Photo by Stephanie Moraca

Search Guest Houses in Winter Springs

  • 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

Compare 25 Guest Houses in Winter Springs with updated reviews, rates, and availability.

SPRING LAKE GETAWAY SUITE (Detached Guest House)
Detached Guesthouse over our 3 Car Garage

SPRING LAKE GETAWAY SUITE (Detached Guest House)

10.0 out of 10, Exceptional, (51)
"This Vrbo is spectacular, it’s in such a nice location and owned by communicative friendly people, who really care for what they do. This is the second time we stayed here and we’re just as impressed as before. Definitely a go to!"
SPRING LAKE GETAWAY SUITE (Detached Guest House)
The Ann Stevens House
Front of property

The Ann Stevens House

3.0 star property
9.4 out of 10, Exceptional, (142)
"Absolutely amazing, we love this place, everything was just exceptional from check in to check out!!"
The price is SAR 522
SAR 587 total
includes taxes & fees
14 Dec - 15 Dec
The Ann Stevens 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
2 Minutes to Universal Studios Theme Parks - Central, Relaxing and Chic 1BR
Room

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

9.8 out of 10, Exceptional, (12)
"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
Pool w/spa. 25/35 dollars a day additional to use pool/spa, pub/game room & gym

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 699
SAR 1,489 total
includes taxes & fees
2 Dec - 3 Dec
Mills Cottage by the Little Lake
Adorable 1bed 1 bath guest house
King bed, dresser, luggage rack, plenty of closet space with full mirror

Adorable 1bed 1 bath guest house

10.0 out of 10, Exceptional, (17)
"I needed a place to stay while my house was being worked on and going to stay here made that experience a little easier for me. And for the price it feels like a great deal for what you get"
Adorable 1bed 1 bath guest house
Downtown Lake Eola Historic House 1 OR 2 BED
Living area

Downtown Lake Eola Historic House 1 OR 2 BED

8.8 out of 10, Excellent, (27)
"Very easy to find, historical home in a quiet neighborhood tucked between the ever growing city. A coffee shop around the corner, and right down the street is Lake Eola for a morning or evening stroll. A Publix grocery store just steps away. The home is very secure, with off street parking, comfortable bed, couch and air conditioning. Everything about our stay was just right. beautiful Lake Eola "
The price is SAR 304
SAR 629 total
includes taxes & fees
29 Nov - 30 Nov
Downtown Lake Eola Historic House 1 OR 2 BED
 Peaceful Two Bedroom Guest House near Wekiva River and State Parks 
Private kitchen

 Peaceful Two Bedroom Guest House near Wekiva River and State Parks 

10.0 out of 10, Exceptional, (77)
"Everything it was clean . The king bed is super comfortable. The host is communicative. The house it’s was surrounding the beautiful springs for hot summer. I recommend Mike cottage. "
 Peaceful Two Bedroom Guest House near Wekiva River and State Parks 
City Guesthouse in beautiful Historic Downtown Sanford

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
Beautiful Villa with Lake Views
Living area

Beautiful Villa with Lake Views

10.0 out of 10, Exceptional, (1)
"UN APPARTEMENT TRES BIEN MEUBLÉ ET BIEN ÉQUIPÉ. UN AGRABLE SÉJOUR."
Beautiful Villa with Lake Views
Casa Catalina☀️ Lakefront Apartment near Downtown
Living area

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!"
The price is SAR 432
SAR 1,236 total
includes taxes & fees
29 Nov - 30 Nov
Casa Catalina☀️ Lakefront Apartment near Downtown
Private Poolside Guest House In Winter Park/Orlando
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
Pool

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
Blissful Guest House
Exterior

Blissful Guest House

3.0 star property
2.0 out of 10, (1)
Blissful Guest House
Cozy Guesthouse in Orlando, Florida! Convenience and comfort!
Living area

Cozy Guesthouse in Orlando, Florida! Convenience and comfort!

10.0 out of 10, Exceptional, (2)
"Amazing location, quiet and close to everything. Great communication "
Cozy Guesthouse in Orlando, Florida! Convenience and comfort!
Dr. Phillips House
Front of property

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
Room

Your Home Away From Home

Your Home Away From Home
Renovated studio/8min Universal/15 Disney/10 Dtown
Outdoor dining

Renovated studio/8min Universal/15 Disney/10 Dtown

Renovated studio/8min Universal/15 Disney/10 Dtown
Cozy Barndominium 1Bdm/1Bth+loft
Exterior

Cozy Barndominium 1Bdm/1Bth+loft

Cozy Barndominium 1Bdm/1Bth+loft
Charming room in Orlando
Room

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.
Don't see what you're looking for?
See all available properties in Winter Springs
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 Springs

The View Studio Suites and Event Venue
Front of property

The View Studio Suites and Event Venue

3.5 star property
8.6 out of 10, Excellent, (565)
"The stay overall was good. We were only there one night, for the price it was good, I just needed a place to sleep so I didn’t expect too fancy. Everyone was friendly, it was clean and bigger than I expected. I struggled with the smell of the room though, normally hotel cleaning chemicals don’t bother me but this was super strong and the whole night was like I was sniffing a bottle of pinesol which led to a migraine. I wish I did a little more research on the location because it is directly next...
The price is SAR 310
SAR 339 total
includes taxes & fees
12 Dec - 13 Dec
The View Studio Suites and Event Venue
Florida Hotel & Conference Center in the Florida Mall
Exterior

Florida Hotel & Conference Center in the Florida Mall

3.5 star property
9.0 out of 10, Wonderful, (1606)
"Using the key to go up to the room on elevator."
The price is SAR 521
SAR 672 total
includes taxes & fees
29 Nov - 30 Nov
Florida Hotel & Conference Center in the Florida Mall
The Point Hotel & Suites
Exterior

The Point Hotel & Suites

3.5 star property
8.0 out of 10, Very Good, (3097)
"Everything was fine, except wrong payment at front"
The price is SAR 344
SAR 422 total
includes taxes & fees
18 Dec - 19 Dec
The Point Hotel & Suites
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.