Kissimmee Vacation Rentals - HolidayHomes base64Hash Kissimmee Vacation Rentals - HolidayHomes

Kissimmee Vacation Rentals

Browse 11,684 available vacation homes and compared across 80 trusted partners

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Top-Rated Vacation rentals in Kissimmee

Book the highest-rated Kissimmee vacation rentals, rated by real guests for comfort, location, cleanliness, services and value for money

Villa Kissimmee

Executive Private Disney Villa, 30 ft Pool, Spa, King, 4K UHD TV, Netflix, Wifi

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House Kissimmee

Family-oriented vacation home with terrace & private pool | Nature view

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House Kissimmee

Vacation home with private pool, garden & barbecue | Lake view

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Villa Kissimmee

Villa with jacuzzi, yard & private pool

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House Kissimmee

9Br/6Ba lake view Pool House from 300/nt, Close To Disney

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House Kissimmee

Family-oriented big vacation home with private pool, patio & yard | Nature view

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House Kissimmee

Brand New 4 Bed, 3bth, Next To Pool, Water Slides, Walk To Oldtown, 6 to Disney.

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Apartment Kissimmee

Holiday apartment with private pool, patio & jacuzzi

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House Kissimmee

House with barbeque, private pool & patio

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House Kissimmee

Waterview, Private Pool, Family Friendly, Spacious and Relaxing

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House Kissimmee

Child-friendly charming vacation home with private pool, garden & hot tub

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House Kissimmee

Brand new private pool with lake view minutes to the parks!

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House Kissimmee

Luxury 15-Bedroom home with Pool, Spa, Theater & Near Theme Parks

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Villa Kissimmee

Lakeside villa, closest to Disney. Full remodel for 2026. New pool!

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Villa Kissimmee

Villa with private pool

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Top 15 most Recommended Vacation Rentals in Kissimmee

Discover your ideal Kissimmee vacation rental with real-time comparisons of 11,684 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

House Kissimmee
House ∙ 8 guests ∙ 4 bedrooms

Vacation home with garden, jacuzzi & heated pool | Nature view | Perfect for remote work

Kissimmee, Osceola County, Florida, United States
This house rental in Kissimmee accommodates 8 guests and features a pool for relaxation and enjoyment.
from $124
per night
(32)
View deal
Villa Kissimmee
Villa ∙ 15 guests ∙ 4 bedrooms

Villa with BBQ & private pool | Nature view

Kissimmee, Osceola County, Florida, United States
This spacious villa in Kissimmee comfortably accommodates 15 guests and features a private pool for relaxation and fun.
from $98
per night
(55)
View deal
House Kissimmee
House ∙ 16 guests ∙ 9 bedrooms

Family-friendly house with private pool

Kissimmee, Osceola County, Florida, United States
This house rental in Kissimmee accommodates 16 guests and features a private pool for a relaxing getaway.
from $307
per night
View deal
House Kissimmee
House ∙ 8 guests ∙ 4 bedrooms

Fully equipped lovely house with jacuzzi & private pool

Kissimmee, Osceola County, Florida, United States
This house rental in Kissimmee accommodates 8 guests and features a private pool for a relaxing getaway.
from $156
per night
(22)
View deal
House Kissimmee
House ∙ 6 guests ∙ 3 bedrooms

House with BBQ, private pool & terrace

Kissimmee, Osceola County, Florida, United States
This house rental in Kissimmee accommodates 6 guests and features a private pool for relaxation and enjoyment.
from $111
per night
(49)
View deal
House Kissimmee
House ∙ 15 guests ∙ 7 bedrooms

Vacation home with BBQ & pool

Kissimmee, Osceola County, Florida, United States
This house rental in Kissimmee accommodates 15 guests and features a family-friendly atmosphere with a private pool.
from $290
per night
(8)
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Villa Kissimmee
Villa ∙ 12 guests ∙ 6 bedrooms

Pleasant villa with private pool | Nature view

Kissimmee, Osceola County, Florida, United States
This spacious villa in Kissimmee accommodates 12 guests and features a private pool for relaxation and enjoyment.
from $156
per night
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Villa Kissimmee
Villa ∙ 8 guests ∙ 4 bedrooms

Villa with heated pool | Lake view

Kissimmee, Osceola County, Florida, United States
This spacious 8-person villa in Kissimmee features a private pool and is perfect for family-friendly vacations.
from $143
per night
(36)
View deal
House Kissimmee
House ∙ 7 guests ∙ 4 bedrooms

Vacation home with grill, patio & private pool | Lake view

Kissimmee, Osceola County, Florida, United States
This house rental in Kissimmee accommodates 7 guests and features a private pool for relaxation and fun.
from $148
per night
(47)
View deal

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