A water fountain, palm trees, and a Ferris wheel.

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Southwest Orlando cottages

A serene landscape with a pond, trees with Spanish moss, and a palm tree.

1. 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 ￥17,561
￥52,237 total
includes taxes & fees
Oct 16 - Oct 17
Shore Steps Cottage - Walking Distance To The Town Of Windermere
A house with a red door, a front porch, and a pathway leading to the entrance.

2. 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 ￥12,810
￥30,971 total
includes taxes & fees
Oct 26 - Oct 27
Downtown Cottage
A white building with large windows and a brick pathway leading to it.

3. 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 ￥25,382
￥52,153 total
includes taxes & fees
Nov 4 - Nov 5
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
A table with a potted plant and a cup of coffee, overlooking a scenic landscape.

4. Romantic Lakefront Getaway with Balcony near Downtown Orlando

Romantic Lakefront Getaway with Balcony near Downtown Orlando
Orlando
The price is ￥12,691
￥31,886 total
includes taxes & fees
Oct 19 - Oct 20
Romantic Lakefront Getaway with Balcony near Downtown Orlando
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 ￥29,031
￥88,334 total
includes taxes & fees
Oct 15 - Oct 16
Chic Orlando Family Getaway w/ Fenced Yard!
A residential property with a well-maintained lawn, a paved driveway, and a small garden area with plants.

6. Gorgeous Cottage near Lake Louisa & mins 2 Disney.

Gorgeous Cottage near Lake Louisa & mins 2 Disney.
Vacation Village
9.4 out of 10, Exceptional, (65 reviews)
"Wonderful time at a property just right for our needs and wants. "
United States
Peter C.
The price is ￥19,671
￥25,008 total
includes taxes & fees
Oct 15 - Oct 16
Gorgeous Cottage near Lake Louisa & mins 2 Disney.
A resort with a large central pool, a smaller circular pool, and a fountain. There are multiple buildings with balconies and a parking lot.

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

Th10 - 3BR House Near Disney and Universal Studios
3.0 star property
Orlando
The price is ￥38,991
￥77,636 total
includes taxes & fees
Oct 28 - Oct 29
Th10 - 3BR House Near Disney and Universal Studios
A single-story mobile home with a front porch and a small deck.

8. Newly Remodeled Tiny Home 20 minutes from Disney!~

Newly Remodeled Tiny Home 20 minutes from Disney!~
Kissimmee
The price is ￥13,484
￥33,041 total
includes taxes & fees
Oct 15 - Oct 16
Newly Remodeled Tiny Home 20 minutes from Disney!~
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 ￥17,292
￥37,698 total
includes taxes & fees
Oct 19 - Oct 20
Walkable Quiet Lakefront Retreat near Downtown Orlando with Private Patio
A single-story building with the number 297, a red door, and a bench outside.

10. 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 ￥15,134
￥38,683 total
includes taxes & fees
Oct 15 - Oct 16
Orlando Pool Days & Hammock Naps Book Your Escape NOW!
A residential area with houses featuring sloped roofs and solar panels.

11. Upstay: Bright Family-friendly Retreat With Patio

Upstay: Bright Family-friendly Retreat With Patio
3.0 star property
Chatham Park
The price is ￥11,422
￥39,791 total
includes taxes & fees
Oct 19 - Oct 20
Upstay: Bright Family-friendly Retreat With Patio
An aerial view of a resort with multiple swimming pools, a dock, and a residential area with houses.

12. Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema

Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema
3.0 star property
Kissimmee
The price is ￥22,834
￥129,498 total
includes taxes & fees
Nov 2 - Nov 3
Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema
A single-story house with a gabled roof, a front porch, and a small front yard with a large agave plant.

13. Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee

Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
Kissimmee
10.0 out of 10, Exceptional, (2 reviews)
"We stayed and visited universal snd drove to Jacksonville it was a cute cottage"
United States
Jennifer b.
The price is ￥14,920
￥49,156 total
includes taxes & fees
Oct 19 - Oct 20
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
A two-story house with a front porch, a brick driveway, and a well-maintained lawn.

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

Fire Pit & Yard: Updated Winter Garden Home!
3.0 star property
Winter Garden
The price is ￥31,569
￥79,180 total
includes taxes & fees
Oct 18 - Oct 19
Fire Pit & Yard: Updated Winter Garden Home!
A mobile home with a paved driveway, a lawn, and a golf cart parked in front.

15. Perfect Place for a Perfect Vacation

Perfect Place for a Perfect Vacation
Kissimmee
10.0 out of 10, Exceptional, (1 review)
The price is ￥12,850
￥30,362 total
includes taxes & fees
Oct 18 - Oct 19
Perfect Place for a Perfect Vacation
A resort with multiple swimming pools, palm trees, and a large building with a red-tiled roof.

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

Th20 - 3BR House With Resort Access Near Parks
3.0 star property
Orlando
The price is ￥38,397
￥76,949 total
includes taxes & fees
Oct 28 - Oct 29
Th20 - 3BR House With Resort Access Near Parks
A patio with outdoor furniture, a wooden deck, and a basketball hoop.

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

Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage
Lake Mary
10.0 out of 10, Exceptional, (22 reviews)
The price is ￥16,657
￥41,183 total
includes taxes & fees
Nov 2 - Nov 3
Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage
A modern living room with a sofa, a large wall clock, and a mirror.

18. Family-Friendly Cottage Near Orlando’s Top Attractions

Family-Friendly Cottage Near Orlando’s Top Attractions
Kissimmee
10.0 out of 10, Exceptional, (1 review)
"Perfect location to enjoy Universal Epic and Islands of Adventure with only a 15 minute ride. The beds were very comfortable and the place is clean. We were welcomed with a cute sign, bottled water and cookies. Will definitely stay here again!"
United States
Joyce R.
The price is ￥14,278
￥32,141 total
includes taxes & fees
Oct 15 - Oct 16
Family-Friendly Cottage Near Orlando’s Top Attractions
A residential property with a red carpet leading to a door, a small garden area with green turf and potted plants, and a wooden fence.

19. Garden in the Cloud- Cottage St. Cloud with WiFi, AC, Free parking

Garden in the Cloud- Cottage St. Cloud with WiFi, AC, Free parking
St. Cloud
10.0 out of 10, Exceptional, (32 reviews)
"Great cute and clean place."
United States
Victoria T.
The price is ￥12,691
￥22,079 total
includes taxes & fees
Nov 9 - Nov 10
Garden in the Cloud- Cottage St. Cloud with WiFi, AC, Free parking
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 Southwest Orlando Hotel Reviews

The Point Hotel & Suites Orlando

The Point Hotel & Suites Orlando

10/10 Excellent
"All of the employees were very friendly and helpful. the room and grounds were kept in great shape and very clean. we will definitely return. have nothing bad to say about the experience at all."
Jacquelyn 2-night trip
Posted less than an hour ago
The Point Hotel & Suites Orlando

Find out more about Southwest Orlando

Southwest Orlando Cottages information

Number of reviews
158
Accommodation
5 Cottages
Lowest Price
￥22,079
Highest Price
￥129,498

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