Bed and Breakfast in Winter Park, FL

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Winter Park, FL bed and breakfast
Choose the perfect holiday accommodation
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16 Bed and Breakfasts in Winter Park, FL

Best Winter Park, FL bed and breakfasts with breakfast included

Comfortable And Quiet Place - Winter Park, FL
9.7 91 reviews
Winter Park, FL
23/06 – 28/06
NZ$140/nighttotal: NZ$700 (5 )

Comfortable And Quiet Place

1 2
B&B , Casselberry
This Casselberry self-catering apartment is conveniently located near Orlando Sanford International Airport, approximately 24-32 km away, offering easy access to numerous restaurants and shopping centres, and less than 80 km from both Walt Disney World and Universal Orlando Resort.
The one-bedroom, one-bathroom apartment sleeps two guests, features a private kitchen with fridge and microwave, complimentary Victor Allen's K-cup coffee and Oasis Bliss amenities, plus fast Wi-Fi and parking; guests benefit from excellent cleanliness and location ratings.

Best Winter Park, FL bed and breakfasts with a garden

St. Hemingway Suite - Winter Park, FL
9.9 354 reviews
Winter Park, FL
28/06 – 18/07
NZ$162/nighttotal: NZ$3240 (20 )

St. Hemingway Suite

1 1
B&B , Altamonte Springs
This lakeside apartment in Altamonte Springs is conveniently located just 30 kilometers from Universal Studios and 50 kilometers from Walt Disney World Resort.
The self-catering apartment features a private entrance, a kitchenette, a private dock, and a swimming pool, ideal for a relaxing getaway for two.
Downtown Lake Eola Historic House 1 Or 2 Bed - Winter Park, FL
9.5 813 reviews
Winter Park, FL
28/07 – 01/08
NZ$223/nighttotal: NZ$892 (4 )

Downtown Lake Eola Historic House 1 Or 2 Bed

2 2
B&B , Orlando
This apartment is ideally located in downtown Orlando, just a short walk from Lake Eola, the Dr. Philips Center and Amway Arena. The surrounding area is lively and vibrant, offering a wide range of restaurants, bars, and shops. Guests have consistently rated this property as excellent for its cleanliness, location, and overall experience.
The apartment is spacious, with 65 square metres of living space and can accommodate up to 4 guests. You can enjoy the convenience of a fully equipped kitchen, a comfortable living space with entertainment options, and a relaxing front porch.
Luxury Suite Near Disney & Downtown Orlando - Winter Park, FL
9.8 282 reviews
Winter Park, FL
28/06 – 18/07
NZ$143/nighttotal: NZ$2860 (20 )

Luxury Suite Near Disney & Downtown Orlando

1 1
B&B , Orlando
This one-bedroom guest suite is situated in a quiet residential neighbourhood just 5 kilometres from Downtown Orlando, offering easy access to the city's attractions, including Universal Studios, Walt Disney World Resort and SeaWorld.
The self-catering apartment features a fully equipped kitchen, a private entrance and a cosy front porch, perfect for relaxing after a day exploring the theme parks.
Comfortable 2-bedroom Place Full Kitchen - Winter Park, FL
9.7 179 reviews
Winter Park, FL
28/06 – 18/07
NZ$184/nighttotal: NZ$3680 (20 )

Comfortable 2-bedroom Place Full Kitchen

1 1
B&B , Fairview Shores
This Fairview Shores duplex, Unit B, enjoys a central location, approximately 19 kilometres from downtown Orlando and 48 kilometres from Walt Disney World.
The two-bedroom property sleeps five, features a fully equipped kitchen with fridge, freezer and microwave, air conditioning, a garden, parking, and benefits from a private entrance.

Frequently asked questions about bed and breakfast in Winter Park, FL

  • What are the must-see sights for first-time visitors on a day trip to Winter Park, FL?

    For a first-time visit, you'll want to see the iconic Winter Park Scenic Boat Tour, a relaxing way to explore the canals. The Charles Hosmer Morse Museum of American Art is a must for art lovers, and the beautiful Rollins College campus is worth strolling around. You can also enjoy some time at the charming Park Avenue, the main shopping and dining district.
  • What are the best bed and breakfasts in Winter Park, FL?

