Hot Winter Haven Cottage Rates

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Cottages in Winter Haven

Lafitte's Landing Lakeview Cottage - Lakefront!

Lafitte's Landing Lakeview Cottage - Lakefront!

3 out of 5
8121 Surf St, Kissimmee, Fl 34747, Usa, Kissimmee, FL
With a stay at this cottage in Kissimmee, you'll be a 4-minute drive from Mystic Dunes Golf Club and 7 minutes from Walt Disney World® Resort.
Lafitte's Landing Lakeview Cottage - Lakefront!
Lake Ida Beach Resort

Lake Ida Beach Resort

3 out of 5
2524 Lake Alfred Rd, Winter Haven, FL
Fully refundableReserve now, pay when you stay
The price is AU$135 per night from 12 Aug to 13 Aug
AU$135
12 Aug - 13 Aug
includes taxes & fees
With a stay at Lake Ida Beach Resort in Winter Haven, you'll be on a lake, within a 15-minute drive of LEGOLAND® Florida and Lake Conine.
Lake Ida Beach Resort
8000 Lost Shaker Lane

8000 Lost Shaker Lane

3 out of 5
8000 Lost Shaker Lane, Kissimmee, FL
With a stay at this cottage in Kissimmee, you'll be a 5-minute drive from Mystic Dunes Golf Club and 8 minutes from Walt Disney World® Resort.
8000 Lost Shaker Lane
Save an average of 15% on thousands of hotels when you're signed in
Family 4BR Home w/ Resort Pool Near Disney

Family 4BR Home w/ Resort Pool Near Disney

3 out of 5
Miramar Avenue 219, Davenport, FL
With a stay at this cottage in Davenport (Regal Palms), you'll be within a 15-minute drive of Flamingo Crossings Town Center and Highland Reserve Golf Club.
Family 4BR Home w/ Resort Pool Near Disney
Amazing Game Room, Harry Potter, Mickey & Princess Room. All new Decor! #7sl1621

Amazing Game Room, Harry Potter, Mickey & Princess Room. All new Decor! #7sl1621

3 out of 5
Nassau Point Trail 1621, Kissimmee, FL
Located in Kissimmee, this cottage is within a 15-minute drive of Flamingo Crossings Town Center and Mystic Dunes Golf Club.
Amazing Game Room, Harry Potter, Mickey & Princess Room. All new Decor! #7sl1621
Gorgeous Cottage w/Private Pool + Balcony, Near Disney!

Gorgeous Cottage w/Private Pool + Balcony, Near Disney!

Kissimmee
With a stay at this cottage in Kissimmee, you'll be a 4-minute drive from Mystic Dunes Golf Club and 7 minutes from Walt Disney World® Resort.
Gorgeous Cottage w/Private Pool + Balcony, Near Disney!
Stunning Villa With Themed Room's and Game Room, Right Across From the Club House #7sl9003

Stunning Villa With Themed Room's and Game Room, Right Across From the Club House #7sl9003

3 out of 5
Kissimmee
Located in Kissimmee, this cottage is within a 15-minute drive of Walt Disney World® Resort and Flamingo Crossings Town Center.
Stunning Villa With Themed Room's and Game Room, Right Across From the Club House #7sl9003
Townhome Splash Pool BBQ Free Water Park!

Townhome Splash Pool BBQ Free Water Park!

3.5 out of 5
8920 Sydney Avenue, Kissimmee, FL
With a stay at this cottage in Kissimmee, you'll be within a 15-minute drive of Walt Disney World® Resort and Flamingo Crossings Town Center.
Townhome Splash Pool BBQ Free Water Park!
Jedi cottage 4 miles from Disney! Mins from universal!

Jedi cottage 4 miles from Disney! Mins from universal!

Kissimmee
With a stay at this cottage in Kissimmee, you'll be a 4-minute drive from Old Town and 9 minutes from Orlando Vineland Premium Outlets.
Jedi cottage 4 miles from Disney! Mins from universal!
Don't see what you're looking for?
See all available properties in Winter Haven
View all properties
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.

Winter Haven Budget-Friendly Cottage Accommodation

Adulting can be rough. You love your job, and your sweetheart is the best, but next time someone says “think outside the box” or “we’ll park that”, you just might throw a fit. When was the last time you had one of those really deep convos with your person, anyway? It sounds like you need a holiday, and you’ve come to the right place. Budget-friendly cottage accommodation in Winter Haven will have you feeling like your SO is the peanut butter to your jelly again in no time.

