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 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Southwest Orlando cottages

A house with a red door, a front porch, and a pathway leading to the entrance.

1. 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 ￥10,701
￥28,465 total
includes taxes & fees
Oct 4 - Oct 5
Downtown Cottage
A table with a potted plant and a cup of coffee, overlooking a scenic landscape.

2. Romantic Lakefront Getaway with Balcony near Downtown Orlando

Romantic Lakefront Getaway with Balcony near Downtown Orlando
Orlando
The price is ￥13,219
￥32,339 total
includes taxes & fees
Oct 5 - Oct 6
Romantic Lakefront Getaway with Balcony near Downtown Orlando
A serene landscape with a pond, trees with Spanish moss, and a palm tree.

3. 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 ￥25,352
￥61,374 total
includes taxes & fees
Oct 5 - Oct 6
Shore Steps Cottage - Walking Distance To The Town Of Windermere
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 ￥24,864
￥51,696 total
includes taxes & fees
Oct 12 - Oct 13
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
A single-story building with the number 297, a red door, and a bench outside.

5. 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, (66 reviews)
"The property was very clean and the host was quick to respond to any questions."
United States
Colette T.
The price is ￥16,288
￥39,961 total
includes taxes & fees
Oct 3 - Oct 4
Orlando Pool Days & Hammock Naps Book Your Escape NOW!
A patio with outdoor furniture, a wooden deck, and a basketball hoop.

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

Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage
Lake Mary
10.0 out of 10, Exceptional, (21 reviews)
The price is ￥14,871
￥38,217 total
includes taxes & fees
Oct 7 - Oct 8
Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage
A two-story house with a front porch, a brick driveway, and a well-maintained lawn.

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

Fire Pit & Yard: Updated Winter Garden Home!
3.0 star property
Winter Garden
The price is ￥33,048
￥80,493 total
includes taxes & fees
Oct 2 - Oct 3
Fire Pit & Yard: Updated Winter Garden Home!
A mobile home with a paved driveway, a lawn, and a golf cart parked in front.

8. Perfect Place for a Perfect Vacation

Perfect Place for a Perfect Vacation
Kissimmee
10.0 out of 10, Exceptional, (1 review)
The price is ￥12,747
￥30,119 total
includes taxes & fees
Oct 4 - Oct 5
Perfect Place for a Perfect Vacation
A single-story mobile home with a front porch and a small deck.

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

Newly Remodeled Tiny Home 20 minutes from Disney!~
Kissimmee
The price is ￥13,376
￥32,777 total
includes taxes & fees
Oct 5 - Oct 6
Newly Remodeled Tiny Home 20 minutes from Disney!~
A single-story house with a gabled roof, a front porch, and a small front yard with a large agave plant.

10. 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 ￥14,801
￥48,291 total
includes taxes & fees
Oct 6 - Oct 7
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
A kitchen with white cabinets, a granite countertop, a stainless steel sink, and a black microwave.

11. Tiny house close to Disney KISSIMMEE

Tiny house close to Disney KISSIMMEE
Kissimmee
8.4 out of 10, Very good, (9 reviews)
"Proximity to theme parks, restaurants, and shopping"
United States
NOLI
The price is ￥9,914
￥26,010 total
includes taxes & fees
Oct 2 - Oct 3
Tiny house close to Disney KISSIMMEE
A modern living room with a sofa, a large wall clock, and a mirror.

12. 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 ￥14,163
￥31,883 total
includes taxes & fees
Oct 4 - Oct 5
Family-Friendly Cottage Near Orlando’s Top Attractions
An aerial view of a resort with multiple swimming pools, a dock, and a residential area with houses.

13. 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 ￥23,732
￥129,880 total
includes taxes & fees
Oct 5 - Oct 6
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.

14. Beautiful Studio cottage in St. Cloud with WiFi, AC, free parking

Beautiful Studio cottage in 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 ￥10,229
￥19,223 total
includes taxes & fees
Oct 5 - Oct 6
Beautiful Studio cottage in St. Cloud with WiFi, AC, free parking
A residential area with houses featuring sloped roofs and solar panels.

15. Upstay: Bright Family-friendly Retreat With Patio

Upstay: Bright Family-friendly Retreat With Patio
3.0 star property
Chatham Park
The price is ￥14,478
￥43,045 total
includes taxes & fees
Oct 21 - Oct 22
Upstay: Bright Family-friendly Retreat With Patio
A multi-story building with a 'STUDIO MOVIE GRILL' sign, parking lot, and surrounding greenery.

16. Serenity - Family & Pet Friendly, Amazing Location

Serenity - Family & Pet Friendly, Amazing Location
3.0 star property
Crestwynd Bay
The price is ￥14,352
￥62,217 total
includes taxes & fees
Oct 6 - Oct 7
Serenity - Family & Pet Friendly, Amazing Location
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)
"The setting was very nice and in a quiet area, but conveniently located to travel around Florida. Cottage was clean and very comfortable. Would definitely stay again."
United States
Brenda P.
The price is ￥21,103
￥45,613 total
includes taxes & fees
Oct 4 - Oct 5
Cozy Lake Front Cottage
A small cabin with a porch and a garage, surrounded by trees and a clear sky.

18. Cozy Forest Retreat Mid-Century Charm Fireplace 20 Min to Disney

Cozy Forest Retreat Mid-Century Charm Fireplace 20 Min to Disney
Davenport
6.8 out of 10, (3 reviews)
"Needs some upgrades. The bed was a full size, very small for a couple, should really think of upgrading to a king. Pans were old and could use replacing. Bugs and ants constant. Shower was small. Very small tv. Stovetop had missing nob and was difficult to operate. Definitely needs upgrading, left a day early, didn’t feel comfortable there. "
United States
Rebecca F.
The price is ￥12,605
￥26,079 total
includes taxes & fees
Oct 2 - Oct 3
Cozy Forest Retreat Mid-Century Charm Fireplace 20 Min to Disney
A compact kitchen with a built-in TV, a dining area with a bench, and a wall decorated with motivational posters.

19. 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 ￥14,588
￥34,623 total
includes taxes & fees
Oct 11 - Oct 12
Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
A single-story house with a brick facade, a garage, and a well-maintained lawn.

20. ~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool

~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool
3.0 star property
Indian Ridge
The price is ￥22,661
￥74,881 total
includes taxes & fees
Oct 2 - Oct 3
~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool
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

Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort

8/10 Good
"We really enjoyed the amenities - the pools, waterslide, firepit, games, bowling, dining, all of it! We were disappointed that we had to purchase our own tubes for the lazy river, so we did not get to enjoy that. Seems like the tubes should be complimentary. Our room was clean, but one hallway was dirty and we saw roaches. Overall, we loved our stay!"
Andrea 2-night trip
Posted less than an hour ago
Universal's Cabana Bay Beach Resort

Find out more about Southwest Orlando

Southwest Orlando Cottages information

Number of reviews
210
Accommodation
5 Cottages
Lowest Price
￥19,223
Highest Price
￥129,880

Explore a world of travel with Expedia