Bed and Breakfast and Inn in Winter Park, FL

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

Best Winter Park, FL bed and breakfasts with breakfast included

Downtown Lake Eola Historic House 1 Or 2 Bed - Winter Park, FL
9.5 813 reviews
Winter Park, FL
03/07 – 10/07
$191/nighttotal: $1337 (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.

Best Winter Park, FL bed and breakfasts with a garden

A Suite Retreat With A Garden View In The City - Winter Park, FL
10 459 reviews
Winter Park, FL
03/09 – 08/09
$125/nighttotal: $625 (5 )

A Suite Retreat With A Garden View In The City

1 2
B&B , Orlando
This College Park guest house is situated near downtown Orlando, a short 5-minute (8 km) drive away, offering easy access to local restaurants and attractions.
The self-contained one-bedroom suite sleeps two, features a kitchenette with microwave, and boasts a private patio plus access to a shared bamboo patio, a queen-size bed, Smart TV and Wi-Fi.
Guesthouse, Walk To Baldwin Lake - 1 Mi To Dining - Winter Park, FL
9.7 292 reviews
Winter Park, FL
28/06 – 18/07
$118/nighttotal: $2360 (20 )

Guesthouse, Walk To Baldwin Lake - 1 Mi To Dining

1 1
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.
St. Hemingway Suite - Winter Park, FL
9.9 354 reviews
Winter Park, FL
03/07 – 10/07
$147/nighttotal: $1029 (7 )

St. Hemingway Suite

1 2
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.
Comfortable 2-bedroom Place Full Kitchen - Winter Park, FL
9.7 179 reviews
Winter Park, FL
28/06 – 18/07
$150/nighttotal: $3000 (20 )

Comfortable 2-bedroom Place Full Kitchen

1 1
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.

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.

Destinations nearby

Best Winter Park, FL bed and breakfasts with parking

Luxury Tiny Home 2 Miles From Downtown Orlando - Winter Park, FL
9.6 192 reviews
Winter Park, FL
08/01 – 29/01
$226/nighttotal: $4746 (21 )

Luxury Tiny Home 2 Miles From Downtown Orlando

1 2
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.
Luxury Suite Near Disney & Downtown Orlando - Winter Park, FL
9.8 282 reviews
Winter Park, FL
28/06 – 18/07
$116/nighttotal: $2320 (20 )

Luxury Suite Near Disney & Downtown Orlando

1 1
B&B , Orlando
This one-bedroom guest suite is situated in a quiet residential neighbourhood just 5 kilometres from Downtown Orlando, offering easy access to the city's attractions, including Universal Studios, Walt Disney World Resort and SeaWorld.
The self-catering apartment features a fully equipped kitchen, a private entrance and a cosy front porch, perfect for relaxing after a day exploring the theme parks.
Centrally Located Guest Suite Retreat - Winter Park, FL
Winter Park, FL
23/06 – 28/06
$156/nighttotal: $780 (5 )

Centrally Located Guest Suite Retreat

1 2
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.
Tiny Unit In Cottage In The Middle Of Downtown - Winter Park, FL
Winter Park, FL
28/07 – 01/08
$123/nighttotal: $492 (4 )

Tiny Unit In Cottage In The Middle Of Downtown

1 2
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

St. Augustine Suite - Winter Park, FL
9.9 387 reviews
Winter Park, FL
28/06 – 18/07
$132/nighttotal: $2640 (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.
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 47 reviews
Winter Park, FL
28/07 – 01/08
$235/nighttotal: $940 (4 )

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

1 2
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.
Guesthouse - Winter Park, FL
9.6 70 reviews
Winter Park, FL
28/06 – 18/07
$118/nighttotal: $2360 (20 )

Guesthouse

1 1
B&B , Orlando
This Orlando guesthouse is situated in a tranquil residential area bordering Winter Park and Baldwin Park, offering easy access to attractions such as Park Avenue (approx. 22.5 km), Mills Avenue (approx. 22.5 km), and Downtown Orlando (approx. 24 km).
The self-catering studio, sleeping two guests, features a well-equipped kitchen (minus an oven), a west-facing patio, and proximity to the Cady Way Trail and Baldwin Park Lake, ideal for walking and cycling.
D` Love Cave  By Airport, Downtown & Theme Park - Winter Park, FL
Winter Park, FL
28/07 – 01/08
$149/nighttotal: $596 (4 )

D` Love Cave By Airport, Downtown & Theme Park

1 2
B&B , Azalea Park
This non-smoking guesthouse in Azalea Park, Orlando, offers convenient access to entertainment, situated just 11 minutes by car from the Kia Center and 21 minutes from the Florida Mall, with proximity to outdoor pursuits.
This B&B accommodates up to three guests, providing air conditioning, Wi-Fi, and on-site parking, alongside a kitchen and one bathroom for a comfortable stay.
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