Bed and Breakfast and Inn in Winter Park, FL

30 available b&b offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • priceline
  • tripadvisor
  • tripcom
  • sonder
  • homestay
  • hostelworld
  • hotelscom
  • agoda
Winter Park, FL B&B
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

30 Bed and Breakfasts and Inn in Winter Park, FL

Best Winter Park, FL bed and breakfasts with breakfast included

Tiny Hidden Cottage - Winter Park, FL
9.5 120 reviews

Tiny Hidden Cottage

B&B, Longwood
The Hidden Tiny Cottage II is located in Longwood, offering a secluded retreat on the back side of a property on Beach Ave. The cottage has received excellent ratings for its cleanliness, location, and overall experience.
This charming cottage offers a comfortable and private stay for two guests. It features a fully equipped kitchen, air conditioning, a Jacuzzi, a garden, a spa, a fitness centre, and parking, making it a perfect choice for a relaxing getaway.

Best Winter Park, FL bed and breakfasts with a garden

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.
Lakefront Downtown Orlando House Suite - Winter Park, FL
9.9 70 reviews

Lakefront Downtown Orlando House Suite

B&B, Orlando
This lakefront B&B offers private guest quarters in downtown Orlando, providing panoramic skyline views and direct lake access within 1 kilometre of the city's core attractions.
This accommodation sleeps up to six guests across one bedroom and a living area with two sofa beds, featuring a kitchenette with a fridge, freezer, and microwave, air conditioning, a swimming pool, garden, parking, and a basketball hoop.
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.
Quiet Garden Retreat Downtown Orlando - Private Apartment, Shared Pool And Patio - Winter Park, FL
9.6 17 reviews

Quiet Garden Retreat Downtown Orlando - Private Apartment, Shared Pool And Patio

B&B, Orlando
This charming bed and breakfast is located in Lake Eola Heights, a peaceful neighbourhood just half a kilometre from Orange Avenue and within easy reach of Orlando's main attractions. The property has received excellent reviews from previous guests, highlighting its tranquil setting and convenient location.
The guest house offers a single bedroom with one bathroom, comfortably accommodating up to two guests. Guests can enjoy a range of amenities, including a swimming pool, a garden, and a terrace, perfect for relaxing and soaking up the Florida sunshine.

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

Atmospheric Studio In The Garden - Winter Park, FL
9.9 261 reviews

Atmospheric Studio In The Garden

B&B, Winter Park
This Winter Park studio apartment is situated in a peaceful residential area, a short drive from Park Avenue and Rollins College.
The self-contained unit, sleeping up to three guests, features a fully equipped kitchenette with a dishwasher, a private garden, and dedicated parking; in-unit laundry facilities are also available for longer stays.
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.
College Park 1 Bed, 1 Bath Gem. - Winter Park, FL
9.4 223 reviews

College Park 1 Bed, 1 Bath Gem.

B&B, Orlando
This College Park apartment is conveniently located 8-16km from both Orlando city centre and Winter Park, and approximately 48km from Walt Disney World.
The self-catering unit features one bedroom, one bathroom, sleeps three (with extra beds available on request), and includes a kitchenette with microwave/convection oven/air fryer, in-unit washer/dryer (for stays over five days), and a private parking space.
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.

Best Winter Park, FL bed and breakfasts with air conditioning

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.
The Bungalow - Winter Park, FL
9.9 407 reviews

The Bungalow

B&B, Altamonte Springs
This Altamonte Springs bungalow is conveniently located near Sanlando Park, offering easy access to walking trails and sports facilities, and is within 48 kilometres of Florida's beaches and natural springs.
The self-contained cottage provides a queen-sized bed, kitchenette, private bathroom, and can accommodate up to two guests, with an air mattress available for extra visitors; keyless entry, private patio, and off-street parking are also included.
©2026 cozycozy.com