Kissimmee, Florida

Vacation Rentals in Kissimmee, Florida

Discover 3,730 vacation rental properties in Kissimmee. From 1 to 42 bedrooms. Average $220/night. 100% have pools.

3,730 verified listings Book securely on VRBO Prices updated March 2026

3,730 properties available

GORGEOUS POOL HOME IN QUIET TRANQUIL SETTING CLOSE TO ATTRACTIONS AND OUTLETS

GORGEOUS POOL HOME IN QUIET TRANQUIL SETTING CLOSE TO ATTRACTIONS AND OUTLETS

3 beds 2 baths
PoolA/CWiFiBalcony
$149/night
View Details → Book on VRBO
My Happy Place with Resort Amenities AND minutes from Disney!!

My Happy Place with Resort Amenities AND minutes from Disney!!

3 beds 2 baths
PoolA/CWiFiBalcony
$157/night
View Details → Book on VRBO
4BR/3BA Villa with Pool & Game Room, 5 min to Disney

4BR/3BA Villa with Pool & Game Room, 5 min to Disney

4 beds 3 baths
PoolA/CWiFiBalcony
$175/night
View Details → Book on VRBO
FREE POOL HEAT! Fantastic 6 Bedroom Resort Villa With Pool

FREE POOL HEAT! Fantastic 6 Bedroom Resort Villa With Pool

6 beds 5 baths
PoolA/CWiFiBalcony
$147/night
View Details → Book on VRBO
**3 MILES TO DISNEY’S MAIN GATE**5STAR 4BD 3BTH HOME w/SOUTH FACING POOL+GAME RM

**3 MILES TO DISNEY’S MAIN GATE**5STAR 4BD 3BTH HOME w/SOUTH FACING POOL+GAME RM

4 beds 3 baths
PoolA/CWiFiBalcony
$147/night
View Details → Book on VRBO
H8536-Single Level Pool Spa Home/5 Bed Near Disney

H8536-Single Level Pool Spa Home/5 Bed Near Disney

5 beds 3 baths
PoolA/CWiFiBalcony
$169/night
View Details → Book on VRBO
Modern Luxury Villa with Everything

Modern Luxury Villa with Everything

8 beds 5 baths
PoolA/CWiFiBalcony
$359/night
View Details → Book on VRBO
Vibrant Townhome near parks!

Vibrant Townhome near parks!

3 beds 3 baths
PoolA/CWiFiBalcony
$100/night
View Details → Book on VRBO
Elegantly Upgraded 4 bedroom Windsor Hills home with COMPLIMENTARY POOL HEAT!

Elegantly Upgraded 4 bedroom Windsor Hills home with COMPLIMENTARY POOL HEAT!

4 beds 4 baths
PoolA/CWiFiBalcony
$305/night
View Details → Book on VRBO
Newly Remodeled 1 bed/1 bath Condo Just 7 miles from Disney!

Newly Remodeled 1 bed/1 bath Condo Just 7 miles from Disney!

2 beds 1 bath
PoolA/CWiFiBalcony
$85/night
View Details → Book on VRBO
Townhome w/ Lanai & Pool Access ~ 10 Mi to Disney!

Townhome w/ Lanai & Pool Access ~ 10 Mi to Disney!

3 beds 2 baths
PoolA/CWiFiBalcony
$70/night
View Details → Book on VRBO
Historic Downtown Kissimmee Beautiful Apartment 2

Historic Downtown Kissimmee Beautiful Apartment 2

1 bed 1 bath
PoolA/CWiFiBalcony
$75/night
View Details → Book on VRBO
VB009 Venetian Bay Wonders

VB009 Venetian Bay Wonders

4 beds 3 baths
PoolA/CWiFiBalcony
$80/night
View Details → Book on VRBO
Lovely remodeled condo close to Magic Kingdom

Lovely remodeled condo close to Magic Kingdom

1 bed 1 bath
PoolA/CWiFiBalcony
$85/night
View Details → Book on VRBO
Renovated Waterfront 4Bd/2Bth Home w/Pool&Spa 15-20Min to Disney/Shops/Universal

Renovated Waterfront 4Bd/2Bth Home w/Pool&Spa 15-20Min to Disney/Shops/Universal

4 beds 2 baths
PoolA/CWiFiBalcony
$146/night
View Details → Book on VRBO
Family-friendly Room with 2 DBL Beds A Short Ride to Theme Parks

