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Check prices for these dates

In two weeks
12 Jun - 14 Jun
In two months
24 Jul - 26 Jul
In three months
21 Aug - 23 Aug
In four months
18 Sept - 20 Sept

Our top choices for Winter Haven cottages

Porch

Lake Ida Beach Resort

Lake Ida Beach Resort
3.0 star property
Winter Haven
7.2 out of 10, Good, (193 reviews)
"Was probably once a great time place. Owner was nice. Night time neighborhood is a bit noisy guess it's just how people act now no respect for property."
United States
wade
The price is £63
includes taxes & fees
29 May - 30 May
Lake Ida Beach Resort
Exterior

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)
"Just what we needed for a weekend trip with our grandsons for the weekend "
United States
Christine B.
The price is £208
includes taxes & fees
26 May - 27 May
Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
House (3 Bedrooms) | Interior

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

Hook, Line & Leisure: Lakefront Gem w/ Porch!
3.0 star property
Winter Haven
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
The price is £315
includes taxes & fees
28 May - 29 May
Hook, Line & Leisure: Lakefront Gem w/ Porch!
House (4 Bedrooms) | Interior

Legoland & Lakes Pool Home Pet Friendly

Legoland & Lakes Pool Home Pet Friendly
3.0 star property
Winter Haven
The price is £418
includes taxes & fees
26 May - 27 May
Legoland & Lakes Pool Home Pet Friendly
House (3 Bedrooms) | Interior

Explore & Relax: Chic & Cozy Retreat in Lakeland!

Explore & Relax: Chic & Cozy Retreat in Lakeland!
3.0 star property
Lakeland
10.0 out of 10, Exceptional, (1 review)
"We had a great time. The house was beautiful. Decor was beautiful and bedding comforting. I sleep so good. The house was family friendly and plenty of rooms. "
United States
Debra
The price is £281
includes taxes & fees
26 May - 27 May
Explore & Relax: Chic & Cozy Retreat in Lakeland!
Interior

Charming Historic Cottage with Cozy Porch and Garden Retreat

Charming Historic Cottage with Cozy Porch and Garden Retreat
Polk City
10.0 out of 10, Exceptional, (2 reviews)
"Stay was amazing. Host was very friendly and very easy to communicate with. 10/10 recommend"
United States
Joseph B.
The price is £155
includes taxes & fees
29 May - 30 May
Charming Historic Cottage with Cozy Porch and Garden Retreat
Microwave, stovetop

Tiny house close to Disney KISSIMMEE

Tiny house close to Disney KISSIMMEE
Kissimmee
8.4 out of 10, Very good, (7 reviews)
"Nice, Cute little place"
United States
Brenda N.
The price is £131
includes taxes & fees
26 May - 27 May
Tiny house close to Disney KISSIMMEE
House (4 Bedrooms) | Interior

Family Resort Home w Pool, BBQ & Game Room

Family Resort Home w Pool, BBQ & Game Room
3.0 star property
Solana
The price is £244
includes taxes & fees
26 May - 27 May
Family Resort Home w Pool, BBQ & Game Room
Exterior

The Cozy Cottage 1 bedroom plus studio bed and 2 bathrooms in charming Lakeland

The Cozy Cottage 1 bedroom plus studio bed and 2 bathrooms in charming Lakeland
East Lake Morton
The price is £81
includes taxes & fees
1 Jun - 2 Jun
The Cozy Cottage 1 bedroom plus studio bed and 2 bathrooms in charming Lakeland
Exterior

"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney

"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
Kissimmee
9.6 out of 10, Exceptional, (10 reviews)
"Great place for a stay, clean and plenty of everything you need. "
United States
Leo C.
The price is £207
includes taxes & fees
8 Jun - 9 Jun
"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
Exterior

Perfect Place for a Perfect Vacation

Perfect Place for a Perfect Vacation
Kissimmee
10.0 out of 10, Exceptional, (1 review)
The price is £145
includes taxes & fees
26 May - 27 May
Perfect Place for a Perfect Vacation
Exterior

MID CENTURY TINY FOREST HOME CLOSE TO DISNEY WORLD

MID CENTURY TINY FOREST HOME CLOSE TO DISNEY WORLD
Davenport
5.0 out of 10, (2 reviews)
"Needs some upgrades. The bed was a full size, very small for a couple, should really think of upgrading to a king. Pans were old and could use replacing. Bugs and ants constant. Shower was small. Very small tv. Stovetop had missing nob and was difficult to operate. Definitely needs upgrading, left a day early, didn’t feel comfortable there. "
United States
Rebecca F.
The price is £119
includes taxes & fees
26 May - 27 May
MID CENTURY TINY FOREST HOME CLOSE TO DISNEY WORLD
Smart TV, books

