Bed and Breakfast in Winter Park, FL

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Winter Park, FL bed and breakfast
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30 Bed and Breakfasts in Winter Park, FL

Best Winter Park, FL bed and breakfasts with breakfast included

Guest Suite Near Full Sail In Winter Park - Winter Park, FL
9.7 245 reviews

Guest Suite Near Full Sail In Winter Park

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.

Best Winter Park, FL bed and breakfasts with a garden

“The Clementine” Boho Home In Orlando’s Food Scene - Winter Park, FL
No reviews

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

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.
Lakefront Studio Apartment (Private Entrance) - Winter Park, FL
10 485 reviews

Lakefront Studio Apartment (Private Entrance)

B&B, Orlando
This studio apartment is situated just a few kilometres from downtown Orlando, offering a peaceful retreat in a residential area with easy access to the lake and pool. The property has consistently received excellent ratings for its location, cleanliness and overall guest experience.
The self-contained apartment comfortably sleeps two guests and features a private outdoor shower, hot tub and canoe for your enjoyment. Guests can also relax in the tropical garden setting with a pool and spa, or unwind inside with modern amenities like a 65-inch TV, Bose Wave Radio and a Mitsubishi air conditioning unit.
Ranch Style Tiny Home Retreat Near Downtown Orlando - Winter Park, FL
9.7 32 reviews

Ranch Style Tiny Home Retreat Near Downtown Orlando

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.
Historic Lakefront Guesthouse - Winter Park, FL
10 13 reviews

Historic Lakefront Guesthouse

B&B, Edgewood
This charming bed and breakfast is ideally located in Orlando, just a short distance from major attractions, the city centre and several lakes and parks. It has received excellent reviews from previous guests, highlighting its comfortable and welcoming atmosphere.
The property spans 102 square metres and comfortably accommodates up to five guests in its single bedroom and bathroom. Guests can enjoy a range of amenities and activities, including a private balcony, a spacious garden, a fire pit, a fitness centre, and the option to bring along their canine companion.

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 day trip, you've got to see the charming Park Avenue district with its shops and restaurants, and the scenic Rollins College campus. And don't miss the beautiful Winter Park Scenic Boat Tour on the chain of lakes, it's a real highlight.
  • 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 Park Avenue district is a popular choice for bed and breakfasts, as it's close to the action. You can also find some lovely options in the more residential areas like Hannibal Square, where it's a bit quieter.
  • 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 most of the year. Summers are hot and rainy, while winters are mild and sunny. You can usually enjoy outdoor activities year-round, but be prepared for some humidity in 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?

    The Park Avenue district has lots of great restaurants for solo travellers, like The Wine Room or Luma on Park. If you're looking for something more casual, there are plenty of cafes and bistros around too.
  • 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 arts scene, with the Charles Hosmer Morse Museum of American Art and the Albin Polasek Museum & Sculpture Gardens being popular choices. The Winter Park Sidewalk Art Festival is a must-see event 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 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?

    There aren't many hiking trails in Winter Park itself, but you can find some good ones in nearby Wekiwa Springs State Park. The scenic Wekiwa Springs Trail is a great option for a leisurely walk.
  • 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?

    Most bed and breakfasts in Winter Park offer a continental breakfast, free Wi-Fi, and private bathrooms. Some also have swimming pools, gardens, and even bike rentals.

Popular destinations

Best Winter Park, FL bed and breakfasts with parking

10 Minutes From Universal - Relaxing Guest Suite - Winter Park, FL
8.5 11 reviews

10 Minutes From Universal - Relaxing Guest Suite

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.
Joe's Grotto - Winter Park, FL
9.5 78 reviews

Joe's Grotto

B&B, Orlando
This Orlando guesthouse offers self-check-in/check-out and sleeps three, featuring a queen bed and bunk beds; its precise location within Orlando is unspecified.
The pet-friendly property includes a fridge, freezer, microwave, washer/dryer, two TVs, a grotto shower, and private outdoor space for barbecues.
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
9.8 47 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.
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.

Best Winter Park, FL bed and breakfasts with air conditioning

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.
Spring Lake Getaway Suite (Detached Guest House) - Winter Park, FL
10 101 reviews

Spring Lake Getaway Suite (Detached Guest House)

B&B, Altamonte Springs
This charming guesthouse is situated in a gated community on Spring Lake in Altamonte Springs, just 5km from the Altamonte Mall and a short drive to downtown Orlando (17km), Universal and Disney Parks (35km), and natural springs (30km). The property has consistently received excellent guest ratings, highlighting its comfortable and romantic atmosphere.
The guesthouse features a private entrance, two balconies, and a dedicated parking space, making it ideal for couples seeking a peaceful getaway. It boasts a king-sized bed, a private bathroom, and a kitchen equipped with a fridge and microwave, along with high-speed internet access. Guests can enjoy the natural beauty of Spring Lake and its recreational activities, or explore the nearby Rock Springs Run State Reserve.
Stylish Location Netflix Parking Wifi - Winter Park, FL
9.7 238 reviews

Stylish Location Netflix Parking Wifi

B&B, Azalea Park
This one-bedroom apartment is located in Azalea Park, just 1.9 kilometres from AdventHealth East Orlando and 2.2 kilometres from Ventura Country Club. It has excellent user, location and cleanliness ratings, making it a great option for travellers visiting the area.
The apartment comfortably sleeps two guests and features a kitchenette with a fridge and microwave. It also has a washing machine, Smart TV, coffee/tea maker, and electric kettle, as well as access to a swimming pool, parking, and a water park.
Pily's Vintage Stay Room Full Bed - Winter Park, FL
8.8 8 reviews

Pily's Vintage Stay Room Full Bed

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.
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