Winter Haven holiday lettings

We found 1,200 holiday rentals — enter your dates for availability

Discover a selection of 127 homes, 31 apartments and other holiday rentals in Winter Haven that are perfect for your trip. Whether you're travelling with your children or with friends, holiday rentals have the amenities that you need and want for your stay, which might include cable TV and a washer and dryer. No matter what you're looking for, you'll be able to choose a property to rent for everyone's needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts - Winter Haven

Showing deals for:12 Dec - 19 Dec

Image gallery for Beautiful Lake Front cottage w/ heated pool & Hot Tub, 23 miles from Disney

Landscaped Drive
9.8 out of 10 rating
Exceptional
(24 reviews)

Beautiful Lake Front cottage w/ heated pool & Hot Tub, 23 miles from Disney

Winter Haven, FL

7% off
Price is £1,796
for 7 nights, 1 home
£257 per night
includes taxes & fees
Beautiful Lake Front cottage w/ heated pool & Hot Tub, 23 miles from Disney

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Find out more about Winter Haven

Find out more about Winter Haven

Why visit Winter Haven

  • Beautiful lakes: Winter Haven is renowned for its stunning lakes, ideal for kayaking and relaxing by the water.
  • Family-friendly attractions: The area boasts lively amusement parks and outdoor activities suitable for all ages.
  • Charming neighbourhoods: Explore welcoming communities that offer a friendly atmosphere and picturesque homes.
  • Budget-friendly getaways: Winter Haven provides diverse experiences at affordable prices, perfect for families.
  • Comfortable accommodations: Choose from a variety of holiday rentals, including villas and condos, to suit your needs.

Popular types of accommodation in Winter Haven

For your next getaway, explore the diverse selection of holiday rentals in Winter Haven. Whether you prefer a private vacation home, a villa, or a cozy condo, we have the perfect accommodation to suit your needs. Ideal for families or groups, our house and home rentals offer exceptional comfort and convenience. Plus, consider our monthly rentals for an extended stay and a chance to truly unwind in this charming destination.

  • Houses: The top choice for holidaymakers in Winter Haven, offering spacious and comfortable stays that cater to families, friends, or couples.
  • Villas: A popular option, these elegant properties provide luxurious amenities and stunning surroundings for a relaxing getaway.
  • Condos: Ideal for those seeking a balance of comfort and convenience, condos are well-situated for easy access to local attractions.
  • Apartments: A practical choice for visitors, offering self-contained living spaces in various locations throughout the area.
  • Cottages: Charming and quaint, these quaint retreats provide a cosy atmosphere for a peaceful holiday experience.**

Top attractions in and around Winter Haven

Winter Haven is an ideal destination for family adventures and outdoor pursuits. The area boasts beautiful lakes, urban parks, and lively amusement parks, making it perfect for those seeking a blend of relaxation and excitement. Whether you’re travelling with family or enjoying a day out, the attractions here provide excellent opportunities for outdoor activities and memorable experiences by the beach.

  • LEGOLAND® Florida: A delightful amusement park filled with interactive rides, themed areas, and captivating LEGO displays, perfect for families seeking outdoor adventure and fun.
  • Auburndale City Park: A charming urban park offering green spaces, playgrounds, and picnic areas, ideal for families looking to enjoy a relaxing day in a city setting.
  • The Circle B Bar Reserve: A stunning nature reserve featuring scenic trails and diverse wildlife, perfect for those seeking an adventurous outdoor experience.

Things to do recommended for couples

For a romantic getaway in Winter Haven, indulge in thrilling water sports at Chain Of Wakes, where adventure awaits. Then, savour exquisite wines at True Blue Winery, just 7.5km away, perfect for a charming afternoon of relaxation and entertainment.

Things to do recommended for families

Families can explore the sports atmosphere at Chain of Lakes Park, enjoy fun-filled activities at Indigo's Billiards, Bowling & Games, and unwind in the serene environment of Sertoma Park, perfect for relaxation and wellness. Winter Haven offers a delightful mix of adventure and leisure for all ages.

