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Compare 111 Cottages in Winter Springs with updated reviews, rates, and availability.

Orlando Lakefront Tiny House Community

3.0 star property
9.4 out of 10, Exceptional, (281)
"Very nice home away from home with a beautiful view"
The price is AED 256
AED 556 total
includes taxes & fees
31 Mar - 1 Apr
Orlando Lakefront Tiny House Community

Florida Guest House with Private pool & WiFi

9.8 out of 10, Exceptional, (29)
"We had a great time. The pool was nice to sit at. The house waa clean and lovely."
The price is AED 569
AED 1,142 total
includes taxes & fees
18 Apr - 19 Apr
Florida Guest House with Private pool & WiFi

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

10.0 out of 10, Exceptional, (12)
"Very inviting and cozy cottage with all amenities to get you started. Amazing cozy home if you're traveling with furry friends, great neighborhood and sites around. Many thanks!"
The price is AED 735
AED 1,361 total
includes taxes & fees
3 Apr - 4 Apr
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!

Tiny Hidden Cottage

9.4 out of 10, Exceptional, (36)
"The cottage was cozy and complete, with even silverware and coffee cups. When the microwave stopped working, the owner went out and bought and set up a new microwave.She asked permission before showing up at the front door!"
The price is AED 345
AED 625 total
includes taxes & fees
28 Apr - 29 Apr
Tiny Hidden Cottage

Downtown Cottage

9.6 out of 10, Exceptional, (4)
"This place was alright. Clean & was exactly as described. Bare concrete floors are a bit of a drawback. "
The price is AED 367
AED 797 total
includes taxes & fees
7 Apr - 8 Apr
Downtown Cottage

Incredible Private Lakefront Cottage Retreat

10.0 out of 10, Exceptional, (25)
"My partner and I were so awestruck by the beauty of the property! The house was immaculately clean and the location was perfect. The lake it sat on was beautiful and serene. We had everything we needed to decompress from the daily grind. We enjoyed the cute and cozy fireplace after visiting nearby botanical gardens. The bed was so comfortable we had a hard time getting up and going. Absolutely one of the best places we have ever stayed, just wish we could have stayed longer! Definitely will be...
The price is AED 511
AED 1,184 total
includes taxes & fees
31 Mar - 1 Apr
Incredible Private Lakefront Cottage Retreat

Private Patio: College Park Cottage in Orlando!

10.0 out of 10, Exceptional, (8)
"We throughly enjoyed our stay! I would highly recommend staying at The Cottage!"
Private Patio: College Park Cottage in Orlando!

The Sanford Foodie Guest House

9.2 out of 10, Wonderful, (9)
"It was a great place to crash for a night. "
The price is AED 275
AED 797 total
includes taxes & fees
31 Mar - 1 Apr
The Sanford Foodie Guest House

2BR COTTAGE IN SANFORD HISTORIC DISTRICT

10.0 out of 10, Exceptional, (98)
"This cottage is a quaint spot, inside and out. Cozy, clean and comfortable. Love the location. Great communication."
2BR COTTAGE IN SANFORD HISTORIC DISTRICT

The Pink Door Cottage-Historic Sanford

10.0 out of 10, Exceptional, (11)
"Fully equipped with everything one could need whilst staying here."
The Pink Door Cottage-Historic Sanford

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

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

Dtwn Winter Garden Home: 12 Mi to Disney!

9.8 out of 10, Exceptional, (9)
"The host was amazing! The house was very comfortable! Quiet neighborhood."
Dtwn Winter Garden Home: 12 Mi to Disney!

Near Disney & Universal: Family Retreat in Orlando

3.0 star property
Near Disney & Universal: Family Retreat in Orlando

5 Mi to Dtwn Orlando: Historic Hideaway!

3.0 star property
5 Mi to Dtwn Orlando: Historic Hideaway!

Resort Townhome: Perfect Orlando Vacation Spot!!

4.0 star property
8.0 out of 10, Very Good, (1)
Resort Townhome: Perfect Orlando Vacation Spot!!

Spring Break Cottage with queen bed & mini golf

10.0 out of 10, Exceptional, (12)
"Great stay ,may stay again another weekend next year when we visit family.Very clean and efficient. "
Spring Break Cottage with queen bed & mini golf

Gator Cove: Quaint 2-bedroom, 1-bath cottage, sleeps 4. Great for a peaceful retreat.

9.6 out of 10, Exceptional, (59)
"Perfect "
Gator Cove: Quaint 2-bedroom, 1-bath cottage, sleeps 4. Great for a peaceful retreat.

~ 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!

Gator Cottage: Cozy 2-bedroom, 1-bath cottage, sleeps 4. Perfect for a small family.

9.4 out of 10, Exceptional, (32)
"Easy to find, nice layout and decor. It was perfect. We liked walking over to see the restaurant, the lake and the alligators! Only a little feedback for your info. The tub was not clean, for bathing. Thank you!"
Gator Cottage: Cozy 2-bedroom, 1-bath cottage, sleeps 4. Perfect for a small family.

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!
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

Florida Hotel & Conference Center in the Florida Mall

3.5 star property
9.2 out of 10, Wonderful, (1844)
"After a very exhausting couple of days of my trip, it was a delight that they allowed me to have a very early check in, so I could take a nap in the middle of the day, much needed. The room was cold and crispy clean. Especially thankfull to Aliya for arraging all of that with me over the phone before leaving at the end of her shift. Definetly my place to stay when going to Orlando. "
The price is AED 615
AED 787 total
includes taxes & fees
10 Apr - 11 Apr
Florida Hotel & Conference Center in the Florida Mall

The View Studio Suites and Event Venue

3.0 star property
8.4 out of 10, Very Good, (980)
"Nice place to stay! "
The price is AED 314
AED 353 total
includes taxes & fees
31 Mar - 1 Apr
The View Studio Suites and Event Venue

Orlando Lakefront Tiny House Community

3.0 star property
9.4 out of 10, Exceptional, (281)
"Very nice home away from home with a beautiful view"
The price is AED 256
AED 556 total
includes taxes & fees
31 Mar - 1 Apr
Orlando Lakefront Tiny House Community
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’ll pay between AED 256 and AED 735 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.