A castle entrance with flags and banners, including a LEGO Kingdoms banner.

Winter Haven Holiday Rentals

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Check prices for these dates

In two weeks
31 Jul - 2 Aug
In two months
11 Sept - 13 Sept
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

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, (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 HK$358
HK$1,832 total
includes taxes & fees
4 Aug - 5 Aug
BlockHaven near Legoland & Disney
Exterior detail

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 HK$572
HK$1,017 total
includes taxes & fees
21 Jul - 22 Jul
Tiny Paradise
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)
"The cabins were great loved it there"
United States
Jennifer
The price is HK$529
HK$593 total
includes taxes & fees
23 Jul - 24 Jul
Lake Ida Beach Resort
Coffee/tea maker, fridge, microwave, oven

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, (67 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$980
HK$2,226 total
includes taxes & fees
20 Jul - 21 Jul
3BR/2BA Lake Mariam Home Near LEGOLAND with Kitchen & Laundry_1724
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.
The price is HK$388
HK$2,077 total
includes taxes & fees
4 Aug - 5 Aug
BlockHaven near Legoland, Disney, Universal Studios, Busch Gardens & SeaWorld !!
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$1,482 total
includes taxes & fees
19 Jul - 20 Jul
Cozy 1 bedroom home in Winter Haven perfect for your getaway.
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, (63 reviews)
"We really enjoyed our stay. Safe, quiet neighborhood, outdoor area was fantastic, beds were comfortable. Would stay again for sure. "
United States
Tara G.
The price is HK$1,305
HK$2,976 total
includes taxes & fees
19 Jul - 20 Jul
Minutes to Legoland. Heated Pool and Private Hot Tub. Relaxation Awaits!
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, (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 HK$941
HK$2,458 total
includes taxes & fees
20 Jul - 21 Jul
The Old Haven - An Enduring Piece of Nostalgia
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)
"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 HK$901
HK$2,209 total
includes taxes & fees
20 Jul - 21 Jul
Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
Smart TV

Large Family Home, Legoland, Pet Friendly, 7 Beds

Large Family Home, Legoland, Pet Friendly, 7 Beds
Winter Haven
10.0 out of 10, Exceptional, (24 reviews)
"Everything was very nice and comfortable. "
United States
Gary B.
The price is HK$1,453
HK$3,508 total
includes taxes & fees
11 Aug - 12 Aug
Large Family Home, Legoland, Pet Friendly, 7 Beds
Coffee/tea maker, fridge, microwave, oven

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 HK$980
HK$2,493 total
includes taxes & fees
19 Jul - 20 Jul
Getaway Clubhouse 5 mil Legoland & .5 mil Downtown
4 bedrooms, iron/ironing board, WiFi, bed sheets

White Door House!

White Door House!
Winter Haven
The price is HK$1,343
HK$3,651 total
includes taxes & fees
19 Jul - 20 Jul
White Door House!
4 bedrooms, free WiFi, bed sheets

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
9.8 out of 10, Exceptional, (7 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 HK$922
HK$2,505 total
includes taxes & fees
20 Jul - 21 Jul
Live Oak Oasis - Getaway Close to Legoland! Sleeps 8 Guests, Fenced yard, Games
Dining

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 HK$956
HK$3,181 total
includes taxes & fees
24 Jul - 25 Jul
Hook, Line & Leisure: Lakefront Gem w/ Porch!
Coffee/tea maker, fridge, microwave, oven

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

Historic Manor, sleeps 10+, 5 Bedroom, huge yard, lake, fishing, parks, events
Winter Haven
9.8 out of 10, Exceptional, (33 reviews)
"Perfect place to stay!"
United States
Rich S.
The price is HK$1,552
HK$3,671 total
includes taxes & fees
11 Aug - 12 Aug
Historic Manor, sleeps 10+, 5 Bedroom, huge yard, lake, fishing, parks, events
Coffee/tea maker, fridge, microwave, oven

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 HK$980
HK$2,311 total
includes taxes & fees
20 Jul - 21 Jul
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, (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 HK$941
HK$2,565 total
includes taxes & fees
21 Jul - 22 Jul
Ricks's Retreat - Downtown Winter Haven Getaway, Near Chain of Lakes
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$1,104
HK$3,345 total
includes taxes & fees
3 Aug - 4 Aug
Spacious 4-bedroom house in pleasant Winter Haven with AC
Interior

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 HK$1,286
HK$3,159 total
includes taxes & fees
24 Jul - 25 Jul
Hook, Line & Leisure: Lakefront Gem w/ Porch!
Smart TV, fireplace

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 HK$1,176
HK$1,952 total
includes taxes & fees
16 Aug - 17 Aug
Charming 3-bedroom 2 bathroom home in brilliant Winter Haven,pet friendly, WiFi
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

Kompose Boutique Resort at Theme Parks

Kompose Boutique Resort at Theme Parks

8/10 Good
"The hotel is very nice, but the layout to get to the rooms is very long. If you're on the upper floors and looking back, you have to walk a lot to get out! The breakfast is very good, the pools are very nice, the only drawback is that they don't have microwaves! The location is perfect! But they should open the back staircase or install an internal elevator! They have an elevator, but you have to walk! For the price and the location, it was worth it! And one more thing: the front desk staff should be a little more cheerful."
Gadiel 7-night trip
Posted 1 hour ago
Kompose Boutique Resort at Theme Parks

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 58 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.