Things to do recommended for groups

Groups visiting Winter Haven can enjoy a captivating show at Theatre Winter Haven, indulge in drinks and fun at Indigo's Family Fun Center, and shop at Northgate Shopping Center for a delightful mix of entertainment and local culture.

What do I need to keep in mind when booking a vacation in 'Winter Haven

If you're travelling with a group, as a family, bringing your pets, or seeking extended stays, be sure to refine your search based on your key priorities. Here are some helpful booking tips for Vrbo.

  • Traveling to Winter Haven with a group: Think about how many bedrooms you require, along with features like a fully-equipped kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Winter Haven with young kids: Venturing out with young children can prove to be quite demanding. It's essential to prioritise their comfort and safety, alongside ensuring access to suitable amenities, like a private swimming pool. Additionally, it's wise to take into account your closeness to attractions that are family-friendly.
  • Taking your pets with you to Winter Haven: For many, a family holiday wouldn’t be the same without their four-legged companion. If this resonates with you, take a look at Vrbo properties that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Winter Haven: If you're seeking holiday rentals with special offers for stays of a month or more, you've come to the perfect place. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include features such as a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in and around Winter Haven

Winter Haven, Florida, offers a delightful blend of family-friendly adventures and outdoor escapades. Explore the stunning lakes, perfect for kayaking and relaxing by the patio. Discover charming homes and welcoming neighbourhoods that embody a friendly atmosphere. With its diverse experiences, Winter Haven is an ideal destination for those seeking a budget-friendly getaway filled with fun and relaxation. Dive into the warmth of this charming city and create unforgettable memories.

  • Eagle Lake: Situated a mere 1.9km from Winter Haven, Eagle Lake is a charming city that offers a delightful blend of family-friendly and outdoor entertainment options. Visitors flock to this area for its vibrant resorts and the nearby amusement park, making it an ideal spot for a fun-filled family day out. The local attractions include a scenic theme park and inviting beaches, perfect for unwinding by the water. Eagle Lake provides a welcoming atmosphere with ample opportunities for shopping and leisure, ensuring a memorable travel experience.
  • Cypress Gardens: Nestled within the Winter Haven vicinity, Cypress Gardens is a picturesque village that is renowned for its adventurous spirit and family-oriented activities. This quaint locale is home to thrilling amusement parks, lush golf courses, and inviting resorts that cater to all ages. Visitors can explore the nearby theme park and relax at the stunning beach or even delve into the cinematic world at the local film studio. Cypress Gardens promises an exhilarating experience where the great outdoors meets exciting attractions.
  • Jan Phyl Village: Located in close proximity to Winter Haven, Jan Phyl Village is a charming community that offers a delightful mix of family, outdoor, and entertainment-themed experiences. This village is known for its vibrant resorts and the exhilarating amusement park, which is sure to delight visitors of all ages. Local highlights include a nearby stadium for sports enthusiasts and a beautiful beach for those seeking relaxation. Jan Phyl Village is a fantastic destination for families looking to enjoy a variety of fun activities in a friendly environment.

Best time to go to Winter Haven

If you're planning a trip to Winter Haven, it's a good idea to check both the weather and property rates. The warmest month is August. Peak season runs in March to April and September, while off-peak times, like August and October to November tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January60.4°F (15.8°C)Light RainMostly SunnyAverageAverage
February64.4°F (18.0°C)No Rain (Dry)Mostly SunnyAverageSlightly Low
March67.5°F (19.7°C)Light RainMostly SunnySlightly HighAverage
April72.9°F (22.7°C)Light RainMostly SunnySlightly HighSlightly High
May77.2°F (25.1°C)Light RainMostly SunnyAverageAverage
June80.6°F (27.0°C)Moderate RainMostly SunnyAverageAverage
July81.7°F (27.6°C)Moderate RainMostly SunnyAverageSlightly High
August81.9°F (27.7°C)Moderate RainMostly SunnySlightly LowAverage
September79.5°F (26.4°C)Moderate RainMostly SunnySlightly HighSlightly Low
October74.7°F (23.7°C)Light RainMostly SunnySlightly LowSlightly Low
November68.0°F (20.0°C)No Rain (Dry)Mostly SunnySlightly LowAverage
December64.2°F (17.9°C)No Rain (Dry)Mostly SunnyAverageSlightly High

