Bed and breakfast in Winter Park, FL

30 available b&b offers

7 nights
2
1
  • airbnb
  • booking
  • stayz
  • expedia
  • hotelscom
  • tripadvisor
  • tripcom
  • agoda
  • homestay
  • tuivillas
  • hostelworld
  • hotelopia
Winter Park, FL bed and breakfast
Choose the perfect holiday 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

Walkable College Park Suite With Full Kitchen - Winter Park, FL
9.9 219 reviews

Walkable College Park Suite With Full Kitchen

hotel, 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.

Best Winter Park, FL bed and breakfasts with a garden

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.
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.
Cozy Suite In Orlando - 17 Min From Airport - Winter Park, FL
9.7 100 reviews

Cozy Suite In Orlando - 17 Min From Airport

B&B, Azalea Park
This Azalea Park guest suite enjoys a central Orlando location, offering easy access to Universal Studios, Disney World, SeaWorld, and the University of Central Florida, all within a 24-43 kilometre radius.
The self-contained apartment features a semi-kitchen, one bedroom, one bathroom, sleeps two guests, and includes private parking, fast Wi-Fi, and essential amenities such as shampoo, towels, and coffee-making facilities.
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.

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.

Popular destinations

Best Winter Park, FL bed and breakfasts with parking

Winter Park Charm - Winter Park, FL
9.9 199 reviews

Winter Park Charm

B&B, Winter Park
This charming bed and breakfast is located in the Winter Park district of Orlando, just a short drive from Church Street Station, Amway Center, and Camping World Stadium. The property enjoys excellent user ratings for location, cleanliness, and overall experience.
The two-bedroom guesthouse offers 46 square metres of space, comfortably accommodating up to four guests. Amenities include air conditioning, a terrace, a garden, free Wi-Fi, a fully equipped kitchen, and a private bathroom.
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.
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.
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.

Best Winter Park, FL bed and breakfasts with air conditioning

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.
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.

Highly Recommended Luxury Bed and Breakfasts in Winter Park, FL

Find luxury B&Bs in Winter Park, FL for a charming premium retreat with personal service.

Tiny Home Barn Style In Backyard With Animals - Winter Park, FL
9.7 34 reviews

Tiny Home Barn Style In Backyard With Animals

B&B, Orlando

Check Out Bed and Breakfasts in the City Centre in Winter Park, FL

Wake up in the heart of it all; choose a charming, centrally located B&B in Winter Park, FL and leave the taxis behind.

Bungalow Near Universal, Disney, And Downtown Orlando - Winter Park, FL
9.3 3 reviews

Bungalow Near Universal, Disney, And Downtown Orlando

B&B, Orlando
Winter Park Charm - Winter Park, FL
9.9 199 reviews

Winter Park Charm

B&B, Winter Park
Guesthouse - Winter Park, FL
9.6 83 reviews

Guesthouse

B&B, Orlando
The Carriage House @ Oasis In Orlando - Winter Park, FL
9.8 56 reviews

The Carriage House @ Oasis In Orlando

B&B, Orlando

Best Winter Park, FL bed and breakfasts with a pool

Among the 30 accommodations in Winter Park, FL, here are the 4 best B&B with a pool

Walkable College Park Suite With Full Kitchen - Winter Park, FL
9.9 219 reviews

Walkable College Park Suite With Full Kitchen

hotel, Orlando
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
Pily's Vintage Stay Room Full Bed - Winter Park, FL
8.8 8 reviews

Pily's Vintage Stay Room Full Bed

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

Lakefront Downtown Orlando House Suite

B&B, Orlando
©2026 cozycozy.com