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Check prices for these dates

Next weekend
2 May - 4 May
In two weeks
9 May - 11 May
In one month
23 May - 25 May
In two months
20 Jun - 22 Jun

Compare 27 Guest Houses in Winter Springs with updated reviews, rates, and availability.

The Ann Stevens House
Exterior

The Ann Stevens House

3.0 star property
9.4 out of 10, Exceptional, (151)
"Beautiful place to stay. "
The price is AED 584
AED 657 total
includes taxes & fees
25 Apr - 26 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 AED 312
AED 631 total
includes taxes & fees
28 Apr - 29 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, (68)
"I'd absolutely stay here again. "
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)
"Super spacious for a tiny house and fit 6 of us perfectly! Had everything we needed"
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)
"Excellent place with everything you could need. Michael is a very thoughtful host. Very close and conveniently located to RBC and Ligonier Ministries! Cannot recommend enough!"
 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)
"Great home away from home"
The price is AED 683
AED 1,420 total
includes taxes & fees
28 Apr - 29 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

8.8 out of 10, Excellent, (16)
"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
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)
"Nice size property great location great host"
The price is AED 312
AED 860 total
includes taxes & fees
25 Apr - 26 Apr
Downtown Orlando Throne Historic Thornton Park
Historic lakefront guesthouse
Interior

Historic lakefront guesthouse

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 AED 481
AED 1,084 total
includes taxes & fees
5 May - 6 May
Historic lakefront guesthouse
Adorable 1bed 1 bath guest house
Smart TV

Adorable 1bed 1 bath guest house

10.0 out of 10, Exceptional, (24)
"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
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-size fridge, microwave, oven, stovetop

Quiet Garden Retreat Downtown Orlando - Private Apartment, Shared Pool and Patio

9.6 out of 10, Exceptional, (15)
"Had a lovely visit in Orlando! Easy to find, host is very nice, communicative and helpful! Would definitely stay again"
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)
"Great place for the 2 of us and awesome location."
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
Quiet 2BR | Remote Work, Pets, Near Airport!
2 bedrooms, desk, iron/ironing board, free WiFi

Quiet 2BR | Remote Work, Pets, Near Airport!

2.0 star property
Quiet 2BR | Remote Work, Pets, Near Airport!
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, (1031)
"Nice place to stay! "
The price is AED 294
AED 330 total
includes taxes & fees
27 Apr - 28 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, (1879)
"Great place to stay "
The price is AED 627
AED 801 total
includes taxes & fees
7 May - 8 May
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, (197)
"Very nice place to stay. "
The price is AED 515
AED 579 total
includes taxes & fees
22 May - 23 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.