This Casselberry self-catering apartment is conveniently located near Orlando Sanford International Airport, approximately 24-32 km away, offering easy access to numerous restaurants and shopping centres, and less than 80 km from both Walt Disney World and Universal Orlando Resort. The one-bedroom, one-bathroom apartment sleeps two guests, features a private kitchen with fridge and microwave, complimentary Victor Allen's K-cup coffee and Oasis Bliss amenities, plus fast Wi-Fi and parking; guests benefit from excellent cleanliness and location ratings.
10 99 reviews
Winter Park, FL
28/06 – 18/07
SG$150/nighttotal: SG$3000 (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.
9.6 192 reviews
Winter Park, FL
28/07 – 01/08
SG$350/nighttotal: SG$1400 (4 )
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.
9.6 136 reviews
Winter Park, FL
28/06 – 18/07
SG$80/nighttotal: SG$1600 (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.
9.5 813 reviews
Winter Park, FL
03/07 – 10/07
SG$175/nighttotal: SG$1225 (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.
9.9 47 reviews
Winter Park, FL
23/06 – 28/06
SG$184/nighttotal: SG$920 (5 )
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.
9.7 179 reviews
Winter Park, FL
03/07 – 10/07
SG$154/nighttotal: SG$1078 (7 )
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.
9.9 354 reviews
Winter Park, FL
28/06 – 18/07
SG$121/nighttotal: SG$2420 (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.
9.9 218 reviews
Winter Park, FL
03/07 – 31/07
SG$112/nighttotal: SG$3136 (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
03/09 – 08/09
SG$138/nighttotal: SG$690 (5 )
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.
9.7 240 reviews
Winter Park, FL
23/06 – 28/06
SG$137/nighttotal: SG$685 (5 )
Guest Suite Near Full Sail In Winter Park
1 2
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.
9.8 308 reviews
Winter Park, FL
03/09 – 08/09
SG$160/nighttotal: SG$800 (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.
Best Winter Park, FL bed and breakfasts with breakfast included
9.0 2 reviews
Winter Park, FL
08/01 – 29/01
SG$201/nighttotal: SG$4221 (21 )
Bungalow Near Universal, Disney, And Downtown Orlando
1 2
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.
Best Winter Park, FL bed and breakfasts with a garden
9.9 233 reviews
Winter Park, FL
28/06 – 18/07
SG$107/nighttotal: SG$2140 (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.
9.9 387 reviews
Winter Park, FL
28/06 – 18/07
SG$122/nighttotal: SG$2440 (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.
9.5 33 reviews
Winter Park, FL
03/07 – 31/07
SG$116/nighttotal: SG$3248 (28 )
Modern Cuartito By Winter Park
1 2
B&B , Maitland
This Maitland Cuartito offers a peaceful escape, situated north of Downtown Orlando and within 4.3km of the Winter Park Scenic Boat Tour. The self-contained apartment sleeps two, features a fully equipped kitchen with dishwasher, a private garden, and keyless entry, plus a shared laundry room.
9.7 42 reviews
Winter Park, FL
03/09 – 08/09
SG$160/nighttotal: SG$800 (5 )
The Tree House @ Oasis In Orlando
1 2
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.
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've got to see the charming Park Avenue district with its shops and restaurants, and the scenic Rollins College campus. And don't miss the beautiful Winter Park Scenic Boat Tour on the chain of lakes, it's a real highlight.
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 Park Avenue district is a popular choice for bed and breakfasts, as it's close to the action. You can also find some lovely options in the more residential areas like Hannibal Square, where it's a bit quieter.
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 most of the year. Summers are hot and rainy, while winters are mild and sunny. You can usually enjoy outdoor activities year-round, but be prepared for some humidity in 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?
The Park Avenue district has lots of great restaurants for solo travellers, like The Wine Room or Luma on Park. If you're looking for something more casual, there are plenty of cafes and bistros around too.
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 arts scene, with the Charles Hosmer Morse Museum of American Art and the Albin Polasek Museum & Sculpture Gardens being popular choices. The Winter Park Sidewalk Art Festival is a must-see event in the spring.
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?
There aren't many hiking trails in Winter Park itself, but you can find some good ones in nearby Wekiwa Springs State Park. The scenic Wekiwa Springs Trail is a great option for a leisurely walk.
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?
Most bed and breakfasts in Winter Park offer a continental breakfast, free Wi-Fi, and private bathrooms. Some also have swimming pools, gardens, and even bike rentals.
Destinations nearby
Best Winter Park, FL bed and breakfasts with parking
9.6 17 reviews
Winter Park, FL
03/09 – 08/09
SG$429/nighttotal: SG$2145 (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
28/06 – 18/07
SG$105/nighttotal: SG$2100 (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.
8.3 13 reviews
Winter Park, FL
28/06 – 18/07
SG$62/nighttotal: SG$1240 (20 )
L12 Private Room With Smart Tv Near Everything
1 1
B&B , Orlando
This Orlando guesthouse is conveniently located near major attractions, approximately 8-21 kilometres from venues such as Camping World Stadium, Church Street Station, and the Florida Mall. The single-bedroom, single-bathroom property sleeps one guest and includes a smart TV, air conditioning, parking, towels, and bed linen; it's a non-smoking establishment.
8.7 10 reviews
Winter Park, FL
03/09 – 08/09
SG$137/nighttotal: SG$685 (5 )
10 Minutes From Universal - Relaxing Guest Suite
1 2
B&B , Azalea Park
This guest house is located in Azalea Park, a short distance from local attractions. This family-friendly accommodation offers 400 square meters of floor area with one bedroom, one bathroom, and can host up to five guests, featuring air conditioning, internet, and parking.
Best Winter Park, FL bed and breakfasts with air conditioning
9.7 292 reviews
Winter Park, FL
28/06 – 18/07
SG$108/nighttotal: SG$2160 (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.
Winter Park, FL
28/07 – 01/08
SG$136/nighttotal: SG$544 (4 )
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.
9.9 105 reviews
Winter Park, FL
28/06 – 18/07
SG$135/nighttotal: SG$2700 (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.
9.6 62 reviews
Winter Park, FL
28/06 – 18/07
SG$109/nighttotal: SG$2180 (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.