467 Holiday rentals and Airbnb in Winter Haven, FL
Winter Haven, FL
01/12 – 28/02
73 €/nighttotal: 6497 € (89 )
Remote Workers 1bed W/full Kitchen & Living Room
1 2
apartment , Winter Haven
This private guest suite is located in Winter Haven, Florida, offering convenient access to local shopping, dining, major roadways, and attractions. This independent apartment accommodates up to three guests and features a queen-sized bedroom, a separate living area, a dining space, and a well-equipped kitchen with a freezer, microwave, and dishwasher, all within easy reach of Winter Haven's amenities.
9.0 13 reviews
Winter Haven, FL
04/07 – 05/07
149 €/nightfor 1 night
Private/spacious 1br Central Near Legoland 2 Miles
1 4
apartment , Cypress Gardens
This one-bedroom duplex apartment is located in Winter Haven, Florida, just 3.2 kilometres from downtown Winter Haven, the hospital, LEGOLAND, and Peppa Pig Theme Park, making it an ideal base for exploring the area. It has received excellent user ratings, with guests praising its cleanliness, safety, and friendly service. The apartment comfortably accommodates five guests and features a private screened-in porch, a large fenced-in yard, and access to nearby golf courses, shopping centres, and entertainment options. Guests can enjoy the Florida weather on the porch, relax in the spacious yard, and easily access attractions like Cypress Gardens, which is just a short drive away.
9.7 651 reviews
Winter Haven, FL
01/12 – 28/02
71 €/nighttotal: 6319 € (89 )
2 - Ships Ahoy Bungalow 2 Bed/2 Bath - Unit 17
1 2
apartment , Winter Haven
This charming cottage is located in Cypress Inlet Vacation Homes and Marina in Winter Haven, Florida, just a short drive from Legoland and other attractions. It has received excellent ratings for its cleanliness, location and overall experience. This two-bedroom property offers a comfortable and stylish living space. Guests can enjoy direct canal access to Lake Eloise, a covered porch, a well-equipped kitchen, three Smart TVs, and a boat ramp on a private canal.
9.9 35 reviews
Winter Haven, FL
01/12 – 28/02
174 €/nighttotal: 15486 € (89 )
Luxury By Legoland 106
1 2
apartment , Winter Haven
This two-bedroom, two-bathroom apartment is situated in a brand-new luxury complex less than 1.6km from LEGOLAND® Florida Resort and Peppa Pig Theme Park in Winter Haven, Florida. The ground-floor flat sleeps six, boasts a fully equipped kitchen with dishwasher, in-unit laundry, and a LEGOLAND®-themed children's bedroom; resort amenities include a heated pool, fitness centre, and BBQ areas.
9.8 7 reviews
Winter Haven, FL
02/07 – 06/07
252 €/nighttotal: 1008 € (4 )
- Hidden Gem - Spacious, Minimal And Clean! Legoland + Disney
4 9
apartment , Winter Haven
This Winter Haven holiday home is conveniently located within 9.6km of Sertoma Park, Winter Haven Hospital, and Inman Park, with Lake Conine and Auburndale City Park also nearby. The four-bedroom, two-bathroom property sleeps nine guests and includes in-house laundry facilities, a hairdryer, and is ideally situated for exploring Winter Haven's attractions.
9.6 230 reviews
Winter Haven, FL
08/07 – 12/07
127 €/nighttotal: 508 € (4 )
Sweet Cottage- 5 Mi To Legoland & 0.5 Mi To Dwntwn
1 3
apartment , Winter Haven
This charming cottage is situated in downtown Winter Haven, just 800 metres from entertainment options and 8.4 kilometres from Legoland, making it a convenient base for exploring the area. It consistently receives excellent ratings for location, cleanliness, and user experience. The two-bedroom property comfortably sleeps up to eight guests. The cottage is well-equipped with a fully-stocked kitchen, a washer and dryer, a desktop computer, and a garden with games, grills, and a foosball table, providing plenty of opportunities for both indoor and outdoor entertainment.
