Kissimmee Vacation Rentals With Private Pool

9,496 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.
Happy House Cheerful 4-B Townhome Championsgate
10

Excellent

·
Kissimmee
·
4 br
·
Sleeps 11
·
Workspace · Balcony · Private Pool ·
From
$171/night
Check availability
Property
House · 4 Beds · 3 baths
Amenities
Private Pool
Air Conditioning
Swimming Pool
Fitness Center
Dishwasher
In Unit Laundry
Wifi
Oven
Other spaces
Workspace, Balcony, Kitchen
Stunning 4 Bd w Pool at Storey Lake Resort 2400
10

Excellent

·
Kissimmee
·
5 br
·
Sleeps 14
·
Pool · Fitness Center · Dishwasher ·
From
$218/night
Check availability
Property
Apartment · 5 Beds · 4 baths
Amenities
Pool
Fitness Center
Dishwasher
Swimming Pool
Private Pool
Furnished
Air Conditioning
Wifi
Other spaces
Kitchen, Outdoor Space
2921DH TOWNHOUSE 4 BEDROOMS & 3 BATHROOMS + POOL
10

Excellent

·
Kissimmee
·
4 br
·
Sleeps 10
·
Workspace · Air Conditioning · Outdoor Space ·
From
$197/night
Check availability
Property
House · 4 Beds · 3 baths
Amenities
Air Conditioning
Private Pool
Wifi
Fitness Center
Free Parking
Assigned Parking
Pool
Dishwasher
Other spaces
Workspace, Outdoor Space, Kitchen
Beautiful 5bedroom house close to Disney 8943
10

Excellent

·
Kissimmee
·
Studio
·
Sleeps 14
·
Dishwasher · Pool · Outdoor Space ·
From
$312/night
Check availability
Property
Apartment · Studio · 5 baths
Amenities
Dishwasher
Pool
Oven
Furnished
Wifi
On Site Laundry
Free Parking
Swimming Pool
Other spaces
Outdoor Space, Kitchen
Beautiful 5 bedroom House with private Pool
10

Excellent

·
Kissimmee
·
Studio
·
Sleeps 16
·
In Unit Laundry · Outdoor Space · Air Conditioning ·
From
$289/night
Check availability
Property
Apartment · Studio · 5 baths
Amenities
In Unit Laundry
Air Conditioning
Private Pool
Pool
Wifi
Free Parking
Furnished
On Site Laundry
Other spaces
Balcony, Kitchen
5bedroom Cozy home close to Disney Resort
9

Excellent

·
Kissimmee
·
5 br
·
Sleeps 14
·
Free Parking · Kitchen · Swimming Pool ·
From
$314/night
Check availability
Property
Apartment · 5 Beds · 5 baths
Amenities
Free Parking
Swimming Pool
Private Pool
Air Conditioning
Pool
Dishwasher
Oven
In Unit Laundry
Other spaces
Kitchen, Outdoor Space

Our Recommended Vacation Rentals in Kissimmee, FL

We analyzed vacation rentals in Kissimmee from many property providers including but not limited to VRBO, Booking.com, Evolve, Blueground and more. We're providing our top recommended offers on the best vacation rentals in Kissimmee to help you find a deal for your next trip.
Charming 4Bd w Private Pool @ Storey Lake Resort 2653

No rating

·
Kissimmee
·
4 br
·
Sleeps 8
·
Pool · Fitness Center · Outdoor Space ·
From
$269/night
Check availability
Property
Apartment · 4 Beds · 3 baths
Amenities
Pool
Fitness Center
Private Pool
Wifi
Free Parking
Furnished
Air Conditioning
Oven
Other spaces
Outdoor Space, Kitchen
Stunning 5Bd Private Pool & Waterpark @ Champions Gate 8913

No rating

·
Kissimmee
·
5 br
·
Sleeps 13
·
Kitchen · Dishwasher · Furnished ·
From
$317/night
Check availability
Property
Apartment · 5 Beds · 5 baths
Amenities
Dishwasher
Furnished
Oven
Wifi
Pool
Free Parking
Air Conditioning
Private Pool
Other spaces
Kitchen, Outdoor Space
Kissimmee Home with Private Pool - 8 Mi to Disney!

No rating

·
Kissimmee
·
4 br
·
Sleeps 12
·
Wifi · Swimming Pool · Free Parking ·
From
$309/night
Check availability
Property
Apartment · 4 Beds · 3 baths
Amenities
Wifi
Swimming Pool
Free Parking
Private Pool
Furnished
Oven
Pool
Dishwasher
Other spaces
Kitchen, Outdoor Space
8462 Secret Key Cove

No rating

·
Kissimmee
·
6 br
·
Sleeps 13
·
Kitchen · Outdoor Space · Dishwasher ·
From
$828/night
Check availability
Property
Apartment · 6 Beds · 5 baths
Amenities
Dishwasher
Wifi
Air Conditioning
Furnished
Swimming Pool
Private Pool
Pool
Oven
Other spaces
Kitchen, Outdoor Space
Incredible townhouse in a beautiful resort

