This Orlando bed and breakfast is situated approximately 9.2 kilometres from Church Street Station, offering straightforward access to downtown attractions and the airport. This accommodation provides a private bedroom and bathroom for up to three guests, featuring air conditioning, complimentary WiFi, and on-site parking, with towels and bed linen supplied.
9.9 216 reviews
Winter Park, FL
03/07 – 31/07
$122/nighttotal: $3416 (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.
Winter Park, FL
28/06 – 18/07
$114/nighttotal: $2280 (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.
9.6 17 reviews
Winter Park, FL
03/09 – 08/09
$466/nighttotal: $2330 (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.
Winter Park, FL
03/09 – 08/09
$157/nighttotal: $785 (5 )
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.
9.6 185 reviews
Winter Park, FL
28/07 – 01/08
$160/nighttotal: $640 (4 )
Balfour Palms
1 2
B&B , Winter Park
This studio apartment is situated in Winter Park, a short distance from Park Avenue and within easy reach of the University of Central Florida, Rollins College, and downtown Orlando. It has received excellent ratings for cleanliness, location, and user experience. The self-catering apartment sleeps two guests and features a kitchenette with modern appliances, a laundry room, and a walk-in shower. Amenities include a king-size bed, FireStick capabilities, and on-site parking.
Winter Park, FL
28/07 – 01/08
$160/nighttotal: $640 (4 )
“The Clementine” Boho Home In Orlando’s Food Scene
1 2
B&B , Orlando
This Boho-style guest house is located in Orlando, within 2.4 kilometres of the city centre, and is 3 kilometres from Church Street Station, 3.4 kilometres from Kia Centre, and 5.3 kilometres from Camping World Stadium. This one-bedroom, one-bathroom accommodation sleeps up to nine guests and offers air conditioning, free Wi-Fi, a kitchen with a fridge and microwave, and a private terrace and garden.
10 99 reviews
Winter Park, FL
28/06 – 18/07
$163/nighttotal: $3260 (20 )
Spring Lake Getaway Suite (Detached Guest House)
1 1
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.
9.6 62 reviews
Winter Park, FL
28/06 – 18/07
$119/nighttotal: $2380 (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.
9.5 137 reviews
Winter Park, FL
28/06 – 18/07
$77/nighttotal: $1540 (20 )
Guest Suite In Orlando-17 Min From Airport
1 1
B&B , Azalea Park
This charming bed and breakfast is conveniently located in Azalea Park, just 17 kilometres from SeaWorld, 22 kilometres from Universal Studios, 27 kilometres from Disney World, and 15 kilometres from the University of Central Florida. The B&B has received excellent ratings for cleanliness, location, and overall experience. The private suite features a semi-kitchen, allowing guests to prepare light meals, and can accommodate up to two guests. The suite comes equipped with everything needed for a comfortable stay, including towels, toiletries, an iron, and kitchenware, as well as coffee, cream, and sugar.
9.6 136 reviews
Winter Park, FL
28/06 – 18/07
$87/nighttotal: $1740 (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.
8.6 7 reviews
Winter Park, FL
03/09 – 08/09
$108/nighttotal: $540 (5 )
Pily's Vintage Stay Room Full Bed
1 2
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.
Best Winter Park, FL bed and breakfasts with breakfast included
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
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.
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.
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.
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?
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?
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?
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
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.
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.
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.
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
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.
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.
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.
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.