Search Guest Houses in Winter Park

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
28 Rab. I - 30 Rab. I
In two weeks
4 Rab. II - 6 Rab. II
In one month
18 Rab. II - 20 Rab. II
In two months
16 Jum. I - 18 Jum. I

Compare 36 Guest Houses in Winter Park with updated reviews, rates, and availability.

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, (29)
"We had an amazing time staying at this property. Everything was clean and the communication with the owner was amazing!"
The price is SAR 319
SAR 645 total
includes taxes & fees
26 Mar - 27 Mar
Downtown Lake Eola Historic House 1 OR 2 BED
SPRING LAKE GETAWAY SUITE (Detached Guest House)
Property grounds

SPRING LAKE GETAWAY SUITE (Detached Guest House)

10.0 out of 10, Exceptional, (63)
"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)
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
 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, (79)
"The house was clean and pretty and perfect!! It’s all updated. Beds were super comfy and warm (it was cold the weekend we stayed). We did have an issue with a couple of minor things but Mike came over instantly and fixed them immediately. He was very attentive and very friendly and I enjoyed talking with him! We stayed for a soccer tournament and it was super close to Seminole Soccer Complex. I would absolutely stay there again! "
 Peaceful Two Bedroom Guest House near Wekiva River and State Parks 
Mills Cottage by the Little Lake
Outdoor pool, a heated pool

Mills Cottage by the Little Lake

10.0 out of 10, Exceptional, (44)
"Upon arriving nice neighborhood drive was seemed small but on our last day with multiple cars on lot it was easy to get out. I was impressed by the whole property, but the vegetation was by far my favorite thing the pool was easy to find there was so many things to keep us occupied if we needed. Owner was quick to respond and even checked in with us. Would definitely stay again!"
The price is SAR 698
SAR 1,491 total
includes taxes & fees
31 Mar - 1 Apr
Mills Cottage by the Little Lake
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)
"Property is in a great location of Thornton Park. We arrived and parked the car. Walking distance to everything, such an awesome weekend."
The price is SAR 319
SAR 856 total
includes taxes & fees
7 Apr - 8 Apr
Downtown Orlando Throne Historic Thornton Park
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

9.2 out of 10, Wonderful, (15)
"This place was good for a two night pre cruise stay. Half of what you would pay staying at a hotel. A rental car is a must have for going anywhere. We just slept and showered here as we were out all day and brought takeout back. They provided a nice bottle of wine. I was disappointed that the bedding was not the nice white bedding pictured and was burgundy instead. A decent place to stay short term if you want to save on accommodations . "
2 Minutes to Universal Studios Theme Parks - Central, Relaxing and Chic 1BR
Beautiful Villa with Lake Views
Interior

Beautiful Villa with Lake Views

10.0 out of 10, Exceptional, (1)
"UN APPARTEMENT TRES BIEN MEUBLÉ ET BIEN ÉQUIPÉ. UN AGRABLE SÉJOUR."
The price is SAR 338
SAR 919 total
includes taxes & fees
7 Apr - 8 Apr
Beautiful Villa with Lake Views
Cozy Guesthouse in Orlando, Florida! Convenience and comfort!
Fridge, oven, stovetop, coffee/tea maker

Cozy Guesthouse in Orlando, Florida! Convenience and comfort!

9.6 out of 10, Exceptional, (4)
"Very convenient location. New fixtures. Very clean. "
Cozy Guesthouse in Orlando, Florida! Convenience and comfort!
Adorable 1bed 1 bath guest house
Smart TV

Adorable 1bed 1 bath guest house

10.0 out of 10, Exceptional, (23)
"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
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)
"Walking distance to Vanguard."
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)
"The unit was nice though the AC was not operating properly. The Hosts were very understanding and immediately offer/processed refund and assisted in instructing us on method of cancelation to get full refund from VRBO. VRBO was also extremely prompt in processing a our full refund. This was a first for us using VRBO and was very skeptical but after this experience I will not have any reservation about using VRBO again as well as booking through this host. The AC issues were out of the hosts...
City Guesthouse in beautiful Historic Downtown Sanford
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
Stunning Black and White 2 Bed APT
2 bedrooms, desk, iron/ironing board, free WiFi

Stunning Black and White 2 Bed APT

2.0 star property
Stunning Black and White 2 Bed APT
Casa Catalina☀️ Lakefront Apartment near Downtown
Beach

Casa Catalina☀️ Lakefront Apartment near Downtown

8.0 out of 10, Very Good, (1)
"So my girlfriends and I stayed for one quick night,which was perfect for one night because just a heads up the air conditioner is not cool in the living room. There is a air conditioner in the bedroom which gets really cool. The bed in the bedroom and the pullout sofa bed were both memory foam which were nice. The small apartment was cute and clean,very nice decor!"
Casa Catalina☀️ Lakefront Apartment near Downtown
Blissful Guest House
Exterior

Blissful Guest House

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

Disney’s Top Villa Resort

Disney’s Top Villa 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.
Don't see what you're looking for?
See all available properties in Winter Park
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Winter Park

Lake Buena Vista Resort Village & Spa
2 outdoor pools, a heated pool, open 8:00 AM to 10:00 PM, pool umbrellas

Lake Buena Vista Resort Village & Spa

4.0 star property
8.4 out of 10, Very Good, (8461)
"Everything was excellent. Will differently being going back."
Lake Buena Vista Resort Village & Spa
Florida Hotel & Conference Center in the Florida Mall
Reception

Florida Hotel & Conference Center in the Florida Mall

3.5 star property
9.2 out of 10, Wonderful, (1834)
"Convenient location to airport."
The price is SAR 684
SAR 867 total
includes taxes & fees
4 Apr - 5 Apr
Florida Hotel & Conference Center in the Florida Mall
Floridays Resort Orlando
2 outdoor pools, a heated pool, open 7:00 AM to 11:00 PM, pool umbrellas

Floridays Resort Orlando

3.5 star property
8.6 out of 10, Excellent, (11277)
"Property location was great. Having 1 remote control to work 3 tvs in 3 different rooms was an inconvenience. The kid had all their electronics but couldn’t connect to the internet. The first hotel or resort where we visited where this happened. The master bathroom had only 1 washcloth. "
The price is SAR 634
SAR 861 total
includes taxes & fees
24 Mar - 25 Mar
Floridays Resort 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.