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

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Southwest Orlando cottages

A modern kitchen with red walls, a dining area with a brown leather couch, and a bar stool.

1. Downtown Cottage

Downtown Cottage
Colonialtown North
8.8 out of 10, Excellent, (16 reviews)
"Clean perfect location for what we needed "
United States
Jerred B.
The price is ￥11,391
￥29,273 total
includes taxes & fees
Nov 1 - Nov 2
Downtown Cottage
A serene landscape with a pond, trees with Spanish moss, and a palm tree.

2. 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 ￥21,142
￥56,225 total
includes taxes & fees
Nov 1 - Nov 2
Shore Steps Cottage - Walking Distance To The Town Of Windermere
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, (55 reviews)
"Everything was super clean and exactly as described. Great location and great stay!"
United States
Garrett S.
The price is ￥23,964
￥50,254 total
includes taxes & fees
Nov 3 - Nov 4
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 ￥12,613
￥31,690 total
includes taxes & fees
Nov 1 - Nov 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. Th10 - 3BR House Near Disney and Universal Studios

Th10 - 3BR House Near Disney and Universal Studios
3.0 star property
Orlando
The price is ￥36,656
￥74,795 total
includes taxes & fees
Nov 1 - Nov 2
Th10 - 3BR House Near Disney and Universal Studios
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 ￥31,374
￥78,691 total
includes taxes & fees
Nov 4 - Nov 5
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 ￥13,401
￥32,995 total
includes taxes & fees
Nov 3 - Nov 4
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 ￥17,185
￥37,307 total
includes taxes & fees
Nov 1 - Nov 2
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 ￥10,650
￥38,769 total
includes taxes & fees
Nov 2 - Nov 3
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, (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 ￥18,588
￥43,364 total
includes taxes & fees
Nov 3 - Nov 4
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 ￥12,455
￥21,763 total
includes taxes & fees
Nov 16 - Nov 17
Garden in the Cloud- Cottage St. Cloud with WiFi, AC, Free parking
A multi-story building with a 'STUDIO MOVIE GRILL' sign, parking lot, and surrounding greenery.

12. Serenity - Family & Pet Friendly, Amazing Location

Serenity - Family & Pet Friendly, Amazing Location
3.0 star property
Crestwynd Bay
The price is ￥14,389
￥62,376 total
includes taxes & fees
Nov 1 - Nov 2
Serenity - Family & Pet Friendly, Amazing Location
A mobile home with a paved driveway, a lawn, and a golf cart parked in front.

13. Perfect Place for a Perfect Vacation

Perfect Place for a Perfect Vacation
Kissimmee
10.0 out of 10, Exceptional, (1 review)
The price is ￥12,770
￥30,174 total
includes taxes & fees
Nov 3 - Nov 4
Perfect Place for a Perfect Vacation
A modern living room with a sofa, a large wall clock, and a mirror.

14. 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 ￥15,293
￥33,353 total
includes taxes & fees
Nov 3 - Nov 4
Family-Friendly Cottage Near Orlando’s Top Attractions
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 ￥38,824
￥77,301 total
includes taxes & fees
Nov 9 - Nov 10
Th60 - 3BR House Near Disney With Pool Access
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 ￥14,828
￥48,537 total
includes taxes & fees
Nov 3 - Nov 4
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
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 ￥18,304
￥42,574 total
includes taxes & fees
Nov 1 - Nov 2
Last-Minute Getaway? 🌴 Private Lanai & Cozy 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 ￥11,210
￥24,539 total
includes taxes & fees
Nov 1 - Nov 2
Cozy Forest Retreat Mid-Century Charm Fireplace 20 Min to Disney
A hammock tied between two wooden posts, a wooden deck, and a view of a lake with trees and a clear sky.

19. 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 ￥26,014
￥52,209 total
includes taxes & fees
Nov 5 - Nov 6
Cozy Lake Front Cottage
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 ￥22,703
￥75,019 total
includes taxes & fees
Oct 31 - Nov 1
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.
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Top Southwest Orlando Hotel Reviews

Coco Key Hotel & Water Park Resort

Coco Key Hotel & Water Park Resort

8/10 Good
"I travelled with my kids for a 3 day trip. Hotel was very conveniently located on I drive. Walking distance to everything. So you don’t need a car. Resort will give you trolley passes to use daily if needed. I loved the shuttle to universal. Wish they had more frequent shuttle to Disney however just 1 at 9:50am Cleanliness was awesome they clean room daily not like other hotels. Resort fees were a bit high. I would stay here again if travelling to Orlando."
Rima 3-night trip
Posted 2 hours ago
Coco Key Hotel & Water Park Resort

Find out more about Southwest Orlando

Southwest Orlando Cottages information

Number of reviews
224
Accommodation
5 Cottages
Lowest Price
￥21,763
Highest Price
￥78,691

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