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Check prices for these dates

Next weekend
23 May - 25 May
In two weeks
30 May - 1 Jun
In one month
13 Jun - 15 Jun
In two months
11 Jul - 13 Jul

Compare 13 B&B in Winter Haven with updated reviews, rates, and availability.

Hotel Styled Bedrooms in a Villa
Outdoor pool

Hotel Styled Bedrooms in a Villa

3.0 star property
5.6 out of 10, (5)
"bad parking quiet hour not observed"
The price is AED 162
AED 434 total
includes taxes & fees
30 May - 31 May
Hotel Styled Bedrooms in a Villa
Movie Night in the Enchanted Forest - Resort Style Pool, Theater & Game Room!
Outdoor pool

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

Movie Night in the Enchanted Forest - Resort Style Pool, Theater & Game Room!
Luxe Penthouse Suite at Opal Oaks Micro Resort
Outdoor pool

Luxe Penthouse Suite at Opal Oaks Micro Resort

3.0 star property
9.4 out of 10, Exceptional, (9)
"We really enjoyed our stay at this unique and beautiful property!"
Luxe Penthouse Suite at Opal Oaks Micro Resort
Queen Room at Opal Oaks Micro Resort - Pool, Hot Tub, Sauna, Billiards
Outdoor pool

Queen Room at Opal Oaks Micro Resort - Pool, Hot Tub, Sauna, Billiards

2.5 star property
10.0 out of 10, Exceptional, (1)
"We stayed two nights 1940's style while attending a concert in Lakeland for our Anniversary. This was so much nicer than a hotel. The only negative is the pool enclosure is still damaged from last years storms. The peacocks were wonderful. "
Queen Room at Opal Oaks Micro Resort - Pool, Hot Tub, Sauna, Billiards
Cozy Home Minutes to I-4 Expressway to Tampa and Orlando
Fridge, microwave, oven, stovetop

Cozy Home Minutes to I-4 Expressway to Tampa and Orlando

2.0 star property
10.0 out of 10, Exceptional, (3)
"The host was very responsive to our needs. The house was nice and also a nice quiet neighborhood. Also 5 minutes from the ballpark was a plus !!"
Cozy Home Minutes to I-4 Expressway to Tampa and Orlando
🛏️ Charming bedroom in pleasant Haines City!!
Microwave, oven, stovetop, dishwasher

🛏️ Charming bedroom in pleasant Haines City!!

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!!
Capernaum Lakeside Lodge
Terrace/patio

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
Cozy private bedroom and private bathroom in Kissimmee. Pets are always welcome!
1 bedroom, WiFi, bed sheets

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

Cozy private bedroom and private bathroom in Kissimmee. Pets are always welcome!
Charming 1bed in the amazing Orlando minutes to Disney.
Fridge, microwave, oven, stovetop

Charming 1bed in the amazing Orlando minutes to Disney.

Charming 1bed in the amazing Orlando minutes to Disney.
Is Simple, Safe, Comfortable and Cheap Rooms for Vacationers
1 bedroom, WiFi

Is Simple, Safe, Comfortable and Cheap Rooms for Vacationers

Is Simple, Safe, Comfortable and Cheap Rooms for Vacationers
Disney Vacation Home
Living area

Disney Vacation Home

Disney Vacation Home
Charming 1bed in the amazing Orlando minutes to Disney.
Microwave, oven, stovetop, dishwasher

Charming 1bed in the amazing Orlando minutes to Disney.

Charming 1bed in the amazing Orlando minutes to Disney.
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

Vacation Village at Parkway
Aerial view

Vacation Village at Parkway

3.0 star property
8.4 out of 10, Very Good, (2090)
"Great stay"
The price is AED 259
AED 357 total
includes taxes & fees
25 May - 26 May
Vacation Village at Parkway
Summer Bay Orlando by Exploria Resorts
5 outdoor pools, pool umbrellas, sun loungers

Summer Bay Orlando by Exploria Resorts

3.5 star property
8.4 out of 10, Very Good, (5413)
"Great place "
The price is AED 446
AED 618 total
includes taxes & fees
26 May - 27 May
Summer Bay Orlando by Exploria Resorts
Margaritaville Cottages Orlando with H2O Waterpark by Rentyl
Interior

Margaritaville Cottages Orlando with H2O Waterpark by Rentyl

4.0 star property
8.8 out of 10, Excellent, (1376)
"Great place to stay"
The price is AED 1,814
AED 2,982 total
includes taxes & fees
2 Jun - 3 Jun
Margaritaville Cottages Orlando with H2O Waterpark by Rentyl
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 Lake Henry 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: Howard Johnson by Wyndham Winter Haven FLBest Western Plus Winter Haven Inn & Suites Home2 Suites By Hilton Winter HavenStaybridge Suites Winter Haven Auburndale by IHGHampton Inn Winter Haven
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 Indigo’s Family Fun Center 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.