Kissimmee Apartments & Vacation Rentals - 2656 Rentals Available
2,656 Vacation rentals

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 51 minutes
$251.00
from $251.00 / 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
Responds fast! Avg. 3 hours 30 minutes
$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 25 minutes
$92.00
from $92.00 / night
Certificate of Excellence
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
Travelers’ Choice award
$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 24 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. 2 hours 43 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. 2 hours 43 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
- min stay varies
- 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
- min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$241.00
from $241.00 / night
Certificate of Excellence
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
Travelers’ Choice award
$121.00
from $121.00 / night
Certificate of Excellence
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
Travelers’ Choice award
$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
$258.00
from $258.00 / 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 24 minutes
$75.00
from $75.00 / night
Spring Hill - 6 Bedroom Luxury Pool Home at Windsor Hills
Kissimmee House
- 6 bedrooms 6
- 4 bathrooms
- sleeps 14 14
- 5 nights min
- Swimming pool
- Child friendly
- Air conditioning
$264.00
from $264.00 / 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
Oakwater Townhome Close To Disney
Kissimmee Townhouse
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 1 night min
- Child friendly
- Air conditioning
Responds fast! Avg. 2 hours 47 minutes
$114.00
from $114.00 / night
Certificate of Excellence
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. 27 minutes
Travelers’ Choice award
$230.00
from $230.00 / 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. 2 hours 26 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
$75.00
from $75.00 / 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
Certificate of Excellence
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
Travelers’ Choice award
$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. 49 minutes
Travelers’ Choice award
$172.00
from $172.00 / night
Certificate of Excellence
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
Travelers’ Choice award
$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
$264.00
from $264.00 / 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
- 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
About Kissimmee
Introduction to Kissimmee
Located just a short hop away from Orlando, Kissimmee is a small city that offers quick and convenient access to a whole range of family friendly activities. When you want to take the kids on a trip to Central Florida but don’t want the stress or expense of vacationing at the theme parks, consider staying at one of the affordable Kissimmee villas. Vacation properties in Kissimmee give you the space to have a good time without breaking the bank.Kissimmee Climate
Like most of Central Florida, Kissimmee enjoys hot, humid summers followed by mild winters. If you visit in December or January, you’ll find temperatures around 60 degrees, while temperatures top out around 90 in July and August.How to Get Around Kissimmee
If you’re flying to Kissimmee, Orlando International Airport is an easy 25-minute drive away. Public busses and private shuttles can transport visitors around the Kissimmee area, but if you want to explore on your own, renting a car is your best bet. You can easily get from your vacation home to the theme parks, or to the natural attractions, on your own schedule with a car.Visit the Parks
The rides and attractions at Disney World are just a short drive away, but Kissimmee also boasts several of its own parks. Right on Lake Tohopekaliga, Kissimmee Lakefront Park features a playground and splash park for kids, BBQ grills for family get togethers, and fishing piers for everyone. If you time your visit right, you can even catch one of the many festivals or events on the park’s outdoor stage.If you’re looking for something more outdoorsy, visit Shingle Creek Regional Park, which encompasses over 1,000 acres. Canoe along the creek, hike the trails, and enjoy a picnic near the park’s historic pioneer homes. Even more impressive is the Disney Wilderness Preserve, which includes 11,500 acres and over 1,000 plant and animal species. Explore wetlands, swamps, and a freshwater marsh while spotting bats, snakes, and even panthers.
Shop and Dine in Old Town
When you’re ready to do some shopping or grab a bite to eat, head straight for Kissimme’s Old Town neighborhood. Here you’ll find everything from souvenir shops to places to stock up on warm weather gear. To fuel up for more adventures, dig into pizza, Tex-Mex, or pub grub. You can even enjoy a night out at one of the live music venues or nightclubs in Old Town.Just a few miles from Disney, Kissimmee offers the best of everything. With parks and preserves that will keep everyone entertained, Kissimmee villas that comfortably fit the whole family, and easy access to all the fun at Disney World, Kissimmee is a great vacation destination.
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Kissimmee, Florida Travel Tips
Beaches and Parks
Theme Parks
Outdoor Adventures
Fun With Kids
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.