Bed and breakfast in Winter Park, FL

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Winter Park, FL bed and breakfast
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16 Bed and Breakfasts and Inn in Winter Park, FL

Best Winter Park, FL bed and breakfasts with breakfast included

G7 Private Room With Smart Tv Near Everything - Winter Park, FL
9.0 24 reviews
Winter Park, FL
21/07 – 04/08
A$68/nighttotal: A$952 (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.

Best Winter Park, FL bed and breakfasts with a garden

Secluded 1br Oasis W/private Patio | Walk To Eola - Winter Park, FL
9.6 60 reviews
Winter Park, FL
28/06 – 18/07
A$121/nighttotal: A$2420 (20 )

Secluded 1br Oasis W/private Patio | Walk To Eola

1 1
B&B , Orlando
This Orlando guest house is situated near downtown, within walking distance of the city centre and nestled in a tropical setting.
The self-contained apartment sleeps two, features a private patio, access to bicycles and a kayak, and offers a shared washer/dryer; optional desk and chair are available for those working remotely.
The Tiny Cottage In The Springs - Winter Park, FL
9.8 26 reviews
Winter Park, FL
21/07 – 04/08
A$612/nighttotal: A$8568 (14 )

The Tiny Cottage In The Springs

1 1
B&B , Altamonte Springs
This charming bed and breakfast is situated just under 3 kilometres from Altamonte Mall and a little over 3 kilometres from Cranes Roost Park, offering easy access to shopping, dining, and outdoor recreation. It has received excellent user ratings, making it a popular choice for travellers.
The inn features a garden, lobby fireplace, and charcoal grills for outdoor relaxation and socialising. Guests can also enjoy free self-parking, a front-desk safe, and change of towels upon request.
St. Hemingway Suite - Winter Park, FL
9.9 354 reviews
Winter Park, FL
28/06 – 18/07
A$134/nighttotal: A$2680 (20 )

St. Hemingway Suite

1 1
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.
Guest Suite! Key West In Altamonte Springs! - Winter Park, FL
9.9 439 reviews
Winter Park, FL
17/06 – 23/06
A$142/nighttotal: A$852 (6 )

Guest Suite! Key West In Altamonte Springs!

1 1
B&B , Altamonte Springs
This Altamonte Springs guest suite, a short walk from Altamonte Mall, offers convenient access to Walt Disney World (approx. 56km) and the Atlantic coast (approx. 72km).
The self-contained ground-floor apartment features a queen-size bed, wet bar, mini-fridge, private courtyard, and driveway parking, sleeping up to two guests in its 30 square metre space.

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 can't miss the charming Park Avenue district with its art galleries, boutiques, and cafes. Take a stroll around the scenic Rollins College campus, and be sure to visit the beautiful Mead Garden, a 50-acre botanical garden with stunning walking trails and a variety of plant life.
  • 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 Rm -2 Downtown Orlando- Owl Cottage Room 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, offering a vibrant atmosphere with plenty of restaurants and shops. For a quieter stay, consider the Hannibal Square district, known for its historic charm and lovely homes.
  • 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 hot, humid summers and mild winters. You can enjoy outdoor activities year-round, but be prepared for high humidity and occasional thunderstorms 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?

    You'll find plenty of charming cafes and restaurants near many bed and breakfasts. Try the popular The Wine Room for a sophisticated atmosphere, or the casual and friendly Park Avenue Eatery for a relaxed meal.
  • 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 events like the Winter Park Sidewalk Art Festival, a major event featuring over 300 artists. The Charles Hosmer Morse Museum of American Art is also a must-visit for art enthusiasts.
  • 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 a short hike, try the scenic trail around the Kraft Azalea Garden. For a longer adventure, head to the Wekiwa Springs State Park, offering over 12 km of trails through beautiful Florida scenery.
  • What are the best bed and breakfasts with parking in Winter Park, FL?

