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Winter Haven B&B
Choose the perfect vacation accommodation
Price per night
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Rating

55 Bed and Breakfast and Inn in Winter Haven

Lollygaggers Lakeside Retreat - Winter Haven
9.4 28 reviews
Winter Haven
07/17 – 07/24
$105/nighttotal: $735 (7 )

Lollygaggers Lakeside Retreat

1 2
B&B, Auburndale
This one-bedroom, one-bathroom lakefront suite in Auburndale, Florida, is located less than 7 miles from LEGOLAND Florida and minutes from downtown.
The fully updated private suite, sleeping up to three guests, boasts a kitchen with a fridge, freezer, microwave, and dishwasher, plus air conditioning, parking, and a tranquil setting ideal for kayaking and jet skiing.
The Lake Alfred Citruswood Cabin - Winter Haven
9.4 16 reviews
Winter Haven
08/21 – 08/30
$134/nighttotal: $1206 (9 )

The Lake Alfred Citruswood Cabin

1 1
B&B, Lake Alfred
Escape to the serene Lake Alfred Citruswood Cabin, where lush greenery and a private outdoor dining area create a secluded oasis. Situated just 4.7 miles from historical railroad stations and 8.9 miles from Legoland Florida, this highly-rated cabin offers easy access to local attractions.
The well-equipped cabin features one bedroom, one bathroom, and a spacious layout with a separate living area. Guests can enjoy modern amenities such as free Wi-Fi, air conditioning, and a flat-screen TV. The cabin's kitchen is fully equipped for home-cooked meals, and the garden provides a peaceful retreat for relaxation.
Chain Of Lakes Cottage - Winter Haven
9.7 18 reviews
Winter Haven
07/03 – 07/07
$192/nighttotal: $768 (4 )

Chain Of Lakes Cottage

1 3
B&B, Winter Haven
Chain of Lakes Cottage in Winter Haven offers a peaceful retreat near Legoland Florida (6.1 miles) and historic railroad stations.
This 800-square-foot house features one bedroom, one bathroom, and a fully equipped kitchen, comfortably accommodating one guest and providing free Wi-Fi.
The Signature Orange Grove King Suite - Winter Haven
9.0 29 reviews
Winter Haven
08/21 – 08/30
$101/nighttotal: $909 (9 )

The Signature Orange Grove King Suite

1 1
B&B, Lake Alfred
The Orange Grove Suite is a short drive from Legoland Florida and several historical railroad stations, offering a peaceful retreat outside the city center. This B&B has consistently received excellent ratings for its location, cleanliness, and overall experience.
The suite offers 500 square feet of space, accommodating up to 3 guests in one bedroom and one bathroom. Amenities include a kitchen with a fridge, microwave, and dishwasher, air conditioning, a terrace, a garden, free WiFi, and private parking.
The Scandinavian Contemporary Goud & Blauw - Winter Haven
9.3 16 reviews
Winter Haven
08/21 – 08/30
$76/nighttotal: $684 (9 )

The Scandinavian Contemporary Goud & Blauw

1 1
B&B, Lake Alfred
The Scandinavian Contemporary Goud is located in Lake Alfred, just a short drive from the historic Swanns Railroad Station and Carters Railroad Station, making it a great base for exploring this charming town. It has received very good ratings for cleanliness, user experience, and location.
This one-bedroom, one-bathroom guesthouse provides 200 square feet of space for two guests. It features a Scandinavian contemporary design, a shared kitchen with modern appliances, a private parking space, an outdoor dining area, a sun terrace, and free Wi-Fi.
Cozy Family Vacation Villa - Winter Haven
9.8 27 reviews
Winter Haven
06/27 – 07/04
$110/nighttotal: $770 (7 )

Cozy Family Vacation Villa

1 2
B&B, Inwood
This Airbnb is located in Inwood, a neighborhood in northern Manhattan, close to Inwood Hill Park and the Harlem River. The house has excellent user, location, and cleanliness ratings.
The home has three bedrooms and one bathroom, comfortably accommodating up to six guests. The property offers amenities like free cooking services, a full kitchen, laundry facilities, and mood lighting, as well as self check-in and ample parking.
🏡Centralprivatekingsuite🏡w/d🏥2miles To Hospital🏥 - Winter Haven
9.6 85 reviews
Winter Haven
07/16 – 07/20
$119/nighttotal: $476 (4 )

