Winter Haven Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
30 Jan - 1 Feb
In two months
13 Mar - 15 Mar
In three months
10 Apr - 12 Apr
In four months
8 May - 10 May

Our top choices for Winter Haven holiday rentals

TV
Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn

Cottage in Winter Haven

Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
2.0 star property
10.0 out of 10, Exceptional, (2 reviews)
"Just what we needed for a weekend trip with our grandsons for the weekend "
United States
Christine B.
The price is HK$896
HK$2,142 total
includes taxes & fees
13 Jan - 14 Jan
Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
Outdoor pool, pool umbrellas, pool loungers
Lake Ida Beach Resort

Cottage in Winter Haven

Lake Ida Beach Resort
3.0 star property
7.2 out of 10, Good, (188 reviews)
"We have stayed here several times. "
United States
Martha
The price is HK$585
HK$655 total
includes taxes & fees
18 Jan - 19 Jan
Lake Ida Beach Resort
Interior
Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn

Cottage in Winter Haven

Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn
3.0 star property
10.0 out of 10, Exceptional, (3 reviews)
"We stayed here because our soccer team had a tournament in the area. We had a couple families stay and the price was much cheaper than hotels around the area. The house is beautiful and spacious inside. Has alot of upgrades. At first we thought the neighborhood looked a little off, but we had no issues at all with our stay. We have some other tournaments in this area later in the year and we will definitely be booking to stay here again."
United States
John
The price is HK$1,333
HK$3,416 total
includes taxes & fees
13 Jan - 14 Jan
Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn
TV, fireplace
Spacious 4-bedroom house in pleasant Winter Haven with AC

Holiday Home in Winter Haven

Spacious 4-bedroom house in pleasant Winter Haven with AC
2.0 star property
10.0 out of 10, Exceptional, (2 reviews)
"An outstanding stay! The house was extremely clean, welcoming, and had all the amenities that made our family vacation unforgettable in our visit to Legoland park"
Mexico
Monica
The price is HK$717
HK$2,791 total
includes taxes & fees
23 Jan - 24 Jan
Spacious 4-bedroom house in pleasant Winter Haven with AC
Smart TV, fireplace, printers
Modern Comfort, Pet Friendly, 2 King Beds

Holiday Home in Winter Haven

Modern Comfort, Pet Friendly, 2 King Beds
2.0 star property
10.0 out of 10, Exceptional, (3 reviews)
"Great welcoming and answered every question I had. Highly recommend this lovely cottage. "
United States
Kristofer G.
The price is HK$650
HK$1,685 total
includes taxes & fees
13 Jan - 14 Jan
Modern Comfort, Pet Friendly, 2 King Beds
Paper towels
Private/Spacious 1BR Central Near LegoLand 2 Miles

Holiday Home in Winter Haven

Private/Spacious 1BR Central Near LegoLand 2 Miles
9.6 out of 10, Exceptional, (7 reviews)
"Location was great. Internet was great. Bed was good. Cleaned and comfortable.."
United States
Maria
The price is HK$631
HK$1,343 total
includes taxes & fees
18 Jan - 19 Jan
Private/Spacious 1BR Central Near LegoLand 2 Miles
4 bedrooms, free WiFi, bed sheets
Live Oak Oasis - Getaway Close to Legoland! Sleeps 8 Guests, Fenced yard, Games

Holiday Home in Winter Haven

Live Oak Oasis - Getaway Close to Legoland! Sleeps 8 Guests, Fenced yard, Games
2.0 star property
10.0 out of 10, Exceptional, (2 reviews)
"This house was perfect for our 1 night stay. We had ecerything we needed. Thank you!"
United States
Stephen and Jenni H.
The price is HK$742
HK$2,256 total
includes taxes & fees
13 Jan - 14 Jan
Live Oak Oasis - Getaway Close to Legoland! Sleeps 8 Guests, Fenced yard, Games
Exterior detail
Tiny Paradise

Apartment in Winter Haven

Tiny Paradise
9.4 out of 10, Exceptional, (8 reviews)
"I have stayed on property a few times, first experience with tiny Paradise very quaint and clean enjoyed my stay."
United States
SUSAN
The price is HK$491
HK$968 total
includes taxes & fees
22 Jan - 23 Jan
Tiny Paradise
Smart TV, table football
*3/2*GorgeousNEWLakeHome2AceLoc*4mi*LEGOLAND*1724

