Kissimmee Apartments & Vacation Rentals with Swimming Pool - 2057 Rentals Available.
2,057 Vacation rentals
Filters applied: Swimming pool

GIANT pool/spa, CLOSE to Disney, GameRm, Free WiFi, Completely private backyard
Kissimmee House
- 8 bedrooms 8
- 6 bathrooms
- sleeps 22 22
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
Responds fast! Avg. 1 hour 29 minutes
$264.00
from $264.00 / night

Disney 5 Star Vacations / The Osprey Villa
Kissimmee Villa
- 5 bedrooms 5
- 4 bathrooms
- sleeps 10 10
- 5 nights min
- Swimming pool
- Child friendly
- Air conditioning
$144.00
from $144.00 / night

CW4- Just 1 mile to Disney, Nice Townhouse in a Gated Community
Kissimmee Townhouse
- 3 bedrooms 3
- 3 bathrooms
- sleeps 8 8
- min stay varies
- Nearest beach 60 mi
- Swimming pool
- Child friendly
$98.00
from $98.00 / night

CW14- 3 Bdrm TownHome 1 mile from Disney
Kissimmee House
- 3 bedrooms 3
- 3 bathrooms
- sleeps 8 8
- min stay varies
- Nearest beach 60 mi
- Swimming pool
- Child friendly
$98.00
from $98.00 / 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
Responds fast! Avg. 39 minutes
$224.00
from $224.00 / night
Summer and fall specials now call for more details or dates
Kissimmee Apartment
- 3 bedrooms 3
- 2 bathrooms
- sleeps 8 8
- 3 nights min
- Nearest beach 72 mi
- Swimming pool
- Child friendly
Responds fast! Avg. 2 hours 22 minutes
$91.00
from $91.00 / night
CW2- 1 mile from Disney, nice town home in Gated Community
Kissimmee Townhouse
- 3 bedrooms 3
- 3 bathrooms
- sleeps 8 8
- min stay varies
- Nearest beach 60 mi
- Swimming pool
- Child friendly
$98.00
from $98.00 / night
Stunning Lake View House 2mls to Disney,games room
Kissimmee House
- 4 bedrooms 4
- 3 bathrooms
- sleeps 8 8
- 5 nights min
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$180.00
from $180.00 / night
NEW 5 BR/Ensuite home w/ private pool in Luxury Resort w/ Lazy River from $213nt
Kissimmee House
- 5 bedrooms 5
- 5 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
Responds fast! Avg. 1 hour 34 minutes
$233.00
from $233.00 / 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
Responds fast! Avg. 1 hour 19 minutes
$98.00
from $98.00 / night
KENNEDY#1 PRIVATE POOL AND SPA! AHHHH!! EAGLE POINTE IN KISSIMMEE
Kissimmee House
- 4 bedrooms 4
- 2 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$104.00
from $104.00 / night
Certificate of Excellence
Themed rooms, lots of space no crowds!
Kissimmee Villa
- 6 bedrooms 6
- 4 bathrooms
- sleeps 14 14
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
Responds fast! Avg. 1 hour 21 minutes
Travelers’ Choice award
$228.00
from $228.00 / night
Check Into a Beautiful Resort w/ Deluxe Room+Premium Living Space+Nearby Disney
Kissimmee Villa
- 7 bedrooms 7
- 5 bathrooms
- sleeps 16 16
- 3 nights min
- Nearest beach 97 mi
- Swimming pool
- Child friendly
$115.00
from $115.00 / night
Windsor Hills 3 Bedroom Condo, Less Than 2 Miles to Disney
Kissimmee Apartment
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Car not necessary
Responds fast! Avg. 1 hour 40 minutes
$114.00
from $114.00 / night
⭐Beautiful Lake View 7BR Villa - Near Orlando Parks and Attractions⭐
Kissimmee Villa
- 7 bedrooms 7
- 5 bathrooms
- sleeps 14 14
- 3 nights min
- Nearest beach 90 mi
- Swimming pool
- Child friendly
$188.00
from $188.00 / 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
Responds fast! Avg. 3 hours 38 minutes
$109.00
from $109.00 / night
Luxury 5 Star 4 Bedroom Waterfront Villa
Kissimmee Villa
- 4 bedrooms 4
- 3 bathrooms
- sleeps 8 8
- 3 nights min
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
Responds fast! Avg. 1 hour 44 minutes
$129.00
from $129.00 / 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
Responds fast! Avg. 3 hours 38 minutes
$172.00
from $172.00 / night
⭐Great Deal - 3 Bedrooms Town Home - Near Disney⭐
Kissimmee Townhouse
- 3 bedrooms 3
- 3 bathrooms
- sleeps 7 7
- 3 nights min
- Nearest beach 90 mi
- Swimming pool
- Child friendly
$70.00
from $70.00 / night
7 Bedroom 5 Bath Lakeview House near Disney
Kissimmee House
- 7 bedrooms 7
- 6 bathrooms
- sleeps 15 15
- 10 nights min
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$264.00
from $264.00 / night
Tropical Seasons-2 master suites-Pool & Spa- game room-6 mi to Disney-South Pool
Kissimmee House
- 4 bedrooms 4
- 3 bathrooms
- sleeps 10 10
- 5 nights min
- Swimming pool
- Child friendly
- Air conditioning
Responds fast! Avg. 57 minutes
$121.00
from $121.00 / 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
$138.00
from $138.00 / night
