Winter Haven holiday rentals

We found 1,067 holiday rentals — enter your dates for availability
Discover a selection of 60 homes 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:11 Dec - 18 Dec

Private kitchen
Terrace/patio
Room
Living area
Exceptional
(29 reviews)

Eagle Haven Lake House

Eagle Lake

8% off
AU$3,149
for 7 nights, 1 home
AU$450 per night
includes taxes & fees
Eagle Haven Lake House
Dining
Pool
Living area
Room
Exceptional
(43 reviews)

Lake Marion Golf Resort Villa

Kissimmee

7% off
AU$1,065
for 7 nights, 1 villa
AU$152 per night
includes taxes & fees
Lake Marion Golf Resort Villa
The large screened lanai has plenty of room to spread out
Spacious kitchen with large island has room for lots of cooks!
Exterior
Large dining room table for 12
Exceptional
(113 reviews)

Beautiful home with white sand beach on stunning Crooked Lake

Babson Park

8% off
AU$5,601
for 7 nights, 1 home
AU$800 per night
includes taxes & fees
Beautiful home with white sand beach on stunning Crooked Lake
Exterior
Outdoor dining
Living area
Private kitchen
Very good
(5 reviews)

Lake View Howell Cottage on Crooked Lake

Babson Park

5% off
AU$2,700
for 7 nights, 1 cottage
AU$386 per night
includes taxes & fees
Lake View Howell Cottage on Crooked Lake
Interior
Interior
Dining
Property grounds
Exceptional
(10 reviews)

Lakefront 3 story 5/3 bungalo with huge yard, great views, a firepit and a dock.

Winter Haven

8% off
AU$2,603
for 7 nights, 1 home
AU$372 per night
includes taxes & fees
Lakefront 3 story 5/3 bungalo with huge yard, great views, a firepit and a dock.
Dining
Exterior
Master bedroom has sliding doors to patio.
Private kitchen
Exceptional
(11 reviews)

Spacious home, in a quiet neighborhood near LEGOLAND®-just a 12-minute drive

Winter Haven

8% off
AU$3,548
for 7 nights, 1 home
AU$507 per night
includes taxes & fees
Spacious home, in a quiet neighborhood near LEGOLAND®-just a 12-minute drive
Terrace/patio
Exterior
Dining
Living area
Wonderful
(11 reviews)

Florida Dream Family Vacation

Haines City

5% off
AU$2,792
for 7 nights, 1 home
AU$399 per night
includes taxes & fees
Florida Dream Family Vacation
Living area
Pool
Exterior
Dining
Exceptional
(67 reviews)

Spacious Exec Villa With Large Private Pool. Stunning Golf Course and Lake Views

Davenport

5% off
AU$2,457
for 7 nights, 1 villa
AU$351 per night
includes taxes & fees
Spacious Exec Villa With Large Private Pool. Stunning Golf Course and Lake Views
Private kitchen
Outdoor dining
Exterior detail
Dining
Wonderful
(10 reviews)

Cute "Treehouse" Apartment

Bartow

9% off
AU$1,059
for 7 nights, 1 apartment
AU$151 per night
includes taxes & fees
Cute "Treehouse" Apartment
2nd Bedroom
Hallway
Newly updated Kitchen fully equipped.
Livingroom
Excellent
(8 reviews)

2 Bed 2 FB Near SEU Midway Disney and Beaches

Lakeland

7% off
AU$1,296
for 7 nights, 1 apartment
AU$185 per night
includes taxes & fees
2 Bed 2 FB Near SEU Midway Disney and Beaches
Dining
Exterior
Exterior detail
Pool
Exceptional
(29 reviews)

Lakefront Lego Land Estate

Winter Haven

12% off
AU$4,658
for 7 nights, 1 home
AU$665 per night
includes taxes & fees
Lakefront Lego Land Estate
Lakeside porch with gas grill
Sunroom
Sunroom
Property grounds
Exceptional
(29 reviews)

Lakefront Howell Bungalow on Crooked Lake, built in 1929, renovated in 2024

Babson Park

5% off
AU$3,301
for 7 nights, 1 home
AU$472 per night
includes taxes & fees
Lakefront Howell Bungalow on Crooked Lake, built in 1929, renovated in 2024
Pool
Pool
Room
Pool
Exceptional
(47 reviews)

Cozy and Clean Condo<br>Lake Marion Golf Resort

Kissimmee

7% off
AU$957
for 7 nights, 1 apartment
AU$137 per night
includes taxes & fees
Cozy and Clean Condo<br>Lake Marion Golf Resort
Pool
Interior
Exterior
Private kitchen
Exceptional
(30 reviews)

