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Search Cottages in Winter Springs

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Compare 88 Cottages in Winter Springs with updated reviews, rates, and availability.

Orlando Lakefront Tiny House Community
Exterior

Orlando Lakefront Tiny House Community

3.0 star property
9.4 out of 10, Exceptional, (240)
"Beautiful, quiet and peaceful. Lots of local wildlife to observe. Simple check in. Hosts were very accommodating and helpful. Would stay here again in the future"
The price is SAR 298
SAR 610 total
includes taxes & fees
14 Jan - 15 Jan
Orlando Lakefront Tiny House Community
Tiny Hidden Cottage
Room

Tiny Hidden Cottage

9.2 out of 10, Wonderful, (25)
"The house was perfect for my weekend stay and I hope to stay again on my next trip"
The price is SAR 338
SAR 622 total
includes taxes & fees
23 Jan - 24 Jan
Tiny Hidden Cottage
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
Orlando oasis ☀️

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

9.8 out of 10, Exceptional, (9)
"It's a lovely, well-appointed, well-located place. The cottage is within easy walking distance of multiple restaurants. The communication was excellent. I hope to stay at the cottage again soon!"
The price is SAR 657
SAR 1,305 total
includes taxes & fees
12 Jan - 13 Jan
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
The Sanford Foodie Guest House
Terrace/patio

The Sanford Foodie Guest House

9.6 out of 10, Exceptional, (4)
"My son and I stayed in Sanford for one night to see a show at Theater West End and I chose this little guest house based mainly on proximity. It was exactly as described in the listing and was perfect to meet our needs. Super cute and convenient. The owner was very professional and communicative. I will definitely stay here again. "
The price is SAR 300
SAR 832 total
includes taxes & fees
7 Jan - 8 Jan
The Sanford Foodie Guest House
Orlando, Florida Guest House with Private pool & WiFi
Pool for your enjoyment.

Orlando, Florida Guest House with Private pool & WiFi

9.8 out of 10, Exceptional, (26)
"I had surgery and stayed here for my recovery, nice quiet area, easily accessible to stores and very comfortable bed. I felt very comfortable while recuperating. Washer and dryer big plus and the pool was beautiful and well kept. I didn't get to use the pool but I sure would have loved to. I will be back when I have to go for my checkups "
The price is SAR 470
SAR 1,027 total
includes taxes & fees
17 Jan - 18 Jan
Orlando, Florida Guest House with Private pool & WiFi
The Pink Door Cottage-Historic Sanford
Exterior detail

The Pink Door Cottage-Historic Sanford

10.0 out of 10, Exceptional, (9)
"A great location in Sanford. Well-stocked house in a historic district near downtown. Close to everything. Great host. Sleeps six comfortably. Large backyard with outdoor patio and bbq. An excellent family unit. 5 stars +."
The Pink Door Cottage-Historic Sanford
Downtown Cottage
Exterior detail

Downtown Cottage

10.0 out of 10, Exceptional, (2)
"Garren’s place had everything we needed: Privacy, plenty of space & being centrally located. My friend and I stayed here for a concert on Mills. We walked to the show, got some food & hit up a couple of bars- all in the same neighborhood. In the morning we went to Bakery 1908, only a 5 min walk from our door. I really appreciated the open kitchen & living room area as well. Felt like a lot of space for the price. Overall we loved staying at Garren’s and can’t wait to come back for the next...
The price is SAR 300
SAR 730 total
includes taxes & fees
9 Jan - 10 Jan
Downtown Cottage
Orlando Home w/ Private Pool: 10 Mi to UCF Campus!
Pool

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

3.0 star property
Orlando Home w/ Private Pool: 10 Mi to UCF Campus!
Luxe Orlando Home w/ Grill & Fenced Yard!
Living area

Luxe Orlando Home w/ Grill & Fenced Yard!

3.0 star property
Luxe Orlando Home w/ Grill & Fenced Yard!
THE HIDEAWAY AT COLLEGE PARK
Property grounds

THE HIDEAWAY AT COLLEGE PARK

8.0 out of 10, Very Good, (1)
"Overall, this was a great stay for my needs. The location was close to where I needed to be. I ABSOLUTELY loved the decor. I had three concerns. We did not know how to use the security code and had to YouTube directions. The second bedroom did not have a "bed" and there is not a curtain so my guest slept in the living room. bedro a bedroom and was very small"
THE HIDEAWAY AT COLLEGE PARK
Dtwn Winter Garden Home: 12 Mi to Disney!
Winter Garden Vacation Rental | 3BR | 2BA | 1,200 Sq Ft | 3 Steps to Enter

Dtwn Winter Garden Home: 12 Mi to Disney!

