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

Search Southwest Orlando Cottage Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

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 ￥19,594
￥54,714 total
includes taxes & fees
Nov 16 - Nov 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 ￥12,089
￥30,094 total
includes taxes & fees
Oct 25 - Oct 26
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 ￥25,283
￥51,949 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 ￥12,648
￥31,778 total
includes taxes & fees
Oct 19 - Oct 20
Romantic Lakefront Getaway with Balcony near Downtown Orlando
A residential property with a well-maintained lawn, a paved driveway, and a small garden area with plants.

5. 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 ￥19,594
￥24,910 total
includes taxes & fees
Nov 15 - Nov 16
Gorgeous Cottage near Lake Louisa & mins 2 Disney.
A single-story mobile home with a front porch and a small deck.

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

Newly Remodeled Tiny Home 20 minutes from Disney!~
Kissimmee
The price is ￥13,432
￥33,071 total
includes taxes & fees
Oct 24 - Oct 25
Newly Remodeled Tiny Home 20 minutes from Disney!~
A single-story building with the number 297, a red door, and a bench outside.

7. 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, (68 reviews)
"The Property was very clean ! Super convenient location and the perfect size for a family with 2 younger children ! Suzy was super nice !"
United States
Gary
The price is ￥15,083
￥38,868 total
includes taxes & fees
Oct 18 - Oct 19
Orlando Pool Days & Hammock Naps Book Your Escape NOW!
A lakeside patio with wooden rocking chairs and a table, overlooking a calm lake and a forested area.

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

Walkable Quiet Lakefront Retreat near Downtown Orlando with Private Patio
Orlando
The price is ￥17,224
￥37,550 total
includes taxes & fees
Oct 25 - Oct 26
Walkable Quiet Lakefront Retreat near Downtown Orlando with Private Patio
A resort with a large central pool, a smaller circular pool, and a fountain. There are multiple buildings with balconies and a parking lot.

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

Th10 - 3BR House Near Disney and Universal Studios
3.0 star property
Orlando
The price is ￥38,912
￥77,476 total
includes taxes & fees
Oct 28 - Oct 29
Th10 - 3BR House Near Disney and Universal Studios
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 ￥31,446
￥78,871 total
includes taxes & fees
Oct 26 - Oct 27
Fire Pit & Yard: Updated Winter Garden Home!
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 ￥11,858
￥40,195 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 ￥22,788
￥129,233 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 residential property with a red carpet leading to a door, a small garden area with green turf and potted plants, and a wooden fence.

13. 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 ￥12,484
￥21,814 total
includes taxes & fees
Nov 16 - Nov 17
Garden in the Cloud- Cottage St. Cloud with WiFi, AC, Free parking
A mobile home with a paved driveway, a lawn, and a golf cart parked in front.

14. Perfect Place for a Perfect Vacation

Perfect Place for a Perfect Vacation
Kissimmee
10.0 out of 10, Exceptional, (1 review)
The price is ￥12,800
￥30,244 total
includes taxes & fees
Oct 18 - Oct 19
Perfect Place for a Perfect Vacation
A modern living room with a sofa, a large wall clock, and a mirror.

15. 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 ￥14,222
￥32,015 total
includes taxes & fees
Oct 18 - Oct 19
Family-Friendly Cottage Near Orlando’s Top Attractions
A single-story house with a gabled roof, a front porch, and a small front yard with a large agave plant.

16. 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 ￥14,862
￥48,964 total
includes taxes & fees
Oct 19 - Oct 20
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
A hammock tied between two wooden posts, a wooden deck, and a view of a lake with trees and a clear sky.

17. Cozy Lake Front Cottage

Cozy Lake Front Cottage
Clermont
10.0 out of 10, Exceptional, (25 reviews)
"Very nice cottage, beautiful view"
United States
rachel c.
The price is ￥23,466
￥49,119 total
includes taxes & fees
Oct 19 - Oct 20
Cozy Lake Front Cottage
A patio with outdoor furniture, a wooden deck, and a basketball hoop.

18. 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 ￥16,592
￥41,022 total
includes taxes & fees
Nov 2 - Nov 3
Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage
A resort with multiple swimming pools, palm trees, and a large building with a red-tiled roof.

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

Th20 - 3BR House With Resort Access Near Parks
3.0 star property
Orlando
The price is ￥38,339
￥76,829 total
includes taxes & fees
Oct 28 - Oct 29
Th20 - 3BR House With Resort Access Near Parks
A single-story house with a brick facade, a garage, and a well-maintained lawn.

20. Kissimmee Pool Home w/ Game Room Near Disney

Kissimmee Pool Home w/ Game Room Near Disney
3.0 star property
Indian Ridge
The price is ￥22,755
￥75,191 total
includes taxes & fees
Oct 18 - Oct 19
Kissimmee Pool Home w/ Game Room Near Disney
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Southwest Orlando Hotel Reviews

Spark by Hilton Orlando near Universal

Spark by Hilton Orlando near Universal

8/10 Good
"Room is clean and staff is helpful and friendly."
Charissa 3-night trip
Posted 5 hours ago
Spark by Hilton Orlando near Universal

Find out more about Southwest Orlando

Southwest Orlando Cottages information

Number of reviews
182
Accommodation
5 Cottages
Lowest Price
￥21,814
Highest Price
￥129,233

Explore a world of travel with Expedia