Family-Friendly Cottage Near Orlando’s Top Attractions

Family-Friendly Cottage Near Orlando’s Top Attractions
Kissimmee
10.0 out of 10, Exceptional, (1 review)
"Perfect location to enjoy Universal Epic and Islands of Adventure with only a 15 minute ride. The beds were very comfortable and the place is clean. We were welcomed with a cute sign, bottled water and cookies. Will definitely stay here again!"
United States
Joyce R.
The price is £153
includes taxes & fees
26 May - 27 May
Family-Friendly Cottage Near Orlando’s Top Attractions
Dining

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
Kissimmee
The price is £166
includes taxes & fees
13 Jun - 14 Jun
Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
House (3 Bedrooms) | Interior

Lakefront Babson Park Escape: Pet Friendly!

Lakefront Babson Park Escape: Pet Friendly!
3.0 star property
Babson Park
The price is £352
includes taxes & fees
23 Jun - 24 Jun
Lakefront Babson Park Escape: Pet Friendly!
House (3 Bedrooms) | Interior

Serenity - Family & Pet Friendly, Amazing Location

Serenity - Family & Pet Friendly, Amazing Location
3.0 star property
Crestwynd Bay
The price is £287
includes taxes & fees
26 May - 27 May
Serenity - Family & Pet Friendly, Amazing Location
House (4 Bedrooms) | Interior

Upstay: Pet-friendly Family Home w Pool & Sundeck

Upstay: Pet-friendly Family Home w Pool & Sundeck
3.0 star property
Kissimmee
The price is £264
includes taxes & fees
1 Jun - 2 Jun
Upstay: Pet-friendly Family Home w Pool & Sundeck
Exterior

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

Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
Kissimmee
10.0 out of 10, Exceptional, (2 reviews)
"We stayed and visited universal snd drove to Jacksonville it was a cute cottage"
United States
Jennifer b.
The price is £226
includes taxes & fees
10 Jun - 11 Jun
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
Interior

1674 Moon Valley DR, Davenport, 6bed

1674 Moon Valley DR, Davenport, 6bed
2.0 star property
Champions Gate
The price is £737
includes taxes & fees
7 Jun - 8 Jun
1674 Moon Valley DR, Davenport, 6bed
House (5 Bedrooms) | Interior

5 Mi to Walt Disney World! Gem w/ Resort Perks

5 Mi to Walt Disney World! Gem w/ Resort Perks
3.0 star property
Kissimmee
8.6 out of 10, Excellent, (4 reviews)
"Property manager was amazing 👏. She responded quickly, even after hours."
United States
Lameka
The price is £398
includes taxes & fees
22 Jun - 23 Jun
5 Mi to Walt Disney World! Gem w/ Resort Perks
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

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

6/10 Okay
"Not worth the price in my opinion. Lamp shape and curtains had some stains on the. Outlets didnt work. Bathroom shower curtain looked cheap and dingy. Got the biggest suite they offer to hold up to 8 people and not enough blankets, pillows or towels. Pull out couch was a joke. Other 2 bedrooms have double beds that can barely fit 2 people ( I am 5 ft 130 lbs so not HUGE) No blackout curtains so sun was beaming in the morning. The pools were equivalent to my condominum pool where I live. Website made them looked bigger as though they were a lagoon. Everything is extra and overpriced. Staff was very friendly and helpful. Parking is super confusing. Wife was TERRIBLE. Got the "resort view" and was a full blow construction view of sand. Either lower the price or dont hype it up"
Amanda 3-night trip
Posted less than an hour ago
The Grove Resort & Water Park Orlando

Find out more about Winter Haven

Winter Haven Cottages information

Number of reviews
230
Accommodation
2122 Cottages
Lowest Price
£63
Highest Price
£737

Frequently asked questions

How much do cottages in Winter Haven cost?
Cottages in Winter Haven range between £63 and £737 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 2122 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 want to slow the pace down in Winter Haven, check the crew in to Lake Ida Beach Resort. With a 3-star rating and handy amenities like laundry facilities and housekeeping services, you'll feel at home at this family-friendly cottage. After checking in and chilling in your cosy new digs, it's time to head out and start sightseeing. Eagle Ridge Mall and Cypresswood Golf and Country Club are fun 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.