Kissimmee Vacation Rental Getaways


Refine Your Search
Check-In 
calendar

Check-Out
calendar
  • Property Options
  • Amenities
  • Location Type
  • Bed
  • Bath
  • Sleeps
Max Price Per Week $
  • Special Offers
  • Online Booking
  • Home/Villa
  • Cottage/Cabin
  • Condo/Townhome
  • Bed & Breakfast
  • Apt/Room/Suite
  • Air Conditioning
  • Washer/Dryer
  • Full Kitchen
  • Satellite/Cable TV
  • Handicap Access
  • High Speed Internet
  • Elevator
  • Maid Service
  • Garage Parking
  • Pets Allowed
  • Private Pool
  • Pool Access
  • Hot Tub
  • Fireplace
  • Smoking allowed
  • Beach Access
  • Beach Front
  • Golf on site
  • Golf nearby
  • Ocean Front
  • Ocean View
  • Lake Front
  • Lake View
  • Ski in/out
  • Walk to Slopes
  • Skiing nearby
 
Sort by: Type BR/BA/Sleeps Price

Disney At Your Doorstep

Kissimmee
This fabulous family 3 bedroom condo is perfectly located on the Windsor Hills Resort in Kissimmee, ...
Condo 3 / 2 / 8

*
Online booking available

$75 - $175
Per Night

$525 - $1225
Per Week

Magical Dreams

Kissimmee
Come and enjoy a family vacation that to cherish forever - when you stay at this spacious and elegan...
Home 5 / 5 / 12

*
Online booking available

$190 - $435
Per Night

$1330 - $3045
Per Week

Natures Haven

Kissimmee
This spacious, family-sized rental town house on the Windsor Palms Resort has a private pool, open p...
Home 3 / 3 / 6

*
Online booking available

$80 - $185
Per Night

$560 - $1295
Per Week

2 bedroom deluxe

Kissimmee
2 bedroom deluxe Unit Description: The 2-bedroom deluxe suite has a king bed in the master bedroom ...
Condo 2 / 2 / 8

*
Online booking available

$199 - $284
Per Night

$1393 - $1988
Per Week

3 bedroom, 3 bathroom, Kissimmee Home (SP2334)

Kissimmee
This lovely 3 bedroom townhouse is in the gated community of Windsor Palms. The bedrooms consist of...
Home 3 / 3 / 8

*
Online booking available

Contact
Owner
Directly
For Rates

2545 Montego Bay Blvd.

Kissimmee
This 3 bedroom 2 bath Orlando vacation home is perfectly placed to maximize your family's vacation f...
Villa 3 / 2 / 8

*
Online booking available

$95 - $140
Per Night

$665 - $980
Per Week

Curacao Three Bedroom Deluxe Villa

Kissimmee
Curacao Three Bedroom Deluxe Villa Unit Description: Three bedroom villas feature 1,600 square feet...
Condo 3 / 2 / 8

*
Online booking available

$95 - $189
Per Night

$665 - $1323
Per Week

2606 Bowring Street

Kissimmee
Located in Windsor Hills, this beautiful home has been furnished and decorated with the utmost atten...
Home 5 / 5 / 10

*
Online booking available

$425 - $575
Per Night

$2975 - $4025
Per Week

8503 La Isla Drive

Kissimmee
A stylish, warm and homey welcome awaits you in our 7 Bedroom true-luxury 2,827sq.ft holiday villa, ...
Home 7 / 5.5 / 14

*
Online booking available

$405 - $535
Per Night

$2835 - $3745
Per Week

2625 Pawnall Street

Kissimmee
Welcome to this stunning 5 Bedroom, 5 Bathroom pool home, with spa, in popular Windsor Hills Resort....
Home 5 / 5 / 12

*
Online booking available

$370 - $500
Per Night

$2590 - $3500
Per Week

Escape2disney

Kissimmee
This delightful 3 bedroom vacation rental is located in Windsor Hills in Orlando, less than 2.5 mile...
Condo 3 / 2 / 6

