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Vacations by Zumper

Kissimmee Vacation House Rentals

Top-Rated Vacation Rentals in Kissimmee, FL

Book a vacation rental in Kissimmee that has the highest visitor rating. Here are 6 of the best vacation rentals in Kissimmee.
Spectacular Tropical Themes at Rum Runner at Margaritaville!
10

Excellent

·
Kissimmee
·
5 br
·
Sleeps 10
·
Assigned Parking · Kitchen · Hot Tub ·
From
$278/night
Check availability
Property
House · 5 Beds · 6 baths
Amenities
Assigned Parking
Hot Tub
Private Pool
Dishwasher
Oven
Swimming Pool
Residents Lounge
Air Conditioning
Other spaces
Kitchen, Balcony, Workspace
Stunning 5 bed property with private south facing deck and pool
10

Excellent

·
Kissimmee
·
5 br
·
Sleeps 12
·
Outdoor Space · Private Pool · Oven ·
From
$229/night
Check availability
Property
House · 5 Beds · 3 baths
Amenities
Private Pool
Oven
Ceiling Fan
Furnished
Air Conditioning
Dishwasher
Wifi
On Site Laundry
Other spaces
Kitchen
Veteran Owned 3bdr/3bath Townhome w/WiFi 3mi to Disney- Late Summer/Fall Special
10

Excellent

·
Kissimmee
·
3 br
·
Sleeps 6
·
Private Pool · Air Conditioning · Fitness Center ·
From
$115/night
Check availability
Property
House · 3 Beds · 3 baths
Amenities
Private Pool
Air Conditioning
Fitness Center
Hot Tub
Furnished
Wheelchair Accessible
On Site Laundry
Dishwasher
Other spaces
Kitchen
Price drop
Serene newly-renovated townhouse next to Disney with private pool!
10

Excellent

·
Kissimmee
·
3 br
·
Sleeps 8
·
Lake · Fitness Center · Outdoor Space ·
From
$239/night
Check availability
Property
House · 3 Beds · 3 baths
Amenities
Lake
Fitness Center
Furnished
Air Conditioning
Waterfront
Oven
Private Pool
Residents Lounge
Other spaces
Kitchen
Price drop
7601 Themed 7BD Villa- Pool&spa - Game room
10

Excellent

·
kissimmee
·
7 br
·
Sleeps 18
·
Swimming Pool · Smoking Allowed · Private Pool ·
From
$294/night
Check availability
Property
House · 7 Beds · 7 baths
Amenities
Swimming Pool
Smoking Allowed
Private Pool
Pool
Oven
Air Conditioning
Furnished
On Site Laundry
Other spaces
Kitchen, Workspace
Price drop
Windsor Oasis | Private Pool and Spa, Custom Games Room, Kids Bedrooms
10

Excellent

·
Kissimmee
·
5 br
·
Sleeps 12
·
Oven · Dishwasher · Kitchen ·
From
$302/night
Check availability
Property
House · 5 Beds · 5 baths
Amenities
Oven
Dishwasher
On Site Laundry
Swimming Pool
Hot Tub
Air Conditioning
Fitness Center
Pool
Other spaces
Kitchen

Budget-Friendly Vacation Rentals in Kissimmee, FL

Traveling on a budget? We've got you covered. Find a great deal on a vacation rental in Kissimmee starting at $40. Use the price filter at the top of the page to search for more specific prices.
Price drop
Cozy Retreat 10 min from Disney

No rating

·
Kissimmee
·
1 br
·
Sleeps 2
·
Wifi · Workspace · Furnished ·
From
$40/night
Check availability
Property
House · 1 Bed · 1 bath
Amenities
Wifi
Furnished
Air Conditioning
Other spaces
Workspace
Price drop
Kissimmee Cottage w/ Resort-Style Amenities!
10

Excellent

·
Kissimmee
·
1 br
·
Sleeps 4
·
Central Heat · Oven · Wifi ·
From
$45/night
Check availability
Property
House · 1 Bed · 1 bath
Amenities
Central Heat
Oven
Wifi
Cable
Ceiling Fan
Dishwasher
Toiletries
Tv
Other spaces
Workspace, Kitchen
Private bedroom and bathroom near to Disney area
10

Excellent

·
Kissimmee
·
1 br
·
Sleeps 2
·
Swimming Pool · Air Conditioning · Kitchen ·
From
$45/night
Check availability
Property
House · 1 Bed · 1 bath
Amenities
Swimming Pool
Air Conditioning
Pool
Furnished
Dishwasher
In Unit Laundry
Wifi
Smoking Allowed
Other spaces
Kitchen
Welcome to Kissimmee!
10