    Among the B&Bs in Winter Park, FL, The Oasis W/pool Access En-suite #1, Sun Room and Downtown Orlando Tranquility Suite are the most popular ones.

  • In which districts of Winter Park, FL should you consider booking a bed and breakfast?

    The most popular areas for bed and breakfasts in Winter Park are the charming areas around Park Avenue, with its shops and restaurants, and the peaceful area around the Rollins College campus. For a more secluded option, you can find some B&Bs in the residential neighbourhoods near the Winter Park Village.
  • What are the best bed and breakfasts with a pool in Winter Park, FL?

  • What is the typical weather in Winter Park, FL, and how does it affect outdoor plans?

    Winter Park has a subtropical climate, with warm, humid summers and mild winters. You can enjoy outdoor activities year-round, though the summer months can be very hot and humid. If you're planning outdoor activities, it's best to go early in the morning or late in the afternoon during the summer.
  • What are the best bed and breakfasts with a jacuzzi in Winter Park, FL?

  • What dining options are recommended for solo travelers staying at bed and breakfasts in Winter Park, FL?

    For solo travelers, there are many great options on Park Avenue. The Wine Room is a popular choice for a casual meal and a glass of wine, while The Ravenous Pig offers a more upscale dining experience. You can also find many cafes and bakeries along Park Avenue for a quick bite.
  • What are the best bed and breakfasts for families and kids in Winter Park, FL?

    The best B&Bs for families and kids in Winter Park, FL are Sun Room , Guesthouse W/private Indoor Pool and Private Guest Suite With Enclosed Porch.

  • What are the best cultural activities and events in and around Winter Park, FL?

    Winter Park is known for its vibrant arts scene. The annual Winter Park Sidewalk Art Festival is a major event, featuring art from local and national artists. The Bach Festival Society of Winter Park hosts classical music concerts throughout the year. And the Winter Park Playhouse offers Broadway-style musicals.
  • What are the best pet friendly bed and breakfasts in Winter Park, FL?

    The best pet friendly B&Bs in Winter Park, FL are Sun Room , Guesthouse W/private Indoor Pool and Private Guest Suite With Enclosed Porch.

  • Which hiking trails are recommended for exploring in and around Winter Park, FL?

    For hiking, head to the Wekiwa Springs State Park just outside of Winter Park. The park has several trails ranging from easy to moderate, offering a chance to explore the Florida wilderness. You can also check out the scenic trails at the Mead Garden, a botanical garden in Winter Park.
  • What are the best bed and breakfasts with parking in Winter Park, FL?

    The Oasis W/pool Access En-suite #1, Sun Room and Downtown Orlando Tranquility Suite are the best B&Bs with parking in Winter Park, FL.

  • What amenities are commonly offered in bed and breakfasts in Winter Park, FL?

    Bed and breakfasts in Winter Park often offer a range of amenities, including a complimentary breakfast, free Wi-Fi, and access to a shared lounge or garden. Some may also have a swimming pool or hot tub. It's best to check the individual B&B's website for specific amenities.

Destinations nearby

Best Winter Park, FL bed and breakfasts with parking

H8 Private Room With Smart Tv Near Everything - Winter Park, FL
Winter Park, FL
28/07 – 01/08
NZ$98/nighttotal: NZ$392 (4 )

H8 Private Room With Smart Tv Near Everything

1 2
B&B , Orlando
This Orlando bed and breakfast is situated approximately 9.2 kilometres from Church Street Station, offering straightforward access to downtown attractions and the airport.
This accommodation provides a private bedroom and bathroom for up to three guests, featuring air conditioning, complimentary WiFi, and on-site parking, with towels and bed linen supplied.
Centrally Located Guest Suite Retreat - Winter Park, FL
Winter Park, FL
23/06 – 28/06
NZ$192/nighttotal: NZ$960 (5 )