    The Oasis W/pool Access En-suite #1, Sun Room and Rm -2 Downtown Orlando- Owl Cottage 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?

    Most bed and breakfasts in Winter Park offer a continental breakfast, free Wi-Fi, and comfortable guest rooms. Some may also have amenities like swimming pools, hot tubs, or gardens.

Destinations nearby

Best Winter Park, FL bed and breakfasts with parking

Charming Getaway Near Downtown & Disney - Winter Park, FL
9.9 216 reviews
Winter Park, FL
03/07 – 31/07
A$124/nighttotal: A$3472 (28 )

Charming Getaway Near Downtown & Disney

1 2
B&B , Orlando
This private guest suite is located in a quiet, family-friendly neighbourhood just a few kilometres from Downtown Orlando, with easy access to restaurants, shops, parks, and major attractions. The accommodation has received excellent ratings for its cleanliness, location, and overall experience.
The suite has one bedroom and one bathroom, comfortably accommodating two guests. Guests can enjoy a fully equipped kitchen, a private entrance, a shared pool, and a garden, along with amenities such as air conditioning, internet access, and a smart TV with Netflix.
Tiny Home Barn Style In Backyard With Animals - Winter Park, FL
9.7 30 reviews
Winter Park, FL
17/06 – 23/06
A$132/nighttotal: A$792 (6 )

Tiny Home Barn Style In Backyard With Animals

1 1
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.
Centrally Located Guest Suite Retreat - Winter Park, FL
Winter Park, FL
17/06 – 23/06
A$187/nighttotal: A$1122 (6 )

Centrally Located Guest Suite Retreat

1 1
B&B , Orlando
This Orlando guest suite, situated 2.3 kilometres from downtown, offers convenient access to attractions including Camping World Stadium (8.3 km), Holy Land Experience (9.7 km), and Church Street Station (5 km).
The 15-square-metre self-catering unit features one bedroom, one bathroom, sleeps two guests, and includes free Wi-Fi, private parking, and air conditioning.
The Tree House @ Oasis In Orlando - Winter Park, FL
9.7 42 reviews
Winter Park, FL
03/09 – 08/09
A$177/nighttotal: A$885 (5 )

The Tree House @ Oasis In Orlando

1 2
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.

Best Winter Park, FL bed and breakfasts with air conditioning

Feast On Modern Southern Fare Art Hamilton’s - Winter Park, FL
10 3 reviews
Winter Park, FL
11/08 – 13/08
A$488/nighttotal: A$976 (2 )

Feast On Modern Southern Fare Art Hamilton’s

1 2
B&B , Winter Park
This guest house is located centrally in Winter Park, providing easy access to local attractions within a 1 kilometre radius.
The Classic Queen room offers 33 square metres of space with two Queen beds, accommodating up to four guests, and includes complimentary WiFi, air conditioning, and a fitness centre.
Quiet Oasis In Lovely Neighborhood - Winter Park, FL
9.8 308 reviews
Winter Park, FL
03/09 – 08/09
A$177/nighttotal: A$885 (5 )

Quiet Oasis In Lovely Neighborhood

1 2
B&B , Orlando
This one-bedroom, one-bathroom house is situated in Southern Oaks, just 1.8km from Lake Conway and within 5km of Orlando Regional Medical Center and Winnie Palmer Hospital for Women and Babies. The property has consistently received excellent ratings for its location, cleanliness, and overall user experience.
The house has a private pool, a spa tub, and a fenced-in yard. Guests can enjoy modern amenities such as a refrigerator, microwave, and patio, as well as complimentary Wi-Fi and a washing machine.
St. Augustine Suite - Winter Park, FL
9.9 387 reviews
Winter Park, FL
28/06 – 18/07
A$135/nighttotal: A$2700 (20 )

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.
Downtown Lake Eola Historic House 1 Or 2 Bed - Winter Park, FL
9.5 813 reviews
Winter Park, FL
03/07 – 10/07
A$194/nighttotal: A$1358 (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.
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