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Search Guest Houses in Winter Springs

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Jul 25 - Jul 27
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Aug 15 - Aug 17
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Sep 12 - Sep 14

Guest Houses in Winter Springs

The Ann Stevens House
Set amidst lush greenery, this two-story house offers a serene retreat.

The Ann Stevens House

3.0 star property
9.4 out of 10, Exceptional, (153)
"Beautiful place to stay. "
$159 nightly
The price is $179
Jul 19 - Jul 20
Total includes taxes and fees
The Ann Stevens House
Winter Park Getaway
Enjoy al fresco dining in this serene outdoor patio area with a table, chairs, and a decorative centerpiece.

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
Stroll along a serene suburban street lined with mature trees and well-manicured lawns.

Downtown Orlando Throne Historic Thornton Park

10.0 out of 10, Exceptional, (3)
"Nice size property great location great host"
$197 nightly
The price is $219
Jul 21 - Jul 22
Total includes taxes and fees
Downtown Orlando Throne Historic Thornton Park
 Peaceful Two Bedroom Guest House near Wekiva River and State Parks 
Enjoy cooking in this well-equipped kitchen with a refrigerator, microwave, and oven.

 Peaceful Two Bedroom Guest House near Wekiva River and State Parks 

10.0 out of 10, Exceptional, (82)
"Excellent place with everything you could need. Michael is a very thoughtful host. Very close and conveniently located to RBC and Ligonier Ministries! Cannot recommend enough!"
 Peaceful Two Bedroom Guest House near Wekiva River and State Parks 
Mills Cottage by the Little Lake
Relax by the serene pool surrounded by lush gardens and shaded lounge chairs.

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."
$307 nightly
The price is $340
Jul 19 - Jul 20
Total includes taxes and fees
Mills Cottage by the Little Lake
Historic lakefront guesthouse
Outdoor pool, a heated pool

Historic lakefront guesthouse

10.0 out of 10, Exceptional, (4)
"Had ana amazing time! The owner is very responsive and the place was a total vibe "
$211 nightly
The price is $235
Jul 23 - Jul 24
Total includes taxes and fees
Historic lakefront guesthouse
SPRING LAKE GETAWAY SUITE (Detached Guest House)
Enjoy meals around the central dining table surrounded by four chairs in this well-appointed kitchen.

SPRING LAKE GETAWAY SUITE (Detached Guest House)

10.0 out of 10, Exceptional, (70)
"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)
Downtown Lake Eola Historic House 1 OR 2 BED
Relax in this inviting living space with a comfortable sofa, coffee table, and side table, surrounded by a potted plant.

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. "
$155 nightly
The price is $172
Jul 23 - Jul 24
Total includes taxes and fees
Downtown Lake Eola Historic House 1 OR 2 BED
2 Minutes to Universal Studios Theme Parks - Central, Relaxing and Chic 1BR
Enjoy outdoor dining or relaxation in the backyard, surrounded by lush greenery and a welcoming atmosphere.

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. "
2 Minutes to Universal Studios Theme Parks - Central, Relaxing and Chic 1BR
Private studio; big outdoor space
Relax in a serene outdoor space surrounded by lush greenery and a soothing water feature.

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
Adorable 1bed 1 bath guest house
Relax in a stylish living space with a tufted sofa, matching ottoman, and a side table.

Adorable 1bed 1 bath guest house

10.0 out of 10, Exceptional, (25)
"Our stay was perfect. The accommodations and hosts were excellent. Will definitely consider it again if/when coming to orlando. "
Adorable 1bed 1 bath guest house
City Guesthouse in beautiful Historic Downtown Sanford
Relax in this stylish living room with a large flat-screen TV, comfortable sofa, and wooden coffee table.

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
Enjoy cooking in this well-equipped kitchen with a gas range, refrigerator, and microwave.

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
Peaceful 2BR Stay • Orlando Comfort • Pets OK
Modern kitchen with oven, microwave, and seating area.

Peaceful 2BR Stay • Orlando Comfort • Pets OK

2.0 star property
Peaceful 2BR Stay • Orlando Comfort • Pets OK
Private Poolside Guest House In Winter Park/Orlando
Relax in a serene backyard oasis surrounded by lush greenery and a pool.

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
Enjoy meals in the compact kitchen with a granite countertop, wooden cabinets, and a stainless steel refrigerator. A dining area with a chair and table is nearby.

Blissful Guest House

3.0 star property
2.0 out of 10, (1)
Blissful Guest House
Dr. Phillips House
Waterfront property with a traditional gabled roof and covered porch overlooking the surrounding trees and water.

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
Relax in this inviting space with a cozy seating area and fully equipped kitchen.

Your Home Away From Home

Your Home Away From Home
Modern 1BR/1BA Guest House by Universal/Parks
Cozy living space with a flat-screen TV, kitchenette, and comfortable sofa.

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

Modern 1BR/1BA Guest House by Universal/Parks
Charming room in Orlando
Classic Room, 1 Queen Bed | Free WiFi

Charming room in Orlando

2.0 star property
Charming room in Orlando
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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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 $172 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.