Cheerful 4 Bed, 3 Bath Home with Screened Pool

Winter Haven

6% off
AU$4,257
for 7 nights, 1 home
AU$608 per night
includes taxes & fees
Cheerful 4 Bed, 3 Bath Home with Screened Pool
Living area
Dining
Private kitchen
Living area
Exceptional
(5 reviews)

Q’s Residence In The Heart of Eagle Lake

Eagle Lake

5% off
AU$1,745
for 7 nights, 1 home
AU$249 per night
includes taxes & fees
Q’s Residence In The Heart of Eagle Lake
Clubhouse at Tower lake - inside
Luxury 4 BR 3 BA Villa - Large Pool Area and Spa, not overlooked, Games Room
Welcome to Calabay Parc at Tower Lake
Drinks at the kitchen counter
Exceptional
(183 reviews)

Luxury 4 BR /3 BA Villa - Pool/Spa Not Overlooked, Games Room

Haines City

7% off
AU$2,096
for 7 nights, 1 villa
AU$299 per night
includes taxes & fees
Luxury 4 BR /3 BA Villa - Pool/Spa Not Overlooked, Games Room
work area with lots of light
open floor plan kitchen and dining
spacious living room
front door with screened-in entryway
Exceptional
(34 reviews)

Family Fun Haven: 3 Bed/2 Bath/6 Mi to Legoland/Pet Friendly!

Winter Haven

17% off
AU$1,627
for 7 nights, 1 home
AU$232 per night
includes taxes & fees
Family Fun Haven: 3 Bed/2 Bath/6 Mi to Legoland/Pet Friendly!
Living area
Outdoor dining
Dining
Exterior
Exceptional
(7 reviews)

Serene, Cozy, Lakefront Home with boat dock and Large Screened in porch!

Winter Haven

7% off
AU$2,174
for 7 nights, 1 apartment
AU$311 per night
includes taxes & fees
Serene, Cozy, Lakefront Home with boat dock and Large Screened in porch!
Breakfast nook/work area overlooking the pool
Upgraded kitchen with everything you could need to cook amazing meals.
Open floor plan with extra high ceilings
Exterior
Exceptional
(17 reviews)

Southern Dunes: pool/spa; air hockey/game room

Haines City

8% off
AU$4,537
for 7 nights, 1 home
AU$648 per night
includes taxes & fees
Southern Dunes: pool/spa; air hockey/game room