Holiday Home in Winter Haven

*3/2*GorgeousNEWLakeHome2AceLoc*4mi*LEGOLAND*1724
9.4 out of 10, Exceptional, (66 reviews)
"The accommodation at this property was exceptional. It felt safe, and was safe Parking was great, proximity to dinning and shopping was withing 5 minutes drive, and the location was peaceful and safe."
United States
Dwight
The price is HK$975
HK$2,160 total
includes taxes & fees
13 Jan - 14 Jan
*3/2*GorgeousNEWLakeHome2AceLoc*4mi*LEGOLAND*1724
Interior
Cozy 1 bedroom home in Winter Haven perfect for your getaway.

Holiday Home in Winter Haven

Cozy 1 bedroom home in Winter Haven perfect for your getaway.
2.0 star property
10.0 out of 10, Exceptional, (1 review)
"Yes the dogs liked it and they enjoyed walking in the neighborhood."
United States
John W.
The price is HK$686
HK$1,273 total
includes taxes & fees
15 Jan - 16 Jan
Cozy 1 bedroom home in Winter Haven perfect for your getaway.
Outdoor dining
⭐️NEAR LEGOLAND+GREAT VALUE⭐️ Cozy Cove Stay 1b1b APT, with PRIVATE entrance

Apartment in Winter Haven

⭐️NEAR LEGOLAND+GREAT VALUE⭐️ Cozy Cove Stay 1b1b APT, with PRIVATE entrance
10.0 out of 10, Exceptional, (3 reviews)
"The place was clean and tidy, accessible to a lot of stores and attractions in the surrounding area, and the hosts were SO nice and easy to contact throughout our stay-even checking in on us to make sure everything was going good. Would totally stay again!"
United States
Kaitlyn F.
The price is HK$807
HK$1,060 total
includes taxes & fees
13 Jan - 14 Jan
⭐️NEAR LEGOLAND+GREAT VALUE⭐️ Cozy Cove Stay 1b1b APT, with PRIVATE entrance
Outdoor dining
Heated Pool and Hot tub-near Legoland, Disney, Theme parks

Holiday Home in Winter Haven

Heated Pool and Hot tub-near Legoland, Disney, Theme parks
9.8 out of 10, Exceptional, (43 reviews)
"We had a great stay!"
United States
Harper B.
The price is HK$1,158
HK$2,724 total
includes taxes & fees
13 Jan - 14 Jan
Heated Pool and Hot tub-near Legoland, Disney, Theme parks
Interior
Family Vacation Home · 8 Minutes from Legoland Florida

Villa in Winter Haven

Family Vacation Home · 8 Minutes from Legoland Florida
10.0 out of 10, Exceptional, (1 review)
"Beautiful clean home. Lots of amenities. However it here were glass decorations on table. We moved them out of reach of 2 and 4 year old. Otherwise BEAUTIFUL! Definitely would stay here again."
United States
Roberta W.
The price is HK$1,024
HK$2,706 total
includes taxes & fees
13 Jan - 14 Jan
Family Vacation Home · 8 Minutes from Legoland Florida
Interior
The Unique cozy studio

Apartment in Winter Haven

The Unique cozy studio
2.0 star property
10.0 out of 10, Exceptional, (1 review)
"Cool little place, love the outdoor private patio.Very close to everything downtown"
United States
Cory M.
The price is HK$624
HK$1,426 total
includes taxes & fees
19 Jan - 20 Jan
The Unique cozy studio
Fridge, microwave, oven, stovetop
Cozy Bungalow - 5 mi Legoland & 0.5 mi Dwntwn

Holiday Home in Winter Haven

Cozy Bungalow - 5 mi Legoland & 0.5 mi Dwntwn
2.0 star property
10.0 out of 10, Exceptional, (1 review)
"Nice place very convenient for us. Would stay again"
United States
John G.
The price is HK$974
HK$2,189 total
includes taxes & fees
13 Jan - 14 Jan
Cozy Bungalow - 5 mi Legoland & 0.5 mi Dwntwn
Fridge, microwave, oven, stovetop
Getaway Clubhouse 5 mil Legoland & .5 mil Downtown