Booking with Vrbo is a breeze

Are you keen to save on your upcoming holiday? Being flexible with your travel dates can be a great way to find better deals, as prices often vary. Additionally, opting for a longer stay can lead to significant savings. To discover the perfect Vrbo property that suits your budget, utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo's cutting-edge Trip Board provides you with a dedicated space to plan new journeys, pick up from where you last stopped, or review and arrange your travel plans. You can easily find the properties you've saved and booked under Potential, Upcoming, or Current Trips. To make the most of the Trip Boards, simply visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Delight in the lakeside landscape of Winter Haven

Enjoy the entertainment and other features of Winter Haven. This city's lake, gardens and baseball games draw many visitors. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Activities and attractions in and around Winter Haven

Are you looking for attractions to visit during your stay? Venture out of your holiday home and experience everything that makes Winter Haven a fun place to get away to. These are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • LEGOLAND® Florida (3.2 mi / 5.2 km)
  • Peppa Pig Theme Park Florida (3.6 mi / 5.8 km)
  • Cypresswood Golf and Country Club (5.2 mi / 8.4 km)
  • Southern Dunes Golf Club (9.8 mi / 15.8 km)
  • Southern Dunes Golf and Country Club (9.9 mi / 15.9 km)
  • Mountain Lake (10.2 mi / 16.5 km)

Exploring the natural landscape of Winter Haven

Travellers enjoy Winter Haven for its lakeside setting and gardens. Whether you're looking for exciting outdoor activities or just want to appreciate the scenery, Winter Haven is a great place to get outside. These are a few of the area's most stunning natural features, all within 30 miles (48.2 km) of the city centre:

  • Auburndale City Park (4.5 mi / 7.3 km)
  • The Circle B Bar Reserve (8.8 mi / 14.2 km)
  • Bok Tower Gardens (11.2 mi / 18 km)
  • Lake Mirror (13.5 mi / 21.8 km)
  • Bryant Stadium (13.8 mi / 22.3 km)
  • Crooked Lake (17.3 mi / 27.8 km)

Transport to and around Winter Haven

Fly into Lakeland Intl. Airport (LAL), the closest airport, located 17.3 mi (27.8 km) from the city centre. If you can't find a flight that's convenient for your trip, you might consider flying into Kissimmee, FL (ISM-Kissimmee Gateway), which is 26 mi (41.9 km) away.

If you'd prefer to travel by train, you can make your way to Winter Haven Station.

Frequently asked questions

What is the best area to stay in Winter Haven when booking a holiday rental?
When considering a holiday rental in Winter Haven, Florida, the downtown area is an excellent choice. This vibrant neighbourhood offers a charming blend of local shops, restaurants, and a friendly setting that's great for visitors looking to immerse themselves in the community. Staying downtown places you within easy reach of the picturesque Chain of Lakes, a prime spot for boating and fishing, as well as the popular LEGOLAND Florida Resort, which promises fun for families and children of all ages.

Another appealing neighbourhood is Cypress Gardens, renowned for its stunning natural beauty and historic significance. Here, you can explore the beautifully landscaped gardens and enjoy outdoor activities around the lakes. This area often features a variety of holiday rentals, giving you plenty of options to choose from, whether you prefer a cosy cottage or a spacious home.

For those seeking a quieter experience, the Eloise area offers a more laid-back vibe. Surrounded by nature, it is ideal for those who enjoy hiking and birdwatching, with the nearby Eloise Nature Park providing ample opportunities to explore the local flora and fauna. This area tends to have a smaller selection of properties, making it a great choice for anyone looking for a serene escape.
How much does it cost to rent a holiday home in Winter Haven?
Prices for holiday rentals in Winter Haven vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Winter Haven to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Winter Haven holiday house rentals?
You can find great discounts on house rentals in Winter Haven on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Winter Haven?
For renting a beach house in Winter Haven, Florida, travellers should focus on the nearby lakes and waterfront areas since Winter Haven itself is not directly on the coast. The area surrounding Lake Eloise provides a picturesque setting with various holiday properties that offer scenic lakefront views. Many of these rentals come equipped with amenities such as private docks, outdoor seating areas, and spacious living rooms, superb for families or groups looking to enjoy water activities.

