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.

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Next weekend

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In two months

"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."

HK$2,920 total

includes taxes & fees

16 Oct - 17 Oct

"We have stayed here several times. "

HK$654 total

includes taxes & fees

12 Oct - 13 Oct

"Just what we needed for a weekend trip with our grandsons for the weekend "

HK$2,162 total

includes taxes & fees

4 Oct - 5 Oct

"We loved staying here! "

HK$1,696 total

includes taxes & fees

16 Oct - 17 Oct

"I love the place ! It was beautiful! Enough room for everyone "

HK$1,681 total

includes taxes & fees

7 Oct - 8 Oct

HK$3,613 total

includes taxes & fees

8 Oct - 9 Oct

"Awesome"

HK$1,733 total

includes taxes & fees

4 Oct - 5 Oct

"We stayed and visited universal snd drove to Jacksonville it was a cute cottage"

HK$1,840 total

includes taxes & fees

13 Oct - 14 Oct

HK$1,672 total

includes taxes & fees

5 Oct - 6 Oct

HK$1,593 total

includes taxes & fees

4 Oct - 5 Oct

HK$1,812 total

includes taxes & fees

4 Oct - 5 Oct

HK$2,122 total

includes taxes & fees

1 Nov - 2 Nov

HK$1,592 total

includes taxes & fees

21 Oct - 22 Oct

HK$2,149 total

includes taxes & fees

25 Oct - 26 Oct

HK$2,486 total

includes taxes & fees

25 Oct - 26 Oct

HK$7,419 total

includes taxes & fees

14 Oct - 15 Oct

HK$2,834 total

includes taxes & fees

5 Oct - 6 Oct

HK$5,223 total

includes taxes & fees

15 Oct - 16 Oct

HK$3,879 total

includes taxes & fees

28 Oct - 29 Oct

"This place is tiny but everything you need for a comfortable stay! Would definitely stay here again."

HK$1,609 total

includes taxes & fees

6 Oct - 7 Oct

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Top Winter Haven Hotel Reviews

Ramada by Wyndham Kissimmee Gateway

10/10 Excellent

"No pets nor children but I am sure it is a great place for them"

Kompose Boutique Resort at Theme Parks

10/10 Excellent

"I recently stayed overnight at Kompose Boutique Resort @ Theme Parks in Orlando, and it was a wonderful experience! From the moment I stepped in, I noticed a beautiful signature scent—it smelled amazing and gave off such a welcoming, upscale vibe. Check‑in was effortless, and the staff were warm, friendly, and attentive. My room was spacious, clean, and had everything I needed. Very well‑maintained. Breakfast the next morning was excellent. The buffet had a wide variety of fresh options to choose from, which I really appreciated. Overall, it was an amazing stay. I’ll definitely recommend Kompose Boutique Resort to others, and I’ll be back next time I’m in Orlando!"

Find out more about Winter Haven

Winter Haven Cottages information

Number of reviews	206
Accommodation	1744 Cottages
Lowest Price	HK$654
Highest Price	HK$7,419

Frequently asked questions

How much do cottages in Winter Haven cost?

Cottages in Winter Haven range between HK$654 and HK$7,419 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 1744 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.

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Search Cottages in Winter Haven

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

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

Lake Ida Beach Resort

Lake Ida Beach Resort

Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn

Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn

Jedi cottage 4 miles from Disney! Mins from universal!

Jedi cottage 4 miles from Disney! Mins from universal!

Disney, Universal and Legoland Getaway

Disney, Universal and Legoland Getaway

161 - 4 bed Gem at Terraverde Resort

161 - 4 bed Gem at Terraverde Resort

Hidden Lake View Cottage 5 miles from Disney!

Hidden Lake View Cottage 5 miles from Disney!

Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee

Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee

Perfect Place for a Perfect Vacation

Perfect Place for a Perfect Vacation

Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC

Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC

Charming cottage 10 mins to Disney, Pool, Mini Golf, Fitness room and more!

Charming cottage 10 mins to Disney, Pool, Mini Golf, Fitness room and more!

Fully-Stocked Cozy Tropical Cottage-4 mi to Disney

Fully-Stocked Cozy Tropical Cottage-4 mi to Disney

Family-Friendly Cottage Near Orlando’s Top Attractions

Family-Friendly Cottage Near Orlando’s Top Attractions

Cozy Lake Cottage - 4 miles to Disney

Cozy Lake Cottage - 4 miles to Disney

**Charming Lakeview Cottage 4 Miles From Disney**

**Charming Lakeview Cottage 4 Miles From Disney**

1209-9-b -mansion Themed With Pool Near Disney

1209-9-b -mansion Themed With Pool Near Disney

Southern Dunes Family Retreat: Hot Tub & Game Room

Southern Dunes Family Retreat: Hot Tub & Game Room

411 Wanderlust Heaven 5bed/pool

411 Wanderlust Heaven 5bed/pool

5180 Spectacular 5bd4ba- Private Pool&spa

5180 Spectacular 5bd4ba- Private Pool&spa

Luxury Cottage Near Legoland & Chain of Lakes

Luxury Cottage Near Legoland & Chain of Lakes

Top Winter Haven Hotel Reviews

Ramada by Wyndham Kissimmee Gateway

Find out more about Winter Haven

Find out more about Winter Haven

Winter Haven Cottages information

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Charming Lakeview Cottage 4 Miles From Disney

Charming Lakeview Cottage 4 Miles From Disney