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.
9.9 354 reviews
Winter Park, FL
28/06 – 18/07
NZ$162/nighttotal: NZ$3240 (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.
9.8 288 reviews
Winter Park, FL
21/07 – 04/08
NZ$157/nighttotal: NZ$2198 (14 )
Guesthouse In Mills 50 With Yard Walking To Bars
1 1
B&B , Orlando
This mid-century modern guesthouse is situated near downtown Orlando, offering easy walking access to local bars and restaurants and a short Uber ride (approximately 1–8 km) to other attractions in Orlando and Winter Park. The self-contained guest house, sleeping two, boasts a full kitchen with fridge, freezer and microwave, a private fenced yard with outdoor seating and fountain, plus a brand new air conditioning unit and August smart lock for keyless entry.
9.8 56 reviews
Winter Park, FL
03/09 – 08/09
NZ$218/nighttotal: NZ$1090 (5 )
The Carriage House @ Oasis In Orlando
1 2
B&B , Orlando
This Orlando apartment, near Downtown Orlando, offers easy access to Universal Studios (18 minutes/29km), Walt Disney World Resort (24 minutes/39km), and Orlando International Airport (20 minutes/32km). The self-catering flat comprises one bedroom, one bathroom, sleeps two, and includes a queen-size memory foam bed, full kitchen with fridge, freezer and microwave, air conditioning, and a garden; nearby restaurants and shops are within walking distance.
10 459 reviews
Winter Park, FL
03/09 – 08/09
NZ$154/nighttotal: NZ$770 (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.
9.9 387 reviews
Winter Park, FL
17/06 – 23/06
NZ$173/nighttotal: NZ$1038 (6 )
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.
9.8 116 reviews
Winter Park, FL
17/06 – 23/06
NZ$165/nighttotal: NZ$990 (6 )
Orlando, Spacious, Quiet, Centrally Located, Suite
1 1
B&B , Casselberry
This Casselberry ground-floor suite, offering a private entrance and located approximately 56km from Walt Disney World Resort, 43km from Universal Orlando Resort, 37km from the Orange County Convention Center, and 72km from the beaches, provides convenient access to major Orlando attractions. The self-catering apartment sleeps four guests comfortably in a king-size bed, queen-size sofa bed, and queen air mattress, and features a well-equipped kitchen, air conditioning, private garden, parking, and excellent guest ratings.
9.4 214 reviews
Winter Park, FL
17/06 – 23/06
NZ$133/nighttotal: NZ$798 (6 )
College Park 1 Bed, 1 Bath Gem.
1 1
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.
9.7 178 reviews
Winter Park, FL
03/07 – 31/07
NZ$174/nighttotal: NZ$4872 (28 )
Comfortable 2-bedroom Place Full Kitchen
1 2
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.
8.1 28 reviews
Winter Park, FL
17/06 – 23/06
NZ$89/nighttotal: NZ$534 (6 )
K11 Private Room With Smart Tv Near Everything
1 1
B&B , Orlando
K11 Private Room, a single-bedroom guesthouse in Orlando, Florida, is situated approximately 8.8km from Orlando International Airport, 8.9km from the Kia Center, and 8.8km from Church Street Station. This self-catering unit offers air conditioning, parking, a smart TV, and sleeps one guest, providing towels, bed linen, and is within reasonable driving distance of other attractions including the Holy Land Experience and Addition Financial Arena.
8.6 7 reviews
Winter Park, FL
17/06 – 23/06
NZ$102/nighttotal: NZ$612 (6 )
Pily's Vintage Stay Room Full Bed
1 1
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.
9.5 813 reviews
Winter Park, FL
21/07 – 04/08
NZ$201/nighttotal: NZ$2814 (14 )
Downtown Lake Eola Historic House 1 Or 2 Bed
2 1
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 breakfast included
9.9 236 reviews
Winter Park, FL
21/07 – 04/08
NZ$115/nighttotal: NZ$1610 (14 )
Private Entrance/bathroom 10 Min From Dt Orlando
1 1
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 a garden
9.7 239 reviews
Winter Park, FL
17/06 – 23/06
NZ$149/nighttotal: NZ$894 (6 )
Guest Suite Near Full Sail In Winter Park
1 1
B&B , Goldenrod
This Goldenrod guest suite, a self-contained studio apartment, is conveniently located 1.6 kilometres from Full Sail University. The 1-bedroom unit offers a kitchenette with fridge, freezer and microwave, a private patio, parking, and accommodates up to 2 guests, providing complete independence and privacy.
9.0 2 reviews
Winter Park, FL
21/07 – 04/08
NZ$175/nighttotal: NZ$2450 (14 )
Bungalow Near Universal, Disney, And Downtown Orlando
1 1
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.
