Kissimmee Apartments & Vacation Rentals with Swimming Pool - 459 Rentals Available.
459 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
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$412.00
from $412.00 / night

Disney 5 Star Vacations / The Osprey Villa
Kissimmee Villa
- 5 bedrooms 5
- 4 bathrooms
- sleeps 10 10
- 5 nights min
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
Responds fast! Avg. 8 minutes
$172.00
from $172.00 / night

CW4- Just 1 mile to Disney, Nice Townhouse in a Gated Community
Kissimmee Townhouse
- 3 bedrooms 3
- 3 bathrooms
- sleeps 8 8
- 2 nights min
- Beach/lakeside relaxation
- Nearest beach 60 mi
- Swimming pool
$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
- Beach/lakeside relaxation
- Nearest beach 60 mi
- Swimming pool
$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
- 3 nights min
- Beach/lakeside relaxation
- Swimming pool
- Ask about children
Responds fast! Avg. 45 minutes
$281.00
from $281.00 / night
CW2- 1 mile from Disney, nice town home in Gated Community
Kissimmee Townhouse
- 3 bedrooms 3
- 3 bathrooms
- sleeps 8 8
- 2 nights min
- Beach/lakeside relaxation
- Nearest beach 60 mi
- Swimming pool
$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
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. 34 minutes
$132.00
from $132.00 / night
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. 3 hours 4 minutes
$252.00
from $252.00 / 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. 2 hours 58 minutes
$126.00
from $126.00 / 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. 2 hours 42 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. 2 hours 58 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
$93.00
from $93.00 / night
6 Bedroom 5 Bath Lakeview House near Disney (Gated Community)
Kissimmee House
- 7 bedrooms 7
- 6 bathrooms
- sleeps 12 12
- min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$275.00
from $275.00 / 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
$161.00
from $161.00 / 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
$407.00
from $407.00 / night
Regal Oaks Resort - 3BR/2BH, 3 miles to Disney,Water slides,WiFi,Behind Old Town
Kissimmee House
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Car not necessary
Responds fast! Avg. 2 hours 25 minutes
$109.00
from $109.00 / night
5 bed 3 bath Disney Villa, Pool, Spa, Netflix
Kissimmee Villa
- 5 bedrooms 5
- 3 bathrooms
- sleeps 11 11
- min stay varies
- Beach/lakeside relaxation
- Nearest beach 115 mi
- Swimming pool
$149.00
from $149.00 / 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 8 8
- 6 nights min
- Swimming pool
- Child friendly
- Car not necessary
Responds fast! Avg. 2 hours 25 minutes
$121.00
from $121.00 / night
Debbie's Florida Retreat a Luxury Vacation Home
Kissimmee House
- 4 bedrooms 4
- 3 bathrooms
- sleeps 8 8
- 4 nights min
- Beach/lakeside relaxation
- Nearest beach 125 mi
- Swimming pool
$217.00
from $217.00 / night
Luxurious Disney Home at Venetian Bay Villages
Kissimmee Townhouse
- 3 bedrooms 3
- 2 bathrooms
- sleeps 8 8
- min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
Responds fast! Avg. 1 hour 58 minutes
$114.00
from $114.00 / night
Superb 4 Bedroom Home, just 3 minutes from Disney
Kissimmee House
- 4 bedrooms 4
- 3 bathrooms
- sleeps 8 8
- 4 nights min
- Nearest beach 72 mi
- Swimming pool
- Child friendly
Responds fast! Avg. 1 hour 10 minutes
$212.00
from $212.00 / night
N7 - BEST PRICE MATCH * Mins to Disney/WaterPark/Arcade/Bar/Gym/Golf/AC/WiFi
Kissimmee House
- 9 bedrooms 9
- 6 bathrooms
- sleeps 24 24
- min stay varies
- Beach/lakeside relaxation
- Nearest beach 70 mi
- Swimming pool
Responds fast! Avg. 3 hours 58 minutes
$516.00
from $516.00 / night
Regal Oaks Resort -Lovely 1900sq 4BR/4BH,Pool & Slides,3Mi to Disney, Free WiFi
