Winter Haven Holiday Rentals

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Check prices for these dates

In two weeks
12 Jun - 14 Jun
In two months
24 Jul - 26 Jul
In three months
21 Aug - 23 Aug
In four months
18 Sept - 20 Sept

Our top choices for Winter Haven holiday rentals

Living area

BlockHaven near Legoland & Disney

BlockHaven near Legoland & Disney
3.5 star property
Winter Haven
10.0 out of 10, Exceptional, (4 reviews)
"Great location. Great communication with host. "
United States
Reid
The price is HK$282
HK$1,747 total
includes taxes & fees
31 May - 1 Jun
BlockHaven near Legoland & Disney
Outdoor pool, pool umbrellas, pool loungers

Lake Ida Beach Resort

Lake Ida Beach Resort
3.0 star property
Winter Haven
7.2 out of 10, Good, (193 reviews)
"Was probably once a great time place. Owner was nice. Night time neighborhood is a bit noisy guess it's just how people act now no respect for property."
United States
wade
The price is HK$619
HK$693 total
includes taxes & fees
31 May - 1 Jun
Lake Ida Beach Resort
Exterior detail

Tiny Paradise

Tiny Paradise
Winter Haven
9.4 out of 10, Exceptional, (13 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$572
HK$1,017 total
includes taxes & fees
1 Jun - 2 Jun
Tiny Paradise
Smart TV, fireplace, printers

Modern Comfort, Pet Friendly, 2 King Beds

Modern Comfort, Pet Friendly, 2 King Beds
Winter Haven
10.0 out of 10, Exceptional, (8 reviews)
"Great welcoming and answered every question I had. Highly recommend this lovely cottage. "
United States
Kristofer G.
Modern Comfort, Pet Friendly, 2 King Beds
TV

Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn

Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
Winter Haven
8.8 out of 10, Excellent, (5 reviews)
"Just what we needed for a weekend trip with our grandsons for the weekend "
United States
Christine B.
The price is HK$901
HK$2,184 total
includes taxes & fees
31 May - 1 Jun
Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
Interior

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 HK$862
HK$1,473 total
includes taxes & fees
21 Jun - 22 Jun
Cozy 1 bedroom home in Winter Haven perfect for your getaway.
Paper towels

Private/Spacious 1BR Central Near LegoLand 2 Miles

Private/Spacious 1BR Central Near LegoLand 2 Miles
Winter Haven
9.0 out of 10, Wonderful, (13 reviews)
"clean room"
United States
sandra
The price is HK$635
HK$1,350 total
includes taxes & fees
7 Jun - 8 Jun
Private/Spacious 1BR Central Near LegoLand 2 Miles
Fridge, microwave, oven, stovetop

Historic, sleeps 10+, 5 Bedroom, huge yard, lake, fishing, parks, events

Historic, sleeps 10+, 5 Bedroom, huge yard, lake, fishing, parks, events
Winter Haven
9.8 out of 10, Exceptional, (32 reviews)
"The host was very attentive, and responsive to our questions and comments. "
United States
Matt O.
The price is HK$1,559
HK$3,749 total
includes taxes & fees
1 Jun - 2 Jun
Historic, sleeps 10+, 5 Bedroom, huge yard, lake, fishing, parks, events
Living area

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 !!
Outdoor dining

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

Hook, Line & Leisure: Lakefront Gem w/ Porch!
Winter Haven
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 HK$964
HK$3,031 total
includes taxes & fees
31 May - 1 Jun
Hook, Line & Leisure: Lakefront Gem w/ Porch!
Outdoor dining

Minutes to Legoland. Heated Pool and Private Hot Tub. Relaxation Awaits!

Minutes to Legoland. Heated Pool and Private Hot Tub. Relaxation Awaits!
Winter Haven
10.0 out of 10, Exceptional, (55 reviews)
"It was pet friendly. "
United States
Ibia
The price is HK$1,442
HK$3,121 total
includes taxes & fees
21 Jun - 22 Jun
Minutes to Legoland. Heated Pool and Private Hot Tub. Relaxation Awaits!
Interior

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

Hook, Line & Leisure: Lakefront Gem w/ Porch!
3.0 star property
Winter Haven
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$1,074
HK$3,136 total
includes taxes & fees
31 May - 1 Jun
Hook, Line & Leisure: Lakefront Gem w/ Porch!
Microwave

Cozy 1-Bedroom Retreat Near Downtown & Legoland

Cozy 1-Bedroom Retreat Near Downtown & Legoland
Winter Haven
10.0 out of 10, Exceptional, (2 reviews)
The price is HK$1,003
HK$1,368 total
includes taxes & fees
30 Jun - 1 Jul
Cozy 1-Bedroom Retreat Near Downtown & Legoland
Terrace/patio

The Old Haven - An Enduring Piece of Nostalgia

The Old Haven - An Enduring Piece of Nostalgia
Winter Haven
9.8 out of 10, Exceptional, (14 reviews)
"Nice location, comfortable stay."
United States
Karthik D.
The price is HK$940
HK$2,331 total
includes taxes & fees
31 May - 1 Jun
The Old Haven - An Enduring Piece of Nostalgia
Fridge, microwave, oven, stovetop

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)
"Great communication from the host; perfect location; well stocked with amenities"
United States
Michele S.
Getaway Clubhouse 5 mil Legoland & .5 mil Downtown
TV, fireplace

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 HK$1,191
HK$3,466 total
includes taxes & fees
8 Jun - 9 Jun
Spacious 4-bedroom house in pleasant Winter Haven with AC
TV, video games

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

Ricks's Retreat - Downtown Winter Haven Getaway, Near Chain of Lakes

Ricks's Retreat - Downtown Winter Haven Getaway, Near Chain of Lakes
Winter Haven
10.0 out of 10, Exceptional, (10 reviews)
"The host was very accommodating and responsive. The house is clean, roomy, cute, and comfortable. There is so much to see and do in Winter Haven - I’ll return and stay at Rick’s Retreat again!"
United States
Mary R.
The price is HK$982
HK$2,618 total
includes taxes & fees
31 May - 1 Jun
Ricks's Retreat - Downtown Winter Haven Getaway, Near Chain of Lakes
Fridge, microwave, stovetop, coffee/tea maker

Cozy Grand Room 1-bedroom apartment with WiFi, AC in charming Winter Haven

Cozy Grand Room 1-bedroom apartment with WiFi, AC in charming Winter Haven
Winter Haven
The price is HK$666
HK$1,135 total
includes taxes & fees
31 May - 1 Jun
Cozy Grand Room 1-bedroom apartment with WiFi, AC in charming Winter Haven
Outdoor dining

Serene, Cozy, Lakefront Home with Jacuzzi/hot tub and covered porch on the Lake!

Serene, Cozy, Lakefront Home with Jacuzzi/hot tub and covered porch on the Lake!
Winter Haven
9.4 out of 10, Exceptional, (6 reviews)
The price is HK$1,206
HK$2,849 total
includes taxes & fees
31 May - 1 Jun
Serene, Cozy, Lakefront Home with Jacuzzi/hot tub and covered porch on the Lake!
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

Delta Hotels by Marriott Orlando Celebration

Delta Hotels by Marriott Orlando Celebration

8/10 Good
"Family friendly and nice poolside bar"
Dominik 1-night trip
Posted less than an hour ago
Delta Hotels by Marriott Orlando Celebration

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:

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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 51 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 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 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.