We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Holiday Rentals in Kissimmee, Florida

Use a credit card to book with our Peace of Mind Protection.
Learn more
Find a rental
Price per night
Min
to
Max
Bedrooms
Any
Amenities
Select
More filters
All 4,240 Rentals in Kissimmee
loading...
Sort by
From
$99
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
Hot Tub, Fitness Room, Pool & more
15 photos Details
Reviews (4) Make Enquiry
From
$106
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
Internet, Air Conditioning, Washer/Dryer & more
13 photos Details
Reviews (2) Make Enquiry
From
$156
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 10
Bookings
Parking, Fitness Room, Grill & more
18 photos Details
Reviews (1) Make Enquiry
Also consider
Luxurious and spacious Design Villa Orlando-Disney
4 Bedrooms, sleeps 8
$119 - $175 / night
Brand New Villa Windsor Hill Resort 2014 $999/WK
6 Bedrooms, sleeps 12
$178 - $390 / night
2719 CALLAWAY
4 Bedrooms, sleeps 8
$1,110 / week
Brand New -4 Bed /3 bath-Pool-WIFI-Game Console
4 Bedrooms, sleeps 10
$106 - $188 / night
From
$112
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 6
Air Conditioning, Private pool, Other outdoor space & more
23 photos Details
Reviews (7) Make Enquiry
From
$211
Per Night
5 Bedrooms, 3 Bathrooms, Sleeps 11
Pool, Private Pool, Heated Pool & more
32 photos Details
Reviews (2) Make Enquiry
From
$167
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 8
Other outdoor space, Washer/Dryer, Air Conditioning & more
24 photos Details
Reviews (12) Make Enquiry
From
$145
Per Night
5 Bedrooms, 5 Bathrooms, Sleeps 10
Grill, Private pool, Other outdoor space & more
40 photos Details
Reviews (6) Make Enquiry
From
$162
Per Night
4 Bedrooms, 2 Bathrooms, Sleeps 8
Fitness Room, Air Conditioning, Hot Tub
21 photos Details
Reviews (2) Make Enquiry
Get the List
From
$215
Per Night
5 Bedrooms, 4 Bathrooms, Sleeps 12
Bookings
Suitable for children
20 photos Details
Reviews (1) Make Enquiry
From
$122
Per Night
5 Bedrooms, 3 Bathrooms, Sleeps 10
Internet, Air Conditioning, Other outdoor space & more
15 photos Details
Reviews (5) Make Enquiry
From
$99
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 8
Booking
Elder access, Suitable for children
18 photos Details
Reviews (1) Make Enquiry
From
$138
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 8
Wi-Fi, Air Conditioning, Parking & more
22 photos Details
Reviews (1) Make Enquiry
From
$95
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 10
Fitness Room, Parking, Grill & more
14 photos Details
Reviews (4) Make Enquiry
From
$184
Per Night
5 Bedrooms, 4 Bathrooms, Sleeps 14
Public pool, Private pool, Internet & more
55 photos Details
Reviews (7) Make Enquiry
From
$155
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 8
Booking
Private Outdoor Pool (Heated), Air Conditioning & more
24 photos Details
Reviews (7) Make Enquiry
From
$109
Per Night
4 Bedrooms, 4 Bathrooms, Sleeps 8
Booking
Washer/Dryer, Suitable for children & more
20 photos Details
Reviews (7) Make Enquiry
From
$195
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 10
Internet
18 photos Details
Reviews (16) Make Enquiry
From
$136
Per Night
5 Bedrooms, 4 Bathrooms, Sleeps 8
Grill, Shared Tennis Court, Washer/Dryer & more
21 photos Details
Reviews (1) Make Enquiry
From
$122
Per Night
4 Bedrooms, 4 Bathrooms, Sleeps 10
Grill, Other outdoor space, Air Conditioning & more
20 photos Details
Reviews (1) Make Enquiry
From
$90
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
Air Conditioning, Private Pool, Internet & more
26 photos Details
Reviews (6) Make Enquiry
From
$195
Per Night
5 Bedrooms, 5 Bathrooms, Sleeps 10
Bookings
Garden, Washer/Dryer, Parking & more
43 photos Details
Reviews (8) Make Enquiry
From
$195
Per Night
6 Bedrooms, 5 Bathrooms, Sleeps 12
Bookings
Grill, Air Conditioning, Suitable for children & more
23 photos Details
Reviews (4) Make Enquiry
From
$95
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 8
Other outdoor space, Internet, Private pool & more
17 photos Details
Reviews (31) Make Enquiry
From
$901
Per Week
4 Bedrooms, 5 Bathrooms, Sleeps 10
Game Room, Other outdoor space & more
24 photos Details
Reviews (6) Make Enquiry
From
$127
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Game Room, Elder access, Air Conditioning & more
24 photos Details
Reviews (10) Make Enquiry
From
$165
Per Night
5 Bedrooms, 3 Bathrooms, Sleeps 10
Bookings
Private pool, Other outdoor space, Parking & more
17 photos Details
Reviews (6) Make Enquiry
From
$109
Per Night
4 Bedrooms, 2 Bathrooms, Sleeps 8
Booking
Suitable for children, Air Conditioning & more
12 photos Details
Reviews (2) Make Enquiry
From
$145
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 10
Internet, Other outdoor space, Private Pool & more
17 photos Details
Reviews (3) Make Enquiry
From
$188
Per Night
5 Bedrooms, 4 Bathrooms, Sleeps 10
Internet, Air Conditioning
20 photos Details
Reviews (1) Make Enquiry
From
$133
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 10
Air Conditioning
16 photos Details
Reviews (1) Make Enquiry
From
$159
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 8
Washer/Dryer, Parking, Hot Tub & more
25 photos Details
Reviews (2) Make Enquiry
From
$279
Per Night
5 Bedrooms, 5 Bathrooms, Sleeps 10
Air Conditioning, Fitness Room, Grill & more
37 photos Details
Reviews (22) Make Enquiry
From
$126
Per Night
4 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
Other outdoor space, Elder access, Wi-Fi & more
12 photos Details
Reviews (4) Make Enquiry
From
$175
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 10
Booking
Parking, Washer/Dryer, Hot Tub & more
22 photos Details
Reviews (2) Make Enquiry
From
$161
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 8
Bookings
Garden, Parking, Game Room & more
16 photos Details
Reviews (3) Make Enquiry
From
$164
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 10
Heated Pool, Pet friendly, Grill & more
15 photos Details
Reviews (18) Make Enquiry
From
$133
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 6
Children's Pool, Shared Outdoor Pool (Heated) & more
18 photos Details
Reviews (18) Make Enquiry
From
$110
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 5
Booking
Washer/Dryer, Air Conditioning, Fitness Room & more
17 photos Details
Reviews (3) Make Enquiry
From
$112
Per Night
4 Bedrooms, 2 Bathrooms, Sleeps 8
Air Conditioning, Fitness Room, Other outdoor space & more
21 photos Details
Reviews (1) Make Enquiry
From
$195
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 10
Internet
16 photos Details
Reviews (17) Make Enquiry
Go to map view
Book Online(2703)
Use filters to find the best results!

