Bed and breakfast in Winter Park, FL

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

Best Winter Park, FL bed and breakfasts with breakfast included

College Park-orlando 5star Villa Oasis - Home Away From Home - Quiet Neighborhood-private Botanical - Winter Park, FL
No reviews

College Park-orlando 5star Villa Oasis - Home Away From Home - Quiet Neighborhood-private Botanical

B&B, Orlando
B&B. This accommodation is based in Orlando.
Services and facilities: a kitchen, an iron and a fridge. Take advantage of the air conditioning in this accommodation!

Best Winter Park, FL bed and breakfasts with a garden

Luxury Tiny Home 2 Miles From Downtown Orlando - Winter Park, FL
9.6 195 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.
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

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

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.
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.
Aqua Room At Bliss House - Winter Park, FL
9.9 103 reviews

Aqua Room At Bliss House

B&B, Orlando
This Orlando property, situated on a secluded 2-acre plot offering a tranquil escape from the theme parks, provides a private guest room with ensuite bathroom and private courtyard.
The self-contained unit features a shared kitchen, saltwater pool, hot tub, and access to a lake with paddleboards and a canoe; it sleeps two guests and offers enhanced security with electronic locks and CCTV.

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

College Park 1 Bed, 1 Bath Gem. - Winter Park, FL
9.4 220 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.
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.
Sunflower Suite At Bliss House - Winter Park, FL
9.9 111 reviews

Sunflower Suite At Bliss House

B&B, Orlando
Bliss House, a private suite near downtown Orlando, offers a tranquil lakefront escape with easy access to the city's attractions, though the precise distance isn't specified.
This self-contained property features a private entrance, bathroom, shared saltwater pool, hot tub, paddle boards, and a fully equipped shared kitchen, accommodating up to two guests.
Private Entrance/bathroom 10 Min From Dt Orlando - Winter Park, FL
9.9 242 reviews

Private Entrance/bathroom 10 Min From Dt Orlando

B&B, Eatonville
This charming bed and breakfast is located just 10 kilometres outside of downtown Orlando, making it a convenient base for exploring both the city and the nearby attractions. It's also just a short drive from Eatonville, a historic town with a rich cultural heritage. The accommodation has consistently received excellent reviews for its cleanliness, location, and overall experience.
The guest house offers a cosy and comfortable double room with a private bathroom, perfect for a couple's getaway. Guests can enjoy a range of amenities including air conditioning, free parking, and complimentary Wi-Fi.

Best Winter Park, FL bed and breakfasts with air conditioning

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.
Spring Lake Getaway Suite (Detached Guest House) - Winter Park, FL
10 101 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.
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.
Comfortable 2-bedroom Place Full Kitchen - Winter Park, FL
9.7 184 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.

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.

Guesthouse In Mills 50 With Yard Walking To Bars - Winter Park, FL
9.8 292 reviews

Guesthouse In Mills 50 With Yard Walking To Bars

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
9.8 221 reviews

Walkable College Park Suite With Full Kitchen

B&B, 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
Orlando Oasis In The Heart Of Thornton Park - Winter Park, FL
9.9 267 reviews

Orlando Oasis In The Heart Of Thornton Park

B&B, Orlando
Minutes To Kia Center + Breakfast. Kitchen. Pool. - Winter Park, FL
9.1 16 reviews

Minutes To Kia Center + Breakfast. Kitchen. Pool.

B&B, Altamonte Springs
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