A castle entrance with flags and banners, including a LEGO Kingdoms banner.

Book Winter Haven Bed & Breakfast

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
Oct 9 - Oct 11
In two weeks
Oct 16 - Oct 18
In one month
Oct 30 - Nov 1
In two months
Nov 27 - Nov 29

Our top choices for Winter Haven bed & breakfast

A swimming pool with blue tiles, a glass-enclosed patio with blue lounge chairs, and a gray sofa with red cushions.

1. Styled Bedrooms in a Resort

Styled Bedrooms in a Resort
2.0 star property
Solterra Resort
5.6 out of 10, (5 reviews)
"I was very comfortable with the people that were staying there. Very nice place. Would recommend anyone to stay."
United States
Jason
$110 nightly
The price is $123
Oct 5 - Oct 6
Total with taxes and fees
Styled Bedrooms in a Resort
A spacious living room with a sectional sofa, a coffee table, and a TV mounted on the wall.

2. Tempo Room Lodgings

Tempo Room Lodgings
3.0 star property
Kissimmee
$109 nightly
The price is $123
Oct 12 - Oct 13
Total with taxes and fees
Tempo Room Lodgings
A pool area with a clear view of the surrounding buildings, a blue inflatable shark, and several lounge chairs.

3. Hotel Styled Bedrooms in a Villa

Hotel Styled Bedrooms in a Villa
3.0 star property
Kissimmee
5.8 out of 10, (8 reviews)
"Parking was almost a mile away. Didn’t even get to stay there and wasted over $200 on the stay. Communication was bad. I tried to get a refund because of the parking situation, they never got back to me. "
United States
Chantal
$110 nightly
The price is $125
Oct 7 - Oct 8
Total with taxes and fees
Hotel Styled Bedrooms in a Villa
A swimming pool with blue tiles, a glass-enclosed patio with blue lounge chairs, and a gray sofa with red cushions.

4. The Gathering Place

The Gathering Place
2.0 star property
Kissimmee
5.0 out of 10, (2 reviews)
"clean room and bathroom"
United States
Matthew
$114 nightly
The price is $129
Nov 2 - Nov 3
Total with taxes and fees
The Gathering Place
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winter Haven Hotel Reviews

Vacation Village Orlando, Celebration

Vacation Village Orlando, Celebration

10/10 Excellent
"I’ve been coming to this resort for the last 18 years and it’s been amazing to see how much it’s grown and and change before the best. An amazing resort with amazing amenities and great value. Our family will continue to come back make many many memories here."
Raquel 2-night trip
Posted 6 hours ago
Vacation Village Orlando, Celebration

Find out more about Winter Haven

Winter Haven B&B information

Number of reviews
10
Accommodation
7 B&B
Lowest Price
$123
Highest Price
$129

Frequently asked questions

What is the nightly rate for a Bed and Breakfast in Winter Haven?
Prices for B&Bs in Winter Haven often vary, but you can find a great deal from $123 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Winter Haven B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
When is the best time to book a Bed and Breakfast in Winter Haven?
The best time to book a B&B in Winter Haven is during the peak season from November to March, particularly when the charming weather draws visitors to the area. This time frame is superb for travelers who appreciate mild temperatures, with daytime highs typically ranging from the upper 60s to mid-70s Fahrenheit, creating ideal conditions for outdoor exploration and sightseeing.

During these months, outdoor enthusiasts can enjoy a variety of activities, including visits to the beautiful Chain of Lakes, which offers stunning views and opportunities for kayaking or paddleboarding. Additionally, Winter Haven's proximity to attractions like Legoland Florida Resort makes it a family-friendly destination, ensuring that every member of your group has something fun to engage in.

For those who are looking for a more budget-friendly option, consider visiting in September. This month presents a lovely transition into fall, with fewer tourists and lower accommodation rates, allowing you to enjoy the scenic beauty of the area without the crowds. The weather remains pleasant, and you can still partake in outdoor activities while savoring the local cuisine at a leisurely pace.
What is the difference between a Winter Haven B&B and a hotel?
Every Winter Haven B&B has its own unique feel. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Winter Haven B&Bs.

Explore a world of travel with Expedia