Winter Haven Cottages

A castle entrance with flags and banners, including a LEGO Kingdoms banner.

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Our top choices for Winter Haven cottages

A small, single-story house with a gray roof and white siding, featuring two white plastic chairs outside.

1. Lake Ida Beach Resort

Winter Haven

Heather

RM325 total

includes taxes & fees

25 Oct - 26 Oct

A two-story house with a front porch, a garage, and a well-maintained lawn.

2. Lakefront Vibes w/ Lanai! Bird-watching Paradise

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

RM1,649 total

includes taxes & fees

19 Oct - 20 Oct

A covered porch with two wooden chairs and a bench, overlooking a road and a body of water.

3. Lakefront Retreat on Lake Ariana w/ EV Charger

Auburndale

Katrina

RM1,433 total

includes taxes & fees

19 Oct - 20 Oct

A two-story house with a garage, surrounded by well-maintained lawns and palm trees.

4. Family Resort Home w Pool, BBQ & Game Room

Solana

RM1,339 total

includes taxes & fees

19 Oct - 20 Oct

A residential area with a well-maintained lawn, a street with parked cars, and a green dumpster.

5. Ei8555 - 3BR House Near Disney

Kissimmee

RM1,328 total

includes taxes & fees

6 Nov - 7 Nov

A multi-story building with a 'STUDIO MOVIE GRILL' sign, parking lot, and surrounding greenery.

6. Serenity - Family & Pet Friendly, Amazing Location

Crestwynd Bay

RM1,614 total

includes taxes & fees

19 Oct - 20 Oct

A residential neighborhood with two houses, a driveway, and a lawn.

7. Walkable Dixieland District Gem With Yard

Dixieland

RM1,135 total

includes taxes & fees

19 Oct - 20 Oct

A two-story house with a garage, a front lawn with palm trees, and a clear blue sky.

8. Family Home With Pool, BBQ & Cinema Near Disney

Kissimmee

RM1,978 total

includes taxes & fees

20 Oct - 21 Oct

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Top Winter Haven Hotel Reviews

Delta Hotels by Marriott Orlando Celebration

10/10 Excellent

"Great hotel the rooms are very spacious. The property is very well located 10 minutes walking to Old Town Disney and same distance to the NiKe Factory I didn't try the breakfast but I found 26.00 per person is too much and they never showed the Menu o what was included"

Margaritaville Resort Orlando with H2O Waterpark

8/10 Good

"Resort is great. The bars closed early. Rooms were nice but basic. Shower on 5th floor had hardly any pressure. The knob for shower on off was broken. Had to report to front desk so I was not charged. We specifically booked two rooms two bites to spend a day at H20 park. I also got a cabana. Got to park and they had a sign with more than half of the park closed. There was no email or info of this given to us. We checked in for cabana. Got settled walked to cabana in the candy cane kids play pool (which we specifically went and got cabana for) and it was closed off. So I walked all the way back and they said they had no idea why the kiddie play area was closed. So spent over $1500 to stay at a resort and could not use the park. My daughter is 2 and was only able to use one slide. If you were gonna shut down whole areas and half of the park you should email people that paid for tickets/cabanas before they get there. If I would have known about the park half closed I would have canceled our trip to this resort and gone to our usual spot in Orlando but figured try something new. Oh and also it was a surprise for our friends visiting us with their 5 year old which was only able to use a couple things."

Kompose Boutique Resort at Theme Parks

10/10 Excellent

"The hotel was great! It felt like a resort with all the fun amenities! Everything was very clean. The staff was so nice, they gave us a complimentary kitchenette upgrade. It was big for just 2 people but for a family of 4 it would be perfect. It also came with a washer/dryer unit, which was very useful. I stayed for 5 night and our towels were changed daily but they were supposed to change the sheets on the 3rd night but never did. But still so worth it! I recommended 2 other families to stay here and they also enjoyed it! The hotel is also conveniently located to all the major parks and it is on the main strip where there are many restaurants in walking distance. So glad I found this hotel. I will be staying here every time I visit Orlando!"

