Winter Haven Holiday Rentals from AU$124: Search Short-Term Rentals

Q: What are some of the best holiday rentals that Winter Haven has to offer?

Formosa Valley Resort by UNE Homes : This holiday home rental outside of Winter Haven is equipped with an outdoor pool, air conditioning and free WiFi to help you feel comfortable during your stay. Kitchen amenities include a full-sized fridge, a dishwasher and a stovetop.

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Our top choices for Winter Haven holiday rentals

A swimming pool with a fence, lounge chairs, and a palm tree.

1. Lake Ida Beach Resort

Winter Haven

Jennifer

includes taxes & fees

14 Sept - 15 Sept

A living room with a large mural of marine life, a ceiling fan, a flat-screen TV, and a dining area in the background.

2. BlockHaven near Legoland & Disney

Winter Haven

Ericka

includes taxes & fees

1 Sept - 2 Sept

A modern living room with a grey sofa, a dining area with a round table and chairs, a kitchen with white cabinets, a clock, and a decorative wall piece.

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

Winter Haven

Christopher V.

includes taxes & fees

11 Sept - 12 Sept

A building with a red door, numbered 132C, and a small porch area with a metal stool and a green bucket with a wooden stick.

4. Tiny Paradise

Winter Haven

Cheryl K.

includes taxes & fees

6 Sept - 7 Sept

A compact living space with a loft bed, a TV mounted on the wall displaying streaming services, a small bathroom, and a wooden floor.

5. Lakefront Tiny Cottage 4 Miles to LEGOLAND.

winter have

Kyle P.

includes taxes & fees

30 Aug - 31 Aug

6. View Private Suite near LEGOLAND & Hospital

Winter Haven

includes taxes & fees

4 Sept - 5 Sept

A modern kitchen with white cabinets, stainless steel appliances, and a central island with bar stools.

7. Getaway Clubhouse 5 mil Legoland & .5 mil Downtown

Winter Haven

Debi K.

includes taxes & fees

12 Sept - 13 Sept

A wooden house with a porch, steps, and a fenced area with plants.

8. The Old Haven - An Enduring Piece of Nostalgia

Winter Haven

Ericka

includes taxes & fees

30 Aug - 31 Aug

A living room with a grey sofa, a wooden coffee table, a patterned rug, a TV, and a wall mural of underwater scenes.

9. BlockHaven near Legoland, Disney, Universal Studios, Busch Gardens & SeaWorld !!

Winter Haven

Patricia M.

10. New Haven 5 mi to Legoland & 0.5 mi to dwntwn

Winter Haven

includes taxes & fees

30 Aug - 31 Aug

11. Charming Lakeside Cottage

Winter Haven

includes taxes & fees

6 Sept - 7 Sept

A spacious living room with a sofa, a recliner, and a glass coffee table. There is a kitchen area in the background with a microwave and refrigerator.

12. Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn

Winter Haven

Rachel B.

includes taxes & fees

11 Sept - 12 Sept

A modern kitchen with stainless steel appliances, a dining area with a wooden bowl centerpiece, and a living room with a sofa and cushions.

13. Modern Comfort, Pet Friendly, 2 King Beds

Winter Haven

Judy A.

includes taxes & fees

1 Sept - 2 Sept

A compact kitchen with white cabinets, a stainless steel dishwasher, a refrigerator, and a microwave.

14. 3BR/2BA Lake Mariam Home Near LEGOLAND with Kitchen & Laundry_1724

Winter Haven

Dwight

includes taxes & fees

30 Aug - 31 Aug

A dining area with a round table, two chairs, a view of a lake, and a decorative wall piece.

15. Hook, Line & Leisure: Lakefront Gem w/ Porch!

Florence Villa

"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

includes taxes & fees

31 Aug - 1 Sept

A living room with two blue sofas, a patterned ottoman, a ceiling fan, and a large abstract painting.

16. Cozy 3br 2ba Winter Haven Getaway Chain of Lakes Downtown

Winter Haven

Felix P.

includes taxes & fees

30 Aug - 31 Aug

An outdoor hot tub area with a pool, surrounded by chairs and a table.

17. Legoland Splash Escape with pool and hot tub!

Winter Haven

Amy

includes taxes & fees

30 Aug - 31 Aug

A neatly arranged bedroom with a bed, nightstand, lamp, and a small cabinet.

18. Charming 3-bedroom 2 bathroom home in brilliant Winter Haven,pet friendly, WiFi

Winter Haven

Emilly D.

includes taxes & fees

30 Aug - 31 Aug

A living room with a brick fireplace, a sofa, a coffee table, and a dining area in the background.

19. Spacious 4-bedroom house in pleasant Winter Haven with AC

Winter Haven

Monica

includes taxes & fees

2 Sept - 3 Sept

20. Hook, Line & Leisure: Lakefront Gem w/ Porch!

Florence Villa

"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."