Family-friendly Room with 2 DBL Beds A Short Ride to Theme Parks

1 bath
PoolA/CWiFiBalcony
$77/night
View Details → Book on VRBO
VB011 Renovated Venetian Bay Townhome In Quiet Location

VB011 Renovated Venetian Bay Townhome In Quiet Location

4 beds 3 baths
PoolA/CWiFiBalcony
$85/night
View Details → Book on VRBO
VB043 4 Bedroom, 3 Bath Townhouse

VB043 4 Bedroom, 3 Bath Townhouse

4 beds 3 baths
PoolA/CWiFiBalcony
$85/night
View Details → Book on VRBO
Southeast Facing Private Pool,lakeside,3 Br-2 Bath,10 Min-disney, Modern

Southeast Facing Private Pool,lakeside,3 Br-2 Bath,10 Min-disney, Modern

3 beds 2 baths
PoolA/CWiFiBalcony
$130/night
View Details → Book on VRBO
VB006 Affordable Venetian Bay Townhouse With Room For Ten

VB006 Affordable Venetian Bay Townhouse With Room For Ten

4 beds 3 baths
PoolA/CWiFiBalcony
$85/night
View Details → Book on VRBO
4BD/3B,EXECUTIVE VILLA WITH SPA,MUST SEE,10 MIN FROM DISNEY

4BD/3B,EXECUTIVE VILLA WITH SPA,MUST SEE,10 MIN FROM DISNEY

4 beds 3 baths
PoolA/CWiFiBalcony
$131/night
View Details → Book on VRBO
Kissimmee Home w/ Private Hot Tub: 6 Mi to Disney!

Kissimmee Home w/ Private Hot Tub: 6 Mi to Disney!

4 beds 3 baths
PoolA/CWiFiBalcony
$93/night
View Details → Book on VRBO
All the amenities you want 6 miles from Disneyworld!

All the amenities you want 6 miles from Disneyworld!

4 beds 2 baths
PoolA/CWiFiBalcony
$113/night
View Details → Book on VRBO
Private Heated Pool! Only 8 miles to Disney! Gated Community

Private Heated Pool! Only 8 miles to Disney! Gated Community

4 beds 3 baths
PoolA/CWiFiBalcony
$204/night
View Details → Book on VRBO
Cozy Coral Cay Resort Condo, 4BR/3BA, 5-mile to Disney, free Wifi, free cable

Cozy Coral Cay Resort Condo, 4BR/3BA, 5-mile to Disney, free Wifi, free cable

4 beds 3 baths
PoolA/CWiFiBalcony
$94/night
View Details → Book on VRBO
Entire townhome near Disney

Entire townhome near Disney

3 beds 2 baths
PoolA/CWiFiBalcony
$105/night
View Details → Book on VRBO
Kissimmee Home w/ Pool ~ 8 Mi to Disney World

Kissimmee Home w/ Pool ~ 8 Mi to Disney World

4 beds 2 baths
PoolA/CWiFiBalcony
$121/night
View Details → Book on VRBO
Great living space within a Resort

Great living space within a Resort

2 beds 1 bath
PoolA/CWiFiBalcony
$121/night
View Details → Book on VRBO
Private Pool on this Peaceful Community

Private Pool on this Peaceful Community

4 beds 2 baths
PoolA/CWiFiBalcony
$108/night
View Details → Book on VRBO
Exquisite Destination. Bay Vista

Exquisite Destination. Bay Vista

6 beds 4 baths
PoolA/CWiFiBalcony
$142/night
View Details → Book on VRBO
Amazing home with many activities besides theme parks close by

Amazing home with many activities besides theme parks close by

4 beds 3 baths
PoolA/CWiFiBalcony
$166/night
View Details → Book on VRBO
Vacation rental with a touch of Class!

Vacation rental with a touch of Class!

