Search Winter Haven Cottages

Start date: Check-in selected.
To Date
End date: Check-out

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
Dec 26 - Dec 28
In two weeks
Jan 2 - Jan 4
In one month
Jan 16 - Jan 18
In two months
Feb 13 - Feb 15

Our top choices for Winter Haven cottages

Porch
Lake Ida Beach Resort

Lake Ida Beach Resort

Lake Ida Beach Resort
3.0 star property
Winter Haven
7.2 out of 10, Good, (187)
"We have stayed here several times. "
United States
Martha
$85 nightly
The price is $95
Jan 15 - Jan 16, 2026
Total with taxes and fees
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

Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
2.0 star property
Winter Haven
10.0 out of 10, Exceptional, (2)
"Just what we needed for a weekend trip with our grandsons for the weekend "
United States
Christine B.
$246 nightly
The price is $271
Jan 1 - Jan 2, 2026
Total with taxes and fees
Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
House (3 Bedrooms) | Interior
Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn

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

Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn
3.0 star property
Winter Haven
10.0 out of 10, Exceptional, (3)
"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
$394 nightly
The price is $438
Dec 27 - Dec 28
Total with taxes and fees
Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn
Microwave, stovetop
Tiny house close to Disney KISSIMMEE

Tiny house close to Disney KISSIMMEE

Tiny house close to Disney KISSIMMEE
2.0 star property
Kissimmee
9.0 out of 10, Wonderful, (2)
"The location was great. We really just needed somewhere to sleep because we spent the day at the Disney Parks. The place had enough beds and was a great price."
United States
Christine M.
$165 nightly
The price is $185
Dec 23 - Dec 24
Total with taxes and fees
Tiny house close to Disney KISSIMMEE
Interior
Family-Friendly Cottage Near Orlando’s Top Attractions

Family-Friendly Cottage Near Orlando’s Top Attractions

Family-Friendly Cottage Near Orlando’s Top Attractions
Kissimmee
10.0 out of 10, Exceptional, (1)
"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.
$180 nightly
The price is $202
Jan 7 - Jan 8, 2026
Total with taxes and fees
Family-Friendly Cottage Near Orlando’s Top Attractions
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

Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
Kissimmee
10.0 out of 10, Exceptional, (2)
"We stayed and visited universal snd drove to Jacksonville it was a cute cottage"
United States
Jennifer b.
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
Terrace/patio
Cozy Tropical Cottage - 4 mi to Disney

Cozy Tropical Cottage - 4 mi to Disney

Cozy Tropical Cottage - 4 mi to Disney
Kissimmee
$255 nightly
The price is $285
Dec 28 - Dec 29
Total with taxes and fees
Cozy Tropical Cottage - 4 mi to Disney
Property grounds
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

Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
Kissimmee
$188 nightly
The price is $211
Jan 5 - Jan 6, 2026
Total with taxes and fees
Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
Private kitchen
Cozy Lake Cottage - 4 miles to Disney

Cozy Lake Cottage - 4 miles to Disney

Cozy Lake Cottage - 4 miles to Disney
Kissimmee
$253 nightly
The price is $283
Dec 22 - Dec 23
Total with taxes and fees
Cozy Lake Cottage - 4 miles to Disney
House (5 Bedrooms) | Interior
Upstay Lakeside Retreat w Private Pool & Game Room

Upstay Lakeside Retreat w Private Pool & Game Room

Upstay Lakeside Retreat w Private Pool & Game Room
3.0 star property
Sandy Ridge
Upstay Lakeside Retreat w Private Pool & Game Room
Interior
Watersong Swanky

Watersong Swanky

Watersong Swanky
3.0 star property
Davenport
$899 nightly
The price is $1,005
Jan 8 - Jan 9, 2026
Total with taxes and fees
Watersong Swanky
Exterior
MID CENTURY TINY FOREST HOME CLOSE TO DISNEY WORLD

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)
"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.
$150 nightly
The price is $166
Dec 28 - Dec 29
Total with taxes and fees
MID CENTURY TINY FOREST HOME CLOSE TO DISNEY WORLD
Exterior
Luxury Cottage Near Legoland & Chain of Lakes