Centrally Located Guest Suite Retreat

1 2
B&B , Orlando
This Orlando guest suite, situated 2.3 kilometres from downtown, offers convenient access to attractions including Camping World Stadium (8.3 km), Holy Land Experience (9.7 km), and Church Street Station (5 km).
The 15-square-metre self-catering unit features one bedroom, one bathroom, sleeps two guests, and includes free Wi-Fi, private parking, and air conditioning.
Tiny Unit In Cottage In The Middle Of Downtown - Winter Park, FL
Winter Park, FL
28/07 – 01/08
NZ$151/nighttotal: NZ$604 (4 )

Tiny Unit In Cottage In The Middle Of Downtown

1 2
house , Orlando
This studio apartment is situated 0.96 kilometres from Orlando's city centre, a 9-minute walk from Church Street Station and a 13-minute walk from the Kia Centre.
This property offers air conditioning, free Wi-Fi, and private parking, with a guest capacity of two people and a check-out time of 11:00 AM.
Pily's Vintage Stay Room Full Bed - Winter Park, FL
8.6 7 reviews
Winter Park, FL
28/07 – 01/08
NZ$133/nighttotal: NZ$532 (4 )

Pily's Vintage Stay Room Full Bed

1 2
B&B , Orlando
Pily's Vintage Stay Room Full Bed is located in Orlando, approximately 13 kilometres from downtown attractions including Church Street Station and the Amway Center.
This Orlando guesthouse offers a 16-square-metre room with a full bed, sleeping up to three guests, and features a shared kitchen, free Wi-Fi, on-site parking, a swimming pool, and a tennis court.

Best Winter Park, FL bed and breakfasts with air conditioning

Large Studio Near The Airport, Downtown, Hospitals - Winter Park, FL
9.9 105 reviews
Winter Park, FL
28/06 – 18/07
NZ$180/nighttotal: NZ$3600 (20 )

Large Studio Near The Airport, Downtown, Hospitals

1 1
B&B , Orlando
This Orlando studio apartment is situated in a residential neighbourhood, approximately 16km from Downtown Orlando, 24km from Orlando International Airport, and within 32-48km of Universal and Disney theme parks.
The self-contained apartment sleeps four guests, offering a queen-size memory foam bed, a full-size sofa bed, a well-equipped kitchenette with a mini-fridge, and a smart TV with streaming services; on-site parking is available.
Balfour Palms - Winter Park, FL
9.6 185 reviews
Winter Park, FL
28/07 – 01/08
NZ$197/nighttotal: NZ$788 (4 )

Balfour Palms

1 2
B&B , Winter Park
This studio apartment is situated in Winter Park, a short distance from Park Avenue and within easy reach of the University of Central Florida, Rollins College, and downtown Orlando. It has received excellent ratings for cleanliness, location, and user experience.
The self-catering apartment sleeps two guests and features a kitchenette with modern appliances, a laundry room, and a walk-in shower. Amenities include a king-size bed, FireStick capabilities, and on-site parking.
Tiny Home Barn Style In Backyard With Animals - Winter Park, FL
9.7 30 reviews
Winter Park, FL
28/07 – 01/08
NZ$198/nighttotal: NZ$792 (4 )

Tiny Home Barn Style In Backyard With Animals

1 2
B&B , Orlando
This unique barn-style guesthouse is located in Orlando, Florida, a short walk (1.3km) from Camping World Stadium and 3.2km from the Kia Forum, with Orlando International Airport 16km away.
This 188 square metre property offers one bedroom, one bathroom, sleeps five guests, and includes a private terrace, free parking, packed lunches for day trips, and on-site staff to arrange airport shuttles.
10 Minutes From Universal - Relaxing Guest Suite - Winter Park, FL
8.7 10 reviews
Winter Park, FL
28/07 – 01/08
NZ$174/nighttotal: NZ$696 (4 )

10 Minutes From Universal - Relaxing Guest Suite

1 2
B&B , Azalea Park
This guest house is located in Azalea Park, a short distance from local attractions.
This family-friendly accommodation offers 400 square meters of floor area with one bedroom, one bathroom, and can host up to five guests, featuring air conditioning, internet, and parking.
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