10 110 reviews
Winter Haven, FL
16/07 – 20/07
101 €/nighttotal: 404 € (4 )
Charming Lakeside Cottage
1 2
house , Winter Haven
This lakeside cottage on Lake Howard in Winter Haven, Florida, offers private dock access and is a short drive (distance unspecified) from Legoland Florida and Walt Disney World Resort. The one-bedroom, one-bathroom property sleeps two guests and features a fully equipped kitchen with freezer, microwave, and dishwasher, air conditioning, parking, and access to the Winter Haven Chain of Lakes.
9.5 12 reviews
Winter Haven, FL
04/07 – 05/07
347 €/nightfor 1 night
The Best House
1 4
apartment , Winter Haven
This four-bedroom house, situated in Winter Haven's Riverwood Circle neighbourhood, is approximately 16km from LEGOLAND Florida Resort and Peppa Pig Theme Park, and close to the Chain of Lakes for watersports. The property boasts a spacious layout sleeping up to 10 guests, offering a swimming pool, garden, fitness centre, parking, and a fully equipped kitchen including a dishwasher, alongside complimentary internet access.
8.0 5 reviews
Winter Haven, FL
02/07 – 06/07
444 €/nighttotal: 1776 € (4 )
Brand New Home Near Legoland & The Chain Of Lakes
1 9
apartment , Eagle Lake
This apartment in Eagle Lake offers a prime location, situated approximately 16 kilometres from Legoland, Peppa Pig World, and Sea Life Aquarium, and a 56-kilometre drive from Disney World. This four-bedroom, two-bathroom residence accommodates up to ten guests and features a resort-style swimming pool, a fitness centre, and convenient access to the chain of lakes and Tampa.
Winter Haven, FL
04/07 – 05/07
161 €/nightfor 1 night
Haven Lake House
1 4
apartment , Winter Haven
This centrally located flat in Winter Haven offers convenient access to major Florida destinations, being approximately 160 kilometres from Tampa, 80 kilometres from Orlando's theme parks, and 120 kilometres from the Gulf Coast beaches of Anna Maria Island. This apartment features two bathrooms and can accommodate up to six guests, with air conditioning and a kitchen, making it an ideal base for families exploring the wider Florida region.
9.9 226 reviews
Winter Haven, FL
27/06 – 04/07
78 €/nighttotal: 546 € (7 )
The Paradise Hide Away
1 2
house , Winter Haven
This one-bedroom home is situated in Winter Haven, a short drive from the city's attractions, offering a quiet retreat with a large backyard. The property has received excellent ratings for its cleanliness, location and overall user experience. The house is ideal for a small group or family of up to three guests. Enjoy the private backyard with a fire pit, hammocks, and cornhole tables, perfect for relaxing and entertaining.
9.5 77 reviews
Winter Haven, FL
04/07 – 05/07
205 €/nightfor 1 night
4 Bedroom In Quiet Neighborhood
1 4
apartment , Winter Haven
This spacious house in Wahneta, Winter Haven, is situated a 6.4km drive from Legoland Florida and Cypress Gardens Boulevard, offering easy access to local taco restaurants. The four-bedroom, two-bathroom property sleeps six guests and features smart TVs, air conditioning, parking, and a kitchen with a fridge; a cleaning fee applies only for excessive mess.
Best family friendly Winter Haven, FL holiday rentals
Among the 467 accommodations in Winter Haven, FL, here are the 4 best family friendly rentals
This one-bedroom apartment is conveniently located in Winter Haven, within a 3-mile radius of Rotary Park, Winter Haven Hospital, Lake Conine, Inman Park, and Winter Haven Women's Hospital. The property has received very good user ratings, making it a popular choice for travellers. The apartment is suitable for up to three guests and includes a fully equipped kitchen with a refrigerator, oven, and microwave. Guests can enjoy free Wi-Fi, a smart TV, and parking, making it a comfortable and convenient choice for exploring Winter Haven.
