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$137 per night from 24 Mar to 25 Mar
NZ$137
includes taxes & fees
24 Mar - 25 Mar
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 Lake Conine are ...
Lake Ida Beach Resort
8081 Knee Deep Rd

8081 Knee Deep Rd

3 out of 5
8081 Knee Deep Rd, 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 ...
8081 Knee Deep Rd
Elegant Family Home w/ Pool, Game Room, Themed Bedrooms

Elegant Family Home w/ Pool, Game Room, Themed Bedrooms

3 out of 5
Sawyer Palm Place 1750, Kissimmee, FL
Stay at this 3-star business-friendly cottage in Kissimmee. Enjoy free parking, a garden, and cable TV channels. Popular attractions Disney's Animal Kingdom® ...
Elegant Family Home w/ Pool, Game Room, Themed Bedrooms
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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
Large Villa W/private Pool & Game Room! Waterpark

Large Villa W/private Pool & Game Room! Waterpark

3.5 out of 5
8997 Rhodes Street, Kissimmee, FL
Stay at this 3.5-star family-friendly cottage in Kissimmee. Enjoy free parking, a lazy river, and a fitness center. Popular attractions Mystic Dunes Golf Club ...
Large Villa W/private Pool & Game Room! Waterpark
Private Pool/spa, Free Waterpark, Lazy River!

Private Pool/spa, Free Waterpark, Lazy River!

4 out of 5
5242 Wildwood Way, Davenport, FL
Stay at this 4-star family-friendly cottage in Davenport. Enjoy free parking, a lazy river, and a fitness center. Popular attractions Reunion Resort Golf Course ...
Private Pool/spa, Free Waterpark, Lazy River!
Lakeland's Charming  Luxury Cottage Retreat Near Downtown Walk Everywhere.

Lakeland's Charming Luxury Cottage Retreat Near Downtown Walk Everywhere.

Lakeland
Stay at this cottage in Lakeland. Enjoy free WiFi, a garden, and patios. Popular attractions RP Funding Center and Publix Field at Joker Marchant Stadium are ...
Lakeland's Charming Luxury Cottage Retreat Near Downtown Walk Everywhere.
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
Cottage w/ Private Pool - Walk to Lake Wales!

Cottage w/ Private Pool - Walk to Lake Wales!

Lake Wales
Stay at this cottage in Lake Wales. Enjoy private pools, a garden, and tennis courts. Our guests praise the property condition in our reviews. Popular attractions ...
Cottage w/ Private Pool - Walk to Lake Wales!
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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
1450 Cottages
Lowest Price
NZ$137
Highest Price
NZ$414
Popular accommodation
Lake Ida Beach Resort, 8081 Knee Deep Rd, Elegant Family Home w/ Pool, Game Room, Themed Bedrooms, 8000 Lost Shaker Lane, Large Villa W/private Pool & Game Room! Waterpark, Private Pool/spa, Free Waterpark, Lazy River!, Lakeland's Charming Luxury Cottage Retreat Near Downtown Walk Everywhere. , Frankly Fintastic - Happy Days in Margaritaville! Min to Resorts, Pet Friendly, Cottage w/ Private Pool - Walk to Lake Wales!

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$296 per night from 23 Mar to 24 Mar
NZ$296
includes taxes & fees
23 Mar - 24 Mar
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, Winter Haven, FL
Fully refundableReserve now, pay when you stay
The price is NZ$215 per night from 6 Apr to 7 Apr
NZ$215
includes taxes & fees
6 Apr - 7 Apr
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
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$414 per night from 23 Mar to 24 Mar
NZ$414
includes taxes & fees
23 Mar - 24 Mar
Stay at this 4-star family-friendly resort in Four Corners. Enjoy free WiFi, 5 outdoor pools, and 3 restaurants. Our guests praise the pool and the helpful staff ...
The Grove Resort & Water Park Orlando
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Vacation Village at Parkway

Vacation Village at Parkway

3 out of 5
2975 Arabian Nights Blvd, Kissimmee, FL
The price is NZ$234 per night from 28 Mar to 29 Mar
NZ$234
includes taxes & fees
28 Mar - 29 Mar
Stay at this 3-star family-friendly condo in Kissimmee. Enjoy free WiFi, 7 outdoor pools, and 7 hot tubs. Our guests praise the helpful staff and the clean rooms ...
Vacation Village at Parkway
Don't see what you're looking for?
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.

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^Subject to availability and chosen travel dates.