Carolyn B.

includes taxes & fees

31 Aug - 1 Sept

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Top Winter Haven Hotel Reviews

Hilton Vacation Club Aqua Sol Orlando West

10/10 Excellent

"Great staff. Pool was great many options. Water park is great for the kids. Good food and food options. One recommendation would be to improve the process for reserving dinner reservations."

The Grove Resort & Water Park Orlando

8/10 Good

"Good spacious room, but the hotel could use new towels and maybe re-do the waterpark (some chairs are broken, the slides have dark spots in it, so a revamp would be nice so it’s more clean. This is a 4 star hotel but more of a 3 star to me. The bathrooms weren’t very clean. The furniture in the unit needs to be replaced. The wood was chipped on almost all the furniture pieces. The shower curtain needs to be changed to plastic and changed after each guest’s stay for hygienic purposes. They also don’t have “free” coffee pods in the unit which was very weird to me as even cheap hotels have free coffee for guests. The hotel could also use some scent spray to make it smell better. While I know “you get what you paid for” the price I paid did not match the photos advertised online. Oh.. the couch in the unit should be leather (not upholstery - due to hygienic purposes as well."

Delta Hotels by Marriott Orlando Celebration

10/10 Excellent

"I enjoy this property very much, I have been coming here since I was a baby for over 30+ years. I've had stays in this hotel in 1994, 1998, 2000, 2002, 2004, 2005, 2009, 2010, 2012, 2013, 2017, 2017 again, 2018, and now 2026. Under the names of Ramada, Radisson, Grand Orlando Resort, and now Delta by Marriott. I was brought here as a kid, celebrated my senior graduation here, proposed to my wife on the eighth floor of the Tower Building; I've come here alone, I've come here with parents, I've come with extended family, and I've come with my fiancée turned wife. I have a strong sentimental affection for this property, it is the main hotel I've stayed at in my life and my main comparison against any hotel I stay at, should I be somewhere other than Celebration. I have made much art inspired by the architecture and aesthetic layout of this property across my life. I tend to visit places that look like this building when I dream even. All of this is to tell you how sincere my adoration is for the 2900 Parkway Boulevard resort, and I wanted to thank you for being its most recent acquirer. I firmly believe that, under the Marriott leadership, this property can attain its greatest years to come."

Find out more about Winter Haven

Everything you need to know about Winter Haven holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winter Haven holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search.

Winter Haven holiday 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winter Haven holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winter Haven holiday rentals we have selected for you start as low as AU$124 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Winter Haven rentals

At Expedia, we put the best Winter Haven holiday 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 holiday.

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.

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?

Formosa Valley Resort by UNE Homes: This holiday home rental outside of Winter Haven is equipped with an outdoor pool, air conditioning and free WiFi to help you feel comfortable during your stay. Kitchen amenities include a full-sized fridge, a dishwasher and a stovetop.

How many holiday rentals are there in Winter Haven?

Choose from 60 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 Peppa Pig Theme Park Florida, 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 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.

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Check prices for these dates

Our top choices for Winter Haven holiday rentals

1. Lake Ida Beach Resort

2. BlockHaven near Legoland & Disney

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

4. Tiny Paradise

5. Lakefront Tiny Cottage 4 Miles to LEGOLAND.

6. View Private Suite near LEGOLAND & Hospital

7. Getaway Clubhouse 5 mil Legoland & .5 mil Downtown

8. The Old Haven - An Enduring Piece of Nostalgia

9. BlockHaven near Legoland, Disney, Universal Studios, Busch Gardens & SeaWorld !!

10. New Haven 5 mi to Legoland & 0.5 mi to dwntwn

11. Charming Lakeside Cottage

12. Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn

13. Modern Comfort, Pet Friendly, 2 King Beds

14. 3BR/2BA Lake Mariam Home Near LEGOLAND with Kitchen & Laundry_1724

15. Hook, Line & Leisure: Lakefront Gem w/ Porch!

16. Cozy 3br 2ba Winter Haven Getaway Chain of Lakes Downtown

17. Legoland Splash Escape with pool and hot tub!

18. Charming 3-bedroom 2 bathroom home in brilliant Winter Haven,pet friendly, WiFi

19. Spacious 4-bedroom house in pleasant Winter Haven with AC

20. Hook, Line & Leisure: Lakefront Gem w/ Porch!

Find holiday rentals that suit your style

Top Winter Haven Hotel Reviews

Hilton Vacation Club Aqua Sol Orlando West

Margaritaville Resort Orlando with H2O Waterpark

The Grove Resort & Water Park Orlando

Kompose Boutique Resort at Theme Parks

Omni Orlando Resort at ChampionsGate

Best Western Plus Winter Haven Inn & Suites

Holiday Inn Club Vacations at Orange Lake Resort by IHG

Delta Hotels by Marriott Orlando Celebration

Howard Johnson by Wyndham Winter Haven FL

Find out more about Winter Haven

Frequently asked questions

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