10 41 reviews
Winter Haven, FL
27/06 – 04/07
143 €/nighttotal: 1001 € (7 )
Newly Vacation Home With Lake View
3 2
apartment , Lake Alfred
This charming lakefront house is situated just 2.4 kilometres from Lions Park, offering a peaceful retreat close to local attractions. The property benefits from excellent user, location and cleanliness ratings, ensuring a comfortable and enjoyable stay. The 149 square metre house comfortably accommodates up to six guests across its three bedrooms and two bathrooms. Guests can enjoy stunning lake views, direct water access, a private yard, a fully equipped kitchen, free Wi-Fi, air conditioning, and a terrace or balcony.
9.4 3 reviews
Winter Haven, FL
27/06 – 04/07
212 €/nighttotal: 1484 € (7 )
15 Minutes To Legoland- Serene Lakeside Cottage Retreat
3 2
apartment , Winter Haven
This Winter Haven waterfront lodge is located within 5km of Lake Henry Golf Club and Willowbrook Golf Course, and within 10km of Inman and Lions Parks. The 179 square metre property boasts three bedrooms, two bathrooms, sleeps six, and includes a fully equipped kitchen, terrace, garden, free Wi-Fi, and parking.
9.9 51 reviews
Winter Haven, FL
07/07 – 12/07
146 €/nighttotal: 730 € (5 )
Getaway Clubhouse 5 Mil Legoland & .5 Mil Downtown
3 4
apartment , Winter Haven
This family-friendly holiday home in Winter Haven, Florida offers three bedrooms and two bathrooms, sleeping up to eight guests, and is conveniently located near various attractions (exact distances require a specific address). The property boasts a fully equipped kitchen including a fridge, freezer, microwave, and dishwasher, plus a garden, air conditioning, internet access, parking, and ample indoor entertainment such as board games and a foosball table.
Best Winter Haven, FL holiday rentals with parking
10 2 reviews
Winter Haven, FL
08/07 – 12/07
254 €/nighttotal: 1016 € (4 )
6 Mi To Legoland Retreat With Pool And Fenced Yard
3 3
house , Winter Haven
This Winter Haven holiday home is situated 4.9 km from Swanns Railroad Station, 9.3 km from Legoland Florida, and 9.6 km from Legoland Retreat, offering convenient access to local attractions. The 202 square metre property sleeps 11 guests and boasts two bathrooms, a private fenced garden, a swimming pool, free Wi-Fi, and a fully equipped kitchen with a dishwasher; ideal for families visiting Legoland.
10 9 reviews
Winter Haven, FL
16/07 – 20/07
308 €/nighttotal: 1232 € (4 )
Family Winter Haven Retreat W/ Pool & Game Room
3 2
apartment , Cypress Gardens
This Winter Haven residence is situated just a 5-minute drive from LEGOLAND® Florida and Chain Of Wakes, with golf courses and shopping centres nearby. This 3-bedroom, 2-bathroom flat for up to 10 guests offers complimentary Wi-Fi, air conditioning, a fully equipped kitchen, and in-unit laundry facilities, alongside access to a communal swimming pool, garden, table tennis, and billiards.
8.6 52 reviews
Winter Haven, FL
27/06 – 04/07
85 €/nighttotal: 595 € (7 )
Central Private King Suit Washer Dryer 2 Miles To Hospital
1 2
apartment , Winter Haven
This Winter Haven apartment is conveniently located 3.2km from a hospital and 8.8km from Legoland Florida, ideal for medical visits or theme park trips. The 42-square-metre self-catering flat features a king suite, a fully equipped kitchenette with microwave and fridge, in-unit laundry, free Wi-Fi, and private parking, sleeping up to five guests.
10 8 reviews
Winter Haven, FL
01/12 – 28/02
293 €/nighttotal: 26077 € (89 )
Modern Comfort, Pet Friendly, 2 King Beds
2 2
apartment , Winter Haven
Chain of Lakes Cottage is situated in Winter Haven, Florida, near LEGOLAND Florida and Chain of Lakes Park, offering easy access to Havendale Plaza and Northgate Shopping Centre, approximately 0.6 km and 1.6 km away respectively. This six-bedroom, three-bathroom holiday home, boasting 175 square metres of floor space, sleeps five guests and includes on-demand linen and towel service, with nearby wildlife viewing opportunities at Circle B Bar Reserve and Sertoma Park.
