503 Results
Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

Apartments
Bungalows
Cabins
Condos
Cottages
Estates
Homes
Townhomes
Villas
Barns
Boats
Castles
Chalets
Farmhouses
Hotels
Lodges
Studios
Yachts

Booking Options

Location Type

Even More Filters

Features

Managed By

503 Results
Cancel Clear Filters Apply Filters
Use filters to narrow your search results!

Kissimmee Area Long Term Villa Rentals(503)

503 Results
$120 - $179
per night
4 - 7 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 8
4 - 7 night minimum stay
(30)
  • 3 BR,
  • 3 BA,
  • Sleeps 8
4 night minimum stay
(83)
  • 4 BR,
  • 2 BA,
  • Sleeps 10
3 night minimum stay
(35)
  • 5 BR,
  • 4 BA,
  • Sleeps 11
5 - 7 night minimum stay
(23)
  • 5 BR,
  • 5 BA,
  • Sleeps 12
5 - 7 night minimum stay
(56)
$224 - $338
per night
4 - 12 night minimum stay
  • 5 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 10
4 - 12 night minimum stay
(15)
  • 6 BR,
  • 4 BA,
  • 2 HF BA,
  • Sleeps 14
3 - 7 night minimum stay
(12)
$175 - $225
per night
5 - 7 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 8
5 - 7 night minimum stay
(71)
$134 - $174
per night
5 - 6 night minimum stay
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
5 - 6 night minimum stay
(28)
  • 4 BR,
  • 3 BA,
  • Sleeps 8
7 - 14 night minimum stay
(35)
  • 6 BR,
  • 3 BA,
  • 2 HF BA,
  • Sleeps 14
5 - 7 night minimum stay
(11)
  • 8 BR,
  • 4 BA,
  • 2 HF BA,
  • Sleeps 19
3 - 7 night minimum stay
(27)
  • 4 BR,
  • 3 BA,
  • Sleeps 9
3 - 7 night minimum stay
(38)
$1,100 - $1,600
per night
5 - 7 night minimum stay
  • 8 BR,
  • 9 BA,
  • 2 HF BA,
  • Sleeps 18
5 - 7 night minimum stay
(19)
  • 5 BR,
  • 5 BA,
  • Sleeps 10
5 - 7 night minimum stay
(12)
  • 4 BR,
  • 2 BA,
  • Sleeps 8
3 - 5 night minimum stay
(58)
$119 - $159
per night
4 - 5 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 9
4 - 5 night minimum stay
(38)
$1,429 - $1,786
per night
5 - 7 night minimum stay
  • 9 BR,
  • 9 BA,
  • 2 HF BA,
  • Sleeps 18
5 - 7 night minimum stay
(11)
$300 - $500
per night
3 - 14 night minimum stay
  • 7 BR,
  • 5 BA,
  • 2 HF BA,
  • Sleeps 16
3 - 14 night minimum stay
(10)
$100 - $130
per night
3 - 7 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 10
3 - 7 night minimum stay
(30)
  • 7 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 16
3 night minimum stay
(22)
$120 - $125
per night
3 - 4 night minimum stay
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
3 - 4 night minimum stay
(16)
$515 - $789
per night
5 - 7 night minimum stay
  • 5 BR,
  • 5 BA,
  • Sleeps 10
5 - 7 night minimum stay
(11)
  • 4 BR,
  • 3 BA,
  • Sleeps 10
(56)
  • 5 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 12
5 - 6 night minimum stay
(22)
  • 4 BR,
  • 2 BA,
  • Sleeps 10
5 - 7 night minimum stay
(23)
  • 6 BR,
  • 5 BA,
  • Sleeps 12
5 - 7 night minimum stay
(12)
  • 4 BR,
  • 3 BA,
  • Sleeps 8
4 - 5 night minimum stay
(7)
$159 - $209
per night
3 night minimum stay
  • 5 BR,
  • 4 BA,
  • Sleeps 14
3 night minimum stay
(17)
$140 - $210
per night
4 - 7 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 8
4 - 7 night minimum stay
(15)
 

Recent Kissimmee Area Reviews

Great Place!

4 of 5
Our family (of six adults) just finished our holiday at Windsor Palms. This villa has a lot of space for six adults. The heated pool was wonderful to come back to after a busy day at the parks. It is also very peaceful after dealing with all the people in the parks. The location is great. Easy to get around. John gives you step by step directions to the villa, which is great when you arrive in the dark and are not sure of the lay out of the land yet! Having a BBQ was also a plus. We would for sure stay here again! Great place!
  • Submitted: Feb 24, 2015
  • Stayed: Feb 2015

Excellent experience.

5 of 5
Our week long stay would have cost us the same amount to stay at a resort hotel and we would of been jammed into a couple hundred square foot room. Making the choice to rent a home is the way to go. Spacious vacation living , washer & dryer , kitchen , private pool. Incredible value for our money.
  • Submitted: Feb 21, 2015
  • Stayed: Feb 2015

VERY ENJOYABLE!

5 of 5
We are a brazilian group travellers and we had a wonderful (the best) vacation at Emerald Island. The house was super nice with fantastic decor. Our stay here was very enjoyable. Very spacious house with plenty of room for a large group. The children enjoyed the awesome games room. The pool was a good size and super warm. The resort is a very high end gated community with visible security. We all loved to stay at this wonderful villa. Thank you Julie for sharing your beautiful house with us! And thank you Dee for the support. Dee was great and answer any questions that I had. We will be back as soon as possible.
  • Submitted: Feb 15, 2015
  • Stayed: Jan 2015