Luxury Cottage Near Legoland & Chain of Lakes

Luxury Cottage Near Legoland & Chain of Lakes
Lake Hamilton
10.0 out of 10, Exceptional, (6)
"This place is tiny but everything you need for a comfortable stay! Would definitely stay here again."
United States
Dallas C.
$186 nightly
The price is $206
Dec 22 - Dec 23
Total with taxes and fees
Luxury Cottage Near Legoland & Chain of Lakes
House (4 Bedrooms) | Interior
~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool

~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool

~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool
3.0 star property
Indian Ridge
$419 nightly
The price is $472
Dec 23 - Dec 24
Total with taxes and fees
~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool
Exterior
"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney

"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney

"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
Kissimmee
9.8 out of 10, Exceptional, (6)
"Wonderful place to stay overnight. Nice furnishings. Good room layout for family. Convenience of washer and dryer. Host was quick and responsive. Thank you for a terrific stay."
United States
George L.
$268 nightly
The price is $300
Jan 7 - Jan 8, 2026
Total with taxes and fees
"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
House, 6 Bedrooms | Exterior
Wellerden at Reunion Resort!by Shine Villas

Wellerden at Reunion Resort!by Shine Villas

Wellerden at Reunion Resort!by Shine Villas
3.5 star property
Reunion
$666 nightly
The price is $755
Dec 22 - Dec 23
Total with taxes and fees
Wellerden at Reunion Resort!by Shine Villas
Exterior
Parrot Bay Cottage with Private Hot Tub near Disney with Margaritaville Resort.

Parrot Bay Cottage with Private Hot Tub near Disney with Margaritaville Resort.

Parrot Bay Cottage with Private Hot Tub near Disney with Margaritaville Resort.
Kissimmee
10.0 out of 10, Exceptional, (1)
"Booked for my friends visiting. Perfect location"
United States
Eric Allan G.
Parrot Bay Cottage with Private Hot Tub near Disney with Margaritaville Resort.
Exterior
Sunrise Cottage near Disney with Margaritaville Resort & Island H20 Waterpark.

Sunrise Cottage near Disney with Margaritaville Resort & Island H20 Waterpark.

Sunrise Cottage near Disney with Margaritaville Resort & Island H20 Waterpark.
Kissimmee
10.0 out of 10, Exceptional, (1)
"Comfy, cozy and room for everyone to have their own space . Easy to get around. Places to eat and shop right outside the property, so convenient."
United States
Marilou J.
Sunrise Cottage near Disney with Margaritaville Resort & Island H20 Waterpark.
Exterior
Dreamy Coral Cottage with Hot Tub near Disney with Margaritaville Resort &.

Dreamy Coral Cottage with Hot Tub near Disney with Margaritaville Resort &.

Dreamy Coral Cottage with Hot Tub near Disney with Margaritaville Resort &.
2.0 star property
Kissimmee
Dreamy Coral Cottage with Hot Tub near Disney with Margaritaville Resort &.
Exterior
Breezy Cottage with Hot Tub near Disney with Margaritaville Resort & Island H2O.

Breezy Cottage with Hot Tub near Disney with Margaritaville Resort & Island H2O.

Breezy Cottage with Hot Tub near Disney with Margaritaville Resort & Island H2O.
Kissimmee
Breezy Cottage with Hot Tub near Disney with Margaritaville Resort & Island H2O.
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winter Haven Hotel Reviews

Delta Hotels by Marriott Orlando Celebration

Delta Hotels by Marriott Orlando Celebration

10/10 Excellent
"Loved our stay! Great hotel and staff. "
isabella 5-night trip
Posted 2 days ago
Delta Hotels by Marriott Orlando Celebration

Find out more about Winter Haven

Winter Haven Cottages information

Number of reviews
198
Accommodation
1731 Cottages
Lowest Price
$95
Highest Price
$1,005

Frequently asked questions

How much do cottages in Winter Haven cost?
Cottages in Winter Haven range between $95 and $1,005 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 1731 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 Center 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 Center, 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.

Explore a world of travel with Expedia