Villas in Kissimmee

Rent your perfect holiday villa: choose from over 100 villas in Kissimmee including villas with private pools and cheap villas

Key holiday destinations in Kissimmee

Our 10 best villas in Kissimmee

Check out our best villas in Kissimmee.
  • Villa in Windsor Hills, Florida: Windsor Hills Retreat
    6 bedroom villa • Sleeps 12

    Windsor Hills villa to rent

    Spacious luxury property situated at the top of the exclusive gated community of Windsor Hills in Kissimmee. Private south facing pool and spa. 2 miles from Disney and Universal is 15 mins drive away.

    From £1,229 per week
    (52)
  • Villa in Emerald, Florida
    4 bedroom villa • Sleeps 8

    Villa with private pool in Kissimmee, Florida

    Stylish and spacious luxury villa set in a private Emerald Island resort in Kissimmee. Private pool and spa with first class games room. 2 miles from Disney and attractions.

    From £152 per week
    (25)
  • Villa in Cumbrian Lakes, Florida
    4 bedroom villa • Sleeps 8

    Cumbrian Lakes holiday villa rental with private pool

    Luxurious 4 bedroom, 3 bathroom villa with private pool and spa located on a beautiful, peaceful gated community within 15 minutes drive of Disney World.

    From £575 per week
    (26)
  • Villa in Vista Del Lago, Florida
    3 bedroom villa • Sleeps 7

    Villa with shared pool in Kissimmee, Florida

    Large and spacious three bedroom villa in Kissimmee. Fully equipped. Minutes from all Disney attractions, restaurants, bars and shops. High speed internet in property.

    From £402 per week
    (30)
  • Villa in Lindfields, Florida: Welcome to our villa
    4 bedroom villa • Sleeps 10

    Villa rental in Kissimmee, Florida, with private pool

    Private pool. PS3 and Video Games. Netflix. Free wireless internet. Unlimited free phone calls worldwide. Outside Grill and covered lanai. So close to Disney you can hear the fireworks.

    From £777 per week
    (9)
  • Villa in Indian Ridge, Florida
    3 bedroom villa • Sleeps 6

    Indian Ridge villa to rent

    A beautiful home away from home situated in Kissimmee, Florida, 30 mins from Airport, less than 10 minutes drive from magical Disney World and all major attractions, restaurants & endless shopping.

    From £679 per week
    (11)
  • Villa in Emerald, Florida
    5 bedroom villa • Sleeps 10

    Villa to rent in Kissimmee, Florida

    A very well maintained villa situated overlooking lush conservation woodland in the the very popular Emerald Island Resort Gated Community.

    From £820 per week
    (6)
  • Villa in Buenaventura Lakes, Florida
    4 bedroom villa • Sleeps 9

    Buenaventura Lakes villa to rent

    Sun drenched 4 bedroom 2 storey vacation home on premier conservation lot offering comfort, convenience and luxury at amazingly good rates ...

    From £664 per week
    (4)
  • Villa in Crescent Lakes, Florida
    6 bedroom villa • Sleeps 12

    Villa with private pool in Kissimmee, Florida

    Stunning south facing pool villa. 6 bed 3 bath. Close to Disney, universal, SeaWorld, wet and wild, Harry Potter, 65 inch HDTV. Sleeps 12

    From £1,024 per week
  • Villa in Oak, Florida
    4 bedroom villa • Sleeps 8

    Villa rental in Kissimmee, Florida, with private pool

    Prestigeous 4 bedroom villa with private south facing pool and conservation lake view, only 3 miles from Disney!

    From £681 per week
    (2)

Villas in Kissimmee with private pools

Enjoy the space and privacy of a villa with a private pool.
  • Villa in Rolling Hills, Florida: View over lanai to pool and lake beyond
    4 bedroom villa • Sleeps 8

    Villa with private pool in Kissimmee, Florida

    Lakeside villa with pool close to Disney and other Orlando attractions. Now with 50" television and high speed internet access.

    Heated private pool
    From £784 per week
    (7)
  • Villa in Doral Woods, Florida
    4 bedroom villa • Sleeps 8

    Villa with private pool in Kissimmee, Florida

    Doral Woods is a select development of family homes on large plots amidst mature trees. It is about 10 mins south of the 192 with its many restaurants and the famous Kissimmee Old Town.

    Heated private pool
    28m x 14m
    From £690 per week
    (3)
  • Villa in Eagle Pointe, Florida: Pool and Lake View
    3 bedroom villa • Sleeps 8

    Villa to rent in Kissimmee, Florida

    «««DISNEY ON YOUR DOORSTEP»»» STAY CLOSE TO THE MAGIC in this Spacious 3 Bed Villa / Family Friendly / SOUTH FACING pool / LAKE VIEWS - BE OUR GUESTS ON EAGLE POINTE

    Private pool
    From £376 per week
    (28)
  • Villa in Sunset Lakes, Florida
    4 bedroom villa • Sleeps 10

    Sunset Lakes villa to rent

    Large lakefront villa with South facing pool, 4 bedrooms ( 2 huge master bedrooms ) very modern decor, Our villa will make your vacation special.