*
Online booking available

$75 - $175
Per Night

$525 - $1225
Per Week

8957 Sugar Palm Road

Kissimmee
On your next trip to the Orlando area, enjoy this distinctively decorated rental town home featuring...
Home 4 / 3 / 8

*
Online booking available

$275 - $405
Per Night

$1925 - $2835
Per Week

Villascape

Kissimmee
Villascape is nestled on the Somerset community, just a short drive from Walt Disney World® Resort i...
Home 6 / 4 / 12

*
Online booking available

$155 - $355
Per Night

$1085 - $2485
Per Week

6 bedroom, 4 bathroom, Kissimmee Villa (ML2712)

Kissimmee
This luxurious spacious 2-storey home is located in the gated community of Windsor Hills, within eas...
Villa 6 / 4 / 12

*
Online booking available

$268 - $339
Per Night

$1876 - $2373
Per Week

Stunning 4 Bed Villa On Lindfields, Newly Furnsihed In Gr...

Kissimmee
Stunning 4 Bed Villa On Lindfields, Newly Furnsihed In Great Area (Av3020Bc) This stunning detached...
Home 4 / 2.5 / 10

*
Online booking available

$141 - $163
Per Night

$963 - $1124
Per Week

One bedroom deluxe villa

Kissimmee
One bedroom deluxe villa Unit Description: This spacious villa features a private bathroom with whi...
Condo 1 / 1 / 4

*
Online booking available

$59 - $261
Per Night

$413 - $1827
Per Week

3 bedroom villa

Kissimmee
3 bedroom villa Unit Description: This villa features a King in the master bedroom with Jacuzzi, t...
Condo 2 / 2 / 8

*
Online booking available

$208 - $312
Per Night

$1456 - $2184
Per Week

180 Hideaway Beach Lane

Kissimmee
Located in the prestigious gated community of Terra Verde, in the heart of Kissimmee. Expect to be i...
Home 7 / 4.5 / 14

*
Online booking available

$250 - $350
Per Night

$1750 - $2450
Per Week

2778 Almaton Loop Unit 105

Kissimmee
We invite you to enjoy our condo on your next trip to Orlando. Absolutely perfect for family groups,...
Condo 3 / 2 / 8

*
Online booking available

$180 - $265
Per Night

$1260 - $1855
Per Week

8571 La Isla Drive

Kissimmee
Gorgeous 7bedroom/6 bath in the upscale resort community Emerald Island. Pool and spa is southeast f...
Home 7 / 6 / 14

*
Online booking available

$595 - $710
Per Night

$4165 - $4970
Per Week

4 Bed 2 Bath Indian Ridge Near Disney With Gameroom Av1506Oh

Kissimmee
Fenced in pool area 4 bed / 2 bath. Master ? Queen. Front bedroom ? Full, Twin beds, Twin bunk beds ...
Home 4 / 2 / 9

*
Online booking available

$146 - $169
Per Night

$1004 - $1164
Per Week

Swan Lake Villa

Kissimmee
This fabulous 4 bedroom vacation rental is located in Windsor Hills in Kissimmee, less than 2.5 mile...
Home 4 / 4 / 10

*
Online booking available

$145 - $335
Per Night

$1015 - $2345
Per Week

The Hidden Mickey

Kissimmee
This high quality family vacation pool home is available for discerning guests. The Hidden Mickey is...
Home 6 / 3 / 14

*
Online booking available

$185 - $425
Per Night

$1295 - $2975
Per Week

Vacation on the Veranda

Kissimmee
Book your loved ones to stay in this fabulous 6 bedroom family pool home that's nestled in a quiet, ...
Home 6 / 4 / 14

*
Online booking available

$165 - $380
Per Night

$1155 - $2660
Per Week

4 bedroom, 2 bathroom, Kissimmee Villa (CPT4665)

Kissimmee
This Villa is ideally located close to all the attractions & shopping. The house is located less tha...
Villa 4 / 2 / 10

*
Online booking available

$88 - $111
Per Night

$616 - $777
Per Week

 

More Getaway Locations and Properties