🏡Centralprivatekingsuite🏡w/d🏥2miles To Hospital🏥

1 2
B&B, Winter Haven
This Winter Haven bed and breakfast is conveniently located just two miles from downtown and the Winter Haven Hospital, and six miles from LEGOLAND. The property enjoys excellent ratings for location, cleanliness, and overall experience.
The suite offers a private entrance, a comfortable king bed, and a sofa bed, making it perfect for couples or small families. Guests can enjoy a private bathroom, a kitchenette with a refrigerator, a washer and dryer, and a covered parking space.
The Tatman Evergreen Suite - Winter Haven
9.0 13 reviews
Winter Haven
07/08 – 07/12
$127/nighttotal: $508 (4 )

The Tatman Evergreen Suite

1 3
B&B, Lake Alfred
This charming bed and breakfast is located in the heart of Lake Alfred, offering picturesque views of the town and easy access to its shops, restaurants, and local attractions. It has earned excellent ratings for its cleanliness, location, and overall experience.
The cozy room features one bedroom and one bathroom, with a total floor area of 360 square feet and a capacity for up to three guests. Amenities include air conditioning, parking, and internet access, along with towels and bed linens, ensuring a comfortable stay.
The Exclusive Tatman Evergreen Suite - Winter Haven
9.9 291 reviews
Winter Haven
06/27 – 07/04
$93/nighttotal: $651 (7 )

The Exclusive Tatman Evergreen Suite

1 2
B&B, Lake Alfred
The Tatman Evergreen Suite is a highly-rated B&B in Lake Alfred, Florida, offering a peaceful stay in a comfortable environment with a private bath and a shared kitchen. It is conveniently located near Adams Estate Wedding and Event Venue, Legoland, Bok Towers, and Orlando theme parks, making it an ideal choice for travelers seeking a relaxing getaway or exploring the surrounding attractions.
With a 24-hour secure keyless private entry, comfortable and cool environment with a 12” memory foam mattress, and a spacious, fully furnished modern kitchen, the B&B offers a range of amenities and features to ensure a memorable stay. Guests can enjoy complimentary Starbucks coffee, Coca-Cola products, and Luzianne Fresh Brewed Iced Tea, as well as in-house complimentary laundry facilities and a comfy living space with a 70-inch Samsung Curve Home Theater System. The B&B also features friendly Golden Retriever dogs on the property, adding a touch of warmth and charm to the overall experience.
Cute & Cozy 1 Bedroom Guesthouse Located In Winter Haven Fl - Winter Haven
10 20 reviews
Winter Haven
08/21 – 08/30
$101/nighttotal: $909 (9 )

Cute & Cozy 1 Bedroom Guesthouse Located In Winter Haven Fl

1 1
B&B, Winter Haven
This smoke-free guesthouse is conveniently located in Winter Haven, within a mile of several attractions including a hospital, family entertainment center, bowling alley, park, and theater. It has earned excellent user ratings, making it a popular choice for travelers.
This charming bed and breakfast can accommodate up to two guests in one bedroom and one bathroom. It offers a range of amenities for a comfortable stay, including a kitchen with a fridge and microwave, air conditioning, a swimming pool, a terrace or balcony, a garden, and parking.
Charming Bed & Breakfast In Wonderful Winter Haven With Wifi, Fitness Room - Winter Haven
Winter Haven
08/21 – 08/30
$95/nighttotal: $855 (9 )

Charming Bed & Breakfast In Wonderful Winter Haven With Wifi, Fitness Room

1 1
B&B, Winter Haven
This Winter Haven guesthouse is conveniently located near LEGOLAND® Florida and Eagle Ridge Mall, an 8-minute drive to each, and offers easy access to Lake Wailes Park (14 minutes) and Bok Tower Gardens (23 minutes).
The one-bedroom, one-bathroom rental features in-house laundry, Wi-Fi, air conditioning, and accommodates one guest, perfect for a solo traveler or couple seeking a relaxing Winter Haven getaway.
Chain Of Lakes 
 2br/1ba Guest Suite - Winter Haven
9.9 188 reviews
Winter Haven
07/08 – 07/12
$124/nighttotal: $496 (4 )

Chain Of Lakes 2br/1ba Guest Suite

1 3
B&B, Winter Haven
This Winter Haven bed and breakfast is situated on a peninsula on the Chain of Lakes, offering beautiful sunset views and direct access to the water. The two-bedroom unit features a private boathouse with AC, fishing gear, and seating, as well as a charcoal grill, picnic table, and canal seating for relaxing by the water.