Kissimmee House
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Child friendly
- Car not necessary
Responds fast! Avg. 2 hours 25 minutes
$115.00
from $115.00 / night
5 Bedroom 4 Bathroom Kissimmee Pool House
Kissimmee House
- 5 bedrooms 5
- 4 bathrooms
- sleeps 12 12
- min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$229.00
from $229.00 / night
⭐Spacious 7 Bedrooms Villa w/ Private Pool - Nearby Disney World⭐
Kissimmee Villa
- 7 bedrooms 7
- 5 bathrooms
- sleeps 18 18
- 3 nights min
- Beach/lakeside relaxation
- Nearest beach 90 mi
- Swimming pool
$265.00
from $265.00 / night
New 8br/6ba pool house, 8 miles to Disney
Kissimmee House
- 8 bedrooms 8
- 6 bathrooms
- sleeps 20 20
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
Responds fast! Avg. 34 minutes
$401.00
from $401.00 / night
Luxury 7 Bed Villa, 4.5 bathrooms, close to Disney World
Kissimmee Villa
- 7 bedrooms 7
- 5 bathrooms
- sleeps 15 15
- 4 nights min
- Nearest beach 112 mi
- Swimming pool
- Child friendly
$258.00
from $258.00 / night
"Affordable Laguna Bay Condo near Disney WIFI"
Kissimmee Condo
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 4 nights min
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$74.00
from $74.00 / night
DisneyVacationRental 3BR 2Bath w Pool heat from $85/night
Kissimmee Villa
- 3 bedrooms 3
- 2 bathrooms
- sleeps 8 8
- 7 nights min
- Beach/lakeside relaxation
- Nearest beach 80 mi
- Swimming pool
$114.00
from $114.00 / night
✦Comfortable 4 Bedrooms Town Home - Nearby Disney World✦
Kissimmee Townhouse
- 4 bedrooms 4
- 3 bathrooms
- sleeps 10 10
- min stay varies
- Beach/lakeside relaxation
- Nearest beach 90 mi
- Swimming pool
$117.00
from $117.00 / night
Magical Disney Vacation Rental
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 38 minutes
$167.00
from $167.00 / night
Venetian Bay Villages 3/2
Kissimmee Townhouse
- 3 bedrooms 3
- 2 bathrooms
- sleeps 7 7
- min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$114.00
from $114.00 / night
✧Near to All Orlando Parks and Attractions! - 4BR Cozy Town Home✧
Kissimmee Townhouse
- 4 bedrooms 4
- 3 bathrooms
- sleeps 10 10
- min stay varies
- Beach/lakeside relaxation
- Nearest beach 90 mi
- Swimming pool
$117.00
from $117.00 / night
Disney World: 2 Room Disney Celebration Villa Suite
Kissimmee Villa
- 1 bedroom 1
- 1 bathroom
- sleeps 6 6
- 2 nights min
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
Responds fast! Avg. 3 hours 42 minutes
$226.00
from $226.00 / night
HarryPotter Theater, Star Wars, Moana, Cinderella, Aladdin. Disney 10 minutes!
Kissimmee House
- 8 bedrooms 8
- 5 bathrooms
- sleeps 20 20
- min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$686.00
from $686.00 / night
4 King Beds! Star Wars Theater, Harry Potter, Pirates, Princess. Disney 5-10 min
Kissimmee House
- 8 bedrooms 8
- 5 bathrooms
- sleeps 22 22
- min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$686.00
from $686.00 / night
⭐Cozy and Simple 3 Bedrooms - Near Disney World⭐
Kissimmee Townhouse
- 3 bedrooms 3
- 3 bathrooms
- sleeps 7 7
- 3 nights min
- Beach/lakeside relaxation
- Nearest beach 90 mi
- Swimming pool
$93.00
from $93.00 / night
Renovated Luxury 4 Bedroom Villa with Salt Pool in 5* Resort 3 miles to Disney
Kissimmee Villa
- 4 bedrooms 4
- 2 bathrooms
- sleeps 8 8
- 4 nights min
- Beach/lakeside relaxation
- Nearest beach 125 mi
- Swimming pool
$190.00
from $190.00 / night
⭐Simple yet Comfortable 4 Bedrooms at Coral Cay Resort⭐
Kissimmee Townhouse
- 4 bedrooms 4
- 3 bathrooms
- sleeps 10 10
- min stay varies
- Beach/lakeside relaxation
- Nearest beach 90 mi
- Swimming pool
$117.00
from $117.00 / 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 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.