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Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Browse Select Winter Springs Cottages

Orlando Lakefront Tiny House Community
The Sunshine Lake Shake

Orlando Lakefront Tiny House Community

3.0 star property
9.4 out of 10, Exceptional, (327)
"We enjoyed our stay."
The price is CA $89
CA $201 total
includes taxes & fees
Sep 8 - Sep 9
Orlando Lakefront Tiny House Community
Tiny Hidden Cottage
Interior

Tiny Hidden Cottage

9.4 out of 10, Exceptional, (48)
"Host provided eggs from chickens that roost on the property - nice extra!"
The price is CA $98
CA $198 total
includes taxes & fees
Aug 10 - Aug 11
Tiny Hidden Cottage
Hidden Garden Cottage-Swim&Spa, Ctrl Orlando Disney Universal Sea World Beaches,
Property grounds

Hidden Garden Cottage-Swim&Spa, Ctrl Orlando Disney Universal Sea World Beaches,

8.4 out of 10, Very good, (15)
"This was a cute place in a nice neighborhood "
Hidden Garden Cottage-Swim&Spa, Ctrl Orlando Disney Universal Sea World Beaches,
Private Patio: College Park Cottage in Orlando!
Exterior

Private Patio: College Park Cottage in Orlando!

10.0 out of 10, Exceptional, (8)
"I stayed here for a month with my dog. It was exactly what I needed! The hosts thought of everything that you could possibly need. There is a ton of space and everything is organized and clean. Location is great being close to local shops, necessities, and major roads."
Private Patio: College Park Cottage in Orlando!
Dtwn Winter Garden Home: 12 Mi to Disney!
Exterior

Dtwn Winter Garden Home: 12 Mi to Disney!

10.0 out of 10, Exceptional, (13)
"We had a wonderful stay in Analia’s home. It was a perfect location and 4 adults were quit comfortable for two weeks. "
Dtwn Winter Garden Home: 12 Mi to Disney!
The Pink Door Cottage-Historic Sanford
Outdoor dining

The Pink Door Cottage-Historic Sanford

9.8 out of 10, Exceptional, (17)
"Fully equipped with everything one could need whilst staying here."
The Pink Door Cottage-Historic Sanford
Labor Day Getaway!! Guest House with Private pool & WiFi
Exterior

Labor Day Getaway!! Guest House with Private pool & WiFi

9.8 out of 10, Exceptional, (40)
"Wonderful stay. This is my second time here and love the accommodations and location. Very quiet. "
Labor Day Getaway!! Guest House with Private pool & WiFi
Lovely Spacious Guesthouse in Mills 50 District, Orlando
Exterior

Lovely Spacious Guesthouse in Mills 50 District, Orlando

10.0 out of 10, Exceptional, (1)
"Loved this space, by great locations. Can’t wait to visit again."
Lovely Spacious Guesthouse in Mills 50 District, Orlando
~ 12 Mi to Disney: Downtown Winter Garden Cottage!
Exterior

~ 12 Mi to Disney: Downtown Winter Garden Cottage!

9.8 out of 10, Exceptional, (43)
"We LOVE staying at Flamingo House. We are a repeat customer and will be back again soon. Suzie and is wonderful to work with and the house is everything we need!"
~ 12 Mi to Disney: Downtown Winter Garden Cottage!
Deltona Lake House, Day Trip to Disney & Universal
House (2 Bedrooms) | Front of property

Deltona Lake House, Day Trip to Disney & Universal

3.0 star property
10.0 out of 10, Exceptional, (3)
"This house was perfect! Very spacious, clean, and felt like a very safe neighborhood for a few women traveling. The ONLY improvements I would suggest would be having more towels, and extra blankets available for guests. And I would replace the pull out couch mattress as it was very uncomfortable. Still a 10/10 overall!"
Deltona Lake House, Day Trip to Disney & Universal
Orlando Home w/ Private Pool: 10 Mi to UCF Campus!
Exterior

Orlando Home w/ Private Pool: 10 Mi to UCF Campus!

3.0 star property
Orlando Home w/ Private Pool: 10 Mi to UCF Campus!
Downtown Cottage
1 bedroom, desk, iron/ironing board, free WiFi

Downtown Cottage

9.6 out of 10, Exceptional, (4)
"Thank you for a wonderful stay. This gem of a guest house is in a perfect location in the Mills50 area of downtown Orlando. A perfectly cozy little home with comfortable beds and a welcoming environment. We look forward to staying again next time we are in Orlando!"
The price is CA $80
CA $234 total
includes taxes & fees
Aug 10 - Aug 11
Downtown Cottage
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
Exterior

The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!

10.0 out of 10, Exceptional, (26)
"Easy and convenient in a nice place "
The price is CA $247
CA $486 total
includes taxes & fees
Aug 11 - Aug 12
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
Orlando Golden Girls Retreat: Prime Location!
House (1 Bedroom) | Interior

Orlando Golden Girls Retreat: Prime Location!

3.0 star property
Orlando Golden Girls Retreat: Prime Location!
Resort Townhome: Perfect Orlando Vacation Spot!!
House (3 Bedrooms) | Property amenity

Resort Townhome: Perfect Orlando Vacation Spot!!

4.0 star property
8.0 out of 10, Very good, (1)
Resort Townhome: Perfect Orlando Vacation Spot!!
Chic Orlando Family Getaway w/ Fenced Yard!
House (4 Bedrooms) | Interior

Chic Orlando Family Getaway w/ Fenced Yard!

3.0 star property
10.0 out of 10, Exceptional, (1)
Chic Orlando Family Getaway w/ Fenced Yard!
Fire Pit & Yard: Updated Winter Garden Home!
House (2 Bedrooms) | Interior

Fire Pit & Yard: Updated Winter Garden Home!

3.0 star property
Fire Pit & Yard: Updated Winter Garden Home!
~ 9 Mi to Universal: Orlando Retreat w/ Sun Porch!
House (3 Bedrooms) | Interior

~ 9 Mi to Universal: Orlando Retreat w/ Sun Porch!

3.0 star property
~ 9 Mi to Universal: Orlando Retreat w/ Sun Porch!
Screened Lanai + Fenced Yard: Luxe Orlando Home
Interior

Screened Lanai + Fenced Yard: Luxe Orlando Home

3.0 star property
Screened Lanai + Fenced Yard: Luxe Orlando Home
The Sanford Foodie Guest House
1 bedroom, desk, WiFi, bed sheets

The Sanford Foodie Guest House

8.6 out of 10, Excellent, (12)
"Great spot if you are visiting the area. The host was nice and helpful!"
The price is CA $76
CA $348 total
includes taxes & fees
Sep 4 - Sep 5
The Sanford Foodie Guest House
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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Top Winter Springs Hotel Reviews

Holiday Inn Express & Suites, International Drive by IHG

Holiday Inn Express & Suites, International Drive by IHG

10/10 Excellent
"Cathrine was very nice. She was willing to help me out unlike the manager. "
Laura 2-night trip
Posted 9 hours ago
Holiday Inn Express & Suites, International Drive by IHG