Winter Haven Vacation Rentals from $109: Search Short-Term Rentals

Q: 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.

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Our top choices for Winter Haven vacation rentals

Outdoor pool, pool umbrellas, sun loungers

Lake Ida Beach Resort

Winter Haven

Martha

$77 nightly

Apr 5 - Apr 6

Total with taxes and fees

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

Winter Haven

"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."

John

$394 nightly

Apr 14 - Apr 15

Total with taxes and fees

Luxury House, 3 Bedrooms, Garden View | Living area | 50-inch Smart TV with digital channels, toys, heated floors

BlockHaven near Legoland & Disney

Winter Haven

Reid

$250 nightly

Apr 12 - Apr 13

Total with taxes and fees

Serene Lake Views: Winter Haven Home

Winter Haven

Harmony Ensuite Room Shared Home No Car

Kissimmee

$104 nightly

Apr 9 - Apr 10

Total with taxes and fees

Lakefront Babson Park Escape: Pet Friendly!

Babson Park

$425 nightly

Apr 1 - Apr 2

Total with taxes and fees

Vacation Village Orlando, Celebration

Kissimmee

Kena

$117 nightly

Apr 26 - Apr 27

Total with taxes and fees

Camp Mack Lodge, Marina & RV Resort

Lake Wales

Tommy

$129 nightly

Apr 1 - Apr 2

Total with taxes and fees

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Top Winter Haven Hotel Reviews

Kompose Boutique Resort at Theme Parks

10/10 Excellent

"Food was excellent and everything was clean "

The Grove Resort & Water Park Orlando

6/10 Okay

"Booked this resort, to try something different from the usual hotel we frequently stay at when visiting Orlando. I have to admit, the photos online make this place seem like a steal for $250 a night. However, after staying there, I am not sure I would again. Came during Spring Break and it was insanely crowded. There was never an option to purchase the “private” seats while we were there - despite several seats staying open the entire time. There is not enough pool chairs - not even by half - for the amount of people that go to the pool. It’s actually ridiculous. We tried the smaller pool & it was ICE cold. My 5 year old couldn’t even stand it (and that says a lot because these kids don’t feel temperatures like we do). So we went to the big pool since we heard it was heated. It wasn’t, by the way … it wasn’t as ice cold as the smaller one though. However, the kids part with the slides was ice cold, so of course my 5 year old was not interested in that. The food at the pool is pretty good. The drinks are super expensive, but that was expected. The restaurant we went to at night, at the resort, was just ok. None of the food was impressive at all. Weird concept too with all these different types of cuisine. Took a long time to be seated and quite awhile for the food to come. It was really like fast food - nothing special. The arcade & put-put area is seriously outdated. It was disappointing. The rooms were ok. The living room & kitchen were nice - outdated but ok. "

Hilton Vacation Club Aqua Sol Orlando West

6/10 Okay

"Upon booking, the room I selected was updated blue with a jacuzzi style tub. I always call ahead as I travel with a service animal, I assume this is why my room was outdated, brown and not the room that I booked. My service animal performs alerting and grounding tasks that are sleep oriented, his training is specifically designated for sleep disturbances (PTSD sleep apnea, sleep walking etc). Therefore, more likely than not I choose to roam day to day without him present all the time. The hotel gave me a flier which the lady who was so nice handed over saying “im sure you’ve seen this before” which no, I have never received a paper about things that are common sense (if damages occur you’re responsible, if the service animal is behaving inappropriately you will be removed from property) However, the paper extensively listed the use of family areas with a service animal is not permitted, seating in restaurants or food areas with a service animal was not permitted, leaving the service animal unattended in the room was not permitted. It made this stay very unaccommodating. I have never experienced this at any hotel, most trained service animals are crated or crate trained and the policy should reflect the use of crating a service animal as acceptable when leaving the room without them. This made my stay entirely taxing & I could not utilize any of the amenities while I stayed. If you are traveling with a service animal, they will allow you to sleep there and nothing else so FYI"

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 $109 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.

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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 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 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.

Winter Haven Vacation Rentals

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Check prices for these dates

Our top choices for Winter Haven vacation rentals

Lake Ida Beach Resort

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

BlockHaven near Legoland & Disney

Serene Lake Views: Winter Haven Home

Harmony Ensuite Room Shared Home No Car

Lakefront Babson Park Escape: Pet Friendly!

Vacation Village Orlando, Celebration

Camp Mack Lodge, Marina & RV Resort

Disney's Animal Kingdom Villas - Kidani Village

Orlando Getaway With Pool View Balcony

Family Friendly Davenport Pool Villa

Adeline Apartments 15m to Parks, Pet Friendly, Free Parking by Heavenly Homes

Barefoot'n Resort Kissimmee Orlando

Margaritaville Cottages Orlando by Rentyl with H2O Waterpark

Serenity - Family & Pet Friendly, Amazing Location

Pet-friendly Lakeland Condo w/ Screened Porch!

Priceless Peace At Serenity By Shine Villas. 081 3 Bedroom Townhouse

4703 Flagler Beach Way, Kissimmee Florida,3bed

Bright 3BR Resort Condo Near Disney + Pools

Lakeview 6Br W/ Pool, Hot Tub & Near Theme Parks

Find vacation rentals that suit your style

Top Winter Haven Hotel Reviews

Kompose Boutique Resort at Theme Parks

Find out more about Winter Haven

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