9.6 133 reviews
Winter Park, FL
28/06 – 18/07
NZ$107/nighttotal: NZ$2140 (20 )
Entire Suite - 17 Min From Airport
1 1
B&B , Azalea Park
This charming bed and breakfast is conveniently located in Azalea Park, just a short drive from major Orlando attractions like Universal Studios (35km), Disney World (43km), SeaWorld (27km), and the University of Central Florida (24km). The peaceful residential neighbourhood provides a quiet escape from the bustling tourist areas. The B&B has consistently received excellent ratings for its cleanliness, location, and overall guest experience. The private suite features a semi-kitchen, perfect for preparing light meals, and is equipped with essential amenities like shampoo, towels, an iron, and silverware. Guests can enjoy a dedicated parking space and a relaxing garden.
9.9 105 reviews
Winter Park, FL
28/06 – 18/07
NZ$180/nighttotal: NZ$3600 (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.
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'll want to see the iconic Winter Park Scenic Boat Tour, a relaxing way to explore the canals. The Charles Hosmer Morse Museum of American Art is a must for art lovers, and the beautiful Rollins College campus is worth strolling around. You can also enjoy some time at the charming Park Avenue, the main shopping and dining district.
What are the best bed and breakfasts in Winter Park, FL?
In which districts of Winter Park, FL should you consider booking a bed and breakfast?
The most popular areas for bed and breakfasts in Winter Park are the charming areas around Park Avenue, with its shops and restaurants, and the peaceful area around the Rollins College campus. For a more secluded option, you can find some B&Bs in the residential neighbourhoods near the Winter Park Village.
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 warm, humid summers and mild winters. You can enjoy outdoor activities year-round, though the summer months can be very hot and humid. If you're planning outdoor activities, it's best to go early in the morning or late in the afternoon during 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?
For solo travelers, there are many great options on Park Avenue. The Wine Room is a popular choice for a casual meal and a glass of wine, while The Ravenous Pig offers a more upscale dining experience. You can also find many cafes and bakeries along Park Avenue for a quick bite.
What are the best bed and breakfasts for families and kids in Winter Park, FL?
What are the best cultural activities and events in and around Winter Park, FL?
Winter Park is known for its vibrant arts scene. The annual Winter Park Sidewalk Art Festival is a major event, featuring art from local and national artists. The Bach Festival Society of Winter Park hosts classical music concerts throughout the year. And the Winter Park Playhouse offers Broadway-style musicals.
What are the best pet friendly bed and breakfasts in Winter Park, FL?
Which hiking trails are recommended for exploring in and around Winter Park, FL?
For hiking, head to the Wekiwa Springs State Park just outside of Winter Park. The park has several trails ranging from easy to moderate, offering a chance to explore the Florida wilderness. You can also check out the scenic trails at the Mead Garden, a botanical garden in Winter Park.
What are the best bed and breakfasts 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 often offer a range of amenities, including a complimentary breakfast, free Wi-Fi, and access to a shared lounge or garden. Some may also have a swimming pool or hot tub. It's best to check the individual B&B's website for specific amenities.
Destinations nearby
Best Winter Park, FL bed and breakfasts with parking
9.9 47 reviews
Winter Park, FL
11/08 – 13/08
NZ$268/nighttotal: NZ$536 (2 )
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.
9.7 30 reviews
Winter Park, FL
03/07 – 10/07
NZ$191/nighttotal: NZ$1337 (7 )
Tiny Home Barn Style In Backyard With Animals
1 2
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.
9.8 278 reviews
Winter Park, FL
28/06 – 18/07
NZ$143/nighttotal: NZ$2860 (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.
Winter Park, FL
28/06 – 18/07
NZ$140/nighttotal: NZ$2800 (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.
Best Winter Park, FL bed and breakfasts with air conditioning
9.9 216 reviews
Winter Park, FL
03/07 – 31/07
NZ$150/nighttotal: NZ$4200 (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.
10 133 reviews
Winter Park, FL
21/07 – 04/08
NZ$149/nighttotal: NZ$2086 (14 )
Top Floor French Style Studio.
1 1
B&B , Casselberry
This Casselberry studio apartment, situated in a building with a sculptor's studio downstairs, offers a peaceful top-floor location. The 400 sq ft (approx. 37 sq m) self-catering apartment features a queen-size bed, 55" LCD TV, fully equipped kitchenette, and private bathroom, comfortably accommodating two guests, with additional guests possible at an extra cost.
Winter Park, FL
17/06 – 23/06
NZ$226/nighttotal: NZ$1356 (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.
9.9 233 reviews
Winter Park, FL
28/06 – 18/07
NZ$144/nighttotal: NZ$2880 (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.
