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Winter Haven Vacation Rentals

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Check prices for these dates

In two weeks
Aug 28 - Aug 30
In two months
Oct 9 - Oct 11
In three months
Nov 6 - Nov 8
In four months
Dec 4 - Dec 6

Our top choices for Winter Haven vacation rentals

Luxury House, 3 Bedrooms, Garden View | Living area | 50-inch Smart TV with digital channels, toys, heated floors

1. BlockHaven near Legoland & Disney

BlockHaven near Legoland & Disney
3.5 star property
Winter Haven
10.0 out of 10, Exceptional, (6 reviews)
"We loved this place! It was perfect for all of us! It was nice and clean as well!"
United States
Ericka
The price is ￥10,097
￥40,111 total
includes taxes & fees
Aug 17 - Aug 18
BlockHaven near Legoland & Disney
Exterior detail

2. Tiny Paradise

Tiny Paradise
Winter Haven
9.6 out of 10, Exceptional, (14 reviews)
"Check in was easy, this little house had everything we needed! Owner very responsive to needs very quickly through app. We would stay again!"
United States
Cheryl K.
The price is ￥11,516
￥20,470 total
includes taxes & fees
Aug 12 - Aug 13
Tiny Paradise
Outdoor pool, pool umbrellas, sun loungers

3. Lake Ida Beach Resort

Lake Ida Beach Resort
3.0 star property
Winter Haven
7.2 out of 10, Good, (194 reviews)
"The cabins were great loved it there"
United States
Jennifer
The price is ￥10,993
￥12,312 total
includes taxes & fees
Aug 15 - Aug 16
Lake Ida Beach Resort
Interior

4. Cozy 1 bedroom home in Winter Haven perfect for your getaway.

Cozy 1 bedroom home in Winter Haven perfect for your getaway.
Winter Haven
10.0 out of 10, Exceptional, (4 reviews)
"This is such a cozy 1 bedroom unit and the side yard was such a great bonus amenity."
United States
Christopher V.
The price is ￥17,354
￥29,975 total
includes taxes & fees
Aug 20 - Aug 21
Cozy 1 bedroom home in Winter Haven perfect for your getaway.
Smart TV

5. View Private Suite near LEGOLAND & Hospital

View Private Suite near LEGOLAND & Hospital
Winter Haven
The price is ￥9,513
￥19,995 total
includes taxes & fees
Aug 27 - Aug 28
View Private Suite near LEGOLAND & Hospital
Terrace/patio

6. The Old Haven - An Enduring Piece of Nostalgia

The Old Haven - An Enduring Piece of Nostalgia
Winter Haven
9.8 out of 10, Exceptional, (15 reviews)
"We loved this place! It was perfect for all of us! It was nice and clean as well!"
United States
Ericka
The price is ￥18,931
￥49,458 total
includes taxes & fees
Aug 14 - Aug 15
The Old Haven - An Enduring Piece of Nostalgia
TV, fireplace

7. Spacious 4-bedroom house in pleasant Winter Haven with AC

Spacious 4-bedroom house in pleasant Winter Haven with AC
Winter Haven
9.6 out of 10, Exceptional, (4 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 ￥14,514
￥58,220 total
includes taxes & fees
Aug 12 - Aug 13
Spacious 4-bedroom house in pleasant Winter Haven with AC
Coffee/tea maker, fridge, microwave, oven

8. Getaway Clubhouse 5 mil Legoland & .5 mil Downtown

Getaway Clubhouse 5 mil Legoland & .5 mil Downtown
Winter Haven
9.8 out of 10, Exceptional, (12 reviews)
"Nice house for our stay."
United States
Debi K.
The price is ￥19,720
￥50,176 total
includes taxes & fees
Aug 22 - Aug 23
Getaway Clubhouse 5 mil Legoland & .5 mil Downtown
Living area

