Hot Winter Haven Cottage Rates

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Featured Cottages in Winter Haven

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$143 per night from 5 Dec to 6 Dec
AU$143
includes taxes & fees
5 Dec - 6 Dec
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
Margarita Porch Paradise

Margarita Porch Paradise

5 out of 5
8121 Surf St, 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.
Margarita Porch Paradise
Private Cottage 10 Minutes To Disney And 15 To Universal!  In- house laundry!!

Private Cottage 10 Minutes To Disney And 15 To Universal! In- house laundry!!

Kissimmee
With a stay at this cottage in Kissimmee, you'll be a 3-minute drive from Old Town and 9 minutes from Walt Disney World® Resort.
Private Cottage 10 Minutes To Disney And 15 To Universal! In- house laundry!!
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Davenport Family Home ~ 10 Mi to Animal Kingdom

Davenport Family Home ~ 10 Mi to Animal Kingdom

3 out of 5
Davenport
With a stay at this cottage in Davenport, you'll be within a 15-minute drive of ChampionsGate Golf Club and Providence Golf Club.
Davenport Family Home ~ 10 Mi to Animal Kingdom
Contemporary Home w/ Hot Tub: 4 Mi to Disney Magic

Contemporary Home w/ Hot Tub: 4 Mi to Disney Magic

Kissimmee
With a stay at this cottage in Kissimmee, you'll be within a 10-minute drive of Walt Disney World® Resort and Mystic Dunes Golf Club.
Contemporary Home w/ Hot Tub: 4 Mi to Disney Magic
Private Pool/spa, Free Waterpark, Lazy River!

Private Pool/spa, Free Waterpark, Lazy River!

4 out of 5
5242 Wildwood Way, Davenport, FL
Located in Davenport, this cottage is within a 15-minute drive of ChampionsGate Golf Club and Reunion Resort Golf Course.
Private Pool/spa, Free Waterpark, Lazy River!
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 ChampionsGate Golf Club.
Stunning Villa With Themed Room's and Game Room, Right Across From the Club House #7sl9003
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 ChampionsGate Golf Club and Mystic Dunes Golf Club.
Amazing Game Room, Harry Potter, Mickey & Princess Room. All new Decor! #7sl1621
Jedi cottage 4 miles from Disney! Mins from universal!

Jedi cottage 4 miles from Disney! Mins from universal!

Kissimmee
The price is AU$351 per night from 23 Nov to 24 Nov
AU$351
includes taxes & fees
23 Nov - 24 Nov
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!
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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
1437 Cottages
Lowest Price
AU$143
Highest Price
AU$351
Popular accommodation
Lake Ida Beach Resort, Margarita Porch Paradise, Private Cottage 10 Minutes To Disney And 15 To Universal! In- house laundry!!, Davenport Family Home ~ 10 Mi to Animal Kingdom, Contemporary Home w/ Hot Tub: 4 Mi to Disney Magic, Private Pool/spa, Free Waterpark, Lazy River!, Stunning Villa With Themed Room's and Game Room, Right Across From the Club House #7sl9003, Amazing Game Room, Harry Potter, Mickey & Princess Room. All new Decor! #7sl1621, Jedi cottage 4 miles from Disney! Mins from universal!

Top trending hotels in Winter Haven

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$213 per night from 1 Dec to 2 Dec
AU$213
includes taxes & fees
1 Dec - 2 Dec
With a stay at Best Western Plus Winter Haven Inn & Suites  in Winter Haven, you'll be within a 5-minute drive of LEGOLAND® Florida and Chain Of Wakes.
Best Western Plus Winter Haven Inn & Suites 
Holiday Inn Winter Haven, an IHG Hotel

Holiday Inn Winter Haven, an IHG Hotel

3 out of 5
200 Cypress Gardens Boulevard, Winter Haven, FL
Fully refundable
The price is AU$170 per night from 1 Dec to 2 Dec
AU$170
includes taxes & fees
1 Dec - 2 Dec
With a stay at Holiday Inn Winter Haven, an IHG Hotel, you'll be centrally located in Winter Haven, within a 10-minute drive of LEGOLAND® Florida and Winter ...
Holiday Inn Winter Haven, an IHG Hotel
Howard Johnson by Wyndham Winter Haven FL

Howard Johnson by Wyndham Winter Haven FL

2 out of 5
1300 3rd St Sw, Cypress Gardens & US 17 South, Winter Haven, FL
Fully refundableReserve now, pay when you stay
The price is AU$175 per night from 24 Nov to 25 Nov
AU$175
includes taxes & fees
24 Nov - 25 Nov
When you stay at Howard Johnson by Wyndham Winter Haven FL in Winter Haven, you'll be in the business district, within a 5-minute drive of Chain of Lakes Park ...
Howard Johnson by Wyndham Winter Haven FL
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The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

4 out of 5
14501 Grove Resort Avenue, Winter Garden, FL
Fully refundableReserve now, pay when you stay
The price is AU$296 per night from 12 Dec to 13 Dec
AU$296
includes taxes & fees
12 Dec - 13 Dec
Located in Four Corners, The Grove Resort & Water Park Orlando is on a lake, a 1-minute drive from Surfari Water Park and 11 minutes from Orange County National ...
The Grove Resort & Water Park Orlando
Don't see what you're looking for?
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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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^Subject to availability and chosen travel dates.