Suitability

  • Wheelchair access (598)
  • Elder access (1,588)
  • Suitable for children (2,323)
  • Pet friendly (175)
  • Smoking allowed (10)

Amenities

  • Air Conditioning (3,016)
  • Internet (2,993)
  • All pools (2,701)
  • Other outdoor space (2,088)
  • Washer/Dryer (2,056)
  • View all amenities
List your property for free!
List your accommodation
for free on our website.
Reach millions worldwide.
Add a Listing


In partnership with
Get the List
Villas in Kissimmee

Kissimmee, near Orlando in Florida, is a great family friendly destination, as it is so near so many of Florida's most famous tourist attractions and theme parks, including Walt Disney World. In addition to these attractions and a glorious sub-tropical climate, the area presents unique opportunities to spot exotic and endangered wildlife. Whether your family are, roller-coaster fanatics or naturalists, or a mixture of both, you will have a packed time in the area, and you can cut down on the expenses by investigating the wide range of villas and holiday rentals on offer.

Things to do in Kissimmee

Kissimmee is within easy reach of Disney World, Sea World Orlando and Universal Studios, but you can also go for lesser known attractions such as Forever Florida, where you can go on safari on horseback or on a coach to spot alligators, black bears and even the incredibly rare Florida panther. Florida is of course also famous for its swamps, so a trip to Boggy Creek is also a perfect day out, you can take a ride in a swamp buggy out to explore the wetlands and see turtles and various exotic birds. These kinds of attractions provide memories which will last a lifetime, and are great for kids. And for a bit of fun, make sure you go to Medieval Times for a dinner show with a difference, as knights joust on horseback. This is an expensive venue, but could be a highpoint of an unforgettable family holiday, and of course you'll be saving a considerable amount of money by renting a villa rather than forking out for a hotel room.

Kissimmee Holiday Rentals

A holiday full of theme parks can be an expensive business with even a small family. But you can make your budget go further by opting to rent a villa, as prices start around £500 a week for villas for up to six people. With air conditioning, pools, broadband and TVs included as standard, you can make yourself completely at home during your stay, and maybe even spend a day in the villa between theme park trips - with the extra space of self-catered accommodation this becomes a real option, whereas in a hotel kids are generally climbing up the walls within twenty minutes! By renting a villa, you can enjoy a low cost holiday in Kissimmee, and probably get to relax a whole lot more!