Winter Haven Vacation Rentals

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Check prices for these dates

Tonight
Dec 31 - Jan 1
Tomorrow
Jan 1 - Jan 2
This weekend
Jan 2 - Jan 4
Next weekend
Jan 9 - Jan 11

Our top choices for Winter Haven vacation rentals

House (3 Bedrooms) | Interior
Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn

Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn

Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn
3.0 star property
Winter Haven
10.0 out of 10, Exceptional, (3)
"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 ￥26,741
￥68,535 total
includes taxes & fees
Jan 3 - Jan 4
Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn
Outdoor pool, pool umbrellas, sun loungers
Lake Ida Beach Resort

Lake Ida Beach Resort

Lake Ida Beach Resort
3.0 star property
Winter Haven
7.2 out of 10, Good, (188)
"We have stayed here several times. "
United States
Martha
The price is ￥13,292
￥14,887 total
includes taxes & fees
Jan 15 - Jan 16
Lake Ida Beach Resort
TV
Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn

Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn

Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
2.0 star property
Winter Haven
10.0 out of 10, Exceptional, (2)
"Just what we needed for a weekend trip with our grandsons for the weekend "
United States
Christine B.
The price is ￥17,984
￥43,435 total
includes taxes & fees
Jan 4 - Jan 5
Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
Pool
Spacious 4-bedroom house in pleasant Winter Haven with AC

Spacious 4-bedroom house in pleasant Winter Haven with AC

Spacious 4-bedroom house in pleasant Winter Haven with AC
2.0 star property
Winter Haven
10.0 out of 10, Exceptional, (1)
"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 ￥14,387
￥57,085 total
includes taxes & fees
Jan 5 - Jan 6
Spacious 4-bedroom house in pleasant Winter Haven with AC
Smart TV, fireplace, printers
Modern Comfort, Pet Friendly, 2 King Beds

Modern Comfort, Pet Friendly, 2 King Beds

Modern Comfort, Pet Friendly, 2 King Beds
2.0 star property
Winter Haven
10.0 out of 10, Exceptional, (3)
"Great welcoming and answered every question I had. Highly recommend this lovely cottage. "
United States
Kristofer G.
The price is ￥16,107
￥37,712 total
includes taxes & fees
Jan 4 - Jan 5
Modern Comfort, Pet Friendly, 2 King Beds
Fridge, microwave, oven, stovetop
*3/2*GorgeousNEWLakeHome2AceLoc*4mi*LEGOLAND*1724

*3/2*GorgeousNEWLakeHome2AceLoc*4mi*LEGOLAND*1724

*3/2*GorgeousNEWLakeHome2AceLoc*4mi*LEGOLAND*1724
Winter Haven
9.4 out of 10, Exceptional, (65)
"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 ￥19,563
￥43,023 total
includes taxes & fees
Jan 10 - Jan 11
*3/2*GorgeousNEWLakeHome2AceLoc*4mi*LEGOLAND*1724
Fridge, microwave, oven, stovetop
Cozy Bungalow - 5 mi Legoland & 0.5 mi Dwntwn

Cozy Bungalow - 5 mi Legoland & 0.5 mi Dwntwn

Cozy Bungalow - 5 mi Legoland & 0.5 mi Dwntwn
2.0 star property
Winter Haven
10.0 out of 10, Exceptional, (1)
"Nice place very convenient for us. Would stay again"
United States
John G.
The price is ￥19,548
￥45,327 total
includes taxes & fees
Jan 4 - Jan 5
Cozy Bungalow - 5 mi Legoland & 0.5 mi Dwntwn
Smart TV
⭐️NEAR LEGOLAND+GREAT VALUE⭐️ Cozy Cove Stay 1b1b APT, with PRIVATE entrance

⭐️NEAR LEGOLAND+GREAT VALUE⭐️ Cozy Cove Stay 1b1b APT, with PRIVATE entrance

⭐️NEAR LEGOLAND+GREAT VALUE⭐️ Cozy Cove Stay 1b1b APT, with PRIVATE entrance
Winter Haven
10.0 out of 10, Exceptional, (3)
"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 ￥16,185
￥21,256 total
includes taxes & fees
Jan 4 - Jan 5
⭐️NEAR LEGOLAND+GREAT VALUE⭐️ Cozy Cove Stay 1b1b APT, with PRIVATE entrance
Private kitchen
Cozy 1 bedroom home in Winter Haven perfect for your getaway.

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

Cozy 1 bedroom home in Winter Haven perfect for your getaway.
2.0 star property
Winter Haven
10.0 out of 10, Exceptional, (1)
"Yes the dogs liked it and they enjoyed walking in the neighborhood."
United States
John W.
The price is ￥13,761
￥25,546 total
includes taxes & fees
Jan 4 - Jan 5
Cozy 1 bedroom home in Winter Haven perfect for your getaway.
Outdoor dining
Getaway Clubhouse 5 mil Legoland & .5 mil Downtown

Getaway Clubhouse 5 mil Legoland & .5 mil Downtown

Getaway Clubhouse 5 mil Legoland & .5 mil Downtown
2.0 star property
Winter Haven
9.8 out of 10, Exceptional, (7)
"Great location, clean and great communication with hosts "
United States
Angie Y.
The price is ￥19,548
￥48,244 total
includes taxes & fees
Jan 3 - Jan 4
Getaway Clubhouse 5 mil Legoland & .5 mil Downtown
Private kitchen
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

