Photo by Stephanie Moraca

Search Guest Houses in Winter Springs

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Featured Guest Houses in Winter Springs and around

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
The Ann Stevens House
Exterior

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 €150
includes taxes & fees
13 Dec - 14 Dec
The Ann Stevens House
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

9.8 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
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 €393
includes taxes & fees
2 Dec - 3 Dec
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, (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
SPRING LAKE GETAWAY SUITE (Detached Guest House)
Property grounds

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)
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, (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 €160
includes taxes & fees
25 Nov - 26 Nov
Downtown Lake Eola Historic House 1 OR 2 BED
 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, (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
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
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."
Beautiful Villa with Lake Views
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!"
The price is €331
includes taxes & fees
27 Nov - 28 Nov
Casa Catalina☀️ Lakefront Apartment near Downtown
Quiet Garden Retreat Downtown Orlando - Private Apartment, Shared Pool and Patio
Full-sized 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
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!
Fridge, oven, stovetop, coffee/tea maker

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
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
Your Home Away From Home
Smart TV

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
Smart TV

Cozy Barndominium 1Bdm/1Bth+loft

Cozy Barndominium 1Bdm/1Bth+loft
Charming room in Orlando
Classic Room, 1 Queen Bed

Charming room in Orlando

2.0 star property
Charming room in Orlando
Modern 1BR/1BA Guest House by Universal/Parks
Smart TV

Modern 1BR/1BA Guest House by Universal/Parks

Modern 1BR/1BA Guest House by Universal/Parks
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

The View Studio Suites and Event Venue
Property entrance

The View Studio Suites and Event Venue

3.5 star property
8.6 out of 10, Excellent, (565)
"They are remodeling the building but is nice and for the price..and the breakfast is a plus"
The price is €89
includes taxes & fees
25 Nov - 26 Nov
The View Studio Suites and Event Venue
Florida Hotel & Conference Center in the Florida Mall
Reception

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 €207
includes taxes & fees
25 Nov - 26 Nov
Florida Hotel & Conference Center in the Florida Mall
The Point Hotel & Suites
Outdoor pool

The Point Hotel & Suites

3.5 star property
8.0 out of 10, Very good, (3097)
"The people next to us were not pleasant..breakfast was quite a joke for what was paid and the lady running it was really rude. "
The price is €110
includes taxes & fees
10 Dec - 11 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.