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 in Winter Park, FL

Best Winter Park, FL bed and breakfasts with breakfast included

Bungalow Near Universal, Disney, And Downtown Orlando - Winter Park, FL
9.0 2 reviews
Winter Park, FL
08/01 – 29/01
SG$201/nighttotal: SG$4221 (21 )

Bungalow Near Universal, Disney, And Downtown Orlando

1 2
B&B , Orlando
This B&B is located in a residential district of Orlando, offering a peaceful alternative to the busy tourist zones and convenient access to the city's major theme parks and entertainment venues.
This 37 square meter guesthouse accommodates up to three guests with one bedroom and one bathroom, featuring complimentary Wi-Fi, air conditioning, a kitchen with a fridge and microwave oven, on-site parking, and a garden with a children's playground.

Best Winter Park, FL bed and breakfasts with a garden

Cozy Orlando Studio • Private Entrance • Queen Bed - Winter Park, FL
9.9 233 reviews
Winter Park, FL
28/06 – 18/07
SG$107/nighttotal: SG$2140 (20 )

Cozy Orlando Studio • Private Entrance • Queen Bed

1 1
B&B , Orlando
This Orlando self-catering apartment boasts a secluded location near Camping World Stadium and Downtown Orlando, within a 16km radius, and is approximately 24km from Universal Studios and 48km from Walt Disney World.
The property offers a queen-sized bed, a fully equipped kitchenette including a microwave and mini-fridge, a private bathroom with a bidet, a full-sized washer and dryer, free parking, and accommodates two guests, enjoying a private entrance and tropical backyard views.
St. Augustine Suite - Winter Park, FL
9.9 387 reviews
Winter Park, FL
28/06 – 18/07
SG$122/nighttotal: SG$2440 (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.
Modern Cuartito By Winter Park - Winter Park, FL
9.5 33 reviews
Winter Park, FL
03/07 – 31/07
SG$116/nighttotal: SG$3248 (28 )

Modern Cuartito By Winter Park

1 2
B&B , Maitland
This Maitland Cuartito offers a peaceful escape, situated north of Downtown Orlando and within 4.3km of the Winter Park Scenic Boat Tour.
The self-contained apartment sleeps two, features a fully equipped kitchen with dishwasher, a private garden, and keyless entry, plus a shared laundry room.
The Tree House @ Oasis In Orlando - Winter Park, FL
9.7 42 reviews
Winter Park, FL
03/09 – 08/09
SG$160/nighttotal: SG$800 (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.

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.

Destinations nearby

Best Winter Park, FL bed and breakfasts with parking

Quiet Garden Retreat Downtown Orlando - Private Apartment, Shared Pool And Patio - Winter Park, FL
9.6 17 reviews
Winter Park, FL
03/09 – 08/09
SG$429/nighttotal: SG$2145 (5 )

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

1 2
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.
Peace In Mind Private Room - Winter Park, FL
Winter Park, FL
28/06 – 18/07
SG$105/nighttotal: SG$2100 (20 )

Peace In Mind Private Room

1 1
B&B , Rio Pinar
This B&B in Orlando's Rio Pinar district is situated 9 kilometres from the Kia Centre and 10 kilometres from Camping World Stadium, with Orlando International Airport located 9 kilometres away.
This accommodation offers one bedroom and one bathroom for two guests, with free Wi-Fi, air conditioning, and on-site parking provided.
L12 Private Room With Smart Tv Near Everything - Winter Park, FL
8.3 13 reviews
Winter Park, FL
28/06 – 18/07
SG$62/nighttotal: SG$1240 (20 )

L12 Private Room With Smart Tv Near Everything

1 1
B&B , Orlando
This Orlando guesthouse is conveniently located near major attractions, approximately 8-21 kilometres from venues such as Camping World Stadium, Church Street Station, and the Florida Mall.
The single-bedroom, single-bathroom property sleeps one guest and includes a smart TV, air conditioning, parking, towels, and bed linen; it's a non-smoking establishment.
10 Minutes From Universal - Relaxing Guest Suite - Winter Park, FL
8.7 10 reviews
Winter Park, FL
03/09 – 08/09
SG$137/nighttotal: SG$685 (5 )

10 Minutes From Universal - Relaxing Guest Suite

1 2
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.

Best Winter Park, FL bed and breakfasts with air conditioning

Guesthouse, Walk To Baldwin Lake - 1 Mi To Dining - Winter Park, FL
9.7 292 reviews
Winter Park, FL
28/06 – 18/07
SG$108/nighttotal: SG$2160 (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.
Private Boutique Suite W/ Pool & Hot Tub Access - Winter Park, FL
Winter Park, FL
28/07 – 01/08
SG$136/nighttotal: SG$544 (4 )

Private Boutique Suite W/ Pool & Hot Tub Access

1 2
B&B , Goldenrod
This studio apartment, Nook Ave, is situated in a tranquil cul-de-sac in East Winter Park, offering a peaceful retreat just a short walk from Park Avenue's amenities.
This accommodation for four guests features a queen bed, sofa bed, kitchenette with an electric cooktop and air fryer, in-suite laundry, a private patio, and access to a shared garden with a swimming pool, hot tub, and fire pit.
Large Studio Near The Airport, Downtown, Hospitals - Winter Park, FL
9.9 105 reviews
Winter Park, FL
28/06 – 18/07
SG$135/nighttotal: SG$2700 (20 )

Large Studio Near The Airport, Downtown, Hospitals

1 1
B&B , Orlando
This Orlando studio apartment is situated in a residential neighbourhood, approximately 16km from Downtown Orlando, 24km from Orlando International Airport, and within 32-48km of Universal and Disney theme parks.
The self-contained apartment sleeps four guests, offering a queen-size memory foam bed, a full-size sofa bed, a well-equipped kitchenette with a mini-fridge, and a smart TV with streaming services; on-site parking is available.
Secluded 1br Oasis W/private Patio | Walk To Eola - Winter Park, FL
9.6 62 reviews
Winter Park, FL
28/06 – 18/07
SG$109/nighttotal: SG$2180 (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.
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