    Heated private pool
    From £878 per week
    (4)
  • Villa in Indian Creek, Florida
    5 bedroom villa • Sleeps 10

    Villa with private pool in Kissimmee, Florida

    A South Facing Spacious property, located just off Formosa Gardens on Highway 192. The Magic Kingdom and other Disney parks are less than ten minutes away.

    Heated private pool
    From £1,050 per week
    (32)
  • Villa in Windsor Hills, Florida
    6 bedroom villa • Sleeps 12

    Villa to rent in Kissimmee, Florida

    Luxury 6 bedroom 4 bathroom pool villa with games room. Just 2 miles from Walt Disney world Orlando Florida. Set within the world renowned gated community of Windsor Hills resort

    Heated private pool
    0.8m to 1.8m deep
    From £1,233 per week
  • Villa in Lakeside, Florida: Luxurious Heated Pool
    4 bedroom villa • Sleeps 9

    Villa rental in Kissimmee, Florida, with private pool

    Luxurious holiday home, which sleeps 9, situated in quiet lakeside residential area, 15 minutes from Orlando Airport and only 20 minutes from Disney.

    Heated private pool
    From £517 per week
    (15)
  • Villa in Emerald, Florida: Viewof villa from  street
    7 bedroom villa • Sleeps 20

    Villa rental in Kissimmee, Florida, with private pool

    Emerald Island Resort-Luxurious 3123 sqft 7bedroom/5.5 bathroom villa. Top Gated Community only 3 miles from Disney. Very private Pool with Lake & Conservation views.

    Heated private pool
    From £1,550 per week
  • Villa in Indian Creek, Florida
    4 bedroom villa • Sleeps 10

    Holiday villa in Kissimmee, Florida, with private pool

    Newer 4 bedroom, 3 bath home just minutes from the Maingate to Walt Disney World with hot tub, wireless hi-speed internet access--top of the line accommodations.

    Private pool
    From £646 per week
    (4)
  • Villa in Emerald, Florida
    6 bedroom villa • Sleeps 13

    Villa to rent in Kissimmee, Florida

    Executive 6 BDR 5.5 BTH Villa, Right at Disney's Doorstep, South West facing Pool with covered lanai, Club house with Gym, Sauna & Cafe, Gated Community, Very Spacious for large families!

    Heated private pool
    From £761 per week

Cheap villas in Kissimmee

Rent one of our cheapest villas in Kissimmee for a low cost holiday.
  • Villa in Vista Del Lago, Florida: Orlando Dreams your home from home
    3 bedroom villa • Sleeps 6

    Holiday villa in Kissimmee, Florida, with shared pool

    A large 1500+ sq ft property with3 bedrooms, 2 bathrooms less than 5 miles from Disney. Set in a quiet, gated, speed restricted, lakeside community.

    From £449 per week
    (5)
  • Villa in Kissimmee, Florida
    3 bedroom villa • Sleeps 8

    Holiday villa in Kissimmee, Florida, with swimming pool

    This 3 bedroom villa with shared pool is located in Kissimmee and sleeps 8 people. It has WiFi, parking nearby and air conditioning.

    From £477 per week
  • Villa in Kissimmee, Florida
    3 bedroom villa • Sleeps 6

    Kissimmee villa to rent

    This 3 bedroom villa with swimming pool is located in Kissimmee and sleeps 6 people. It has parking nearby and air conditioning.

    From £477 per week
  • Villa in Venetian Bay, Florida
    3 bedroom villa • Sleeps 6

    Venetian Bay holiday villa rental with shared pool

    Lake Front Home @ Venetian Bay Villages Kissimmee Close to DisneyWorld And Universal Parks 4 Swimming Pools, Gym & Games Room Great Location in the Heart of Orlando Ideal for Couples & Families.

    From £512 per week
  • Villa in Indian Ridge, Florida: South Facing Screened Pool
    4 bedroom villa • Sleeps 8

    Indian Ridge holiday villa rental with private pool

    Luxury 4 bedroom villa with south facing private pool, just 5 minutes from Walt Disney World

    From £549 per week
    (1)
  • Villa in High Grove, Florida: 26ft Pool and Spa
    4 bedroom villa • Sleeps 10

    Villa with private pool in Kissimmee, Florida

    Luxury 4 bed/3 bath villa, private pool and spa,games room & FREE broadband & national phone calls. Gated community+club house. Junction of 192/Highway 27, 10 mins. Disney.

