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Check prices for these dates

Next weekend
25 Jul - 27 Jul
In two weeks
1 Aug - 3 Aug
In one month
15 Aug - 17 Aug
In two months
12 Sep - 14 Sep

Cottages in Winter Springs

Orlando Lakefront Tiny House Community
The Club House | 2 bedrooms, individually decorated, individually furnished

Orlando Lakefront Tiny House Community

3.0 star property
9.4 out of 10, Exceptional, (323)
"We enjoyed our stay, I loved the the view of the lake from the main bedroom ,it’s a beautiful and relaxing place."
The price is AED 233
AED 530 total
includes taxes & fees
22 Jul - 23 Jul
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 AED 290
AED 563 total
includes taxes & fees
21 Jul - 22 Jul
Tiny Hidden Cottage
Florida Guest House with Private pool & WiFi
Outdoor pool

Florida Guest House with Private pool & WiFi

9.8 out of 10, Exceptional, (38)
"Wonderful stay. This is my second time here and love the accommodations and location. Very quiet. "
The price is AED 374
AED 897 total
includes taxes & fees
26 Jul - 27 Jul
Florida Guest House with Private pool & WiFi
Private Patio: College Park Cottage in Orlando!
Outdoor dining

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!
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
2 bedrooms, in-room safe, desk, iron/ironing board

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

10.0 out of 10, Exceptional, (24)
"Easy and convenient in a nice place "
The price is AED 641
AED 1,274 total
includes taxes & fees
28 Jul - 29 Jul
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
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
Deltona Lake House, Day Trip to Disney & Universal
House (2 Bedrooms) | Interior

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!
Paper towels

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

3.0 star property
Orlando Home w/ Private Pool: 10 Mi to UCF Campus!
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!
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 AED 264
AED 681 total
includes taxes & fees
21 Jul - 22 Jul
Downtown Cottage
Chic Orlando Family Getaway w/ Fenced Yard!
House (4 Bedrooms) | Front of property

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!
Near Kayak Launch: Riverfront Home in Sanford!
House (2 Bedrooms) | Interior

Near Kayak Launch: Riverfront Home in Sanford!

3.0 star property
Near Kayak Launch: Riverfront Home in Sanford!
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, (14)
"This was a cute place in a nice neighborhood "
The price is AED 503
AED 1,188 total
includes taxes & fees
21 Jul - 22 Jul
Hidden Garden Cottage-Swim&Spa, Ctrl Orlando Disney Universal Sea World Beaches,
5014 Tideview Circle #9
House (3 Bedrooms) | Property amenity

5014 Tideview Circle #9

3.0 star property
5014 Tideview Circle #9
Garden House - jacuzzi, skylights, window seat, near restaurants & culture
Exterior

Garden House - jacuzzi, skylights, window seat, near restaurants & culture

Garden House - jacuzzi, skylights, window seat, near restaurants & culture
The Sanford Foodie Guest House
1 bedroom, desk, WiFi, bed sheets

The Sanford Foodie Guest House

9.2 out of 10, Wonderful, (11)
"Great spot if you are visiting the area. The host was nice and helpful!"
The price is AED 225
AED 979 total
includes taxes & fees
22 Jul - 23 Jul
The Sanford Foodie Guest House
Dtwn Winter Garden Home: 12 Mi to Disney!
Fridge, microwave, stovetop, dishwasher

Dtwn Winter Garden Home: 12 Mi to Disney!

10.0 out of 10, Exceptional, (12)
"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!
Lovely Spacious Guesthouse in Mills 50 District, Orlando
Exterior detail

Lovely Spacious Guesthouse in Mills 50 District, Orlando

Lovely Spacious Guesthouse in Mills 50 District, Orlando
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

Rosen Inn at Pointe Orlando

Rosen Inn at Pointe Orlando

10/10 Excellent
"Great front desk, perfect location, great value"
Captain BF 3-night trip
Posted 11 hours ago
Rosen Inn at Pointe Orlando

Frequently asked questions

How much do cottages in Winter Springs cost?
You'll pay between AED 225 and AED 641 per night for cottages in Winter Springs. Whatever your budget, an ideal stay is only a few clicks away on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
Why book your cottage in Winter Springs with Expedia?
Expedia has some terrific cottages in Winter Springs, so start packing your bags for a memorable vacation on nature's doorstep. If you're sticking to a budget, select how much you want to spend and the star rating of your property. Or take advantage of our filters to search for cottages with a hot tub or a kitchen. We'll help you find the perfect pad whatever your trip looks like.
How can I find cheap cottages in Winter Springs?
A good way to find cheap cottages in Winter Springs is with Expedia's useful filter tool. Tailor your search results by star rating, amenities and budget to access unbeatable rates with only a few clicks.