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

College Park-orlando 5star Villa Oasis - Home Away From Home - Quiet Neighborhood-private Botanical - Winter Park, FL
No reviews

College Park-orlando 5star Villa Oasis - Home Away From Home - Quiet Neighborhood-private Botanical

B&B, Orlando
B&B. You will be in Orlando.
Services and facilities include free parking, a garden and an iron. This accommodation is very convenient for families.

Best Winter Park, FL bed and breakfasts with a garden

Estudio Privado Y Acogedor - Winter Park, FL
9.4 22 reviews

Estudio Privado Y Acogedor

B&B, Azalea Park
This elegant guest suite is situated in the quiet Azalea Park neighbourhood, offering a peaceful retreat with a private entrance for convenience.
This one-bedroom, one-bathroom apartment accommodates two guests and features a full kitchen, air conditioning, and parking, with essential appliances including a tea maker, mini-fridge, and microwave.
The Tree House @ Oasis In Orlando - Winter Park, FL
9.7 48 reviews

The Tree House @ Oasis In Orlando

B&B, Orlando
This Orlando treehouse apartment is situated near Downtown Orlando, a 29km drive from Universal Studios Florida, 39km from Walt Disney World Resort, and 32km from Orlando International Airport.
The self-catering dwelling boasts a queen-size bed, full bathroom, and kitchen with fridge, freezer, and microwave, sleeping up to two guests, and features a garden and parking.
Comfortable 2-bedroom Place Full Kitchen - Winter Park, FL
9.7 185 reviews

Comfortable 2-bedroom Place Full Kitchen

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.
Luxury Tiny Home 2 Miles From Downtown Orlando - Winter Park, FL
9.6 194 reviews

Luxury Tiny Home 2 Miles From Downtown Orlando

B&B, Orlando
This charming bed and breakfast is located just 3.2 kilometres from Orlando's city centre, offering easy access to attractions like Church Street Station, Amway Center, and Camping World Stadium. The property has consistently received excellent ratings for cleanliness, location, and guest satisfaction.
The cosy guesthouse features a single bedroom and bathroom, spanning a total of 9 square metres. Guests can enjoy a range of amenities including a fully equipped kitchen, air conditioning, a garden, and free Wi-Fi, making it a comfortable and convenient choice for travellers.

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.

Popular destinations

Best Winter Park, FL bed and breakfasts with parking

Private Unit Near Downtown Orlando & Ucf - Winter Park, FL
9.5 64 reviews

Private Unit Near Downtown Orlando & Ucf

B&B, Azalea Park
This Azalea Park guesthouse, conveniently located within 19km of Downtown Orlando and 16km from Winter Park, offers easy access to Universal Studios and International Drive, all within a 32km radius.
The self-contained studio, sleeping two guests, features a fully equipped kitchen with microwave, oven and air fryer, a queen-size bed, 65" Roku TV, and a private balcony; on-site parking is provided.
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.
Private Entrance/bathroom 10 Min From Dt Orlando - Winter Park, FL
9.9 242 reviews

Private Entrance/bathroom 10 Min From Dt Orlando

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.
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.

Best Winter Park, FL bed and breakfasts with air conditioning

Guesthouse, Walk To Baldwin Lake - 1 Mi To Dining - Winter Park, FL
9.7 301 reviews

Guesthouse, Walk To Baldwin Lake - 1 Mi To Dining

B&B, Orlando
This Orlando studio apartment is situated near Baldwin Park, a short walk from Baldwin Park Lake and the Cady Way Trail.
The self-contained unit, sleeping two guests, boasts a 43" smart TV, kitchenette, private patio, and oversized bathroom with a rain shower; enjoy nearby dining and jogging opportunities.
Spring Lake Getaway Suite (Detached Guest House) - Winter Park, FL
No 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.
St. Hemingway Suite - Winter Park, FL
9.9 358 reviews

St. Hemingway Suite

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.
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.
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