Live Oak Oasis - Getaway Close to Legoland! Sleeps 8 Guests, Fenced yard, Games
2.0 star property
Winter Haven
10.0 out of 10, Exceptional, (2)
"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 ￥21,893
￥54,670 total
includes taxes & fees
Jan 5 - Jan 6
Live Oak Oasis - Getaway Close to Legoland! Sleeps 8 Guests, Fenced yard, Games
Golf
Family Vacation Home · 8 Minutes from Legoland Florida

Family Vacation Home · 8 Minutes from Legoland Florida

Family Vacation Home · 8 Minutes from Legoland Florida
Winter Haven
10.0 out of 10, Exceptional, (1)
"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 ￥21,215
￥55,662 total
includes taxes & fees
Jan 4 - Jan 5
Family Vacation Home · 8 Minutes from Legoland Florida
Fridge, microwave, oven, stovetop
LEGOLAND! Disney, Universal &+! Your Home Away from Home in Winter Haven, FLA!

LEGOLAND! Disney, Universal &+! Your Home Away from Home in Winter Haven, FLA!

LEGOLAND! Disney, Universal &+! Your Home Away from Home in Winter Haven, FLA!
Winter Haven
9.0 out of 10, Wonderful, (2)
"I'm town for family graduation party. Perfect place to stay"
United States
John S.
The price is ￥33,778
￥61,445 total
includes taxes & fees
Jan 2 - Jan 3
LEGOLAND! Disney, Universal &+! Your Home Away from Home in Winter Haven, FLA!
Outdoor pool
Heated Pool and Hot tub-near Legoland, Disney, Theme parks

Heated Pool and Hot tub-near Legoland, Disney, Theme parks

Heated Pool and Hot tub-near Legoland, Disney, Theme parks
Winter Haven
9.8 out of 10, Exceptional, (40)
"We had a great stay!"
United States
Harper B.
The price is ￥23,222
￥53,877 total
includes taxes & fees
Jan 12 - Jan 13
Heated Pool and Hot tub-near Legoland, Disney, Theme parks
Luxury House, 3 Bedrooms, Garden View | Living area | 50-inch Smart TV with digital channels, toys, heated floors
BlockHaven near Legoland & Disney

BlockHaven near Legoland & Disney

BlockHaven near Legoland & Disney
3.5 star property
Winter Haven
The price is ￥14,600
￥44,899 total
includes taxes & fees
Jan 3 - Jan 4
BlockHaven near Legoland & Disney
1 bedroom, iron/ironing board, WiFi, bed sheets
Tiny Paradise

Tiny Paradise

Tiny Paradise
Winter Haven
9.4 out of 10, Exceptional, (8)
"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 ￥9,852
￥19,416 total
includes taxes & fees
Jan 6 - Jan 7
Tiny Paradise
Property grounds
The Unique cozy studio

The Unique cozy studio

The Unique cozy studio
2.0 star property
Winter Haven
10.0 out of 10, Exceptional, (1)
"Cool little place, love the outdoor private patio.Very close to everything downtown"
United States
Cory M.
The price is ￥12,510
￥28,617 total
includes taxes & fees
Jan 19 - Jan 20
The Unique cozy studio
Interior
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

Charming 3-bedroom 2 bathroom home in brilliant Winter Haven,pet friendly, WiFi
Winter Haven
10.0 out of 10, Exceptional, (2)
"Wonderful home "
United States
Joshlynn
The price is ￥25,474
￥31,659 total
includes taxes & fees
Jan 5 - Jan 6
Charming 3-bedroom 2 bathroom home in brilliant Winter Haven,pet friendly, WiFi
Interior
Historic, sleeps 10+, 5 Bedroom, huge yard, lake, fishing, parks, events

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, (25)
"Awesome look forward to future stay "
United States
cheryl d.
The price is ￥30,963
￥65,767 total
includes taxes & fees
Jan 3 - Jan 4
Historic, sleeps 10+, 5 Bedroom, huge yard, lake, fishing, parks, events
Smart TV
Cozy 1-Bedroom Retreat Near Downtown & Legoland

Cozy 1-Bedroom Retreat Near Downtown & Legoland

Cozy 1-Bedroom Retreat Near Downtown & Legoland
Winter Haven
10.0 out of 10, Exceptional, (2)
The price is ￥20,017
￥27,298 total
includes taxes & fees
Jan 2 - Jan 3
Cozy 1-Bedroom Retreat Near Downtown & Legoland
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

Hilton Vacation Club Aqua Sol Orlando West

Hilton Vacation Club Aqua Sol Orlando West

10/10 Excellent
"Everything walking distance! Perfect for kids!"
Giulia 4-night trip
Posted 8 hours ago
Hilton Vacation Club Aqua Sol Orlando West

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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  • 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 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?

The Berkley, Orlando: This vacation home rental outside of Winter Haven offers a furnished patio, a terrace, and a barbecue grill 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 vacation with an arcade game room and a hot tub.

How many vacation rentals are there in Winter Haven?

Choose from 63 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 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 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.