Frequently asked questions about holiday rentals in Winter Haven, FL
What are the top family-friendly attractions in Winter Haven, FL?
For families, Legoland Florida is a top choice. You can also visit the Polk Museum of Art, which has a dedicated children's gallery, and the Winter Haven Public Library, which hosts regular events for kids. For a day outdoors, head to the Chain of Lakes for a picnic or a boat ride.
What are the best Airbnb and holiday rentals in Winter Haven, FL?
When is the best time to book a vacation rental in Winter Haven, FL?
The best time to book a vacation rental in Winter Haven is during the shoulder seasons, from April to May and September to October. The weather is still pleasant, and you'll find fewer crowds and more affordable prices compared to peak season.
What are the most popular Airbnbs in Winter Haven, FL?
What events or festivals should visitors check out in and around Winter Haven, FL?
Winter Haven hosts several events throughout the year, including the annual Winter Haven Art Festival, which showcases local artists and craftspeople. You can also check out the Cypress Gardens Festival of Lights during the holiday season. If you're looking for something a bit further afield, the Sun 'n Fun International Fly-In & Expo in Lakeland is a major event for aviation enthusiasts.
What are the best holiday rentals with a pool in Winter Haven, FL?
What are the best budget-friendly activities in Winter Haven, FL?
Winter Haven offers plenty of budget-friendly activities. You can enjoy a walk or bike ride along the Chain of Lakes, visit the Winter Haven Public Library, or explore the historic downtown area. You can also pack a picnic and enjoy a day at one of the many parks, such as the Chain of Lakes Park or the Lake Alfred Public Beach.
What are the best rentals for families and kids in Winter Haven, FL?
What are the best restaurants with local dishes in Winter Haven, FL?
For local dishes, try The Terrace Restaurant at the Chain of Lakes, which serves classic Florida cuisine with a modern twist. For a more casual dining experience, head to The Boathouse Restaurant, which offers fresh seafood and waterfront views.
What are the best rentals or Airbnbs with a jacuzzi in Winter Haven, FL?
What are the best walking or cycling routes in Winter Haven, FL?
The Chain of Lakes Trail is a popular walking and cycling route that winds its way through the city, offering scenic views of the lakes and parks. For a shorter route, try the Winter Haven Linear Park, which follows the CSX railroad line and features a variety of native plants and wildlife.
Are there pet-friendly attractions in Winter Haven, FL?
Yes, many places in Winter Haven are pet-friendly. The Chain of Lakes Park has a designated dog park, and many restaurants and shops welcome furry friends. You can also find pet-friendly vacation rentals in the area.
What are the benefits of choosing a vacation rental in Winter Haven, FL?
Vacation rentals offer more space and privacy compared to hotels, and you'll often find them to be more affordable, especially for families or groups. They also provide a more home-like experience, allowing you to cook your own meals and relax in a comfortable setting.
What are the top sports attractions and facilities in Winter Haven, FL?
Winter Haven is home to the Chain of Lakes, which offers a variety of watersports, including boating, fishing, and swimming. You can also find golf courses, tennis courts, and other recreational facilities throughout the city.
Destinations nearby
Best Winter Haven, FL holiday rentals with a balcony
10 2 reviews
Winter Haven, FL
16/07 – 20/07
97 €/nighttotal: 388 € (4 )
Winter Haven Apt: 1 Mi To Polk State College!
1 2
apartment , Winter Haven
This Winter Haven apartment is conveniently located within 1.6km of Rotary Park and Winter Haven Hospital, and within 4.8km of Winter Haven Women's Hospital and Indigo's Family Fun Centre. The self-catering flat offers free Wi-Fi, parking, a private balcony, and is close to various amenities including a hospital and family entertainment.