Excellent

·
Kissimmee
·
2 br
·
Sleeps 1
·
Workspace · Air Conditioning · Swimming Pool ·
From
$50/night
Check availability
Property
House · 2 Beds · 1 bath
Amenities
Air Conditioning
Swimming Pool
On Site Laundry
Dishwasher
Carpet
Oven
Fireplace
Wifi
Other spaces
Workspace, Kitchen
Price drop
Tasteful Room with 2 DBL Beds Near Local-favorite Spots
10

Excellent

·
Kissimmee
·
Studio
·
Sleeps 4
·
Wheelchair Accessible · Pool · Air Conditioning ·
From
$53/night
Check availability
Property
House · Studio · 1 bath
Amenities
Wheelchair Accessible
Pool
Air Conditioning
Residents Lounge
Business Center
Swimming Pool
Wifi
Assigned Parking
Other spaces
Workspace, Balcony
Price drop
Peaceful Room with 2 DBL Beds A Short Ride to Theme Parks
10

Excellent

·
Kissimmee
·
Studio
·
Sleeps 4
·
Wifi · Furnished · Pool ·
From
$53/night
Check availability
Property
House · Studio · 1 bath
Amenities
Wifi
Furnished
Pool
Swimming Pool
Elevator
Air Conditioning
Business Center
Fitness Center
Other spaces
Balcony, Workspace

Vacation Rentals With AC and/or Heat in Kissimmee, FL

Whether you need air conditioning or central heating, these vacation rentals are for you.
Kissimmee Getaway ~ 4 Mi to Walt Disney World
10

Excellent

·
Kissimmee
·
4 br
·
Sleeps 10
·
Central Heat · Furnished · On Site Laundry ·
From
$172/night
Check availability
Property
House · 4 Beds · 3 baths
Amenities
Central Heat
Furnished
On Site Laundry
Oven
Wifi
Pool
Swimming Pool
Walk In Closets
Other spaces
Kitchen
Price drop
3 Bed Disney/Orlando Vacation Home with Gorgeous LAKE VIEW!
10

Excellent

·
Kissimmee
·
3 br
·
Sleeps 6
·
Waterfront · Air Conditioning · Outdoor Space ·
From
$159/night
Check availability
Property
House · 3 Beds · 2 baths
Amenities
Waterfront
Air Conditioning
Dishwasher
Pool
Swimming Pool
On Site Laundry
Assigned Parking
Fitness Center
Other spaces
Kitchen
4-Bed Disney Area*Beautiful Water View*HotTub*Outdoor Deck!
10

Excellent

·
Kissimmee
·
4 br
·
Sleeps 8
·
Central Heat · Wifi · Assigned Parking ·
From
$233/night
Check availability
Property
House · 4 Beds · 3 baths
Amenities
Central Heat
Wifi
Assigned Parking
Waterfront
Pool
Dishwasher
Swimming Pool
Hot Tub
Other spaces
Kitchen, Balcony

Family-Friendly Vacation Rentals in Kissimmee, FL

Heading to Kissimmee for your next family vacation? Check out these family-friendly vacation rentals, which have more bedrooms and more space for you and your loved ones. Use the filters at the top of the page to narrow your search and find what you need.
Price drop
Beautiful Paradise Palms Home W private pool
10

Excellent

·
Kissimmee
·
Studio
·
Sleeps 10
·
Furnished · Outdoor Space · On Site Laundry ·
From
$219/night
Check availability
Property
House · Studio · 1 bath
Amenities
Furnished
On Site Laundry
Fireplace
Fitness Center
Pool
Oven
Dishwasher
Air Conditioning
Other spaces
Workspace, Kitchen
Disney Getaway W pool, spa, wifi, and Game Room
10

Excellent

·
Kissimmee
·
Studio
·
Sleeps 12
·
Furnished · Oven · Kitchen ·
From
$203/night
Check availability
Property
House · Studio · 1 bath
Amenities
Furnished
Oven
Air Conditioning
On Site Laundry
Wifi
Dishwasher
Swimming Pool
Package Service
Other spaces
Kitchen
Holiday Inn Orange lake Resort near at Disney's Animal Kingdom Theme Park

No rating

·
Kissimmee
·
1 br
·
Sleeps 4
·
Pool · Concierge Service · On Site Laundry ·
From
$166/night
Check availability
Property
House · 1 Bed · 1 bath
Amenities
Pool
Concierge Service
On Site Laundry
Swimming Pool
Air Conditioning
Private Pool
Waterfront
Elevator
Other spaces
Balcony, Kitchen
Expand your search criteria to see more vacation rentals near Kissimmee.
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Updated: September 21, 2023