Search Guest Houses in Winter Park

    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
13 Jun - 15 Jun
In two weeks
20 Jun - 22 Jun
In one month
4 Jul - 6 Jul
In two months
1 Aug - 3 Aug

Compare 38 Guest Houses in Winter Park with updated reviews, rates, and availability.

Winter Park Getaway
Terrace/patio

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
Historic lakefront guesthouse
Interior

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 "
The price is AED 360
AED 966 total
includes taxes & fees
7 Jul - 8 Jul
Historic lakefront guesthouse
SPRING LAKE GETAWAY SUITE (Detached Guest House)
Property grounds

SPRING LAKE GETAWAY SUITE (Detached Guest House)

10.0 out of 10, Exceptional, (69)
"Nice residential gated community. Excellent welcoming host!"
SPRING LAKE GETAWAY SUITE (Detached Guest House)
 Peaceful Two Bedroom Guest House near Wekiva River and State Parks 
Fridge, microwave, oven, stovetop

 Peaceful Two Bedroom Guest House near Wekiva River and State Parks 

10.0 out of 10, Exceptional, (81)
"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 
Downtown Orlando Throne Historic Thornton Park
Microwave, coffee/tea maker, cookware/dishes/utensils

Downtown Orlando Throne Historic Thornton Park

10.0 out of 10, Exceptional, (3)
"Nice size property great location great host"
The price is AED 281
AED 803 total
includes taxes & fees
9 Jun - 10 Jun
Downtown Orlando Throne Historic Thornton Park
Downtown Lake Eola Historic House 1 OR 2 BED
Miscellaneous

Downtown Lake Eola Historic House 1 OR 2 BED

8.8 out of 10, Excellent, (30)
"We had an amazing time staying at this property. Everything was clean and the communication with the owner was amazing!"
The price is AED 312
AED 631 total
includes taxes & fees
3 Jul - 4 Jul
Downtown Lake Eola Historic House 1 OR 2 BED
2 Minutes to Universal Studios Theme Parks - Central, Relaxing and Chic 1BR
Smart TV, books

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

8.8 out of 10, Excellent, (16)
"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
Mills Cottage by the Little Lake
Outdoor pool, a heated pool

Mills Cottage by the Little Lake

10.0 out of 10, Exceptional, (44)
"Awesome property, kind host, great location… 1mile to food and drinks, 15 minutes to universal studios."
The price is AED 529
AED 1,246 total
includes taxes & fees
15 Jun - 16 Jun
Mills Cottage by the Little Lake
Adorable 1bed 1 bath guest house
Smart TV

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
Fridge, microwave, stovetop, dishwasher

Private studio; big outdoor space

10.0 out of 10, Exceptional, (20)
"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
Cozy 1BR apt-Pool/Tennis/Gym/Near attractions
Outdoor pool

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

Cozy 1BR apt-Pool/Tennis/Gym/Near attractions
Private Poolside Guest House In Winter Park/Orlando
A heated 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
Quiet Garden Retreat Downtown Orlando - Private Apartment, Shared Pool and Patio
Full-size fridge, microwave, oven, stovetop

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
City Guesthouse in beautiful Historic Downtown Sanford
TV

City Guesthouse in beautiful Historic Downtown Sanford

9.8 out of 10, Exceptional, (8)
"Great place for the 2 of us and awesome location."
City Guesthouse in beautiful Historic Downtown Sanford
2BR Orlando Escape • Pets OK + Comfort
2 bedrooms, desk, iron/ironing board, free WiFi

2BR Orlando Escape • Pets OK + Comfort

2.0 star property
2BR Orlando Escape • Pets OK + Comfort
Blissful Guest House
Exterior

Blissful Guest House

3.0 star property
2.0 out of 10, (1)
Blissful Guest House
Disney’s Top Villa Resort
Outdoor pool

Disney’s Top Villa Resort

Disney’s Top Villa Resort
Tree House
Exterior

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
Exterior

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
Exterior

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

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