Further along, the Cypress Gardens area is another option, where visitors can find charming cottages and homes that feature amenities like fully equipped kitchens, barbecues, and access to community pools. This locale is particularly appealing for those interested in boating and fishing, as the nearby lakes offer plenty of opportunities to enjoy the outdoors.
What is the most popular type of holiday rental accomodation in Winter Haven?
In Winter Haven, holiday houses are the most popular type of rental, with approximately 124 available throughout the area. These properties are often situated in family-friendly neighbourhoods, providing ample space and amenities for travellers. Most holiday houses feature multiple bedrooms, fully equipped kitchens, and spacious living areas, making them ideal for families or larger groups. Additionally, many homes include outdoor spaces such as patios or gardens, superb for enjoying the warm Florida weather after a day at the nearby attractions like Legoland Florida Resort and the scenic Chain of Lakes.
Are there any family house rentals in Winter Haven?
In Winter Haven, there are numerous family-friendly house rentals available, with around 127 options to choose from. This area is well-known for its beautiful chain of lakes, offering ample opportunities for outdoor activities such as fishing, boating, and swimming. Many of these homes boast spacious living areas, fully equipped kitchens for preparing family meals, and outdoor patios or gardens superb for children to play in.
Can I rent a holiday home with a pool or hot tub in Winter Haven?
In Winter Haven, there are a variety of holiday homes available for rent featuring pools and hot tubs, with around 77 options to consider. This charming city is known for its beautiful chain of lakes and a family-friendly atmosphere, making it an excellent choice for travellers seeking relaxation and recreation. Many of the properties come equipped with private swimming pools and inviting hot tubs, great for unwinding after a day of exploring the local attractions.
Can I find long-stay holiday rentals in Winter Haven?
A long-stay holiday rental in Winter Haven is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Winter Haven?
In Winter Haven, travellers will find numerous pet-friendly house rentals available, with around 50 options to choose from. The area is known for its beautiful lakes and outdoor recreational opportunities, making it a great choice for those travelling with pets. Many of these holiday rentals come equipped with essential amenities such as fully equipped kitchens, spacious living areas, and outdoor spaces where pets can roam freely.
Are there any remote work holiday rentals in Winter Haven?
In Winter Haven, Florida, there are numerous remote work holiday rentals available, with around 159 options for travellers seeking a conducive workspace. Many of these properties cater specifically to remote workers, featuring dedicated office spaces with desks, comfortable chairs, and high-speed Wi-Fi to ensure productivity during your stay. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Winter Haven holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Winter Haven with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Winter Haven?
In Winter Haven, popular holiday rental amenities include fully equipped kitchens, allowing guests to prepare their meals comfortably. Most rentals also offer complimentary Wi-Fi in the rooms, ensuring connectivity for leisure or work. Additionally, travellers can expect essential cookware, dishware, and utensils, making dining in easy and convenient. Refrigerators and microwaves are standard features as well, providing flexibility for storing and reheating food.
When is the best time to visit Winter Haven for a holiday rental?
March is the most popular time to visit Winter Haven, where visitors flock to enjoy the delightful Florida sunshine and the area's vibrant attractions. The peak season spans from February to April, making it an ideal period for travellers, as the pleasant temperatures and numerous activities create a great holiday atmosphere.

During these months, temperatures generally hover around the mid to high 20s Celsius, encouraging outdoor adventures like exploring the scenic Chain of Lakes or indulging in the fun at nearby theme parks such as Legoland Florida. The bustling parks and beautiful weather make it a prime time for sightseeing and enjoying the natural beauty of the region.

If you're looking for a more budget-friendly option, consider visiting in November. This month offers a quieter experience, allowing you to appreciate the charm of Winter Haven without the crowds. Enjoy the milder temperatures and fewer tourists as you explore local parks or stroll around the picturesque downtown area.
How early should I book a Winter Haven holiday rental?
Book your Winter Haven holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Can I change or cancel my Winter Haven home rental booking on Vrbo?
To find Winter Haven holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Winter Haven holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.

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