9. BlockHaven near Legoland, Disney, Universal Studios, Busch Gardens & SeaWorld !!

BlockHaven near Legoland, Disney, Universal Studios, Busch Gardens & SeaWorld !!
Winter Haven
10.0 out of 10, Exceptional, (1 review)
"Awesome quiet and cozy place The host is very communicative and the house had everything we need"
United States
Patricia M.
The price is ￥10,507
￥45,145 total
includes taxes & fees
Aug 17 - Aug 18
BlockHaven near Legoland, Disney, Universal Studios, Busch Gardens & SeaWorld !!
Coffee/tea maker, fridge, microwave, oven

10. 3BR/2BA Lake Mariam Home Near LEGOLAND with Kitchen & Laundry_1724

3BR/2BA Lake Mariam Home Near LEGOLAND with Kitchen & Laundry_1724
Winter Haven
9.4 out of 10, Exceptional, (68 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 ￥19,720
￥44,804 total
includes taxes & fees
Aug 20 - Aug 21
3BR/2BA Lake Mariam Home Near LEGOLAND with Kitchen & Laundry_1724
Outdoor dining

11. Legoland Splash Escape with pool and hot tub!

Legoland Splash Escape with pool and hot tub!
Winter Haven
10.0 out of 10, Exceptional, (66 reviews)
"We had a wonderful stay. Property was as listed and pool and activities were great for our family. "
United States
Christy H.
The price is ￥19,878
￥51,638 total
includes taxes & fees
Aug 17 - Aug 18
Legoland Splash Escape with pool and hot tub!
TV

12. Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn

Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
Winter Haven
9.0 out of 10, Wonderful, (6 reviews)
"Wonderful little cottage filled with fun for the whole family. Cozy backyard to enjoy some sunshine and read a book. Close to downtown shops and restaurants. Owners were quick to respond to questions. Would happily stay here again."
United States
Rachel B.
The price is ￥18,142
￥44,448 total
includes taxes & fees
Aug 19 - Aug 20
Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
4 bedrooms, WiFi (free), bed sheets

13. Live Oak Oasis - Getaway Close to Legoland! Sleeps 8 Guests, Fenced yard, Games

Live Oak Oasis - Getaway Close to Legoland! Sleeps 8 Guests, Fenced yard, Games
Winter Haven
9.6 out of 10, Exceptional, (8 reviews)
"Wonderful stay in Winter Haven for our family Legoland trip, including our dog!The house was spotless, cozy, and easily accommodated all of us.Close to the park, would definitely stay again."
United States
Oscar G.
The price is ￥19,436
￥51,868 total
includes taxes & fees
Aug 20 - Aug 21
Live Oak Oasis - Getaway Close to Legoland! Sleeps 8 Guests, Fenced yard, Games
TV

14. Cozy 3br 2ba Winter Haven Getaway Chain of Lakes Downtown

Cozy 3br 2ba Winter Haven Getaway Chain of Lakes Downtown
Winter Haven
10.0 out of 10, Exceptional, (12 reviews)
"The house was really great. It was also very clean, updated, comfortable and very close to great restaurants. Highly recommend this house."
United States
Felix P.
The price is ￥19,720
￥49,852 total
includes taxes & fees
Aug 20 - Aug 21
Cozy 3br 2ba Winter Haven Getaway Chain of Lakes Downtown
Smart TV, fireplace, printers

15. Modern Comfort, Pet Friendly, 2 King Beds

Modern Comfort, Pet Friendly, 2 King Beds
Winter Haven
10.0 out of 10, Exceptional, (9 reviews)
"Great place. Perfect for my small group on a short visit. Shower is amazing. Had all amenities. Christopher was fantastic. "
United States
Judy A.
The price is ￥19,603
￥42,925 total
includes taxes & fees
Sep 9 - Sep 10
Modern Comfort, Pet Friendly, 2 King Beds
Coffee/tea maker, fridge, microwave, oven

16. Cozy Bungalow - 5 mi Legoland & 0.5 mi Dwntwn

Cozy Bungalow - 5 mi Legoland & 0.5 mi Dwntwn
Winter Haven
10.0 out of 10, Exceptional, (2 reviews)
"Nice place very convenient for us. Would stay again"
United States
John G.
The price is ￥19,720
￥46,358 total
includes taxes & fees
Sep 10 - Sep 11
Cozy Bungalow - 5 mi Legoland & 0.5 mi Dwntwn
Smart TV, fireplace