Hilton Vacation Club Mystic Dunes Orlando

8/10 Good

"Clean, large places convenient to pool and golf course. Nice property. Receiving packages is terrible! Our important Amazon arrived. We drove to the gate within 15 minutes of arrival. They would not give it to us. They said it needed to be checked in at their warehouse after first denying that it was there. We had to call all over the place the following day which delayed our trip to the theme park. They couldn’t locate the package. We had a picture of the delivery from Amazon and then they finally said that it was still sitting in the check-in station. It hadn’t gone anywhere. They delivered it, but it took another hour and a half. We also had some rain ponchos that were delivered. Again… They could not find the package. It took three days and we finally got it when we checked out. Terrible terrible service. They need to have another system for receiving parcels. Also… When you are checking in, they want you to commit to a timeshare presentation. We declined and then they called the room at least three times."

Find out more about Winter Haven

Winter Haven Cottages information

Number of reviews	4
Accommodation	1936 Cottages
Lowest Price	RM325
Highest Price	RM1,978

Frequently asked questions

How much do cottages in Winter Haven cost?

Cottages in Winter Haven range between RM325 and RM1,978 per night. These properties offer a chance to get in tune with nature — at a price you can afford. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.

How many cottages are there in Winter Haven?

Pack your suitcases and pick from 1936 cottages in Winter Haven. Thinking about a place where you can get in touch with nature? Expedia can help you find your ideal stay in only a click or two.

Are there any family-friendly cottages in Winter Haven?

If you're looking to get back to nature in Winter Haven, you can't beat Lake Ida Beach Resort. With a 3-star rating and amenities like housekeeping services and WiFi, you'll find it easy to relax at this family-friendly cottage. After checking in and chilling out in your comfy new digs, it's time to head out and start exploring. LEGOLAND® Florida and Indigo's Family Fun Centre are among the best family-friendly attractions in Winter Haven.

Why book your cottage in Winter Haven with Expedia?

Booking a cottage in Winter Haven is as simple as working out your travel dates and picking your ideal place for a getaway in nature. From chic retreats to low-cost stays and cottages that have amenities like laundry facilities, Expedia has something for all tastes and styles. As for the best offers around? We've got them too!

How can I find cheap cottages in Winter Haven?

A great way to track down cheap cottages in Winter Haven is with Expedia's useful filter tool. Tailor your search results by star rating, amenities and budget to discover unbeatable bargains in a few clicks.

What is there to do in Winter Haven near my cottage?

You'll find plenty of fabulous things that'll fill up your itinerary in Winter Haven. Head for top attractions like Indigo's Family Fun Centre, Lake Henry Golf Club and Cypresswood Golf and Country Club. LEGOLAND® Florida, Chain of Lakes Park and Theatre Winter Haven are other must-see's.

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Winter Haven cottages

1. Lake Ida Beach Resort

2. Lakefront Vibes w/ Lanai! Bird-watching Paradise

3. Lakefront Retreat on Lake Ariana w/ EV Charger

4. Family Resort Home w Pool, BBQ & Game Room

5. Ei8555 - 3BR House Near Disney

6. Serenity - Family & Pet Friendly, Amazing Location

7. Walkable Dixieland District Gem With Yard

8. Family Home With Pool, BBQ & Cinema Near Disney

Find holiday rentals that suit your style

Top Winter Haven Hotel Reviews

Delta Hotels by Marriott Orlando Celebration

Vacation Village Orlando, Celebration

Holiday Inn Resort Kissimmee by the Parks by IHG

Margaritaville Resort Orlando with H2O Waterpark

Kompose Boutique Resort at Theme Parks

The Grove Resort & Water Park Orlando

Legoland Florida Hotel

Holiday Inn & Suites Orlando SW - Celebration Area by IHG

Hilton Vacation Club Mystic Dunes Orlando

Find out more about Winter Haven

Winter Haven Cottages information

Frequently asked questions

Explore a world of travel with Expedia

Search Cottages in Winter Haven

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Winter Haven cottages

1. Lake Ida Beach Resort

2. Lakefront Vibes w/ Lanai! Bird-watching Paradise

3. Lakefront Retreat on Lake Ariana w/ EV Charger

4. Family Resort Home w Pool, BBQ & Game Room

5. Ei8555 - 3BR House Near Disney

6. Serenity - Family & Pet Friendly, Amazing Location

7. Walkable Dixieland District Gem With Yard

8. Family Home With Pool, BBQ & Cinema Near Disney

Find holiday rentals that suit your style

Top Winter Haven Hotel Reviews

Delta Hotels by Marriott Orlando Celebration

Find out more about Winter Haven

Winter Haven Cottages information

Frequently asked questions

Explore a world of travel with Expedia