Bed and Breakfast and Inn in Winter Park, FL

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

Best Winter Park, FL bed and breakfasts with breakfast included

Lakefront Artist's Loft - Isolate In Luxury! - Winter Park, FL
9.8 105 reviews

Lakefront Artist's Loft - Isolate In Luxury!

B&B, Orlando
This charming house is located in College Park, a short distance from the Camping World Stadium, Kia Center, and Orlando Science Center, offering easy access to the city's attractions. The property has consistently received excellent ratings for its location, cleanliness, and overall experience.
The house is a comfortable and well-equipped property, with 28 square metres of space and a capacity of two guests. Enjoy a private pool, a spa tub, and a garden, perfect for relaxing after a day of exploring the city.

Best Winter Park, FL bed and breakfasts with a garden

The Carriage House @ Oasis In Orlando - Winter Park, FL
9.8 56 reviews

The Carriage House @ Oasis In Orlando

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.
St. Augustine Suite - Winter Park, FL
9.9 394 reviews

St. Augustine Suite

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.
Downtown Lake Eola Historic House 1 Or 2 Bed - Winter Park, FL
9.5 822 reviews

Downtown Lake Eola Historic House 1 Or 2 Bed

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.
The Orlando Oasis - Winter Park, FL
No reviews

The Orlando Oasis

B&B, Pine Hills
The Orlando Oasis, a guest house in Pine Hills, is located in Orlando, offering a homestay experience with convenient access to local amenities. This B&B provides a comfortable and personal atmosphere with complimentary WiFi, air-conditioning, on-site private parking, tea and coffee making facilities, and a garden area for relaxation, accommodating up to three guests in one bedroom and one bathroom.

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.

Popular destinations

Best Winter Park, FL bed and breakfasts with parking

Nook Ave Studio| Priv Patio| Pool & Hot Tub Access - Winter Park, FL
10 11 reviews

Nook Ave Studio| Priv Patio| Pool & Hot Tub Access

B&B, Goldenrod
This studio apartment, Nook Ave, is situated in a tranquil cul-de-sac in East Winter Park, offering a peaceful retreat just a short walk from Park Avenue's amenities.
This accommodation for four guests features a queen bed, sofa bed, kitchenette with an electric cooktop and air fryer, in-suite laundry, a private patio, and access to a shared garden with a swimming pool, hot tub, and fire pit.
Room In Downtown Orlando! Close To Everything! - Winter Park, FL
10 1 review

Room In Downtown Orlando! Close To Everything!

B&B, Orlando
This downtown Orlando guest house is situated just over 1.6 kilometres from Church Street Station and Camping World Stadium, and a 17-minute walk from the Kia Centre.
The B&B offers one bedroom, one bathroom, and accommodation for two guests, with free Wi-Fi, air conditioning, and on-site parking provided by a private host.
Your Great Stay - Winter Park, FL
No reviews

Your Great Stay

B&B, Rio Pinar
This guest house in Rio Pinar, Orlando, is situated approximately 9 kilometres from Orlando International Airport and within a 24-kilometre radius of attractions including Church Street Station, Amway Centre, and Universal Studios Florida.
Offering a homestay experience for up to two guests in one bedroom with one bathroom, this property provides complimentary WiFi, air conditioning, and private on-site parking, with multilingual reception staff available.
A Space For Peace - Winter Park, FL
No reviews

A Space For Peace

B&B, Rio Pinar
This Orlando homestay in Rio Pinar is located approximately 9 kilometres from Orlando International Airport and 14 kilometres from Church Street Station and Amway Center.
This comfortable B&B offers a peaceful retreat with one bedroom and one bathroom for up to one guest, featuring free WiFi, air conditioning, on-site parking, and kitchen facilities, with Universal Islands of Adventure 24 kilometres away and Florida Mall 19 kilometres distant.

Best Winter Park, FL bed and breakfasts with air conditioning

Tiny Unit In Cottage In The Middle Of Downtown - Winter Park, FL
No reviews

Tiny Unit In Cottage In The Middle Of Downtown

B&B, 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.
College Park-orlando 5star Villa Oasis - Home Away From Home - Quiet Neighborhood-private Botanical Courtyard - Mins From Eola,dt, Winter Park - Free Parking & Ev Plug In - Winter Park, FL
9.9 46 reviews

College Park-orlando 5star Villa Oasis - Home Away From Home - Quiet Neighborhood-private Botanical Courtyard - Mins From Eola,dt, Winter Park - Free Parking & Ev Plug In

B&B, Orlando
The College Park-Orlando 5Star Guesthouse with Private Patio and Grill is located in the College Park district of Orlando, just 5km from Church Street Station and 6km from Amway Center, offering a peaceful retreat in a vibrant area. It has received excellent ratings for location, cleanliness, and overall experience.
The guesthouse features a single bedroom and bathroom, spanning 61 square metres and comfortably accommodating two guests. It offers a range of amenities, including a private patio with a grill, free bikes for exploring the neighbourhood, and a shared terrace with a barbecue.
Bungalow Near Universal, Disney, And Downtown Orlando - Winter Park, FL
9.3 3 reviews

Bungalow Near Universal, Disney, And Downtown Orlando

B&B, Orlando
This B&B is located in a residential district of Orlando, offering a peaceful alternative to the busy tourist zones and convenient access to the city's major theme parks and entertainment venues.
This 37 square meter guesthouse accommodates up to three guests with one bedroom and one bathroom, featuring complimentary Wi-Fi, air conditioning, a kitchen with a fridge and microwave oven, on-site parking, and a garden with a children's playground.
New Mid Century-modern Studio - Winter Park, FL
9.9 323 reviews

New Mid Century-modern Studio

B&B, Orlando
This College Park studio apartment is conveniently located near Edgwater Drive, a 24km drive from Orlando city centre, and within a 48km radius of major theme parks, also a short distance from the historic Dubsdread Golf Club.
The pet-friendly property, sleeping two guests, includes a kitchen with fridge, freezer and microwave, air conditioning, a private courtyard, laundry facilities and the use of two bikes (on request), all within walking distance of local restaurants and bars.
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