17. Charming 3-bedroom 2 bathroom home in brilliant Winter Haven,pet friendly, WiFi

Charming 3-bedroom 2 bathroom home in brilliant Winter Haven,pet friendly, WiFi
Winter Haven
9.6 out of 10, Exceptional, (4 reviews)
"Everything was very clean! "
United States
Emilly D.
The price is ￥21,298
￥36,475 total
includes taxes & fees
Aug 16 - Aug 17
Charming 3-bedroom 2 bathroom home in brilliant Winter Haven,pet friendly, WiFi
Dining

18. Hook, Line & Leisure: Lakefront Gem w/ Porch!

Hook, Line & Leisure: Lakefront Gem w/ Porch!
Florence Villa
9.6 out of 10, Exceptional, (29 reviews)
"The house is well updated and comfortable. Everything was very clean and well appointed. Kitchen well stocked for cooking and eating in. Lovely view of the lake from 2 bedrooms, living room and screened porch. Host was very responsive and checked in to see if we needed anything. Caretakers of property across street and also helpful and welcoming. Only 40-45 minutes from Disney. Was a good home base for our 12 day stay. Neighborhood generally quiet and friendly."
United States
Carolyn B.
The price is ￥20,667
￥66,234 total
includes taxes & fees
Sep 8 - Sep 9
Hook, Line & Leisure: Lakefront Gem w/ Porch!
Outdoor dining

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

Serene, Cozy, Lakefront Home with boat dock and Large Screened in porch!
Winter Haven
9.6 out of 10, Exceptional, (7 reviews)
"Everything was just as it was listed great place to stay"
United States
Renee T.
The price is ￥26,977
￥61,009 total
includes taxes & fees
Aug 20 - Aug 21
Serene, Cozy, Lakefront Home with boat dock and Large Screened in porch!
House (3 Bedrooms) | Interior

20. Hook, Line & Leisure: Lakefront Gem w/ Porch!

Hook, Line & Leisure: Lakefront Gem w/ Porch!
3.0 star property
Florence Villa
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 ￥27,450
￥65,328 total
includes taxes & fees
Aug 31 - Sep 1
Hook, Line & Leisure: Lakefront Gem w/ Porch!
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.
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Top Winter Haven Hotel Reviews

Staybridge Suites Winter Haven Auburndale by IHG

Staybridge Suites Winter Haven Auburndale by IHG

10/10 Excellent
"Lovely Hotel!!!!! If I could have stayed longer I would. Amazing staff very nice and helpful, and Great cooks. Rooms SPOTLESS!! Clean and well organized and put together. Would definitely come back again."
Edwina 1-night trip
Posted less than an hour ago
Staybridge Suites Winter Haven Auburndale by IHG

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

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Frequently asked questions

Can I find a vacation rental in Winter Haven?

Yes, there are vacation rentals in Winter Haven close to LEGOLAND® Florida, or you can choose a more secluded option if you'd like a relaxing place to 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's the top vacation rental that Winter Haven has to offer?

Formosa Valley Resort by UNE Homes: This vacation home rental outside of Winter Haven is equipped with an outdoor pool, air-conditioning, and free WiFi to help you feel comfortable during your stay. Kitchen amenities include a full-sized fridge, a dishwasher, and a stovetop.

How many vacation rentals are there in Winter Haven?

Choose from 56 Expedia vacation rentals in Winter Haven for a memorable vacation.

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 Rotary 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 vacation rentals like in Winter Haven?

Vacation rentals are private properties you can book for a few days or a quick weekend in Winter Haven. Vacation rentals offer extras such as hot tubs, fire pits, and patios so you'll have everything you want. If you're concerned about cleanliness, a vacation rental can offer a sense of privacy away from public hotel elevators and bustling concierge desks while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular option for a small group gathering.