⭐Beautiful 8 BR - Near to Disney / Universal / SeaWorld - Great Deal!⭐
Kissimmee Villa
- 8 bedrooms 8
- 6 bathrooms
- sleeps 18 18
- 3 nights min
- Nearest beach 90 mi
- Swimming pool
- Child friendly
$306.00
from $306.00 / 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
Responds fast! Avg. 2 hours 33 minutes
$75.00
from $75.00 / night
5 bed 3 bath Disney Villa, Pool, Spa, Netflix
Kissimmee Villa
- 5 bedrooms 5
- 3 bathrooms
- sleeps 11 11
- min stay varies
- Nearest beach 115 mi
- Swimming pool
- Child friendly
$125.00
from $125.00 / night
Lake Berkley- Lakefront Home w/ Pool, HotTub,10 miles to Disney
Kissimmee Villa
- 6 bedrooms 6
- 4 bathrooms
- sleeps 12 12
- 7 nights min
- Beach/lakeside relaxation
- Nearest beach 120 mi
- Swimming pool
Responds fast! Avg. 19 minutes
$229.00
from $229.00 / 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
Responds fast! Avg. 2 hours 24 minutes
$81.00
from $81.00 / night
Certificate of Excellence
Debbie's Florida Retreat a Luxury Vacation Home
Kissimmee House
- 4 bedrooms 4
- 3 bathrooms
- sleeps 8 8
- 3 nights min
- Nearest beach 125 mi
- Swimming pool
- Child friendly
Responds fast! Avg. 3 hours 8 minutes
Travelers’ Choice award
$144.00
from $144.00 / night
Luxurious Disney Home at Venetian Bay Villages
Kissimmee Townhouse
- 3 bedrooms 3
- 2 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$86.00
from $86.00 / night
2 miles to Disney, Beautiful Home that Sleeps 8 (2 families)
Kissimmee Townhouse
- 3 bedrooms 3
- 3 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$68.00
from $68.00 / 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
Responds fast! Avg. 1 hour 56 minutes
$115.00
from $115.00 / night
Affordable luxury! 3 bdrm pet friendly pool home 4 mi from Disney.
Kissimmee House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 8 8
- 3 nights min
- Swimming pool
- Child friendly
- Air conditioning
$132.00
from $132.00 / night
Certificate of Excellence
Superb 4 Bedroom Home, just 3 minutes from Disney
Kissimmee House
- 4 bedrooms 4
- 3 bathrooms
- sleeps 8 8
- 5 nights min
- Nearest beach 72 mi
- Swimming pool
- Child friendly
Responds fast! Avg. 50 minutes
Travelers’ Choice award
$172.00
from $172.00 / night
4 Bedroom 2 Bath with Pool & Spa
Kissimmee House
- 4 bedrooms 4
- 2 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$104.00
from $104.00 / night
New Upgraded Luxury Villa w/ Frozen & Star Wars Rooms at Encore!
Kissimmee House
- 6 bedrooms 6
- 7 bathrooms
- sleeps 16 16
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$401.00
from $401.00 / night
♥ 5 Min To Disney - Game Room, Salt Water Pool W/ Free Pool Heat, BBQ, Baby Gear
Kissimmee House
- 6 bedrooms 6
- 4 bathrooms
- sleeps 16 16
- min stay varies
- Nearest beach 114 mi
- Swimming pool
- Child friendly
$295.00
from $295.00 / night
The Kennedy #5
Kissimmee House
- 4 bedrooms 4
- 3 bathrooms
- sleeps 8 8
- min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$98.00
from $98.00 / 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
Responds fast! Avg. 2 hours 24 minutes
$81.00
from $81.00 / night
3/2 Condo in Resort with Community Pool and Spa
Kissimmee Condo
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$86.00
from $86.00 / night
5 Bedroom 4 Bathroom Kissimmee Pool House
Kissimmee House
- 5 bedrooms 5
- 4 bathrooms
- sleeps 12 12
- 10 nights min
- Swimming pool
- Child friendly
- Air conditioning
$258.00
from $258.00 / night
- Chatham Park
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- The Hamlets
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- Creekside
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- Indian Creek
- Fiesta Key
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- Villasol
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- Coral Cay
- Westside
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- Lindfields
- Remington
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- Regal Oaks
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- Heritage Key
- Veranda Palms
- Legacy Dunes Resort
- Crystal Cove Resort
- Tuscany, Florida
- Lucaya Village
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- Indian Ridge
- Vista del lago
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- Calabria, Orlando
- Doral Woods
- Bass Lakes Estate
- Indian Point
- Country Creek
- Hamilton's Reserve
What is Travelers’ Choice award?
Tripadvisor gives a Travelers’ Choice award to accommodations, attractions and restaurants that consistently earn great reviews from travellers and are ranked within the top 10% of properties on Tripadvisor.