Best Winter Haven bed and breakfasts with breakfast included

Chain Of Lakes 
 2br/1ba Guest Suite - Winter Haven
9.9 188 reviews
Winter Haven
07/08 – 07/12
$124/nighttotal: $496 (4 )

Chain Of Lakes 2br/1ba Guest Suite

1 3
B&B, Winter Haven
This Winter Haven bed and breakfast is situated on a peninsula on the Chain of Lakes, offering beautiful sunset views and direct access to the water. The two-bedroom unit features a private boathouse with AC, fishing gear, and seating, as well as a charcoal grill, picnic table, and canal seating for relaxing by the water.

Best Winter Haven bed and breakfasts with a garden

Cute & Cozy 1 Bedroom Guesthouse Located In Winter Haven Fl - Winter Haven
10 20 reviews
Winter Haven
08/21 – 08/30
$101/nighttotal: $909 (9 )

Cute & Cozy 1 Bedroom Guesthouse Located In Winter Haven Fl

1 1
B&B, Winter Haven
This smoke-free guesthouse is conveniently located in Winter Haven, within a mile of several attractions including a hospital, family entertainment center, bowling alley, park, and theater. It has earned excellent user ratings, making it a popular choice for travelers.
This charming bed and breakfast can accommodate up to two guests in one bedroom and one bathroom. It offers a range of amenities for a comfortable stay, including a kitchen with a fridge and microwave, air conditioning, a swimming pool, a terrace or balcony, a garden, and parking.
The Lake Alfred Citruswood Cabin - Winter Haven
9.4 16 reviews
Winter Haven
08/21 – 08/30
$134/nighttotal: $1206 (9 )

The Lake Alfred Citruswood Cabin

1 1
B&B, Lake Alfred
Escape to the serene Lake Alfred Citruswood Cabin, where lush greenery and a private outdoor dining area create a secluded oasis. Situated just 4.7 miles from historical railroad stations and 8.9 miles from Legoland Florida, this highly-rated cabin offers easy access to local attractions.
The well-equipped cabin features one bedroom, one bathroom, and a spacious layout with a separate living area. Guests can enjoy modern amenities such as free Wi-Fi, air conditioning, and a flat-screen TV. The cabin's kitchen is fully equipped for home-cooked meals, and the garden provides a peaceful retreat for relaxation.
Chain Of Lakes 
 2br/1ba Guest Suite - Winter Haven
9.9 188 reviews
Winter Haven
07/08 – 07/12
$124/nighttotal: $496 (4 )

Chain Of Lakes 2br/1ba Guest Suite

1 3
B&B, Winter Haven
This Winter Haven bed and breakfast is situated on a peninsula on the Chain of Lakes, offering beautiful sunset views and direct access to the water. The two-bedroom unit features a private boathouse with AC, fishing gear, and seating, as well as a charcoal grill, picnic table, and canal seating for relaxing by the water.
Cozy Family Vacation Villa - Winter Haven
9.8 27 reviews
Winter Haven
06/27 – 07/04
$110/nighttotal: $770 (7 )

Cozy Family Vacation Villa

1 2
B&B, Inwood
This Airbnb is located in Inwood, a neighborhood in northern Manhattan, close to Inwood Hill Park and the Harlem River. The house has excellent user, location, and cleanliness ratings.
The home has three bedrooms and one bathroom, comfortably accommodating up to six guests. The property offers amenities like free cooking services, a full kitchen, laundry facilities, and mood lighting, as well as self check-in and ample parking.

Frequently Asked Questions about bed and breakfast in Winter Haven

Destinations nearby

Top Bed and Breakfasts with Parking in Winter Haven

Park up and enjoy the city center, as every B&B in Winter Haven on this list comes with a free on-site parking spot.

Chain Of Lakes Cottage - Winter Haven
9.7 18 reviews
Winter Haven
07/03 – 07/07
$192/nighttotal: $768 (4 )

Chain Of Lakes Cottage

1 3
B&B, Winter Haven
Chain of Lakes Cottage in Winter Haven offers a peaceful retreat near Legoland Florida (6.1 miles) and historic railroad stations.
This 800-square-foot house features one bedroom, one bathroom, and a fully equipped kitchen, comfortably accommodating one guest and providing free Wi-Fi.
Chain Of Lakes 
 2br/1ba Guest Suite - Winter Haven
9.9 188 reviews
Winter Haven
07/08 – 07/12
$124/nighttotal: $496 (4 )

