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Search Guest Houses in Winter Springs

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Compare 22 Guest Houses in Winter Springs with updated reviews, rates, and availability.

Front of property
The Ann Stevens House
3.0 star property
9.4 out of 10, Exceptional, (139)
"My spouse and I stayed for the weekend for our wedding anniversary and we were in awww with the property. So beautiful and comfortable. The owners are super nice and I just love how she tells the story of the history of the home and surrounding town. The room was more than amazing with its own bathroom with a jet tub and balcony We didn’t get to experience any of the amenities such as their Tavern bar they promote nor were they serving breakfast due to electrical issues which is understandable....
The price is AED 584
AED 657 total
includes taxes & fees
30 May - 31 May
The Ann Stevens House
Private kitchen
 Peaceful Three Bedroom Guest House near Wekiva River and State Parks 
10.0 out of 10, Exceptional, (71)
"This experience couldn’t have been better. The home was in perfect condition and had everything that we needed. We were very comfortable and will definitely be back."
 Peaceful Three Bedroom Guest House near Wekiva River and State Parks 
Property grounds
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
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King bed, dresser, luggage rack, plenty of closet space with full mirror
Adorable 1bed 1 bath guest house
10.0 out of 10, Exceptional, (13)
"Property was easy to find and easy to access. It was clean and decorated nicely."
Adorable 1bed 1 bath guest house
Living area
Tiny Cottage Farm House!
9.8 out of 10, Exceptional, (15)
"Not only was the tiny farmhouse great, it was Super Cute!! All the thoughtfulness put into everything including the funny signs all over made my trip very enjoyable! Tanya was very responsive and respectful of my privacy (she lives on the property) I felt very safe and comfortable. Would highly recommend her place. Thanks again Tanya for creating a wonderful space 🤗"
Tiny Cottage Farm House!
Detached Guesthouse over our 3 Car Garage
SPRING LAKE GETAWAY SUITE (Detached Guest House)
10.0 out of 10, Exceptional, (44)
"We really enjoyed our stay. Great location for what we needed. Pictures and descriptions accurate. I would recommend this property for 1-2 guests."
SPRING LAKE GETAWAY SUITE (Detached Guest House)
Room
2 Minutes to Universal Studios Theme Parks - Central, Relaxing and Chic 1BR
9.8 out of 10, Exceptional, (11)
"EASY! Convenient. Quiet nice neighborhood!"
The price is AED 283
AED 578 total
includes taxes & fees
9 Jun - 10 Jun
2 Minutes to Universal Studios Theme Parks - Central, Relaxing and Chic 1BR
Pool
Paradise in a country setting. 2 BDRM 1100 SQ FT apartment. 1 King ,1 Queen
10.0 out of 10, Exceptional, (5)
"Beautiful neighborhood, was perfectly centered for us to travel to a tigers game and cape Canaveral . There was a manned launch on one of the nights and we could see it from the deck. Friendly attentive owners, would definitely recommend."
Paradise in a country setting. 2 BDRM 1100 SQ FT apartment. 1 King ,1 Queen
Exterior
Downtown Orlando Throne Historic Thornton Park
10.0 out of 10, Exceptional, (1)
"Nice size property great location great host"
The price is AED 312
AED 853 total
includes taxes & fees
11 Jun - 12 Jun
Downtown Orlando Throne Historic Thornton Park
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, (42)
"My family and I wanted to have fun during the day at all the Disney parks but was interested in staying somewhere quaint and quiet in the evenings. This place was perfect and we would recommend it to everyone. Great price, great location and great host!"
The price is AED 676
AED 1,463 total
includes taxes & fees
4 Jun - 5 Jun
Mills Cottage by the Little Lake
Tiny Cottage - 3 MI to Downtwn w/ Grill & Hammocks
10.0 out of 10, Exceptional, (3)
"The property was fantastic. The bed and bedding was so comfortable. Zero complaints. Highly recommended. Great communication with the owners. "
The price is AED 224
AED 682 total
includes taxes & fees
4 Jun - 5 Jun
Tiny Cottage - 3 MI to Downtwn w/ Grill & Hammocks
City Guesthouse in beautiful Historic Downtown Sanford
9.6 out of 10, Exceptional, (4)
"Perfect"
The price is AED 367
AED 905 total
includes taxes & fees
6 Jun - 7 Jun
City Guesthouse in beautiful Historic Downtown Sanford
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
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 AED 422
AED 1,235 total
includes taxes & fees
30 May - 31 May
Casa Catalina☀️ Lakefront Apartment near Downtown
Interior
Modern and Romantiv Villa
10.0 out of 10, Exceptional, (7)
"You can stop looking…this one is perfect! Very clean, quiet, private outdoor sitting area, well equipped, beautiful, modern accommodations!"
Modern and Romantiv Villa
Exterior
Quiet Garden Retreat Downtown Orlando - Private Apartment, Shared Pool and Patio
9.6 out of 10, Exceptional, (14)
"We had a wonderful stay! Cheryl and Eric were beyond kind and welcoming upon our arrival and showed us all around the guesthouse. They were very helpful and very quick to respond via messaging, but not intrusive at all, as we never saw them during our stay. The guesthouse was fun and ecclectic and a wonderful space. We were in town for th Olympic Marathon Trials so we parked the car and then were on foot throughout the weekend. Its such an amazing location to be able to walk everywhere! Quiet...
Quiet Garden Retreat Downtown Orlando - Private Apartment, Shared Pool and Patio
Exterior
Blissful Guest House
3.0 star property
2.0 out of 10, (1)
Blissful Guest House
Pool
Luxury Comfortable Guest Suite in Altamonte Springs - Large Pool
Luxury Comfortable Guest Suite in Altamonte Springs - Large Pool
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
Room
Your Home Away From Home
Your Home Away From Home
Don't see what you're looking for?
See all available properties in Winter Springs
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.

Other property types in Winter Springs

Pool
Avanti International Resort
3.0 star property
7.8 out of 10, Good, (2114)
"Excellent service "
The price is AED 345
AED 450 total
includes taxes & fees
6 Jun - 7 Jun
Avanti International Resort
Rooftop pool
Hyatt Regency Orlando International Airport
4.0 star property
9.4 out of 10, Exceptional, (4866)
"Enjoyed some well needed rest! Everyone was wonderful!"
The price is AED 731
AED 810 total
includes taxes & fees
1 Jun - 2 Jun
Hyatt Regency Orlando International Airport
Room
CoCo Key Hotel and Water Resort 
3.5 star property
7.4 out of 10, Good, (3771)
"We thoroughly enjoyed our time including the water park and the pool/hot tub area. Wished the water park had longer hours but we did enjoy it. Close by everything, and the staff was exceptional at keeping areas cleaned and numerous towels available. Had a great stay, will stay again! "
The price is AED 334
AED 544 total
includes taxes & fees
30 May - 31 May
CoCo Key Hotel and Water Resort 
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.

Recent reviews of Winter Springs hotels
Expedia verified reviews

Universal's Endless Summer Resort - Dockside Inn and Suites

Universal's Endless Summer Resort - Dockside Inn and Suites

5/5 Excellent
"Very nice "
A verified traveler stayed at Universal's Endless Summer Resort - Dockside Inn and Suites
Posted 5 hours ago
Universal's Endless Summer Resort - Dockside Inn and Suites