Bed and Breakfast and Inn in Winter Park, FL

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Winter Park, FL B&B
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16 Bed and Breakfasts and Inn in Winter Park, FL

Best Winter Park, FL bed and breakfasts with breakfast included

Private Entrance/bathroom 10 Min From Dt Orlando - Winter Park, FL
9.9 236 reviews
Winter Park, FL
11/08 – 13/08
$116/nighttotal: $232 (2 )

Private Entrance/bathroom 10 Min From Dt Orlando

1 2
B&B , Eatonville
This charming bed and breakfast is located just 10 kilometres outside of downtown Orlando, making it a convenient base for exploring both the city and the nearby attractions. It's also just a short drive from Eatonville, a historic town with a rich cultural heritage. The accommodation has consistently received excellent reviews for its cleanliness, location, and overall experience.
The guest house offers a cosy and comfortable double room with a private bathroom, perfect for a couple's getaway. Guests can enjoy a range of amenities including air conditioning, free parking, and complimentary Wi-Fi.

Best Winter Park, FL bed and breakfasts with a garden

Downtown Lake Eola Historic House 1 Or 2 Bed - Winter Park, FL
9.5 813 reviews
Winter Park, FL
03/07 – 10/07
$191/nighttotal: $1337 (7 )

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.
Guest Suite Near Full Sail In Winter Park - Winter Park, FL
9.7 239 reviews
Winter Park, FL
17/06 – 23/06
$121/nighttotal: $726 (6 )

Guest Suite Near Full Sail In Winter Park

1 1
B&B , Goldenrod
This Goldenrod guest suite, a self-contained studio apartment, is conveniently located 1.6 kilometres from Full Sail University.
The 1-bedroom unit offers a kitchenette with fridge, freezer and microwave, a private patio, parking, and accommodates up to 2 guests, providing complete independence and privacy.
St. Augustine Suite - Winter Park, FL
9.9 387 reviews
Winter Park, FL
17/06 – 23/06
$141/nighttotal: $846 (6 )

St. Augustine Suite

1 1
B&B , Altamonte Springs
This one-bedroom apartment is situated in Spring Valley, a peaceful community in Altamonte Springs, just 40 km from Walt Disney World Resort.
The property boasts a private entrance and bathroom, lakefront views, a swimming pool, and a garden, ideal for a relaxing getaway for two.
Lovely Spacious Guesthouse In Mills 50 District - Winter Park, FL
8.9 25 reviews
Winter Park, FL
03/09 – 08/09
$123/nighttotal: $615 (5 )

Lovely Spacious Guesthouse In Mills 50 District

1 2
B&B , Orlando
This Orlando guesthouse is located in the Mills 50 District, 4.5km from Camping World Stadium and approximately 18km from Universal Studios Florida.
The 23-square-metre self-catering unit sleeps three, featuring a kitchenette, private bathroom, terrace, and garden with outdoor play equipment; free Wi-Fi is provided.

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 can't miss the charming Park Avenue, with its shops and restaurants. A walk around the scenic Rollins College campus is a must, and the beautiful Kraft Azalea Garden is a real treat, especially in the spring.
  • 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, Tropical King Room Private Entrance Pool and Sun Room are the most popular ones.

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

    The areas around Park Avenue and the charming Hannibal Square are great for finding bed and breakfasts. You'll be close to the action, but still enjoy a peaceful atmosphere.
  • 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, so it's warm and humid for most of the year. Summers are hot and rainy, while winters are mild. You can enjoy outdoor activities year-round, but be prepared for the heat and humidity during the summer months.
  • 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 plenty of charming cafes and restaurants along Park Avenue, like The Wine Room or The Ravenous Pig, offering a relaxed atmosphere and delicious food.
  • 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 has a thriving arts scene. Check out the events at the Charles Hosmer Morse Museum of American Art, or the Winter Park Sidewalk Art Festival, which happens in the spring.
  • What are the best pet friendly bed and breakfasts in Winter Park, FL?

    The best pet friendly B&Bs in Winter Park, FL are Tropical King Room Private Entrance Pool, Sun Room and Guesthouse W/private Indoor Pool.

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

    For hiking, head to the Wekiwa Springs State Park, just outside Winter Park. The trails there are perfect for a morning or afternoon hike.
  • What are the best bed and breakfasts with parking in Winter Park, FL?