8.3 1815 reviews
Winter Haven, FL
08/07 – 12/07
363 €/nighttotal: 1452 € (4 )
Legoland® Florida Resort
1 3
resort , Winter Haven
LEGOLAND® Florida Resort is located in Winter Haven, Florida, just a short drive from attractions like Historic Bok Tower Gardens and Davidson of Dundee candy factory. The resort is highly rated for its location, cleanliness, and overall experience, making it a popular choice for families. The resort offers a variety of accommodation options, including themed rooms and bungalows. Guests can enjoy a range of amenities, including swimming pools, restaurants, bars, and a concierge service. There are also family-friendly activities such as treasure hunts, LEGO® model building sessions, and nightly entertainment.
9.8 10 reviews
Winter Haven, FL
08/07 – 12/07
219 €/nighttotal: 876 € (4 )
Peaceful Lakeside Retreat
3 3
house , Winter Haven
Peaceful Lakeside Retreat, a three-bedroom house in Winter Haven, Florida, enjoys a tranquil lakeside location 9.3km from Legoland Florida and approximately 18km from several railway stations. This 172 square metre property boasts two living rooms, a fully equipped kitchen, a terrace, garden, spa, parking, and accommodates up to 17 guests, offering excellent value for families or large groups.
9.4 13 reviews
Winter Haven, FL
01/12 – 28/02
319 €/nighttotal: 28391 € (89 )
5 Br Home With Pool And Outdoor Fun
5 2
house , Cypress Gardens
This five-bedroom holiday home is situated in Winter Haven, Florida, approximately 12 kilometres from Swanns Railroad Station and 18 kilometres from Phosmico Railroad Station, offering easy access to Legoland Florida and Cypress Gardens. The 177-square-metre property boasts a private pool, terrace, and fully equipped kitchen, accommodating up to 19 guests and featuring free Wi-Fi and private parking.
Best Winter Haven, FL holiday rentals with air conditioning
10 5 reviews
Winter Haven, FL
03/07 – 07/07
184 €/nighttotal: 736 € (4 )
Grammy's House On Lake Buckeye
3 3
apartment , Winter Haven
This mid-century flat is directly situated on the lake in Winter Haven, offering picturesque views and waterfront access, with convenient access to Winter Haven's renowned chain of lakes and local attractions. This spacious accommodation, ideal for families and accommodating up to six guests, features three bedrooms, two bathrooms, air conditioning, and a kitchen equipped with a fridge and dishwasher, perfect for both short and extended stays.
8.0 5 reviews
Winter Haven, FL
01/12 – 28/02
71 €/nighttotal: 6319 € (89 )
Winter Haven Relax Enjoy
1 2
apartment , Winter Haven
This one-bedroom apartment is situated in a gated community in Winter Haven, close to a lakefront clubhouse with amenities and within easy driving distance of attractions like Legoland Florida and Bok Tower Gardens. The apartment is perfect for a couple seeking a comfortable and convenient base for exploring the area. The apartment features a queen bed, a walk-in closet, a Jack & Jill bathroom with a garden tub and separate shower, and a Roku TV. Guests can enjoy the Florida sunshine on either of the two outdoor patios and relax by the pool, play tennis, or make use of the spa facilities within the community.
10 300 reviews
Winter Haven, FL
16/07 – 20/07
192 €/nighttotal: 768 € (4 )
Roe Family Lake House (Lake Mcleod)
1 2
apartment , Eagle Lake
This charming cottage is located in Eagle Lake, Florida, just 10 kilometres from Legoland and less than an hour's drive from Tampa or Disney World. It has received excellent ratings for location, cleanliness, and overall experience. The two-bedroom cottage comfortably accommodates up to five guests. It features a fully equipped kitchen, air conditioning, a private garden, and a detached garage, perfect for enjoying the Florida sunshine and exploring the local area.
10 17 reviews
Winter Haven, FL
27/06 – 04/07
179 €/nighttotal: 1253 € (7 )
2-bedroom, 2-bath Unit Offers A Family-friendly Retreat Just Mins From Legoland.
2 2
apartment , Winter Haven
This two-bedroom, two-bathroom apartment in a gated Winter Haven community is located minutes (approximately 1.6km) from LEGOLAND Florida. The 119 square metre ground-floor property sleeps six, boasts a fully equipped kitchen, in-unit laundry, smart TVs, and access to a heated pool, fitness centre, tennis court, and children's playground within the complex.