3 beds 2 baths
PoolA/CWiFiBalcony
$122/night
View Details → Book on VRBO
Lake Front Authentic Disney Collection Edition 4 Bedroom Townhome

Lake Front Authentic Disney Collection Edition 4 Bedroom Townhome

4 beds 3 baths
PoolA/CWiFiBalcony
$113/night
View Details → Book on VRBO
12 person,5 m to Disney, 5BR 3BA pool & SPA,Gated, lakeview; Xbox Wii, Air fryer

12 person,5 m to Disney, 5BR 3BA pool & SPA,Gated, lakeview; Xbox Wii, Air fryer

5 beds 3 baths
PoolA/CWiFiBalcony
$126/night
View Details → Book on VRBO
Great value 5BR/3BA townhome with hot tub/ lake View, Close to Disney, Seaworld

Great value 5BR/3BA townhome with hot tub/ lake View, Close to Disney, Seaworld

5 beds 3 baths
PoolA/CWiFiBalcony
$113/night
View Details → Book on VRBO
Florida Haven Villa - Newly Refurbished, Great location, Sleeps 8

Florida Haven Villa - Newly Refurbished, Great location, Sleeps 8

3 beds 2 baths
PoolA/CWiFiBalcony
$119/night
View Details → Book on VRBO
Gorgeous!☀ 4Bed 3.5Ba with Splash Pool by Disney

Gorgeous!☀ 4Bed 3.5Ba with Splash Pool by Disney

4 beds 3 baths
PoolA/CWiFiBalcony
$150/night
View Details → Book on VRBO
Relaxing 3 bedroom home near Disney 4564

Relaxing 3 bedroom home near Disney 4564

3 beds 2 baths
PoolA/CWiFiBalcony
$119/night
View Details → Book on VRBO
Game Room, Hot Tub, Every room w/ En Suite Bathroom. Perfect Family Getaway

Game Room, Hot Tub, Every room w/ En Suite Bathroom. Perfect Family Getaway

6 beds 6 baths
PoolA/CWiFiBalcony
$297/night
View Details → Book on VRBO
4br/3ba TownHome with lake View,Near Disney,Sea World,Convention Center

4br/3ba TownHome with lake View,Near Disney,Sea World,Convention Center

4 beds 3 baths
PoolA/CWiFiBalcony
$104/night
View Details → Book on VRBO
Near Disney,Seaworld,Convention Center,5br/3ba townhome with hot tub/lake view

Near Disney,Seaworld,Convention Center,5br/3ba townhome with hot tub/lake view

5 beds 3 baths
PoolA/CWiFiBalcony
$118/night
View Details → Book on VRBO
Family Townhome - 3beds/2baths

Family Townhome - 3beds/2baths

3 beds 2 baths
PoolA/CWiFiBalcony
$121/night
View Details → Book on VRBO
4br/3ba townhome with private hot tub,Near Disney,Seaworld,Convention Center

4br/3ba townhome with private hot tub,Near Disney,Seaworld,Convention Center

4 beds 3 baths
PoolA/CWiFiBalcony
$103/night
View Details → Book on VRBO
Last minute! Book now and get big discount!

Last minute! Book now and get big discount!

4 beds 2 baths
PoolA/CWiFiBalcony
$127/night
View Details → Book on VRBO
Tranquil Times: Theater, Heated pool, Outdoor BBQ 6 miles from Disney

Tranquil Times: Theater, Heated pool, Outdoor BBQ 6 miles from Disney

4 beds 2 baths
PoolA/CWiFiBalcony
$196/night
View Details → Book on VRBO
5br/3ba townhome with hot tub,Near Disney,Seaworld and Convention Center

5br/3ba townhome with hot tub,Near Disney,Seaworld and Convention Center

5 beds 3 baths
PoolA/CWiFiBalcony
$116/night
View Details → Book on VRBO
Amazing Townhone at Bella Vida Resort

Amazing Townhone at Bella Vida Resort

3 beds 2 baths
PoolA/CWiFiBalcony
$142/night
View Details → Book on VRBO
YOS-Pool home, 4BR, 2 Masters, game room sleep 8

YOS-Pool home, 4BR, 2 Masters, game room sleep 8

4 beds 3 baths
PoolA/CWiFiBalcony
$192/night
View Details → Book on VRBO

Showing 48 of 3,730 properties

More destinations in Florida

Panama City Beach (4614) Davenport (2507) Miami Beach (1899) Key West (1835) Cape Coral (1809) Sarasota (1719) Marco Island (1375) Naples (1355) Siesta Key (936) Holmes Beach (770) Clearwater (768) Bradenton (551) Orlando (458) Miami (425) Anna Maria (386) Rotonda West (381) Clearwater Beach (361) Santa Rosa Beach (358) Destin (250) Gulf Shores (250)