9.6 out of 10, Exceptional, (5)
"We evacuated from Helene. Because we were unable to return to our home, we ended up having to rent multiple vacation rentals. This is the first home that actually looked like it did online--really lovely. (I agree, yard can use some TLC) I liked the retro touches throughout. Comfortable furniture and beds. Luxury towels and linens. Really nice! Walk west and cross over Dillard two block then three blocks north to Plant street and you'll find many wonderful restaurants and shops. Saturday...
Dtwn Winter Garden Home: 12 Mi to Disney!
Resort Townhome: Perfect Orlando Vacation Spot!!
Living area

Resort Townhome: Perfect Orlando Vacation Spot!!

4.0 star property
8.0 out of 10, Very Good, (1)
Resort Townhome: Perfect Orlando Vacation Spot!!
~ 12 Mi to Disney: Downtown Winter Garden Cottage!
Winter Garden Vacation Rental | 2BR | 1BA | 3 Steps Required for Entry

~ 12 Mi to Disney: Downtown Winter Garden Cottage!

9.8 out of 10, Exceptional, (42)
"We wanted something special on a short trip to Winter Garden. We were combining the trip with a visit to our new grand-daughter and spending time in a lovely area of the city."
~ 12 Mi to Disney: Downtown Winter Garden Cottage!
Orlando Golden Girls Retreat: Prime Location!
Living area

Orlando Golden Girls Retreat: Prime Location!

3.0 star property
Orlando Golden Girls Retreat: Prime Location!
Chic Orlando Family Getaway w/ Fenced Yard!
Living area

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!
3 Mi to Lake Harney: Home on 6 Acres w/ Fire Pit
Living area

3 Mi to Lake Harney: Home on 6 Acres w/ Fire Pit

3.0 star property
3 Mi to Lake Harney: Home on 6 Acres w/ Fire Pit
Lake Mary, Florida Cottage with queen bed & fire pit.
Family Room

Lake Mary, Florida Cottage with queen bed & fire pit.

10.0 out of 10, Exceptional, (8)
"Nice and clean, and small"
Lake Mary, Florida Cottage with queen bed & fire pit.
Deltona Lake House, Day Trip to Disney & Universal
Exterior

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
Apopka Single-story Home w/ Private Lanai + Pool!
Pool

Apopka Single-story Home w/ Private Lanai + Pool!

3.0 star property
Apopka Single-story Home w/ Private Lanai + Pool!
Lake Marion Home w/ Canoe in Altamonte Springs!
Living area

Lake Marion Home w/ Canoe in Altamonte Springs!

3.0 star property
Lake Marion Home w/ Canoe in Altamonte 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.
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Other property types in Winter Springs

The View Studio Suites and Event Venue
Front of property

The View Studio Suites and Event Venue

3.5 star property
8.4 out of 10, Very Good, (684)
"The hotel is definitely dated.. but the price reflects that. Regardless, my room and bedding were clean and comfortable. The breakfast was simple but good. Parking was easy. Access to highways and expressways were also easy. I didn’t need much and didn’t spend much time at the hotel as I was out and about most days of my stay.. so it was perfect for me. No complaints."
The price is SAR 287
SAR 323 total
includes taxes & fees
13 Jan - 14 Jan
The View Studio Suites and Event Venue
Florida Hotel & Conference Center in the Florida Mall
Exterior

Florida Hotel & Conference Center in the Florida Mall

3.5 star property
9.0 out of 10, Wonderful, (1667)
"This property is connected to the Florida Mall which is a great convenience for families traveling with children. "
The price is SAR 634
SAR 810 total
includes taxes & fees
4 Jan - 5 Jan
Florida Hotel & Conference Center in the Florida Mall
The Point Hotel & Suites
Exterior

The Point Hotel & Suites

3.5 star property
8.0 out of 10, Very Good, (3118)
"Not clean"
The price is SAR 409
SAR 504 total
includes taxes & fees
15 Jan - 16 Jan
The Point Hotel & Suites
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.

Frequently asked questions

How much do cottages in Winter Springs cost?
You can expect to pay between SAR 298 and SAR 657 per night for cottages in Winter Springs. No matter your budget, a wonderful stay is only a click 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?
We think that vacays should be stress-free, so if you’re looking for cottages in Winter Springs at an affordable rate, Expedia has got your back. Save those pennies and stay in a wallet-friendly option far away from the hustle and bustle, or splurge on an upmarket cottage to really spoil your favorite people.
How can I find cheap cottages in Winter Springs?
The simplest way to locate cheap cottages in Winter Springs is with Expedia’s handy filter tool. Narrow your search results by budget, star rating and amenities to discover awesome rates with only a few clicks.