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Winter Haven Vacation Rentals

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  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

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

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, (6 reviews)
"We loved this place! It was perfect for all of us! It was nice and clean as well!"
United States
Ericka
$214 nightly
The price is $240
Aug 4 - Aug 5
Total with taxes and fees
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.
$113 nightly
The price is $124
Jul 19 - Jul 20
Total with taxes and fees
Tiny Paradise
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)
"The cabins were great loved it there"
United States
Jennifer
$73 nightly
The price is $81
Jul 28 - Jul 29
Total with taxes and fees
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
$256 nightly
The price is $283
Jul 19 - Jul 20
Total with taxes and fees
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.
$240 nightly
The price is $265
Aug 4 - Aug 5
Total with taxes and fees
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.
$171 nightly
The price is $189
Jul 19 - Jul 20
Total with taxes and fees
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.
$335 nightly
The price is $370
Aug 2 - Aug 3
Total with taxes and fees
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
$286 nightly
The price is $314
Jul 20 - Jul 21
Total with taxes and fees
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.
$254 nightly
The price is $279
Jul 18 - Jul 19
Total with taxes and fees
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.
$391 nightly
The price is $432
Aug 12 - Aug 13
Total with taxes and fees
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.
$290 nightly
The price is $318
Jul 19 - Jul 20
Total with taxes and fees
Getaway Clubhouse 5 mil Legoland & .5 mil Downtown
4 bedrooms, iron/ironing board, WiFi, bed sheets

White Door House!

White Door House!
Winter Haven
$417 nightly
The price is $461
Jul 19 - Jul 20
Total with taxes and fees
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.
$288 nightly
The price is $319
Jul 18 - Jul 19
Total with taxes and fees
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.
$358 nightly
The price is $396
Jul 26 - Jul 27
Total with taxes and fees
Hook, Line & Leisure: Lakefront Gem w/ Porch!
Fridge, microwave, oven, stovetop

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)
"The house was great!"
United States
Kristin H.
$430 nightly
The price is $475
Jul 19 - Jul 20
Total with taxes and fees
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.
$269 nightly
The price is $295
Jul 20 - Jul 21
Total with taxes and fees
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 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.
$296 nightly
The price is $327
Jul 21 - Jul 22
Total with taxes and fees
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
$386 nightly
The price is $427
Aug 3 - Aug 4
Total with taxes and fees
Spacious 4-bedroom house in pleasant Winter Haven with AC
House (3 Bedrooms) | 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
$360 nightly
The price is $403
Jul 24 - Jul 25
Total with taxes and fees
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.
$225 nightly
The price is $249
Aug 16 - Aug 17
Total with taxes and fees
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

Best Western Plus Winter Haven Inn & Suites 

Best Western Plus Winter Haven Inn & Suites 

10/10 Excellent
"I’ve stayed here at least 4 times this year and it’s always a terrific experience. The staff is awesome, the rooms always very clean, it feels safe and the prices are great. You can’t beat the convenience to legoland and a ton of restaurants, coffee places and multiple Walmarts and Publix’s within 5 minutes. We’ll be back soon!"
Marianne 1-night trip
Posted 1 hour ago
Best Western Plus Winter Haven Inn & Suites 

Find out more about Winter Haven

Everything you need to know about Winter Haven vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winter Haven vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winter Haven vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winter Haven vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winter Haven. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Winter Haven in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $95 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winter Haven rentals

At Expedia, we put the best Winter Haven vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Winter Haven rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winter Haven vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winter Haven. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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 55 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 Peppa Pig Theme Park Florida, 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.