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.
9.9 354 reviews
Winter Park, FL
28/06 – 18/07
$132/nighttotal: $2640 (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.
9.4 214 reviews
Winter Park, FL
17/06 – 23/06
$108/nighttotal: $648 (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.
9.8 308 reviews
Winter Park, FL
03/09 – 08/09
$174/nighttotal: $870 (5 )
Quiet Oasis In Lovely Neighborhood
1 2
B&B , Orlando
This one-bedroom, one-bathroom house is situated in Southern Oaks, just 1.8km from Lake Conway and within 5km of Orlando Regional Medical Center and Winnie Palmer Hospital for Women and Babies. The property has consistently received excellent ratings for its location, cleanliness, and overall user experience. The house has a private pool, a spa tub, and a fenced-in yard. Guests can enjoy modern amenities such as a refrigerator, microwave, and patio, as well as complimentary Wi-Fi and a washing machine.
9.7 290 reviews
Winter Park, FL
03/07 – 10/07
$130/nighttotal: $910 (7 )
Guesthouse, Walk To Baldwin Lake - 1 Mi To Dining
1 2
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.
Winter Park, FL
17/06 – 23/06
$184/nighttotal: $1104 (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.
9.9 139 reviews
Winter Park, FL
11/08 – 13/08
$144/nighttotal: $288 (2 )
The Paradise Bird Cottage
1 2
B&B , Orlando
This cosy guest suite is conveniently located near Orlando International Airport, offering easy access to Baldwin Park, Downtown Orlando, and Winter Park. The self-contained unit sleeps two, features a fridge and microwave, air conditioning, parking, and boasts a peaceful wildlife theme with private garden access (pool available upon arrangement).
Winter Park, FL
03/07 – 10/07
$68/nighttotal: $476 (7 )
H8 Private Room With Smart Tv Near Everything
1 2
B&B , Orlando
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.
10 133 reviews
Winter Park, FL
03/07 – 31/07
$111/nighttotal: $3108 (28 )
Top Floor French Style Studio.
1 2
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.
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.
9.9 252 reviews
Winter Park, FL
03/09 – 08/09
$431/nighttotal: $2155 (5 )
Mills Cottage By The Little Lake
2 2
B&B , Orlando
This family-friendly guesthouse is located in Orlando, close to Lake Eola and within a mile of Orlando Regional Medical Center, offering a peaceful lakeside setting near the city centre. The guesthouse has received excellent ratings for user experience, location, and cleanliness. The guesthouse offers two bedrooms and one bathroom across 65 square metres, comfortably accommodating up to four guests. Guests can enjoy amenities such as a swimming pool, jacuzzi, sauna, fitness centre, and a garden, perfect for relaxing and unwinding after a day exploring Orlando.
9.8 116 reviews
Winter Park, FL
17/06 – 23/06
$134/nighttotal: $804 (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.
Best Winter Park, FL bed and breakfasts with breakfast included
9.9 236 reviews
Winter Park, FL
11/08 – 13/08
$116/nighttotal: $232 (2 )
Private Entrance/bathroom 10 Min From Dt Orlando
1 2
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
9.5 813 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.
9.7 239 reviews
Winter Park, FL
17/06 – 23/06
$121/nighttotal: $726 (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.
9.9 387 reviews
Winter Park, FL
17/06 – 23/06
$141/nighttotal: $846 (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.
8.9 25 reviews
Winter Park, FL
03/09 – 08/09
$123/nighttotal: $615 (5 )
Lovely Spacious Guesthouse In Mills 50 District
1 2
B&B , Orlando
This Orlando guesthouse is located in the Mills 50 District, 4.5km from Camping World Stadium and approximately 18km from Universal Studios Florida. The 23-square-metre self-catering unit sleeps three, featuring a kitchenette, private bathroom, terrace, and garden with outdoor play equipment; free Wi-Fi is provided.
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
Winter Park, FL
21/07 – 04/08
$158/nighttotal: $2212 (14 )
“The Clementine” Boho Home In Orlando’s Food Scene
1 1
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.
8.6 7 reviews
Winter Park, FL
17/06 – 23/06
$83/nighttotal: $498 (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.
9.0 24 reviews
Winter Park, FL
21/07 – 04/08
$67/nighttotal: $938 (14 )
G7 Private Room With Smart Tv Near Everything
1 1
B&B , Orlando
This Orlando guesthouse is conveniently located near Church Street Station, approximately 8-19 kilometres from attractions such as Camping World Stadium and Orlando International Airport. The single-bedroom, en-suite room offers air conditioning, a Smart TV, and sleeps one guest; towels and linen are provided, and guests can enjoy proximity to various entertainment venues.
9.8 278 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.
Best Winter Park, FL bed and breakfasts with air conditioning
8.1 28 reviews
Winter Park, FL
17/06 – 23/06
$72/nighttotal: $432 (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.
9.8 288 reviews
Winter Park, FL
21/07 – 04/08
$127/nighttotal: $1778 (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.
9.9 105 reviews
Winter Park, FL
28/06 – 18/07
$146/nighttotal: $2920 (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.
9.8 56 reviews
Winter Park, FL
03/09 – 08/09
$178/nighttotal: $890 (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.