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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)
  • Lake Myrtle Sports Complex (7.4 mi / 12 km)
  • Southern Dunes Golf and Country Club (9.9 mi / 15.9 km)
  • White Heron Golf Club (13.6 mi / 21.9 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)
  • Star Lake (10.1 mi / 16.3 km)
  • Sanlan Bird and Wildlife Sanctuary (10.2 mi / 16.5 km)
  • Bok Tower Gardens (11.2 mi / 18 km)
  • Lake Parker (12.5 mi / 20.1 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, a popular area to stay is the downtown vicinity. This charming neighbourhood offers a delightful mix of local shops, restaurants, and a vibrant setting. One of the top attractions here is the beautiful Chain of Lakes, where visitors can enjoy scenic views, boating, and picnicking along the waterfront. Additionally, the nearby LEGOLAND Florida Resort provides a fun-filled experience for families and those young at heart, featuring rides, shows, and interactive attractions.Another great option is the picturesque Cypress Gardens area, known for its stunning botanical gardens and serene landscapes. This area, steeped in history, is superb for those looking to unwind amidst nature while still being close to various amenities.
What is the most popular type of holiday rental accomodation in Winter Haven?
In Winter Haven, holiday houses are the most popular type of holiday rental, with around 440 available throughout the area. These properties typically offer spacious living arrangements, multiple bedrooms, and fully equipped kitchens, making them ideal for families or larger groups. Many also feature outdoor spaces such as private gardens or patios, great for enjoying the warm Florida weather. Additionally, there are about 100 apartments, which provide a more compact option for couples or solo travellers, often including amenities like pools and fitness centres. Cottages and villas, with 64 and 16 options respectively, offer a more quaint and relaxed atmosphere, while several condos can also be found, providing yet another alternative for visitors.
Are there any family house rentals in Winter Haven?
In Winter Haven, Florida, there is a substantial selection of family-friendly houses available, with around 101 options to choose from. This charming city is renowned for its beautiful chain of lakes, making it an appealing destination for families looking to enjoy water-based activities. Many of the homes feature spacious living areas, full kitchens, and outdoor patios or gardens, great for barbecues or simply unwinding after a day of adventure.Families will find amenities such as Wi-Fi, air conditioning, and laundry facilities common in these properties, ensuring a comfortable and convenient stay. Additionally, the locale is near popular attractions like LEGOLAND Florida, which offers fun for all ages, and the serene Bok Tower Gardens, where visitors can explore lush landscapes and enjoy the famous carillon music.
Can I rent a holiday home with a pool or hot tub in Winter Haven?
In Winter Haven, there are many holiday homes available for rent that come with pools and hot tubs, with approximately 61 options to choose from. This picturesque city, known for its chain of lakes and pleasant weather, features various neighbourhoods where these rentals can be found, including the tranquil areas near Lake Eloise and the more vibrant spots close to Lake Howard.Travellers can expect a range of amenities in these properties, such as private swimming pools, relaxing hot tubs, spacious outdoor patios, and fully equipped kitchens, ideal for enjoying both relaxation and social gatherings.
Are there pet-friendly house rentals in Winter Haven?
In Winter Haven, there is a wide selection of pet-friendly house rentals available, with around 54 options to choose from. These holiday homes often come equipped with amenities such as spacious backyards, modern kitchens, and comfortable living areas, making them ideal for families or groups travelling with pets. Many properties feature additional conveniences like laundry facilities, outdoor seating areas, and even private pools, enhancing the overall experience for pet owners.The area is known for its beautiful lakes and parks, providing ample opportunities for outdoor activities with pets. Nearby, you can explore the scenic Chain of Lakes, which offers walking trails and picnic spots, superb for enjoying the Florida sunshine with your four-legged friends. Additionally, local pet-friendly cafes and shops contribute to a friendly setting for those travelling with pets.
Are there any remote work holiday rentals in Winter Haven?
In Winter Haven, there are numerous options for remote work holiday rentals, with around 572 available throughout the area. Many of these properties cater specifically to those needing a productive work environment, featuring amenities such as high-speed Wi-Fi, dedicated work desks, and comfortable chairs to ensure an efficient workspace.The city is known for its picturesque Chain of Lakes, offering opportunities for outdoor activities during breaks from work. Additionally, many rentals include fully equipped kitchens, allowing guests to prepare meals conveniently. For those seeking a balanced work-life experience, the nearby attractions, such as Legoland Florida Resort and beautiful parks, provide ample opportunities for relaxation after a day of remote working. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Winter Haven?
In Winter Haven, popular holiday rental amenities include well-equipped kitchens, ensuring guests can prepare their own meals. Onsite parking is typically available, making it convenient for those travelling with cars. Many rentals also feature coffee and tea makers, allowing visitors to enjoy a warm drink at their leisure. Additionally, outdoor spaces like decks or patios are common, providing a pleasant area to relax and unwind after a day of exploring the local attractions.
When is the best time to visit Winter Haven for a holiday rental?
The ideal time to visit Winter Haven for a holiday rental is during the peak season from February to April, with March standing out as the most popular month. This vibrant period attracts visitors looking for warmer weather and an abundance of outdoor activities. With temperatures typically ranging from 15 to 28 degrees Celsius, it's superb for enjoying the area's famous attractions, including the stunning Legoland Florida Resort and the beautiful Chain of Lakes.During these months, you can expect a buzzing atmosphere filled with travellers, all eager to partake in the numerous recreational opportunities. From boating and fishing to exploring the local parks, there's something for everyone to enjoy in the mild sunshine.If you're looking for a more budget-friendly option, November is a wonderful time to visit Winter Haven. This month offers a quieter experience, allowing you to explore the area's charming attractions without the crowds. The weather remains pleasant, making it a great time for leisurely strolls and enjoying the scenic views.Ultimately, the best time to book your holiday rental in Winter Haven depends on your preferences for social atmosphere and outdoor activities.
What are the top attractions in Winter Haven?
In Winter Haven, visitors can enjoy a variety of attractions that highlight the area's unique charm. The most top is Legoland Florida Resort, a family-friendly set-up park that offers rides, shows, and interactive experiences based on the popular LEGO toy brand. This park is a major draw for families staying in the area and is located near several rental options.For those interested in nature, the Chain of Lakes provides opportunities for boating, fishing, and scenic walks along the water. The surrounding parks, such as Lake Howard Nature Park, feature walking trails and picnic areas, superb for outdoor enthusiasts.Additionally, downtown Winter Haven boasts a selection of shops, cafes, and restaurants, allowing visitors to experience local cuisine and culture. The historic area is also home to the beautiful theatre, which often hosts community events and performances.
Are all fees included in the Winter Haven holiday homes prices shown on Stayz?
Stayz 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.
Are there any Winter Haven holiday homes with parking?
Stayz offers a wide selection of holiday homes 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 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.
Are there any discounts for Winter Haven holiday homes?
You can find great discounts on holiday homes in Winter Haven on Stayz, 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.
Can I change or cancel my Winter Haven holiday home booking on Stayz?
To find Winter Haven holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Winter Haven?
A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Winter Haven holiday home?
Book your Winter Haven holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Winter Haven?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Winter Haven to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz 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, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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