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Check prices for these dates

Next weekend
7 Feb - 9 Feb
In two weeks
14 Feb - 16 Feb
In one month
28 Feb - 2 Mar
In two months
28 Mar - 30 Mar

Compare 11 B&B in Winter Haven with updated reviews, rates, and availability.

Luxe Penthouse Suite at Opal Oaks Micro Resort
Interior

Luxe Penthouse Suite at Opal Oaks Micro Resort

3.0 star property
10.0 out of 10, Exceptional, (2)
"I absolutely loved the quality of the bed and sheets as well as the comforter! I loved the thick plush bath towels to go with the extordinary bathroom! It was so quiet,we slept so sound. Then when we woke up and was thrilled to have my favorite creamer for our coffee as we sat outside on the outstanding balcony listening to birds singing! It was breath taking! Every area of this home was welcoming and will be on our top list of places to stay! A must be place to add to your list of experiences!...
Luxe Penthouse Suite at Opal Oaks Micro Resort
Hotel Styled Bedrooms in a Villa
Pool

Hotel Styled Bedrooms in a Villa

3.0 star property
6.8 out of 10, (3)
"I didn’t know it was a house being shared by like 6 other tenants and parking was a pain"
The price is AED 220
AED 500 total
includes taxes & fees
1 Mar - 2 Mar
Hotel Styled Bedrooms in a Villa
1 BDR, 1BA in gated community with pool/playground access
Exterior detail

1 BDR, 1BA in gated community with pool/playground access

9.8 out of 10, Exceptional, (41)
"The room was clean and had several ammenities. There was items to cook with including toaster oven and microwave. The hosts were excellent and always responded to any questions or issues. Would rent again for sure."
1 BDR, 1BA in gated community with pool/playground access
Charming Cottage Minutes to I-4 Expressway to Tampa and Orlando
Living room with front entrance

Charming Cottage Minutes to I-4 Expressway to Tampa and Orlando

2.0 star property
Charming Cottage Minutes to I-4 Expressway to Tampa and Orlando
Movie Night in the Enchanted Forest - Resort Style Pool, Theater & Game Room!
Interior

Movie Night in the Enchanted Forest - Resort Style Pool, Theater & Game Room!

Movie Night in the Enchanted Forest - Resort Style Pool, Theater & Game Room!
Vintage Vacation - Time Travel in a Retro Room at Opal Oaks Micro Resort
Vintage Vacation

Vintage Vacation - Time Travel in a Retro Room at Opal Oaks Micro Resort

2.5 star property
Vintage Vacation - Time Travel in a Retro Room at Opal Oaks Micro Resort
🛏️ Charming bedroom in pleasant Haines City with WiFi, AC
Room

🛏️ Charming bedroom in pleasant Haines City with WiFi, AC

2.0 star property
10.0 out of 10, Exceptional, (1)
"Had a pleasant stay. Everything was clean and organized. Host had excellent communication. "
🛏️ Charming bedroom in pleasant Haines City with WiFi, AC
Disney Vacation Home
Pool

Disney Vacation Home

Disney Vacation Home
Cozy private bedroom and private bathroom in Kissimmee. Pets are always welcome!
Room

Cozy private bedroom and private bathroom in Kissimmee. Pets are always welcome!

Cozy private bedroom and private bathroom in Kissimmee. Pets are always welcome!
Capernaum Lakeside Lodge
Outdoor wedding area

Capernaum Lakeside Lodge

3.5 star property
8.6 out of 10, Excellent, (139)
"New owner as of few weeks ago. Restoration work being done. Beautiful setting, Pecky cypress ceilings in main area. Wood floors with beautiful carpeting up stairways and through halls. Very clean. My room appeared to be recently painted. Very comfortable. Wi-fi iffy. Staff very pleasant & helpful. Continental breakfast. Apparently lightning strike on chimney has created some problems. Staff said that plans are to closed and complete repairs after June 17th. When that is done, this...
Capernaum Lakeside Lodge
Is Simple, Safe, Comfortable and Cheap Rooms for Vacationers
Room

Is Simple, Safe, Comfortable and Cheap Rooms for Vacationers

Is Simple, Safe, Comfortable and Cheap Rooms for Vacationers
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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Other property types in Winter Haven

Margaritaville Resort Orlando Cottages by Rentyl
Front of property

Margaritaville Resort Orlando Cottages by Rentyl

4.0 star property
8.8 out of 10, Excellent, (1179)
"This is our 3rd time staying here. We did not love this cottage as much as we did the others. Although each room had a bathroom there was not one outside the bedrooms. We had 6 people and there was limited seating & small living room area The master bathroom shower leaked all over the floor Wish we were told there was a hot tub do we could have brought bathing suits We liked that it was less than a 10 minute walk to the Salty Rim and the shuttle to the promenade was very quick & convenient"
Margaritaville Resort Orlando Cottages by Rentyl
Summer Bay Orlando by Exploria Resorts
Property amenity

Summer Bay Orlando by Exploria Resorts

3.5 star property
8.4 out of 10, Very Good, (5118)
"Very clean, quiet & spacious apartments. Staff very prompt and courteous. A lot of practical amenities & entertainments. I’m very happy with my stay. "
The price is AED 446
AED 618 total
includes taxes & fees
23 Feb - 24 Feb
Summer Bay Orlando by Exploria Resorts
Vacation Village at Parkway
Outdoor pool

Vacation Village at Parkway

3.0 star property
8.4 out of 10, Very Good, (1428)
"Very staff, clean room and great pool and hot tub"
The price is AED 295
AED 390 total
includes taxes & fees
12 Feb - 13 Feb
Vacation Village at Parkway
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.

Frequently asked questions

Searching for B&Bs in Winter Haven?
If you want to find a place to stay with fewer rooms than a hotel and an intimate environment, a B&B may be the perfect thing for your vacation to Winter Haven. If you’re looking to play some golf while in Winter Haven, you can perfect your swing at Cypresswood Golf and Country Club and Baytree Golf Club.
How do you know if a B&B is the best choice for your stay?
Every B&B has a unique charm. Whether it’s a picturesque garden or a beautiful breakfast room, the quaint details are what make bed and breakfasts the perfect escape.
What are the best bed and breakfasts in Winter Haven?
You might be interested in one of these choices if you’re hoping to find a place to stay where breakfast is included with your stay: Best Western Plus Winter Haven Inn & Suites Howard Johnson by Wyndham Winter Haven FLStaybridge Suites Winter Haven Auburndale, an IHG HotelHampton Inn Winter HavenLegoland Beach Retreat
What's the best time of year to book my B&B in Winter Haven?
When you’re planning your trip to Winter Haven, be sure to take into account the year-round temperatures. The hottest months are usually August and July with an average temp of 81°F, while the coldest months are January and February with an average of 64°F. The rainiest months in Winter Haven are August, July, September, and June, with each month seeing an average of 8 inches of rainfall.
What is there to do in Winter Haven?
Travelers enjoy Winter Haven for its beautiful lakeside setting and array of dining options. Spend some time exploring The Circle B Bar Reserve and Rotary Park if you’re hoping to see some of the area’s natural features. You might put LEGOLAND® Florida and Theatre Winter Haven on your list if you want to see more of the area.
How can I get to and around Winter Haven?
You can map out your trip in and around Winter Haven ahead of time with these transportation options. Fly into Lakeland Intl. Airport (LAL), which is located 17.3 mi (27.8 km) away from the heart of the city. You can also search for flights into Kissimmee, FL (ISM-Kissimmee Gateway), which is 26 mi (41.9 km) away. If you’d like to explore around the area, consider renting a car to take in more sights.