotel or resort. They can range from small cottages to luxurious villas, and are often located in popular tourist destinations such as beaches or mountains. One of the main benefits is the privacy and flexibility that comes with having your own space. Unlike a hotel room, a holiday home provides you with a living area, kitchen, and sometimes even outdoor space, allowing you to cook your own meals, relax in comfort, and enjoy the company of your friends or family without the interruptions of other guests.
Holiday homes often offer more space than a hotel room. This can be particularly useful for families or groups of friends traveling together, who may need more than one room or want to avoid the cramped feeling of a single hotel room. They can also provide a more authentic travel experience, allowing guests to immerse themselves in the local culture and lifestyle. This can be particularly appealing for those who prefer to stay in quieter, residential areas away from the hustle and bustle of tourist hotspots.
Find the best Holiday home in Winter Haven for your needs
Holiday homes should offer a comfortable and enjoyable stay, providing all the necessary amenities and conveniences to make your vacation experience memorable. At a minimum, your holiday home in Winter Haven should offer a clean and well-maintained living space with comfortable furnishings, adequate lighting, and climate control.
In addition to basic amenities such as a fully equipped kitchen, comfortable bedding, and clean linens and towels, holiday homes should also offer modern conveniences such as Wi-Fi, cable or streaming TV, and laundry facilities. A private outdoor space, such as a balcony or terrace, can also add to the overall enjoyment. They can also offer additional features such as a swimming pool, hot tub, or outdoor grill. Location is also important, for example, close to popular tourist attractions, restaurants and shopping areas.
Accommodation data and pictures provided by Booking.com