Search Guest Houses in Winter Park from CA $105

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Aug 8 - Aug 10
In two weeks
Aug 15 - Aug 17
In one month
Aug 29 - Aug 31
In two months
Sep 26 - Sep 28

Browse Select Winter Park Guest Houses

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
 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, (83)
"Nice area, nice place. Will definitely be back to visit family"
 Peaceful Two Bedroom Guest House near Wekiva River and State Parks 
Historic lakefront guesthouse
Outdoor pool, a heated pool

Historic lakefront guesthouse

10.0 out of 10, Exceptional, (5)
"Great location - property seas very clean and comfortable!"
The price is CA $141
CA $405 total
includes taxes & fees
Aug 11 - Aug 12
Historic lakefront guesthouse
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."
The price is CA $199
CA $469 total
includes taxes & fees
Aug 7 - Aug 8
Mills Cottage by the Little Lake
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. "
The price is CA $105
CA $224 total
includes taxes & fees
Aug 5 - Aug 6
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
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, (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)
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
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
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
Cozy 1BR apt-Pool/Tennis/Gym/Near attractions
Relax by the pool surrounded by a shaded area with lounge chairs and a table.

Cozy 1BR apt-Pool/Tennis/Gym/Near attractions

The price is CA $112
CA $287 total
includes taxes & fees
Aug 8 - Aug 9
Cozy 1BR apt-Pool/Tennis/Gym/Near attractions
Comfortable 2BR Orlando Home • Pet-Friendly
Modern kitchen with oven, microwave, and seating area.

Comfortable 2BR Orlando Home • Pet-Friendly

2.0 star property
Comfortable 2BR Orlando Home • Pet-Friendly
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
Tree House
Relax on the balcony with a glass door, taking in the natural surroundings from this cozy cabin.

Tree House

10.0 out of 10, Exceptional, (1)
"Erik at the beehive treehouse was the best host we’ve had in a while. He met us at the spot and showed us everything we needed to know and even bought flowers as a surprise because I told him it was my wife’s birthday. The treehouse is AMAZING, built with love and you feel it in every detail. Peaceful, serene, and quant. Couldn’t have asked for a better mini vacation spot. Thank you Erik!"
Tree 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
2 Bed/2 Bath Villa @ Walt Disney's Grand Floridian Resort
Experience the grandeur of this luxurious hotel, featuring a stunning facade with red roofs and multiple balconies, and a charming water feature with teapots and cups.

2 Bed/2 Bath Villa @ Walt Disney's Grand Floridian Resort

2 Bed/2 Bath Villa @ Walt Disney's Grand Floridian Resort
Disney’s Top Villa Resort
Relax by the pool surrounded by lush gardens and a gazebo.

Disney’s Top Villa Resort

Disney’s Top Villa Resort
Marriott Resort Timeshare Near DisneyWorld
Stroll through the beautifully landscaped gardens, featuring a serene water feature and a paved walkway leading to the hotel.

Marriott Resort Timeshare Near DisneyWorld

Marriott Resort Timeshare Near DisneyWorld
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winter Park Hotel Reviews

Drury Plaza Hotel Orlando - Disney Springs Area

Drury Plaza Hotel Orlando - Disney Springs Area

10/10 Excellent
"Great amenities! Excellent location. Very satisfying."
William 2-night trip
Posted 3 hours ago
Drury Plaza Hotel Orlando - Disney Springs Area