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Check prices for these dates

In two weeks
31 Jul - 2 Aug
In two months
11 Sept - 13 Sept
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

Our top choices for Winter Haven cottages

House (3 Bedrooms) | Interior

Oasis Near Disney w Golf View, Family&pet Friendly

Oasis Near Disney w Golf View, Family&pet Friendly
3.0 star property
Reunion
The price is £271
includes taxes & fees
20 Jul - 21 Jul
Oasis Near Disney w Golf View, Family&pet Friendly
Porch

Lake Ida Beach Resort

Lake Ida Beach Resort
3.0 star property
Winter Haven
7.2 out of 10, Good, (193 reviews)
"The cabins were great loved it there"
United States
Jennifer
The price is £60
includes taxes & fees
21 Jul - 22 Jul
Lake Ida Beach Resort
House (6 Bedrooms) | Interior

Upstay Spacious Home w Private Pool & Hot Tub

Upstay Spacious Home w Private Pool & Hot Tub
3.0 star property
Solana
The price is £341
includes taxes & fees
14 Jul - 15 Jul
Upstay Spacious Home w Private Pool & Hot Tub
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 £256
includes taxes & fees
19 Jul - 20 Jul
Family Resort Home w Pool, BBQ & Game Room
House (3 Bedrooms) | Interior

Golf, Dine & Unwind Poolside! Haines City Getaway

Golf, Dine & Unwind Poolside! Haines City Getaway
3.0 star property
Haines City
The price is £340
includes taxes & fees
18 Jul - 19 Jul
Golf, Dine & Unwind Poolside! Haines City Getaway
House (4 Bedrooms) | Interior

8 Mi to Disney World: Home w/ Lanai + Game Room!

8 Mi to Disney World: Home w/ Lanai + Game Room!
3.0 star property
Eagle Pointe South
The price is £319
includes taxes & fees
17 Jul - 18 Jul
8 Mi to Disney World: Home w/ Lanai + Game Room!
House (5 Bedrooms) | Interior

Spacious Family Home w Pool, Hot Tub & BBQ

Spacious Family Home w Pool, Hot Tub & BBQ
3.0 star property
Kissimmee
The price is £343
includes taxes & fees
16 Jul - 17 Jul
Spacious Family Home w Pool, Hot Tub & BBQ
House (3 Bedrooms) | Interior

Davenport Basecamp! 3BR Family Home w/ Patio

Davenport Basecamp! 3BR Family Home w/ Patio
3.0 star property
Davenport
The price is £274
includes taxes & fees
31 Jul - 1 Aug
Davenport Basecamp! 3BR Family Home w/ Patio
House (4 Bedrooms) | Interior

Upstay: Crystal Cove Resort Villa w/ Pool & Games

Upstay: Crystal Cove Resort Villa w/ Pool & Games
3.0 star property
Crystal Cove
The price is £346
includes taxes & fees
16 Jul - 17 Jul
Upstay: Crystal Cove Resort Villa w/ Pool & Games
House (6 Bedrooms) | Interior

Family Fun Villa w Pool, Hot Tub & Game Room

Family Fun Villa w Pool, Hot Tub & Game Room
3.0 star property
Solterra Resort
The price is £444
includes taxes & fees
16 Jul - 17 Jul
Family Fun Villa w Pool, Hot Tub & Game Room
House (3 Bedrooms) | Interior

Artsy Bungalow on St Anne Lake: Pool, Dock & Deck

Artsy Bungalow on St Anne Lake: Pool, Dock & Deck
3.0 star property
Lake Wales
The price is £356
includes taxes & fees
15 Jul - 16 Jul
Artsy Bungalow on St Anne Lake: Pool, Dock & Deck
Exterior

Refurbished Lux 6 Bed Golf Views at Reunion Resort by Shine Villas

Refurbished Lux 6 Bed Golf Views at Reunion Resort by Shine Villas
3.5 star property
Reunion
The price is £554
includes taxes & fees
6 Aug - 7 Aug
Refurbished Lux 6 Bed Golf Views at Reunion Resort by Shine Villas
House (6 Bedrooms) | Interior

Upstay: New Solara Resort Home w/ Pool & Hot Tub

Upstay: New Solara Resort Home w/ Pool & Hot Tub
3.0 star property
Kissimmee
The price is £534
includes taxes & fees
16 Jul - 17 Jul
Upstay: New Solara Resort Home w/ Pool & Hot Tub
House (2 Bedrooms) | Interior

Walkable Dixieland District Gem With Yard

Walkable Dixieland District Gem With Yard
2.0 star property
Dixieland
The price is £213
includes taxes & fees
2 Aug - 3 Aug
Walkable Dixieland District Gem With Yard
House (3 Bedrooms) | Interior

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

Hook, Line & Leisure: Lakefront Gem w/ Porch!
3.0 star property
Florence Villa
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 £293
includes taxes & fees
26 Jul - 27 Jul
Hook, Line & Leisure: Lakefront Gem w/ Porch!
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

Quality Inn & Suites Kissimmee near Main Gate

Quality Inn & Suites Kissimmee near Main Gate

8/10 Good
"Toilet was clogged. Called at 12 noon for maintenance and they did not arrive until 10pm. Besides that experience was fine."
Lohaiza 3-night trip
Posted less than an hour ago
Quality Inn & Suites Kissimmee near Main Gate

Find out more about Winter Haven

Winter Haven Cottages information

Number of reviews
196
Accommodation
2186 Cottages
Lowest Price
£60
Highest Price
£554

Frequently asked questions

How much do cottages in Winter Haven cost?
Cottages in Winter Haven range between £60 and £554 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 2186 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.