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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Winter Springs cottages

A single-story building with the number 297, a red door, and a bench outside.

1. Orlando Pool Days & Hammock Naps Book Your Escape NOW!

Orlando Pool Days & Hammock Naps Book Your Escape NOW!
Lake Mary
9.8 out of 10, Exceptional, (67 reviews)
"The property was very clean and the host was quick to respond to any questions."
United States
Colette T.
The price is NZ$428
includes taxes & fees
15 Oct - 16 Oct
Orlando Pool Days & Hammock Naps Book Your Escape NOW!
A patio with outdoor furniture, a wooden deck, and a basketball hoop.

2. Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage

Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage
Lake Mary
10.0 out of 10, Exceptional, (22 reviews)
"Easy access, perfect location, perfectly appointed. Will stay again :-)"
United States
Tricia S.
The price is NZ$387
includes taxes & fees
8 Oct - 9 Oct
Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage
A house with a red door, a front porch, and a pathway leading to the entrance.

3. Downtown Cottage

Downtown Cottage
Colonialtown North
8.8 out of 10, Excellent, (15 reviews)
"Clean perfect location for what we needed "
United States
Jerred B.
The price is NZ$332
includes taxes & fees
12 Oct - 13 Oct
Downtown Cottage
A white building with large windows and a brick pathway leading to it.

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

The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
College Park
10.0 out of 10, Exceptional, (54 reviews)
"Everything was super clean and exactly as described. Great location and great stay!"
United States
Garrett S.
The price is NZ$582
includes taxes & fees
12 Oct - 13 Oct
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
A residential house with a front yard, a palm tree, and a garage.

5. Chic Orlando Family Getaway w/ Fenced Yard!

Chic Orlando Family Getaway w/ Fenced Yard!
3.0 star property
Rosemont
10.0 out of 10, Exceptional, (2 reviews)
"The house was well supplied with amenities, family friendly and it was very fun to use the pool and games. There’s a super Walmart and other shops close by."
United States
Jennifer
The price is NZ$990
includes taxes & fees
15 Oct - 16 Oct
Chic Orlando Family Getaway w/ Fenced Yard!
A table with a potted plant and a cup of coffee, overlooking a scenic landscape.

6. Romantic Lakefront Getaway with Balcony near Downtown Orlando

Romantic Lakefront Getaway with Balcony near Downtown Orlando
Orlando
The price is NZ$358
includes taxes & fees
3 Nov - 4 Nov
Romantic Lakefront Getaway with Balcony near Downtown Orlando
A serene landscape with a pond, trees with Spanish moss, and a palm tree.

7. Shore Steps Cottage - Walking Distance To The Town Of Windermere

Shore Steps Cottage - Walking Distance To The Town Of Windermere
Windermere
10.0 out of 10, Exceptional, (1 review)
The price is NZ$584
includes taxes & fees
14 Oct - 15 Oct
Shore Steps Cottage - Walking Distance To The Town Of Windermere
A resort with a large central pool, a smaller circular pool, and a fountain. There are multiple buildings with balconies and a parking lot.

8. Th130 - 3BR House Near Disney and Universal Parks

Th130 - 3BR House Near Disney and Universal Parks
3.0 star property
Orlando
The price is NZ$834
includes taxes & fees
12 Oct - 13 Oct
Th130 - 3BR House Near Disney and Universal Parks
A lakeside patio with wooden rocking chairs and a table, overlooking a calm lake and a forested area.

9. Walkable Quiet Lakefront Retreat near Downtown Orlando with Private Patio

Walkable Quiet Lakefront Retreat near Downtown Orlando with Private Patio
Orlando
The price is NZ$419
includes taxes & fees
19 Oct - 20 Oct
Walkable Quiet Lakefront Retreat near Downtown Orlando with Private Patio
A two-story house with a front porch, a brick driveway, and a well-maintained lawn.

10. Fire Pit & Yard: Updated Winter Garden Home!

Fire Pit & Yard: Updated Winter Garden Home!
3.0 star property
Winter Garden
The price is NZ$887
includes taxes & fees
18 Oct - 19 Oct
Fire Pit & Yard: Updated Winter Garden Home!
A multi-story residential building with balconies, a lawn, and outdoor seating.

11. Th10 - 3BR House Near Disney and Universal Studios

Th10 - 3BR House Near Disney and Universal Studios
3.0 star property
Orlando
The price is NZ$872
includes taxes & fees
28 Oct - 29 Oct
Th10 - 3BR House Near Disney and Universal Studios
A resort with a large central pool, a smaller circular pool, and a fountain. There are multiple buildings with balconies and a parking lot.

12. Th20 - 3BR House With Resort Access Near Parks

Th20 - 3BR House With Resort Access Near Parks
3.0 star property
Orlando
The price is NZ$868
includes taxes & fees
28 Oct - 29 Oct
Th20 - 3BR House With Resort Access Near Parks
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

Spark by Hilton Orlando near Universal

Spark by Hilton Orlando near Universal

10/10 Excellent
"I’d book here again"
Andrea 4-night trip
Posted 10 hours ago
Spark by Hilton Orlando near Universal

Find out more about Winter Springs

Winter Springs Cottages information

Number of reviews
123
Accommodation
146 Cottages
Lowest Price
NZ$332
Highest Price
NZ$990

Frequently asked questions

How much do cottages in Winter Springs cost?
You'll pay between NZ$332 and NZ$990 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.
What is there to do in Winter Springs near my cottage?
After you've unpacked your things and settled in, head out and discover the cool things Winter Springs has to offer. Tuscawilla Golf Course is a popular attraction to add to your itinerary.