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
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

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 ￥16,910
￥49,143 total
includes taxes & fees
Nov 16 - Nov 17
Shore Steps Cottage - Walking Distance To The Town Of Windermere
A modern kitchen with red walls, a dining area with a brown leather couch, and a bar stool.

2. Downtown Cottage

Downtown Cottage
Colonialtown North
8.8 out of 10, Excellent, (17 reviews)
"Clean perfect location for what we needed "
United States
Jerred B.
The price is ￥10,737
￥27,297 total
includes taxes & fees
Nov 4 - Nov 5
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, (56 reviews)
"Great location, well stocked and beds were very comfortable."
United States
Raegan S.
The price is ￥23,949
￥48,174 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
10.0 out of 10, Exceptional, (1 review)
"Cozy and nice place. It was very clean. Comunication with host was easy. Great view and sitting area from balcony to the lake. Very relaxing!"
United States
jacqueline M.
The price is ￥14,684
￥32,941 total
includes taxes & fees
Dec 1 - Dec 2
Romantic Lakefront Getaway with Balcony near Downtown Orlando
A resort with multiple swimming pools, palm trees, and a large building with a red-tiled roof.

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

Th20 - 3BR House With Resort Access Near Parks
3.0 star property
Orlando
Th20 - 3BR House With Resort Access Near Parks
A two-story house with a front porch, a brick driveway, and a well-maintained lawn.

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

Fire Pit & Yard: Updated Winter Garden Home!
3.0 star property
Winter Garden
The price is ￥31,354
￥78,641 total
includes taxes & fees
Nov 9 - Nov 10
Fire Pit & Yard: Updated Winter Garden Home!
A single-story mobile home with a front porch and a small deck.

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

Newly Remodeled Tiny Home 20 minutes from Disney!~
Kissimmee
The price is ￥13,421
￥31,623 total
includes taxes & fees
Nov 4 - Nov 5
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.

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 ￥17,210
￥36,098 total
includes taxes & fees
Nov 17 - Nov 18
Walkable Quiet Lakefront Retreat near Downtown Orlando with Private Patio
A residential area with houses featuring sloped roofs and solar panels.

9. Upstay: Bright Family-friendly Retreat With Patio

Upstay: Bright Family-friendly Retreat With Patio
3.0 star property
Chatham Park
The price is ￥11,605
￥39,874 total
includes taxes & fees
Nov 30 - Dec 1
Upstay: Bright Family-friendly Retreat With 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, (69 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 ￥18,331
￥41,058 total
includes taxes & fees
Nov 16 - Nov 17
Orlando Pool Days & Hammock Naps Book Your Escape NOW!
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.

11. 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 ￥12,473
￥20,532 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.

12. Perfect Place for a Perfect Vacation

Perfect Place for a Perfect Vacation
Kissimmee
10.0 out of 10, Exceptional, (1 review)
The price is ￥12,789
￥28,955 total
includes taxes & fees
Nov 4 - Nov 5
Perfect Place for a Perfect Vacation
A modern living room with a sofa, a large wall clock, and a mirror.

13. 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 ￥15,315
￥31,980 total
includes taxes & fees
Nov 4 - Nov 5
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.

14. 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 ￥15,000
￥46,726 total
includes taxes & fees
Nov 4 - Nov 5
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
A resort with multiple swimming pools, palm trees, and a large building with a red-tiled roof.

15. Th60 - 3BR House Near Disney With Pool Access

Th60 - 3BR House Near Disney With Pool Access
3.0 star property
Orlando
The price is ￥37,104
￥75,361 total
includes taxes & fees
Nov 9 - Nov 10
Th60 - 3BR House Near Disney With Pool Access
A compact kitchen with a built-in TV, a dining area with a bench, and a wall decorated with motivational posters.

16. Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC

Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
Kissimmee
The price is ￥14,636
￥33,158 total
includes taxes & fees
Nov 7 - Nov 8
Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
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, (23 reviews)
"We had an amazing stay! The place was beautiful, cozy, and incredibly comfortable. Even though we had to leave earlier than planned, we truly enjoyed our time here. The host was kind, responsive, and made everything easy from start to finish. We would definitely stay here again and look forward to returning in the future. Highly recommend!"
United States
Chiann M.
The price is ￥16,544
￥38,697 total
includes taxes & fees
Dec 4 - Dec 5
Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage
A hammock tied between two wooden posts, a wooden deck, and a view of a lake with trees and a clear sky.

18. Cozy Lake Front Cottage

Cozy Lake Front Cottage
Clermont
10.0 out of 10, Exceptional, (27 reviews)
"Very nice cottage, beautiful view"
United States
rachel c.
The price is ￥23,447
￥46,553 total
includes taxes & fees
Nov 5 - Nov 6
Cozy Lake Front Cottage
A two-story house with a garage, surrounded by well-maintained lawns and palm trees.

19. Family Resort Home w Pool, BBQ & Game Room

Family Resort Home w Pool, BBQ & Game Room
3.0 star property
Solana
The price is ￥16,421
￥51,813 total
includes taxes & fees
Nov 29 - Nov 30
Family Resort Home w Pool, BBQ & Game Room
A multi-story building with a 'STUDIO MOVIE GRILL' sign, parking lot, and surrounding greenery.

20. Serenity - Family & Pet Friendly, Amazing Location

Serenity - Family & Pet Friendly, Amazing Location
3.0 star property
Crestwynd Bay
The price is ￥16,042
￥64,288 total
includes taxes & fees
Nov 4 - Nov 5
Serenity - Family & Pet Friendly, Amazing Location
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

Hotel Monreale Express International Drive Orlando

Hotel Monreale Express International Drive Orlando

10/10 Excellent
"Hotel cerca de todo los parques"
Jose 3-night trip
Posted 1 hour ago
Hotel Monreale Express International Drive Orlando

Find out more about Southwest Orlando

Southwest Orlando Cottages information

Number of reviews
159
Accommodation
5 Cottages
Lowest Price
￥20,532
Highest Price
￥78,641

Explore a world of travel with Expedia