    The Oasis W/pool Access En-suite #1, Tropical King Room Private Entrance Pool and Sun Room 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 usually offer a continental breakfast, private bathrooms, and some even have swimming pools or hot tubs. Many also have beautiful gardens or patios.

Destinations nearby

Best Winter Park, FL bed and breakfasts with parking

“The Clementine” Boho Home In Orlando’s Food Scene - Winter Park, FL
Winter Park, FL
21/07 – 04/08
$158/nighttotal: $2212 (14 )

“The Clementine” Boho Home In Orlando’s Food Scene

1 1
B&B , Orlando
This Boho-style guest house is located in Orlando, within 2.4 kilometres of the city centre, and is 3 kilometres from Church Street Station, 3.4 kilometres from Kia Centre, and 5.3 kilometres from Camping World Stadium.
This one-bedroom, one-bathroom accommodation sleeps up to nine guests and offers air conditioning, free Wi-Fi, a kitchen with a fridge and microwave, and a private terrace and garden.
Pily's Vintage Stay Room Full Bed - Winter Park, FL
8.6 7 reviews
Winter Park, FL
17/06 – 23/06
$83/nighttotal: $498 (6 )

Pily's Vintage Stay Room Full Bed

1 1
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.
G7 Private Room With Smart Tv Near Everything - Winter Park, FL
9.0 24 reviews
Winter Park, FL
21/07 – 04/08
$67/nighttotal: $938 (14 )

G7 Private Room With Smart Tv Near Everything

1 1
B&B , Orlando
This Orlando guesthouse is conveniently located near Church Street Station, approximately 8-19 kilometres from attractions such as Camping World Stadium and Orlando International Airport.
The single-bedroom, en-suite room offers air conditioning, a Smart TV, and sleeps one guest; towels and linen are provided, and guests can enjoy proximity to various entertainment venues.
Luxury Suite Near Disney & Downtown Orlando - Winter Park, FL
9.8 278 reviews
Winter Park, FL
28/06 – 18/07
$116/nighttotal: $2320 (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.

Best Winter Park, FL bed and breakfasts with air conditioning

K11 Private Room With Smart Tv Near Everything - Winter Park, FL
8.1 28 reviews
Winter Park, FL
17/06 – 23/06
$72/nighttotal: $432 (6 )

K11 Private Room With Smart Tv Near Everything

1 1
B&B , Orlando
K11 Private Room, a single-bedroom guesthouse in Orlando, Florida, is situated approximately 8.8km from Orlando International Airport, 8.9km from the Kia Center, and 8.8km from Church Street Station.
This self-catering unit offers air conditioning, parking, a smart TV, and sleeps one guest, providing towels, bed linen, and is within reasonable driving distance of other attractions including the Holy Land Experience and Addition Financial Arena.
Guesthouse In Mills 50 With Yard Walking To Bars - Winter Park, FL
9.8 288 reviews
Winter Park, FL
21/07 – 04/08
$127/nighttotal: $1778 (14 )

Guesthouse In Mills 50 With Yard Walking To Bars

1 1
B&B , Orlando
This mid-century modern guesthouse is situated near downtown Orlando, offering easy walking access to local bars and restaurants and a short Uber ride (approximately 1–8 km) to other attractions in Orlando and Winter Park.
The self-contained guest house, sleeping two, boasts a full kitchen with fridge, freezer and microwave, a private fenced yard with outdoor seating and fountain, plus a brand new air conditioning unit and August smart lock for keyless entry.
Large Studio Near The Airport, Downtown, Hospitals - Winter Park, FL
9.9 105 reviews
Winter Park, FL
28/06 – 18/07
$146/nighttotal: $2920 (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.
The Carriage House @ Oasis In Orlando - Winter Park, FL
9.8 56 reviews
Winter Park, FL
03/09 – 08/09
$178/nighttotal: $890 (5 )

The Carriage House @ Oasis In Orlando

1 2
B&B , Orlando
This Orlando apartment, near Downtown Orlando, offers easy access to Universal Studios (18 minutes/29km), Walt Disney World Resort (24 minutes/39km), and Orlando International Airport (20 minutes/32km).
The self-catering flat comprises one bedroom, one bathroom, sleeps two, and includes a queen-size memory foam bed, full kitchen with fridge, freezer and microwave, air conditioning, and a garden; nearby restaurants and shops are within walking distance.
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