We’re not here to tell you what you want—we think you already know. You want a spot that’s totally relaxing, but still has plenty of things to do, you know, if you feel like it. You want great scenery, and you want food that’s worthy of your number one hashtag: #nomnom. Cottage getaways to Winter Haven definitely fit the bill.

Yes, the scenery is stunning, but on a romantic cottage holiday, it’s what’s inside that counts. Today’s cottages are filled with those little touches of luxury, like fine bath amenities and gourmet kitchens. You know the saying about how the way to someone’s heart is through their stomach? Don’t miss your chance to impress this holiday—even if that just means remembering their favourite wine. (Hey, that still counts!)

Before you can check out entirely, you’ve got a few last bits of adulting to take care of: pick your perfect cheap country cottage in Winter Haven, then type up that email to your boss and request your annual leave. We’re sure they’ll understand.

Winter Haven Cottages essential information

Accommodation
1755 Cottages
Lowest Price
AU$119
Highest Price
AU$218
Popular accommodation
Lafitte's Landing Lakeview Cottage - Lakefront!, Lake Ida Beach Resort, 8000 Lost Shaker Lane, Family 4BR Home w/ Resort Pool Near Disney, Amazing Game Room, Harry Potter, Mickey & Princess Room. All new Decor! #7sl1621, Gorgeous Cottage w/Private Pool + Balcony, Near Disney!, Stunning Villa With Themed Room's and Game Room, Right Across From the Club House #7sl9003, Townhome Splash Pool BBQ Free Water Park!, Jedi cottage 4 miles from Disney! Mins from universal!

Top trending hotels in Winter Haven

Staybridge Suites Winter Haven Auburndale by IHG

Staybridge Suites Winter Haven Auburndale by IHG

3 out of 5
305 5th St NW and Avenue D NW, Winter Haven, FL
Fully refundable
The price is AU$218 per night from 13 Aug to 14 Aug
AU$218
13 Aug - 14 Aug
includes taxes & fees
With a stay at Staybridge Suites Winter Haven Auburndale by IHG in Winter Haven, you'll be in a shopping district, within a 10-minute drive of LEGOLAND® Florida ...
Staybridge Suites Winter Haven Auburndale by IHG
Holiday Inn Winter Haven by IHG

Holiday Inn Winter Haven by IHG

3 out of 5
200 Cypress Gardens Boulevard, Winter Haven, FL
Fully refundable
The price is AU$160 per night from 17 Aug to 18 Aug
AU$160
17 Aug - 18 Aug
includes taxes & fees
With a stay at Holiday Inn Winter Haven by IHG, you'll be centrally located in Winter Haven, within a 10-minute drive of LEGOLAND® Florida and Theatre Winter ...
Holiday Inn Winter Haven by IHG
Best Western Plus Winter Haven Inn & Suites 

Best Western Plus Winter Haven Inn & Suites 

3.5 out of 5
5801 Roosevelt Dr, Winter Haven, FL
Fully refundableReserve now, pay when you stay
The price is AU$217 per night from 13 Aug to 14 Aug
AU$217
13 Aug - 14 Aug
includes taxes & fees
With a stay at Best Western Plus Winter Haven Inn & Suites  in Winter Haven, you'll be within a 15-minute walk of LEGOLAND® Florida and Peppa Pig Theme Park ...
Best Western Plus Winter Haven Inn & Suites 
Save an average of 15% on thousands of hotels when you're signed in
Kompose Boutique Resort at Theme Parks

Kompose Boutique Resort at Theme Parks

3 out of 5
7491 W Irlo Bronson Memorial Hwy, Kissimmee, FL
Fully refundableReserve now, pay when you stay
The price is AU$119 per night from 17 Aug to 18 Aug
AU$119
17 Aug - 18 Aug
includes taxes & fees
With a stay at Kompose Boutique Resort at Theme Parks in Kissimmee, you'll be a 5-minute drive from Walt Disney World® Resort and 7 minutes from Old Town.
Kompose Boutique Resort at Theme Parks
Don't see what you're looking for?
See all available properties in Winter Haven
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.