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Check prices for these dates

In two weeks
9 Jan - 11 Jan
In two months
20 Feb - 22 Feb
In three months
20 Mar - 22 Mar
In four months
17 Apr - 19 Apr

Our top choices for Southwest Orlando cottages

House (3 Bedrooms) | Interior
Upstay: Bright Family-friendly Retreat With Patio

Upstay: Bright Family-friendly Retreat With Patio

Upstay: Bright Family-friendly Retreat With Patio
3.0 star property
Chatham Park
The price is 2.369.970 ₫
7.143.220 ₫ total
includes taxes & fees
8 Jan - 9 Jan 2026
Upstay: Bright Family-friendly Retreat With Patio
Exterior
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

Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema
3.0 star property
Kissimmee
The price is 12.739.905 ₫
31.685.714 ₫ total
includes taxes & fees
29 Dec - 30 Dec
Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema
Interior
Watersong Swanky

Watersong Swanky

Watersong Swanky
3.0 star property
Davenport
The price is 8.909.206 ₫
26.455.629 ₫ total
includes taxes & fees
8 Jan - 9 Jan 2026
Watersong Swanky
House (2 Bedrooms) | Interior
Fire Pit & Yard: Updated Winter Garden Home!

Fire Pit & Yard: Updated Winter Garden Home!

Fire Pit & Yard: Updated Winter Garden Home!
3.0 star property
Winter Garden
The price is 4.815.645 ₫
13.384.862 ₫ total
includes taxes & fees
28 Dec - 29 Dec
Fire Pit & Yard: Updated Winter Garden Home!
House (6 Bedrooms) | Interior
Upstay: 6BR Resort Home w Pool & Basketball Court

Upstay: 6BR Resort Home w Pool & Basketball Court

Upstay: 6BR Resort Home w Pool & Basketball Court
3.0 star property
Kissimmee
Upstay: 6BR Resort Home w Pool & Basketball Court
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

Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort

10/10 Excellent
"Clean rooms, great staff, food court was a bit pricey but to be expected at a resort- plus food was great! 10/10 for affordable family vacation. "
Ariel 7-night trip
Posted 1 day ago
Universal's Cabana Bay Beach Resort

Find out more about Southwest Orlando

Southwest Orlando Cottages information

Number of reviews
Accommodation
5 Cottages
Lowest Price
13.384.862 ₫
Highest Price
31.685.714 ₫