Photo by Stephanie Moraca

Search Guest Houses in Winter Springs

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Compare 22 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, (54)
"Very nice stay. Clean place and nice area. Hosts were very helpful and receptive. Will definitely stay again if I need to stay in that area!!"
SPRING LAKE GETAWAY SUITE (Detached 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 AED 281
AED 596 total
includes taxes & fees
6 Jan - 7 Jan
Downtown Lake Eola Historic House 1 OR 2 BED
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, (13)
"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!"
Mills Cottage by the Little Lake
The Ann Stevens House
Front of property

The Ann Stevens House

3.0 star property
9.4 out of 10, Exceptional, (143)
"Absolutely amazing, we love this place, everything was just exceptional from check in to check out!!"
The price is AED 584
AED 657 total
includes taxes & fees
7 Jan - 8 Jan
The Ann Stevens House
 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 
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, (19)
"Hello. I stayed here with my son, while we were visiting my daughter and her husband and daughter. It's close to her house, so a very convenient location for us. "
Adorable 1bed 1 bath guest house
Tiny Cottage Farm House!
Living area

Tiny Cottage Farm House!

9.8 out of 10, Exceptional, (16)
"The tiny cottage was very well prepared and so cute. It is in a perfect area very quiet and calm. I would highly recommend for a small family for a mini vacation. "
Tiny Cottage Farm House!
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
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 "
The price is AED 275
AED 1,028 total
includes taxes & fees
6 Jan - 7 Jan
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.
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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
8.4 out of 10, Very Good, (688)
"Rooms were spacious and breakfast was good, freshly made. Only issue i felt was the bathroom was small and no locks on the door"
The price is AED 250
AED 281 total
includes taxes & fees
6 Jan - 7 Jan
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, (1675)
"Great place to stay."
The price is AED 620
AED 792 total
includes taxes & fees
10 Jan - 11 Jan
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, (3119)
"Not clean"
The price is AED 400
AED 493 total
includes taxes & fees
15 Jan - 16 Jan
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.