    From £554 per week
    (5)
  • Villa in Venetian Bay, Florida
    3 bedroom villa • Sleeps 8

    Villa rental in Kissimmee, Florida, with shared pool

    Luxurious Villa/Townhome in Venetian Bay Villages sleeping 8 and just a few minutes from Walt Disney World, Sea World and Universal Studios !

    From £572 per week
    (1)
  • Villa in Kissimmee, Florida
    4 bedroom villa • Sleeps 10

    Villa with swimming pool in Kissimmee, Florida

    This 4 bedroom villa with shared pool is located in Kissimmee and sleeps 10 people. It has WiFi, parking nearby and air conditioning.

    From £573 per week
  • Villa in Kissimmee, Florida
    4 bedroom villa • Sleeps 8

    Villa with swimming pool in Kissimmee, Florida

    This 4 bedroom villa with shared pool is located in Kissimmee and sleeps 8 people. It has WiFi, parking nearby and air conditioning.

    From £573 per week
  • Villa in Cumbrian Lakes, Florida: Front Elevation
    4 bedroom villa • Sleeps 8

    Villa to rent in Kissimmee, Florida

    Gorgeous villa, private swimming pool, a private corner plot garden and a patio area. Ample private parking, smashing surrounds! Fantastic!

    From £575 per week
    (10)

Reviews of our villas in Kissimmee

We have 326 reviews of our villas in Kissimmee.

Explore Kissimmee holiday lettings

Villa rentals

Prices and Availability for villas in Kissimmee

Cheapest monthSeptember 2021 average weekly price £1,68540% of villas are available
High seasonDecember 2021 average weekly price £2,30536% of villas are available
Most popular destinationEmerald IslandAverage weekly price £2,020
Cheapest destinationSunset LakesAverage weekly price £992

All data is for the next 12 months and all the prices are the average weekly cost (Saturday - Saturday).

Price information for villas in Kissimmee (2021 - 2022)

£0£2,850£2,137£1,425£712AprilMayJuneJulyAugustSeptemberOctoberNovemberDecemberJanuaryFebruaryMarch
Average weekly price

Average weekly prices for villas in Kissimmee

The prices graph for villas in Kissimmee shows you the average weekly price for one of our villas over the next twelve months. December and February are the most expensive months to rent a villa in Kissimmee where the average price is £2,305 in December and £2,226 in February. The cheapest month to rent a villa is in September where the average weekly price is £1,657 (18/09 - 25/09). The average price of a villa in Kissimmee varies considerably between regions, distance from the nearest beach and the size of the villa. See the graph for average weekly prices for our top destinations in Kissimmee below.

Availability for villas in Kissimmee (2021 - 2022)

0%100%75%50%25%AprilMayJuneJulyAugustSeptemberOctoberNovemberDecemberJanuaryFebruaryMarch
Average available villas

Weekly availability for villas in Kissimmee

The graph above shows the availability of our villa holiday rentals in Kissimmee over the next twelve months. April (10/04 - 17/04) is the busiest time to rent a villa in Kissimmee where only 178 of our villas are available to book. The quietest time to visit Kissimmee at the moment is in December (04/12 - 11/12) where 48% of our villas have availability.

Prices for top villa destinations in Kissimmee (2021 - 2022)

£0£2,020£1,515£1,010£505EmeraldIslandIndianCreekLakeBerkleyLindfieldsSunsetLakesWindsorHills
Average weekly price for destination

Average weekly prices for top destinations in Kissimmee

This graph shows the average weekly prices for villas in our most popular destinations in Kissimmee. Our cheapest popular destination to rent a villa in Kissimmee is in Sunset Lakes where the average weekly rental price is £992. In comparison, Emerald Island costs an average of £2,020 per week and Windsor Hills £1,864 per week.

Travel guide

Villas in Kissimmee

Just south of Orlando, Kissimmee is one of the most popular areas to stay due to its many surrounding activities and proximity to the theme parks. Right in the middle of all the excitement, Kissimmee offers lots of attractive villa options that are perfect for families and groups.

The city is also home to several golf courses and nature parks including Kissimmee Lakefront Park: a great place to walk around the lake, take a relaxing bike ride or enjoy a boat trip to see the local wildlife, head here for breathtaking sunsets. Other lovely nature areas to visit in Kissimmee are Shingle Creek Regional Park and The Disney Wilderness Preserve.

Full of entertainment, Kissimmee is crammed with family activities such as mini golf, ice skating, swamp airboat tours, dinner theatre, petting farms, zip wires plus a variety of restaurants and bars to choose from.

Discover Kissimmee

Take a look at our blog posts about where to go in Kissimmee and what to do on your holiday in Kissimmee.