Kissimmee Apartments & Vacation Rentals with Swimming Pool - 395 Rentals Available.
395 Vacation rentals
Filters applied: Swimming pool
Fall Special !! Up to 20 ppl - 7BR(4 King)/5.5BA-3miles to Disney
Kissimmee Villa
- 7 bedrooms 7
- 6 bathrooms
- Sleeps 20 20
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$149
from $149 / night
5 Bedroom 4 Bathroom Kissimmee Pool House
Kissimmee House
- 5 bedrooms 5
- 4 bathrooms
- Sleeps 12 12
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$100
from $100 / night
Certificate of Excellence
Superb 4 Bedroom Home, just 3 minutes from Disney
Kissimmee House
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 8 8
- Min stay varies
- Nearest beach 72 mi
- Swimming pool
- Child friendly
Certificate of Excellence
$145
from $145 / night
Brand New 8 beds/6baths pool house, 6 mi to Disney
Kissimmee House
- 8 bedrooms 8
- 6 bathrooms
- Sleeps 18 18
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$289
from $289 / night
Brand New Disney Vacation Home,6BR,5BA,Pool/Spa
Kissimmee Villa
- 6 bedrooms 6
- 5 bathrooms
- Sleeps 14 14
- Min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$169
from $169 / night
4 Bedroomed Luxury Villa 4 miles from Disney
Kissimmee House
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 8 8
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$114
from $114 / night
4BD/3BA,RENOVATED,EXECUTIVE VILLA WITH SPA,MUST SEE,10 MIN FROM DISNEY
Kissimmee Villa
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 8 8
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$95
from $95 / night
Stunning Lake View House 2mls to Disney,games room
Kissimmee House
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 8 8
- Min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$157
from $157 / night
7 Beds/7 Baths,SOUTH FACING POOL WITH WATER VIEW,ALL NEW FURNITURE,10 MIN. DISNEY
Kissimmee Villa
- 7 bedrooms 7
- 7 bathrooms
- Sleeps 16 16
- Min stay varies
- Beach/lakeside relaxation
- Nearest beach 113 mi
- Swimming pool
$150
from $150 / night
Lion King condo at Windsor Palms Resort, 2 miles from Disney, heated pool, gym
Kissimmee Villa
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 8 8
- 5 nights min
- Swimming pool
- Child friendly
- Air conditioning
$79
from $79 / night
Regal Oaks Resort - 3BR/2BH, 3 miles to Disney,Water slides,WiFi,Behind Old Town
Kissimmee House
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 8 8
- Min stay varies
- Swimming pool
- Child friendly
- Car not necessary
$65
from $65 / night
Regal Oaks Resort -Lovely 1900sq 4BR/4BH,Pool & Slides,3Mi to Disney, Free WiFi
Kissimmee House
- 4 bedrooms 4
- 4 bathrooms
- Sleeps 10 10
- Min stay varies
- Swimming pool
- Child friendly
- Car not necessary
$39
from $39 / night
Certificate of Excellence
Updated and Modern Home in Reunion. Disney Perfect
Kissimmee Townhouse
- 3 bedrooms 3
- 4 bathrooms
- Sleeps 6 6
- 1 night min
- Swimming pool
- Child friendly
- Air conditioning
Certificate of Excellence
$100
from $100 / night
CW2 - 1 mile from Disney, New town home in Gated Comm
Kissimmee Townhouse
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 8 8
- Min stay varies
- Nearest beach 60 mi
- Swimming pool
- Child friendly
$79
from $79 / night
19-204 Fun Jungle Safari Condo Rental, near Walt Disney World, POOL, gym, gated
Kissimmee Apartment
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 6 6
- 5 nights min
- Swimming pool
- Child friendly
- Air conditioning
$79
from $79 / night
7 Bedroom 5 Bath Lakeview House near Disney
Kissimmee House
- 7 bedrooms 7
- 6 bathrooms
- Sleeps 16 16
- Min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$180
from $180 / night
GIANT pool/spa, CLOSE to Disney, GameRm, Free WiFi, Completely private backyard
Kissimmee House
- 6 bedrooms 6
- 4 bathrooms
- Sleeps 15 15
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$149
from $149 / night
DISNEY ORLANDO LAKE 4 BED LUXURY POOL VILLA
Kissimmee Villa
- 4 bedrooms 4
- 2 bathrooms
- Sleeps 8 8
- 5 nights min
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$120
from $120 / night
Mickey's Oasis - SPLASH PAD!!!
Kissimmee Villa
- 7 bedrooms 7
- 6 bathrooms
- Sleeps 14 14
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$375
from $375 / night
CW14- 3 Bdrm TownHome 1 mile from Disney
Kissimmee House
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 8 8
- 2 nights min
- Nearest beach 60 mi
- Swimming pool
- Child friendly
$90
from $90 / night
Regal Oaks Resort - Beautiful 4 BR/4BT,1900Sq.3 Mi to Disney,New Pool/Slide,WiFi
Kissimmee Villa
- 4 bedrooms 4
- 4 bathrooms
- Sleeps 10 10
- Min stay varies
- Swimming pool
- Child friendly
- Car not necessary
$69
from $69 / night
Distinctively Orlando Palms, Pet-Friendly Home
Kissimmee Villa
- 4 bedrooms 4
- 2 bathrooms
- Sleeps 8 8
- 4 nights min
- Nearest beach 105 mi
- Swimming pool
- Child friendly
$100
from $100 / night
SUMMER $275 NIGHTLY! Potter, Star Wars, Princesses, Pirates. Disney 2 miles!