No rating

·
Kissimmee
·
4 br
·
Sleeps 8
·
Oven · In Unit Laundry · Kitchen ·
From
$191/night
Check availability
Property
House · 4 Beds · 3 baths
Amenities
Oven
In Unit Laundry
Pool
Swimming Pool
Wifi
Garage Parking
On Site Laundry
Dishwasher
Other spaces
Kitchen
2405 Amazing 5BD Townhome for Your Vacation

No rating

·
Kissimmee
·
1 br
·
Sleeps 15
·
Air Conditioning · Oven · Private Pool ·
From
$337/night
Check availability
Property
House · 1 Bed
Amenities
Air Conditioning
Oven
Private Pool
Swimming Pool
Dishwasher
Wifi
Fitness Center
Furnished
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 $29. Use the price filter at the top of the page to search for more specific prices.
Near Disney Vacation Private Room in shared Villa
7.7

Very good

·
Kissimmee
·
1 br
·
Sleeps 2
·
Outdoor Space · Furnished · In Unit Laundry ·
From
$29/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Furnished
In Unit Laundry
Wheelchair Accessible
Oven
Private Pool
Pool
Free Parking
Air Conditioning
Other spaces
Outdoor Space, Kitchen, Workspace
4 Bed 3 Bath Vacation home in Kissimmee
7.7

Very good

·
Kissimmee
·
4 br
·
Sleeps 8
·
In Unit Laundry · Furnished · Air Conditioning ·
From
$69/night
Check availability
Property
Apartment · 4 Beds · 3 baths
Amenities
In Unit Laundry
Furnished
Air Conditioning
Wifi
Pool
Swimming Pool
Private Pool
Fitness Center
Other spaces
Kitchen, Outdoor Space
❤️ Lake view condo 🐶🐱FREE Pet fee under 25lbs
10

Excellent

·
Kissimmee
·
2 br
·
Sleeps 6
·
Free Parking · Furnished · Private Pool ·
From
$71/night
Check availability
Property
Condo · 2 Beds · 2 baths
Amenities
Free Parking
Furnished
Private Pool
Wifi
Business Center
Concierge Service
Oven
Dishwasher
Other spaces
Balcony, Kitchen
A luxurious Oasis

No rating

·
Kissimmee
·
2 br
·
Sleeps 6
·
Outdoor Space · Oven · Private Pool ·
From
$71/night
Check availability
Property
Apartment · 2 Beds · 2 baths
Amenities
Oven
Private Pool
In Unit Laundry
Free Parking
Air Conditioning
Wifi
Dishwasher
Pool
Other spaces
Kitchen, Balcony, Workspace
4BR Cozy Resort Townhome Private pool & BBQ

No rating

·
Kissimmee
·
4 br
·
Sleeps 8
·
Wifi · Oven · Private Pool ·
From
$74/night
Check availability
Property
House · 4 Beds · 3 baths
Amenities
Wifi
Oven
Private Pool
Furnished
On Site Laundry
Carpet
Air Conditioning
In Unit Laundry
Other spaces
Outdoor Space, Kitchen
Charming Holiday Condo, Only 7 Min. to Disney
10

Excellent

·
Kissimmee
·
2 br
·
Sleeps 6
·
Onsite Management · Hot Tub · In Unit Laundry ·
From
$75/night
Check availability
Property
Condo · 2 Beds · 2 baths
Amenities
Onsite Management
Hot Tub
In Unit Laundry
Wheelchair Accessible
Fitness Center
Wifi
Dishwasher
Air Conditioning
Other spaces
Workspace, Kitchen, Balcony

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

Whether you need air conditioning or central heating, these vacation rentals are for you.
Sun-Soaked Kissimmee Escape
9.7

Excellent

·
Kissimmee
·
3 br
·
Sleeps 6
·
Toiletries · Kitchen · Air Conditioning ·
From
$125/night
Check availability
Property
House · 3 Beds · 3 baths
Amenities
Toiletries
Air Conditioning
Oven
Microwave
Cable
Free Parking
Wifi
Pool
Other spaces
Kitchen, Walk In Closets, Outdoor Space
Kissimmee Retreat w/ Pool Access, 10 Mi to Disney!
9

Excellent

·
Kissimmee
·
3 br
·
Sleeps 6
·
Cable · Air Conditioning · Toiletries ·
From
$55/night
Check availability
Property
House · 3 Beds · 2 baths
Amenities
Cable
Air Conditioning
Toiletries
Fitness Center
Swimming Pool
Oven
Free Parking
Pool
Other spaces
Workspace, Walk In Closets, Kitchen, Outdoor Space
Disney Escape with Arcade, Pool & Themed Rooms!
10

Excellent

·
Kissimmee
·
4 br
·
Sleeps 10
·
Microwave · Air Conditioning · Walk In Closets ·
From
$165/night
Check availability
Property
House · 4 Beds · 3 baths
Amenities
Microwave
Air Conditioning
Cable
Wifi
Residents Lounge
Oven
Private Pool
Pool
Other spaces
Walk In Closets, Workspace, Outdoor Space, Kitchen
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Updated: March 5, 2024