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

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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 ￥10,035
￥27,720 total
includes taxes & fees
Sep 30 - Oct 1
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 ￥12,593
￥31,640 total
includes taxes & fees
Sep 30 - Oct 1
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 ￥22,525
￥57,887 total
includes taxes & fees
Sep 30 - Oct 1
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 ￥24,871
￥49,191 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 place was beautiful, cozy and so clean!!!! loved the pool and enjoyed spending my birthday there! will visit again soon!"
United States
Sara L.
The price is ￥15,442
￥39,019 total
includes taxes & fees
Sep 30 - Oct 1
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)
"Easy access, perfect location, perfectly appointed. Will stay again :-)"
United States
Tricia S.
The price is ￥14,155
￥36,615 total
includes taxes & fees
Oct 1 - Oct 2
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 ￥33,056
￥80,514 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 ￥12,750
￥30,126 total
includes taxes & fees
Sep 30 - Oct 1
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 ￥13,369
￥32,601 total
includes taxes & fees
Sep 30 - Oct 1
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 ￥14,804
￥48,302 total
includes taxes & fees
Sep 30 - Oct 1
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 ￥9,917
￥26,017 total
includes taxes & fees
Sep 30 - Oct 1
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 ￥14,155
￥31,707 total
includes taxes & fees
Oct 11 - Oct 12
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 ￥23,569
￥129,721 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 ￥10,232
￥19,228 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 ￥14,009
￥42,520 total
includes taxes & fees
Oct 20 - Oct 21
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 ￥13,097
￥60,806 total
includes taxes & fees
Sep 30 - Oct 1
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 ￥23,454
￥48,544 total
includes taxes & fees
Oct 5 - Oct 6
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 ￥11,192
￥24,499 total
includes taxes & fees
Sep 30 - Oct 1
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 ￥14,592
￥34,002 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 ￥22,667
￥74,900 total
includes taxes & fees
Sep 30 - Oct 1
~ 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.
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Top Southwest Orlando Hotel Reviews

Coco Key Hotel & Water Park Resort

Coco Key Hotel & Water Park Resort

10/10 Excellent
"Hagwgbe"
BRANLY 3-night trip
Posted less than an hour ago
Coco Key Hotel & Water Park Resort

Find out more about Southwest Orlando

Southwest Orlando Cottages information

Number of reviews
210
Accommodation
5 Cottages
Lowest Price
￥19,228
Highest Price
￥129,721

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