Holiday Home in Winter Haven

Getaway Clubhouse 5 mil Legoland & .5 mil Downtown
2.0 star property
9.8 out of 10, Exceptional, (7 reviews)
"Great location, clean and great communication with hosts "
United States
Angie Y.
The price is HK$974
HK$2,381 total
includes taxes & fees
13 Jan - 14 Jan
Getaway Clubhouse 5 mil Legoland & .5 mil Downtown
Fridge, microwave, stovetop, coffee/tea maker
Cozy Grand Room 1-bedroom apartment with WiFi, AC in charming Winter Haven

Apartment in Winter Haven

Cozy Grand Room 1-bedroom apartment with WiFi, AC in charming Winter Haven
The price is HK$663
HK$1,129 total
includes taxes & fees
31 Jan - 1 Feb
Cozy Grand Room 1-bedroom apartment with WiFi, AC in charming Winter Haven
Living area
BlockHaven near Legoland & Disney

Holiday Home in Winter Haven

BlockHaven near Legoland & Disney
3.5 star property
The price is HK$530
HK$2,017 total
includes taxes & fees
2 Feb - 3 Feb
BlockHaven near Legoland & Disney
Living area
BlockHaven near Legoland, Disney, Universal Studios, Busch Gardens & SeaWorld !!

Holiday Home in Winter Haven

BlockHaven near Legoland, Disney, Universal Studios, Busch Gardens & SeaWorld !!
The price is HK$491
HK$2,168 total
includes taxes & fees
13 Jan - 14 Jan
BlockHaven near Legoland, Disney, Universal Studios, Busch Gardens & SeaWorld !!
Dining
Home Away from Home Winter Haven! Disney, Legoland, Bok Tower, Golf, Medical Ctr

Holiday Home in Winter Haven

Home Away from Home Winter Haven! Disney, Legoland, Bok Tower, Golf, Medical Ctr
9.0 out of 10, Wonderful, (2 reviews)
"I'm town for family graduation party. Perfect place to stay"
United States
John S.
The price is HK$1,559
HK$2,806 total
includes taxes & fees
13 Jan - 14 Jan
Home Away from Home Winter Haven! Disney, Legoland, Bok Tower, Golf, Medical Ctr
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winter Haven Hotel Reviews

Best Western Plus Winter Haven Inn & Suites 

Best Western Plus Winter Haven Inn & Suites 

10/10 Excellent
"All clean and good"
Carol 1-night trip
Posted 14 hours ago
Best Western Plus Winter Haven Inn & Suites 

Find out more about Winter Haven

Search for holiday rentals in Winter Haven on Expedia! You can easily find your home rentals, villas, holiday apartments in Winter Haven using one of the methods below:

  • View our selection of featured holiday rentals in Winter Haven
  • Use the map to find apartments and other holiday homes in the Winter Haven neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Winter Haven while they last

Look no further and take a look at our great range of rental properties in Winter Haven!

Frequently asked questions

Can I find a holiday rental in Winter Haven?

Yes, there are holiday rentals in Winter Haven close to LEGOLAND® Florida, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to Winter Haven speak positively about the scenic lakeside and top-notch restaurants in this destination. Leave time to check out the gardens and entertainment venues during your visit.

What are some of the best holiday rentals that Winter Haven has to offer?

The Berkley, Orlando: This holiday home rental outside of Winter Haven offers a furnished patio, a terrace and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a full-sized fridge, a microwave and a coffee maker. You can relax into your holiday with an arcade/games room and 1 hot tub.

How many holiday rentals are there in Winter Haven?

Choose from 66 Expedia holiday rentals in Winter Haven for a memorable holiday.

What can I see and do in Winter Haven?

Family-friendly attractions include LEGOLAND® Florida and Indigo's Family Fun Center, whereas The Circle B Bar Reserve and Inman Park are a couple of great spots to enjoy the outdoors. Theatre Winter Haven and Chain of Lakes Park are other places to visit while you're in town.

What are holiday rentals like in Winter Haven?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winter Haven. Holiday rentals offer amenities such as kitchens and laundry facilities to help you enjoy your stay. If you're concerned about a clean environment, holiday rentals can provide a sense of seclusion away from shared hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a great choice for a family trip.