Kissimmee House
- 8 bedrooms 8
- 5 bathrooms
- Sleeps 22 22
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$275
from $275 / night
Only $119 per night, 6 bedrooms, 5 star-rated house less than 4 miles to Disney
Kissimmee House
- 6 bedrooms 6
- 6 bathrooms
- Sleeps 18 18
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$119
from $119 / night
Ladybug Villa 6 Bed 5.5 Bath Heated Pool and Spa
Kissimmee Villa
- 6 bedrooms 6
- 6 bathrooms
- Sleeps 16 16
- Min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$225
from $225 / night
Executive Villa, 8 Bedrooms, 4.5 Baths (Sleeps 19)
Kissimmee Villa
- 8 bedrooms 8
- 5 bathrooms
- Sleeps 19 19
- Min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$169
from $169 / night
Affordable Luxury for Your Family Next to Disney
Kissimmee Apartment
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 8 8
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$90
from $90 / night
4 Bed/3 bath Condo with only 2 miles to Disney
Kissimmee Apartment
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 8 8
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$80
from $80 / night
1-304 Poolside Zen themed 1BR condo near Disney World, heated pool, gym, tennis
Kissimmee Apartment
- 1 bedroom 1
- 1 bathroom
- Sleeps 4 4
- 5 nights min
- Swimming pool
- Child friendly
- Air conditioning
$90
from $90 / night
Private Secluded Pool - 8 Miles to Disney
Kissimmee Villa
- 4 bedrooms 4
- 2 bathrooms
- Sleeps 8 8
- 3 nights min
- Swimming pool
- Child friendly
- Air conditioning
$100
from $100 / night
Spring Hill - 6 Bedroom Luxury Pool Home at Windsor Hills
Kissimmee House
- 6 bedrooms 6
- 4 bathrooms
- Sleeps 14 14
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$200
from $200 / night
Disney World... Minutes Away! Luxury 6 BR/4 BA
Kissimmee Villa
- 6 bedrooms 6
- 4 bathrooms
- Sleeps 14 14
- 2 nights min
- Swimming pool
- Ask about children
- Air conditioning
$185
from $185 / night
10 min to Disney"Minnies Villa"sleeps 12 - 4 BR+Kids Dbl bunk room-Lgr So Pool
Kissimmee House
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 12 12
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$106
from $106 / night
3 Miles to Disney/Gated Resort/South-Facing Pool/SPA/6BR/5.5BA(4masters)/WiFi
Kissimmee House
- 6 bedrooms 6
- 6 bathrooms
- Sleeps 17 17
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$195
from $195 / night
Orlando,lovely condo close to Disney, sleep 4
Kissimmee Apartment
- 1 bedroom 1
- 1 bathroom
- Sleeps 4 4
- 3 nights min
- Swimming pool
- Child friendly
- Air conditioning
$65
from $65 / night
Aug/Sept $275 nightly! Potter, Star Wars, Princess, Narnia, Nemo. Disney 2 mile
Kissimmee House
- 8 bedrooms 8
- 5 bathrooms
- Sleeps 23 23
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$275
from $275 / night
Luxury Pool Home Sleeps 12 - Windsor Hills
Kissimmee House
- 6 bedrooms 6
- 4 bathrooms
- Sleeps 12 12
- Min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$183
from $183 / night
Family Friendly Home Near Disney!
Kissimmee House
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 8 8
- 4 nights min
- Swimming pool
- Child friendly
- Air conditioning
$120
from $120 / night
16-201 Deep Sea Blue Four Bedrooms at Legacy Dunes Resort, POOL heated
Kissimmee Apartment
- 4 bedrooms 4
- 2 bathrooms
- Sleeps 8 8
- 5 nights min
- Swimming pool
- Child friendly
- Air conditioning
$99
from $99 / night
Summer Breeze, Ideal Vacation Home in Kissimmee
Kissimmee Villa
- 7 bedrooms 7
- 6 bathrooms
- Sleeps 16 16
- Min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$180
from $180 / night
- Chatham Park
- Cumbrian Lakes
- Eagle Pointe
- Kissimmee City
- Lake Berkley
- Lake Marion
- Rolling Hills at Formosa
- Terra Verde Resort
- The Hamlets
- Windsor Palms
- Emerald Isle Kissimmee
- Formosa Gardens
- Seasons Resort
- Winward Cay
- Creekside
- Liberty Village
- Venetian Bay Villages
- Windsor Hills Resort
- Indian Ridge Oaks
- Bellavida Resort
- Indian Creek
- Fiesta Key
- Trafalgar Village
- Crescent Lakes
- Villasol
- Sunset Lakes
- Cane Island
- Coral Cay
- Westside
- Oak Island Cove
- Paradise Palms
- Lindfields
- Remington
- Encantada Resort
- Compass Bay
- Regal Oaks
- Crestwynd Bay
- Heritage Key
- Veranda Palms
- Legacy Dunes Resort
- Crystal Cove Resort
- Tuscany, Florida
- Lucaya Village
- Oak Island Harbor
- Indian Ridge
- Vista del lago
- Orange Lake Resort
- Calabria, Orlando
- Doral Woods
- Bass Lakes Estate
- Indian Point
- Country Creek
- Hamilton's Reserve
What is Certificate of Excellence?
TripAdvisor gives a Certificate of Excellence to accommodations, attractions and restaurants that consistently earn great reviews from travelers.