Photo by Stephanie Moraca

Search Guest Houses in Winter Springs

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Check prices for these dates

Next weekend
18 Apr - 20 Apr
In two weeks
25 Apr - 27 Apr
In one month
9 May - 11 May
In two months
6 Jun - 8 Jun

Featured Guest Houses in Winter Springs and around

The Ann Stevens House
Exterior

The Ann Stevens House

3.0 star property
9.4 out of 10, Exceptional, (151)
"What a beautiful, serene, magical place this is! The owners are so friendly and helpful and full of so much knowledge about the area. We loved our stay and wanted to stay longer!! "
The price is €159
includes taxes & fees
14 Apr - 15 Apr
The Ann Stevens 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, (30)
"This was a great option for my friend and I who were traveling. It had two separate bedrooms, a decent kitchen, and a nice seating area. It’s pretty much in downtown, we walked very easily to the Orlando magic stadium and there’s plenty of restaurants within walking distance around the home. would definitely stay here again, and I really appreciated the communication from the property management company. "
The price is €157
includes taxes & fees
21 Apr - 22 Apr
Downtown Lake Eola Historic House 1 OR 2 BED
SPRING LAKE GETAWAY SUITE (Detached Guest House)
Property grounds

SPRING LAKE GETAWAY SUITE (Detached Guest House)

10.0 out of 10, Exceptional, (65)
"Elegant and cozy. "
SPRING LAKE GETAWAY SUITE (Detached Guest 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 Tiny Cottage Farm House!
Terrace/patio

Cozy Tiny Cottage Farm House!

9.8 out of 10, Exceptional, (20)
"I needed a convenient place to stay while visiting family in Longwood, and this rental was perfect. Tucked away from the main road in a quiet neighborhood, the house was easy to find and check-in was effortless. The efficient space was well-appointed with all I needed for a cozy spot to sleep, have breakfast, and wash a small load of laundry before setting out to spend my day with family. I will be back."
Cozy Tiny Cottage Farm House!
 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, (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 
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 €361
includes taxes & fees
23 Apr - 24 Apr
Mills Cottage by the Little Lake
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

9.2 out of 10, Wonderful, (15)
"This place was good for a two night pre cruise stay. Half of what you would pay staying at a hotel. A rental car is a must have for going anywhere. We just slept and showered here as we were out all day and brought takeout back. They provided a nice bottle of wine. I was disappointed that the bedding was not the nice white bedding pictured and was burgundy instead. A decent place to stay short term if you want to save on accommodations . "
2 Minutes to Universal Studios Theme Parks - Central, Relaxing and Chic 1BR
Downtown Orlando Throne Historic Thornton Park
Microwave, coffee/tea maker, cookware/dishes/utensils

Downtown Orlando Throne Historic Thornton Park

10.0 out of 10, Exceptional, (3)
"Property is in a great location of Thornton Park. We arrived and parked the car. Walking distance to everything, such an awesome weekend."
The price is €207
includes taxes & fees
16 Apr - 17 Apr
Downtown Orlando Throne Historic Thornton Park
Beautiful Villa with Lake Views
Interior

Beautiful Villa with Lake Views

10.0 out of 10, Exceptional, (2)
"Overall wonderful stay in a great historic neighborhood! The area was quiet, safe and enjoyable for morning walks or coffee on the balcony with lake views. The villa itself was a lot more spacious than the pictures indicate and all the furnishings and accommodations included were just right for either a short- or long-term stay. The location was in close proximity to many local attractions, shopping, and restaurants, but did not feel crowded. Our host, Jason, was responsive to any questions and...
The price is €269
includes taxes & fees
29 Apr - 30 Apr
Beautiful Villa with Lake Views
Adorable 1bed 1 bath guest house
Smart TV

Adorable 1bed 1 bath guest house

10.0 out of 10, Exceptional, (24)
"Samson and Sunny clearly put in the effort to make sure I felt welcome during my stay. The check in and check out processes were very simple (not always the case with properties!) which I really appreciated. "
Adorable 1bed 1 bath guest house
Private studio; big outdoor space
Fridge, microwave, stovetop, dishwasher

Private studio; big outdoor space

10.0 out of 10, Exceptional, (20)
"We were very pleased with our hosts and their responsiveness to any concerns we had. The property worked very well for us as we spent our days with family and returned to our quiet place in the evenings. "
Private studio; big outdoor space
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
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
Private Poolside Guest House In Winter Park/Orlando
A heated 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
Elegant Black & White 2BR | Pet-Friendly
2 bedrooms, desk, iron/ironing board, free WiFi

Elegant Black & White 2BR | Pet-Friendly

2.0 star property
Elegant Black & White 2BR | Pet-Friendly
Blissful Guest House
Exterior

Blissful Guest House

3.0 star property
2.0 out of 10, (1)
Blissful Guest House
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
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
Your Home Away From Home
Smart TV

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
Exterior

The View Studio Suites and Event Venue

3.0 star property
8.4 out of 10, Very good, (1011)
"Away from the city center, made it a quite stay. "
The price is €73
includes taxes & fees
13 Apr - 14 Apr
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
9.2 out of 10, Wonderful, (1865)
"The property/our room was clean. Tue ENTIRE staff we communicated with were all so friendly and helpful. I unfortunately didn’t get everyone’s names but I did communicate with with a Sebastian. Super nice people. "
The price is €222
includes taxes & fees
12 Apr - 13 Apr
Florida Hotel & Conference Center in the Florida Mall
Sonder Vista Cay
Outdoor pool

Sonder Vista Cay

3.5 star property
9.0 out of 10, Wonderful, (192)
"Apartment was clean. "
The price is €157
includes taxes & fees
4 May - 5 May
Sonder Vista Cay
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.