Photo by Stephanie Moraca

Search Guest Houses in Winter Springs

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Compare 28 Guest Houses in Winter Springs with updated reviews, rates, and availability.

The Ann Stevens House

3.0 star property
9.4 out of 10, Exceptional, (151)
"What a beautiful, serene, magical place this is! The owners are so friendly and helpful and full of so much knowledge about the area. We loved our stay and wanted to stay longer!! "
The price is SAR 521
SAR 587 total
includes taxes & fees
12 Apr - 13 Apr
The Ann Stevens House

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 287
SAR 609 total
includes taxes & fees
3 Apr - 4 Apr
Downtown Lake Eola Historic House 1 OR 2 BED

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

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

Cozy Tiny Cottage Farm House!

9.8 out of 10, Exceptional, (20)
"I needed a convenient place to stay while visiting family in Longwood, and this rental was perfect. Tucked away from the main road in a quiet neighborhood, the house was easy to find and check-in was effortless. The efficient space was well-appointed with all I needed for a cozy spot to sleep, have breakfast, and wash a small load of laundry before setting out to spend my day with family. I will be back."
Cozy Tiny Cottage Farm House!

 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

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 1,446 total
includes taxes & fees
7 Apr - 8 Apr
Mills Cottage by the Little Lake

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 . "
The price is SAR 323
SAR 645 total
includes taxes & fees
3 Apr - 4 Apr
2 Minutes to Universal Studios Theme Parks - Central, Relaxing and Chic 1BR

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

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 364
SAR 949 total
includes taxes & fees
20 Apr - 21 Apr
Beautiful Villa with Lake Views

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

10.0 out of 10, Exceptional, (24)
"Samson and Sunny clearly put in the effort to make sure I felt welcome during my stay. The check in and check out processes were very simple (not always the case with properties!) which I really appreciated. "
Adorable 1bed 1 bath guest house

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

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

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

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

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

Elegant Black & White 2BR | Pet-Friendly

2.0 star property
Elegant Black & White 2BR | Pet-Friendly

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
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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Other property types in Winter Springs

Florida Hotel & Conference Center in the Florida Mall

3.5 star property
9.2 out of 10, Wonderful, (1840)
"After a very exhausting couple of days of my trip, it was a delight that they allowed me to have a very early check in, so I could take a nap in the middle of the day, much needed. The room was cold and crispy clean. Especially thankfull to Aliya for arraging all of that with me over the phone before leaving at the end of her shift. Definetly my place to stay when going to Orlando. "
The price is SAR 652
SAR 831 total
includes taxes & fees
11 Apr - 12 Apr
Florida Hotel & Conference Center in the Florida Mall

The View Studio Suites and Event Venue

3.0 star property
8.4 out of 10, Very Good, (976)
"Limited opcions for breakfast. We could not have eggs and pancakes at the same time, it was one are the other. Other than that, everything was ok."
The price is SAR 314
SAR 354 total
includes taxes & fees
9 Apr - 10 Apr
The View Studio Suites and Event Venue

Sonder at The Point

4.0 star property
8.4 out of 10, Very Good, (684)
"We enjoyed this property. We did not have to interact with any staff. We were sent all instructions 3 days before and had no issues with codes or communication. The construction around property was difficult to maneuver around but in time that will pass. Room was spacious and clean. Would absolutely stay there again."
The price is SAR 357
SAR 402 total
includes taxes & fees
24 Apr - 25 Apr
Sonder at The Point
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.