Chain Of Lakes 2br/1ba Guest Suite

1 3
B&B, Winter Haven
This Winter Haven bed and breakfast is situated on a peninsula on the Chain of Lakes, offering beautiful sunset views and direct access to the water. The two-bedroom unit features a private boathouse with AC, fishing gear, and seating, as well as a charcoal grill, picnic table, and canal seating for relaxing by the water.
The Tatman Evergreen Suite - Winter Haven
9.0 13 reviews
Winter Haven
07/08 – 07/12
$127/nighttotal: $508 (4 )

The Tatman Evergreen Suite

1 3
B&B, Lake Alfred
This charming bed and breakfast is located in the heart of Lake Alfred, offering picturesque views of the town and easy access to its shops, restaurants, and local attractions. It has earned excellent ratings for its cleanliness, location, and overall experience.
The cozy room features one bedroom and one bathroom, with a total floor area of 360 square feet and a capacity for up to three guests. Amenities include air conditioning, parking, and internet access, along with towels and bed linens, ensuring a comfortable stay.
The Signature Orange Grove King Suite - Winter Haven
9.0 29 reviews
Winter Haven
08/21 – 08/30
$101/nighttotal: $909 (9 )

The Signature Orange Grove King Suite

1 1
B&B, Lake Alfred
The Orange Grove Suite is a short drive from Legoland Florida and several historical railroad stations, offering a peaceful retreat outside the city center. This B&B has consistently received excellent ratings for its location, cleanliness, and overall experience.
The suite offers 500 square feet of space, accommodating up to 3 guests in one bedroom and one bathroom. Amenities include a kitchen with a fridge, microwave, and dishwasher, air conditioning, a terrace, a garden, free WiFi, and private parking.

Best Winter Haven bed and breakfasts with air conditioning

Cute & Cozy 1 Bedroom Guesthouse Located In Winter Haven Fl - Winter Haven
10 20 reviews
Winter Haven
08/21 – 08/30
$101/nighttotal: $909 (9 )

Cute & Cozy 1 Bedroom Guesthouse Located In Winter Haven Fl

1 1
B&B, Winter Haven
This smoke-free guesthouse is conveniently located in Winter Haven, within a mile of several attractions including a hospital, family entertainment center, bowling alley, park, and theater. It has earned excellent user ratings, making it a popular choice for travelers.
This charming bed and breakfast can accommodate up to two guests in one bedroom and one bathroom. It offers a range of amenities for a comfortable stay, including a kitchen with a fridge and microwave, air conditioning, a swimming pool, a terrace or balcony, a garden, and parking.
Charming Bed & Breakfast In Wonderful Winter Haven With Wifi, Fitness Room - Winter Haven
Winter Haven
08/21 – 08/30
$95/nighttotal: $855 (9 )

Charming Bed & Breakfast In Wonderful Winter Haven With Wifi, Fitness Room

1 1
B&B, Winter Haven
This Winter Haven guesthouse is conveniently located near LEGOLAND® Florida and Eagle Ridge Mall, an 8-minute drive to each, and offers easy access to Lake Wailes Park (14 minutes) and Bok Tower Gardens (23 minutes).
The one-bedroom, one-bathroom rental features in-house laundry, Wi-Fi, air conditioning, and accommodates one guest, perfect for a solo traveler or couple seeking a relaxing Winter Haven getaway.
Chain Of Lakes 
 2br/1ba Guest Suite - Winter Haven
9.9 188 reviews
Winter Haven
07/08 – 07/12
$124/nighttotal: $496 (4 )

Chain Of Lakes 2br/1ba Guest Suite

1 3
B&B, Winter Haven
This Winter Haven bed and breakfast is situated on a peninsula on the Chain of Lakes, offering beautiful sunset views and direct access to the water. The two-bedroom unit features a private boathouse with AC, fishing gear, and seating, as well as a charcoal grill, picnic table, and canal seating for relaxing by the water.
🏡Centralprivatekingsuite🏡w/d🏥2miles To Hospital🏥 - Winter Haven
9.6 85 reviews
Winter Haven
07/16 – 07/20
$119/nighttotal: $476 (4 )

🏡Centralprivatekingsuite🏡w/d🏥2miles To Hospital🏥

1 2
B&B, Winter Haven
This Winter Haven bed and breakfast is conveniently located just two miles from downtown and the Winter Haven Hospital, and six miles from LEGOLAND. The property enjoys excellent ratings for location, cleanliness, and overall experience.
The suite offers a private entrance, a comfortable king bed, and a sofa bed, making it perfect for couples or small families. Guests can enjoy a private bathroom, a kitchenette with a refrigerator, a washer and dryer, and a covered parking space.
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