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Search Guest Houses in Winter Springs from CA $105

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Browse Select Winter Springs Guest Houses

SPRING LAKE GETAWAY SUITE (Detached Guest House)

10.0 out of 10, Exceptional, (71)
"Perfect house, perfect location, and the host is very pleasant and easy to get in contact with. A great stay."
SPRING LAKE GETAWAY SUITE (Detached Guest House)

The Ann Stevens House

3.0 star property
9.4 out of 10, Exceptional, (154)
"Beautiful place to stay. "
The price is CA $219
CA $246 total
includes taxes & fees
Sep 8 - Sep 9
The Ann Stevens House

Winter Park Getaway

10.0 out of 10, Exceptional, (3)
"The host was very helpful and welcoming without being overbearing as some can be. The space was clean, cute, and well stocked."
Winter Park Getaway

Downtown Orlando Throne Historic Thornton Park

8.4 out of 10, Very good, (5)
"Nice size property great location great host"
The price is CA $105
CA $307 total
includes taxes & fees
Sep 1 - Sep 2
Downtown Orlando Throne Historic Thornton Park

Historic lakefront guesthouse

10.0 out of 10, Exceptional, (6)
"Great location - property seas very clean and comfortable!"
The price is CA $125
CA $384 total
includes taxes & fees
Sep 3 - Sep 4
Historic lakefront guesthouse

Adorable 1bed 1 bath guest house

10.0 out of 10, Exceptional, (26)
"The apartment was perfect for us! It was clean and spacious and very well appointed with everything needed for the few days we were here. Samson was very accommodating and even allowed us to check in early. We will definitely stay here again as our daughter will be in law school near by for the next 3 years. "
Adorable 1bed 1 bath guest house

Mills Cottage by the Little Lake

10.0 out of 10, Exceptional, (45)
"Awesome property, kind host, great location… 1mile to food and drinks, 15 minutes to universal studios."
The price is CA $223
CA $501 total
includes taxes & fees
Aug 30 - Aug 31
Mills Cottage by the Little Lake

Downtown Lake Eola Historic House 1 OR 2 BED

8.8 out of 10, Excellent, (30)
"This was a great option for my friend and I who were traveling. It had two separate bedrooms, a decent kitchen, and a nice seating area. It’s pretty much in downtown, we walked very easily to the Orlando magic stadium and there’s plenty of restaurants within walking distance around the home. would definitely stay here again, and I really appreciated the communication from the property management company. "
The price is CA $117
CA $236 total
includes taxes & fees
Sep 1 - Sep 2
Downtown Lake Eola Historic House 1 OR 2 BED

2 Minutes to Universal Studios Theme Parks - Central, Relaxing and Chic 1BR

8.8 out of 10, Excellent, (17)
"One bedroom with comfortable foldout futon in small living room. Small fridge, microwave, kettle were ideal for my stay. "
The price is CA $114
CA $232 total
includes taxes & fees
Aug 31 - Sep 1
2 Minutes to Universal Studios Theme Parks - Central, Relaxing and Chic 1BR

 Peaceful Two Bedroom Guest House near Wekiva River and State Parks 

10.0 out of 10, Exceptional, (83)
"Very clean and well kept. The house had everything we needed for our stay and then some. The owner was very welcoming too! We will definitely stay here again the next time we are in the area. "
 Peaceful Two Bedroom Guest House near Wekiva River and State Parks 

2BR Orlando Retreat • Pets + Wi-Fi Near Disney

2.0 star property
2BR Orlando Retreat • Pets + Wi-Fi Near Disney

City Guesthouse in beautiful Historic Downtown Sanford

9.8 out of 10, Exceptional, (8)
"Very clean and perfect location. Historic Sanford is awesome."
City Guesthouse in beautiful Historic Downtown Sanford

Quiet Garden Retreat Downtown Orlando - Private Apartment, Shared Pool and Patio

9.6 out of 10, Exceptional, (15)
"Had a lovely visit in Orlando! Easy to find, host is very nice, communicative and helpful! Would definitely stay again"
Quiet Garden Retreat Downtown Orlando - Private Apartment, Shared Pool and Patio

Private studio; big outdoor space

10.0 out of 10, Exceptional, (22)
"We were very pleased with our hosts and their responsiveness to any concerns we had. The property worked very well for us as we spent our days with family and returned to our quiet place in the evenings. "
Private studio; big outdoor space

Private Poolside Guest House In Winter Park/Orlando

8.0 out of 10, Very good, (2)
"The property, the location and host are all top notch."
Private Poolside Guest House In Winter Park/Orlando

Blissful Guest House

3.0 star property
2.0 out of 10, (1)
Blissful Guest House

Dr. Phillips House

3.0 star property
8.2 out of 10, Very good, (13)
"AWESOME LOCATION AND A GREAT PLACE TO STAY. THE ROOM WAS ABSOLUTELY AMAZING!! NO TURN DOWN OR TOWELS AFTER THE FIRST NIGHT STAY ALTHOUGH IT WAS AT THE BEGINNING OF CORONA."
Dr. Phillips House

Your Home Away From Home

Your Home Away From Home

Renovated studio/8min Universal/15 Disney/10 Dtown

Renovated studio/8min Universal/15 Disney/10 Dtown

Modern 1BR/1BA Guest House by Universal/Parks

Modern 1BR/1BA Guest House by Universal/Parks
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Winter Springs Hotel Reviews

Find out more about Winter Springs

Find out more about Winter Springs

Winter Springs Guest Houses information

Number of reviews
71
Accommodation
24 Guest Houses
Lowest Price
CA $105
Highest Price
CA $223

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

What is the nightly rate for a guest house in Winter Springs?
Rates for Winter Springs guest houses vary, but travelers can find great-value prices from CA $105 with Expedia. A range of factors can affect nightly rates, such as the location, the breakfast offering, and the range of amenities. Travelers looking for a good deal should consider looking for a midweek stay, as weekend rates at Winter Springs guest houses tend to be higher. Remember to also use our filters to sort prices from low to high.
What's the difference between a Winter Springs guest house and a B&B?
A guest house in Winter Springs is typically a larger establishment with more rooms, offering a more hotel-like experience, and may provide additional amenities including luxury bedding. In contrast, a B&B is usually a smaller property that focuses primarily on providing a room and breakfast. A B&B is often more personal, and breakfast is typically included as part of the stay, but other services might be more limited compared to a guest house.