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 NZ$175 per night from 2 Jan to 3 Jan
NZ$175
includes taxes & fees
2 Jan - 3 Jan 2025
Stay at this 3-star cottage in Winter Haven. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions LEGOLAND® Florida and Inman Park are ...
Lake Ida Beach Resort
Enchanted Cottage with Pool and Mini-Golf Near Disney

Enchanted Cottage with Pool and Mini-Golf Near Disney

Kissimmee
Book a stay at this family-friendly cottage in Kissimmee. Enjoy free WiFi, a fitness center, and a garden. Popular attractions Old Town and Disney Springs™ are ...
Enchanted Cottage with Pool and Mini-Golf Near Disney
Lakeview Cottage Escape.  Close to BOK Tower Gardens, Legoland and Disney

Lakeview Cottage Escape. Close to BOK Tower Gardens, Legoland and Disney

Babson Park
Stay at this cottage in Babson Park. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Ridge Audubon Nature Reserve and Garden Club Park ...
Lakeview Cottage Escape. Close to BOK Tower Gardens, Legoland and Disney
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Frankly Fintastic - Happy Days in Margaritaville! Min to Resorts, Pet Friendly

Frankly Fintastic - Happy Days in Margaritaville! Min to Resorts, Pet Friendly

Kissimmee
Book a stay at this family-friendly cottage in Kissimmee. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Disney's Animal Kingdom® ...
Frankly Fintastic - Happy Days in Margaritaville! Min to Resorts, Pet Friendly
Up to Scale With Margaritas

Up to Scale With Margaritas

3 out of 5
8021 Sandy Toes Way, Kissimmee, FL
Stay at this 3-star cottage in Kissimmee. Enjoy free WiFi, free parking, and furnished patios. Popular attractions Disney's Animal Kingdom® Theme Park and ESPN ...
Up to Scale With Margaritas
Lake Wales Vacation Rental w/ Screened-In Porch!

Lake Wales Vacation Rental w/ Screened-In Porch!

Lake Wales
Stay at this cottage in Lake Wales. Enjoy an in-room coffeemaker and air conditioning. Popular attractions Crystal Lake Park and Lake Wales History Museum are ...
Lake Wales Vacation Rental w/ Screened-In Porch!
8000 Lost Shaker Lane

8000 Lost Shaker Lane

3 out of 5
8000 Lost Shaker Lane, Kissimmee, FL
Stay at this 3-star cottage in Kissimmee. Enjoy free parking, balconies, and cable TV channels. Popular attractions Disney's Animal Kingdom® Theme Park and ESPN ...
8000 Lost Shaker Lane
Davenport Family Home ~ 10 Mi to Animal Kingdom

Davenport Family Home ~ 10 Mi to Animal Kingdom

3 out of 5
Davenport
Stay at this 3-star cottage in Davenport. Enjoy free parking, air conditioning, and an outdoor pool. Popular attractions Reunion Resort Golf Course and ChampionsGate ...
Davenport Family Home ~ 10 Mi to Animal Kingdom
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
Stay at this 3-star cottage in Kissimmee. Enjoy free parking, a garden, and cable TV channels. Popular attractions Disney's Animal Kingdom® Theme Park and ESPN ...
Stunning Villa With Themed Room's and Game Room, Right Across From the Club House #7sl9003
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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
1443 Cottages
Lowest Price
NZ$175
Highest Price
NZ$366
Popular accommodation
Lake Ida Beach Resort, Enchanted Cottage with Pool and Mini-Golf Near Disney, Lakeview Cottage Escape. Close to BOK Tower Gardens, Legoland and Disney , Frankly Fintastic - Happy Days in Margaritaville! Min to Resorts, Pet Friendly, Up to Scale With Margaritas, Lake Wales Vacation Rental w/ Screened-In Porch!, 8000 Lost Shaker Lane, Davenport Family Home ~ 10 Mi to Animal Kingdom, Stunning Villa With Themed Room's and Game Room, Right Across From the Club House #7sl9003

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 NZ$262 per night from 24 Dec to 25 Dec
NZ$262
includes taxes & fees
24 Dec - 25 Dec
Stay at this 3.5-star business-friendly hotel in Winter Haven. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Best Western Plus Winter Haven Inn & Suites 
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 NZ$202 per night from 25 Dec to 26 Dec
NZ$202
includes taxes & fees
25 Dec - 26 Dec
Stay at this motel in Winter Haven. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Howard Johnson by Wyndham Winter Haven FL
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 NZ$248 per night from 13 Jan to 14 Jan
NZ$248
includes taxes & fees
13 Jan - 14 Jan 2025
Stay at this 3-star business-friendly hotel in Winter Haven. Enjoy free WiFi, free parking, and room service. Our guests praise the breakfast and the helpful ...
Holiday Inn Winter Haven, an IHG Hotel
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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 NZ$366 per night from 24 Dec to 25 Dec
NZ$366
includes taxes & fees
24 Dec - 25 Dec
Stay at this 4-star family-friendly resort in Four Corners. Enjoy free WiFi, 3 outdoor pools, and 3 restaurants. Our guests praise the pool and the helpful staff ...
The Grove Resort & Water Park Orlando
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See all available properties in Winter Haven
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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.

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