Photo by Stephanie Moraca

Search Guest Houses in Winter Springs

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Check prices for these dates

Next weekend
21 Feb - 23 Feb
In two weeks
28 Feb - 2 Mar
In one month
14 Mar - 16 Mar
In two months
11 Apr - 13 Apr

Compare 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, (59)
"Great location. Love that it is gated. Gina has everything we needed and was extremely friendly but not hovering! We’ll be back!"
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, (28)
"Great little 2-story house smack downtown & walking distance to Dr. Phillips Center. It’s old, though, so there are a few eccentricities… Parking was a breeze."
The price is AED 281
AED 596 total
includes taxes & fees
13 Feb - 14 Feb
Downtown Lake Eola Historic House 1 OR 2 BED
The Ann Stevens House
Front of property

The Ann Stevens House

3.0 star property
9.4 out of 10, Exceptional, (146)
"Beautiful property with a very kind host. Very comfortable room in the building behind the main house. Enjoyed the walking trails behind the property. "
The price is AED 511
AED 574 total
includes taxes & fees
22 Feb - 23 Feb
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
Cozy Guesthouse in Orlando, Florida! Convenience and comfort!
Living area

Cozy Guesthouse in Orlando, Florida! Convenience and comfort!

9.6 out of 10, Exceptional, (4)
"Very convenient location. New fixtures. Very clean. "
The price is AED 511
AED 1,337 total
includes taxes & fees
20 Feb - 21 Feb
Cozy Guesthouse in Orlando, Florida! Convenience and comfort!
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
 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, (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 
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

9.2 out of 10, Wonderful, (14)
"One bedroom with comfortable foldout futon in small living room. Small fridge, microwave, kettle were ideal for my stay. "
The price is AED 312
AED 627 total
includes taxes & fees
13 Feb - 14 Feb
2 Minutes to Universal Studios Theme Parks - Central, Relaxing and Chic 1BR
Tiny Cottage Farm House!
Dining

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!
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."
The price is AED 573
AED 1,067 total
includes taxes & fees
12 Mar - 13 Mar
Beautiful Villa with Lake Views
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, (22)
"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
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
Stunning Black and White 2 Bed APT
living room, dining room, tv

Stunning Black and White 2 Bed APT

2.0 star property
Stunning Black and White 2 Bed APT
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
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
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!"
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
Charming 1BR Vintage Treehouse Garage Apartment
Living area

Charming 1BR Vintage Treehouse Garage Apartment

2.0 star property
Charming 1BR Vintage Treehouse Garage Apartment
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
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, (824)
"The staff was so great, very kind and helpful. There is also a local cat that hangs out that is very sweet!"
The price is AED 377
AED 424 total
includes taxes & fees
13 Feb - 14 Feb
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, (1735)
"Hotel was overall great! Location is great and the amenities were good. The only problem I experienced was that the shower handle came off as soon as I touched it to turn shower on."
The price is AED 730
AED 916 total
includes taxes & fees
14 Feb - 15 Feb
Florida Hotel & Conference Center in the Florida Mall
Sonder at The Point
Room

Sonder at The Point

4.0 star property
8.4 out of 10, Very Good, (645)
"This is our third time staying here and its always clean and perfect! "
The price is AED 341
AED 383 total
includes taxes & fees
17 Feb - 18 Feb
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.