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Winter Haven Vacation Rentals

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Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

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 AED 223
AED 921 total
includes taxes & fees
21 Sep - 22 Sep
BlockHaven near Legoland & Disney
Outdoor pool, pool umbrellas, sun loungers

2. Lake Ida Beach Resort

Lake Ida Beach Resort
3.0 star property
Winter Haven
7.2 out of 10, Good, (196 reviews)
"Clean room and private area loved it"
United States
Heather
The price is AED 253
AED 284 total
includes taxes & fees
21 Oct - 22 Oct
Lake Ida Beach Resort
Exterior detail

3. Tiny Paradise

Tiny Paradise
Winter Haven
9.6 out of 10, Exceptional, (15 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 AED 268
AED 477 total
includes taxes & fees
21 Sep - 22 Sep
Tiny Paradise
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 AED 404
AED 698 total
includes taxes & fees
3 Oct - 4 Oct
Cozy 1 bedroom home in Winter Haven perfect for your getaway.
Coffee/tea maker, fridge, microwave, oven

5. New Haven 5 mi to Legoland & 0.5 mi to dwntwn

New Haven 5 mi to Legoland & 0.5 mi to dwntwn
Winter Haven
10.0 out of 10, Exceptional, (1 review)
The price is AED 404
AED 1,014 total
includes taxes & fees
25 Sep - 26 Sep
New Haven 5 mi to Legoland & 0.5 mi to dwntwn
Interior

6. Lakefront Tiny Cottage 4 Miles to LEGOLAND.

Lakefront Tiny Cottage 4 Miles to LEGOLAND.
winter have
9.0 out of 10, Wonderful, (42 reviews)
"Awesome location, very nice"
United States
Kyle P.
The price is AED 257
AED 547 total
includes taxes & fees
21 Sep - 22 Sep
Lakefront Tiny Cottage 4 Miles to LEGOLAND.
Smart TV

7. View Private Suite near LEGOLAND & Hospital

View Private Suite near LEGOLAND & Hospital
Winter Haven
The price is AED 231
AED 477 total
includes taxes & fees
21 Sep - 22 Sep
View Private Suite near LEGOLAND & Hospital
TV

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

Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
Winter Haven
9.2 out of 10, Wonderful, (7 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 AED 422
AED 1,035 total
includes taxes & fees
21 Sep - 22 Sep
Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
Coffee/tea maker, fridge, microwave, oven

9. Charming Lakeside Cottage

Charming Lakeside Cottage
Winter Haven
The price is AED 314
AED 631 total
includes taxes & fees
21 Sep - 22 Sep
Charming Lakeside Cottage
Coffee/tea maker, fridge, microwave, oven

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

Getaway Clubhouse 5 mil Legoland & .5 mil Downtown
Winter Haven
9.8 out of 10, Exceptional, (13 reviews)
"Nice house for our stay."
United States
Debi K.
The price is AED 459
AED 1,146 total
includes taxes & fees
21 Sep - 22 Sep
Getaway Clubhouse 5 mil Legoland & .5 mil Downtown
Terrace/patio

11. 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 AED 441
AED 1,111 total
includes taxes & fees
21 Sep - 22 Sep
The Old Haven - An Enduring Piece of Nostalgia
4 bedrooms, WiFi (free), bed sheets

12. 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.
Live Oak Oasis - Getaway Close to Legoland! Sleeps 8 Guests, Fenced yard, Games
House (3 Bedrooms) | Interior

13. 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 AED 606
AED 1,484 total
includes taxes & fees
21 Sep - 22 Sep
Hook, Line & Leisure: Lakefront Gem w/ Porch!
Living area

14. 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.
BlockHaven near Legoland, Disney, Universal Studios, Busch Gardens & SeaWorld !!
TV, fireplace

15. 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 AED 417
AED 1,455 total
includes taxes & fees
21 Sep - 22 Sep
Spacious 4-bedroom house in pleasant Winter Haven with AC
TV

16. 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, (14 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 AED 533
AED 1,254 total
includes taxes & fees
21 Sep - 22 Sep
Cozy 3br 2ba Winter Haven Getaway Chain of Lakes Downtown
Smart TV, fireplace, printers

17. Modern Comfort, Pet Friendly, 2 King Beds

Modern Comfort, Pet Friendly, 2 King Beds
Winter Haven
9.8 out of 10, Exceptional, (11 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 AED 360
AED 877 total
includes taxes & fees
21 Sep - 22 Sep
Modern Comfort, Pet Friendly, 2 King Beds
Smart TV, fireplace

18. 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 AED 595
AED 986 total
includes taxes & fees
26 Sep - 27 Sep
Charming 3-bedroom 2 bathroom home in brilliant Winter Haven,pet friendly, WiFi
Smart TV

19. Private King Suite with W/D near LEGOLAND & Winter Haven Hospital

Private King Suite with W/D near LEGOLAND & Winter Haven Hospital
Winter Haven
8.4 out of 10, Very good, (9 reviews)
"Minor issues with the toilet but it was taken care of immediately. Overall a pleasant stay."
Canada
Mike S.
The price is AED 349
AED 670 total
includes taxes & fees
21 Sep - 22 Sep
Private King Suite with W/D near LEGOLAND & Winter Haven Hospital
Dining

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

Hook, Line & Leisure: Lakefront Gem w/ Porch!
Florence Villa
9.6 out of 10, Exceptional, (29 reviews)
"Nice place to stay for a weekend, had plenty of beds and baths, was clean and close to Lake Silver."
United States
Kelley K.
The price is AED 452
AED 1,505 total
includes taxes & fees
21 Sep - 22 Sep
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

Vacation Village Orlando, Celebration

Vacation Village Orlando, Celebration

10/10 Excellent
"Ideal location short drive to all theme parks and restaurants. Clean room with great balcony view, laundry and full kitchen. Super friendly and welcoming staff. Kid friendly, comfortable and convenient. Always a pleasure to stay."
Liz 2-night trip
Posted 3 hours ago
Vacation Village Orlando, Celebration

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 59 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 Inman Park and The Circle B Bar Reserve 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.