Winter Haven Vacation Rentals

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Check prices for these dates

In two weeks
Jul 10 - Jul 12
In two months
Aug 21 - Aug 23
In three months
Sep 18 - Sep 20
In four months
Oct 16 - Oct 18

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

BlockHaven near Legoland & Disney

BlockHaven near Legoland & Disney
3.5 star property
Winter Haven
10.0 out of 10, Exceptional, (5 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 ￥7,377
￥37,796 total
includes taxes & fees
Jun 28 - Jun 29
BlockHaven near Legoland & Disney
Outdoor pool, pool umbrellas, sun 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 ￥11,065
￥12,392 total
includes taxes & fees
Jun 29 - Jun 30
Lake Ida Beach Resort
House (3 Bedrooms) | 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 ￥22,001
￥65,092 total
includes taxes & fees
Jul 13 - Jul 14
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, (57 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 ￥23,296
￥56,539 total
includes taxes & fees
Jun 29 - Jun 30
Minutes to Legoland. Heated Pool and Private Hot Tub. Relaxation Awaits!
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, (6 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 ￥19,024
￥52,174 total
includes taxes & fees
Jun 27 - Jun 28
Live Oak Oasis - Getaway Close to Legoland! Sleeps 8 Guests, Fenced yard, Games
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 ￥17,795
￥30,413 total
includes taxes & fees
Jun 29 - Jun 30
Cozy 1 bedroom home in Winter Haven perfect for your getaway.
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 ￥11,809
￥20,991 total
includes taxes & fees
Jun 29 - Jun 30
Tiny Paradise
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 ￥31,898
￥74,874 total
includes taxes & fees
Jun 29 - Jun 30
Large Family Home, Legoland, Pet Friendly, 7 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)
"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 ￥18,604
￥45,256 total
includes taxes & fees
Jun 28 - Jun 29
Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
Fridge, microwave, oven, stovetop

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 ￥20,221
￥45,457 total
includes taxes & fees
Jun 29 - Jun 30
3BR/2BA Lake Mariam Home Near LEGOLAND with Kitchen & Laundry_1724
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, (33 reviews)
"The house was great!"
United States
Kristin H.
The price is ￥32,030
￥76,575 total
includes taxes & fees
Jun 29 - Jun 30
Historic, sleeps 10+, 5 Bedroom, huge yard, lake, fishing, parks, events
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 ￥19,412
￥48,110 total
includes taxes & fees
Jun 28 - Jun 29
The Old Haven - An Enduring Piece of Nostalgia
4 bedrooms, iron/ironing board, WiFi, bed sheets

White Door House!

White Door House!
Winter Haven
White Door House!
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 ￥19,736
￥63,375 total
includes taxes & fees
Jul 13 - Jul 14
Hook, Line & Leisure: Lakefront Gem w/ Porch!
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 ￥8,153
￥43,192 total
includes taxes & fees
Jun 28 - Jun 29
BlockHaven near Legoland, Disney, Universal Studios, Busch Gardens & SeaWorld !!
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)
"Nice house for our stay."
United States
Debi K.
The price is ￥20,221
￥50,553 total
includes taxes & fees
Jun 28 - Jun 29
Getaway Clubhouse 5 mil Legoland & .5 mil Downtown
Fridge, microwave, oven, stovetop

3br Modern home w/hot tub>5min from LEGOLAND

3br Modern home w/hot tub>5min from LEGOLAND
Winter Haven
10.0 out of 10, Exceptional, (26 reviews)
"Great property!"
United States
Glenn C.
The price is ￥35,592
￥72,575 total
includes taxes & fees
Jul 9 - Jul 10
3br Modern home w/hot tub>5min from LEGOLAND
Fridge, microwave, oven, stovetop

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 ￥20,221
￥47,212 total
includes taxes & fees
Jun 28 - Jun 29
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, (11 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 ￥22,648
￥56,879 total
includes taxes & fees
Jun 28 - Jun 29
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 ￥30,251
￥77,559 total
includes taxes & fees
Jul 26 - Jul 27
Spacious 4-bedroom house in pleasant Winter Haven with AC
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

Galleria Palms Hotel

Galleria Palms Hotel

10/10 Excellent
"Nos gustó mucho la atención del personal del restaurante y principalmente de la Sra sol"
José Gabriel 7-night trip
Posted less than an hour ago
Galleria Palms Hotel

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?

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 57 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.