Villas in Kissimmee

Rent a villa in Kissimmee and get the most out of your holiday. Browse over 120 villas and narrow down your search by filtering on the number of bedrooms, bathrooms and other facilities

Our 10 best villas in Kissimmee

Rent a great villa in Kissimmee for a wonderful holiday.
  • Villa in Eagle Pointe, Florida
    3 bedroom villa • Sleeps 6

    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

    From £711 per week
    (44)
  • 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 £679 per week
    (35)
  • 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 £1,737 per week
    (63)
  • Villa in Emerald, Florida: Felicitys Villa
    6 bedroom villa • Sleeps 14

    Villa with private pool in Kissimmee, Florida

    Home from home villa situated in the Emerald Island gated resort in Kissimmee. Private pool and games room. Full use of the club house amenities. Minutes from Disney main gate.

    From £1,338 per week
    (30)
  • 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 £890 per week
    (26)
  • Villa in Emerald, Florida
    7 bedroom villa • Sleeps 14

    Emerald villa to rent

    Disney World, Orlando, Kissimmee, Four Corners, Emerald Islands, Margaritaville

    From £1,299 per week
    (1)
  • Villa in Emerald, Florida: South facing private pool with outstanding lake and conservation view
    7 bedroom villa • Sleeps 20

    Holiday villa 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.

    From £1,275 per week
  • 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.

    From £784 per week
    (13)
  • Villa in Emerald, Florida
    8 bedroom villa • Sleeps 12

    Villa to rent in Kissimmee, Florida

    Emerald Island Safari 8 Bedroom with gameroom with AC and More

    From £1,002 per week
  • 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 £523 per week
    (9)

Villas in Kissimmee with private pools

Enjoy the space and privacy of a villa with a private pool.
  • Villa in Windsor Palms, Florida
    4 bedroom villa • Sleeps 8

    Holiday villa in Kissimmee, Florida, with private pool

    Immaculate 4 bedrooms 3 bathroom is exceptional for your next vacation. The entrance invites you through an open floor plan through the family room/dining room combo leading to the spacious kitchen.

    Private pool
    From £1,127 per week
    (1)
  • Villa in Indian Creek, Florida
    5 bedroom villa • Sleeps 10

    Holiday villa in Kissimmee, Florida, with private pool

    5 Bedroom/4 bathroom villa with pool and spa. Two themed children's bedrooms and a games room with pool table and football table. Close to Disney, shopping, bars and dining.

    Heated private pool
    10m x 3m and 1m to 2m deep
    From £1,024 per week
    (3)
  • Villa in Emerald, Florida
    4 bedroom villa • Sleeps 8

    Villa rental in Kissimmee, Florida, with private pool

    Enjoy a magical vacation at the elegant Emerald Island Resort. This new luxurious private holiday villa includes a custom-built pool with Jacuzzi/spa directly across from a public children playground.

    Private pool
    From £890 per week
  • Villa in Sunset Lakes, Florida
    4 bedroom villa • Sleeps 8

    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 £1,097 per week
    (5)
  • Villa in Emerald, Florida
    7 bedroom villa • Sleeps 13

    Emerald holiday villa rental with private pool

    South Facing pool and hot tub Spa.Huge 3900 sq ft of living and playing space.7 Bed 5.5 bath Disney in 10 minutes.

    Heated private pool
    10m x 5m and 0.1m to 1.8m deep
    From £1,000 per week
    (1)
  • Villa in Emerald, Florida
    6 bedroom villa • Sleeps 13

    Holiday villa in Kissimmee, Florida, with private pool

    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 £1,334 per week
  • Villa in Windsor Palms, Florida
    6 bedroom villa • Sleeps 12

    Windsor Palms holiday villa rental with private pool

    Windsor Palms is located in the Formosa Gardens area, minutes from Margaritaville close to Disney and is one of the premier vacation spots in the Orlando area.

    Heated private pool
    From £1,127 per week
  • Villa in Lake Berkley, Florida
    7 bedroom villa • Sleeps 14

    Villa to rent in Kissimmee, Florida

    7 Bed Lakefront DISNEY THEME VILLA - Private Pool/Spa/Gameroom on Gated and Guarded Resort Near all Parks. TVs all bedrooms, 5 King Beds 2 sets Disney Twin Rooms. Stunning views -Fast Internet.

    Heated private pool
    1m to 1.8m deep
    From £1,364 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!

    Private pool
    From £679 per week
    (14)
  • 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 £1,483 per week

Cheap villas in Kissimmee

Rent one of our cheapest villas in Kissimmee for a low cost holiday.
  • Villa in Kissimmee, Florida
    3 bedroom villa • Sleeps 6

    Kissimmee holiday villa rental with shared pool

    This 3 bedroom villa with shared pool is located in Four Corners and sleeps 6 people. It has a garden, parking nearby and air conditioning.

    From £461 per week
  • Villa in Kissimmee, Florida
    3 bedroom villa • Sleeps 6

    Kissimmee villa to rent

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

    From £618 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 £622 per week
    (1)
  • Villa in Kissimmee, Florida
    2 bedroom villa • Sleeps 6

    Villa in Kissimmee, Florida

    This 2 bedroom villa is located in Four Corners and sleeps 6 people. It has parking nearby and air conditioning.

    From £626 per week
  • Villa in Lakeside, Florida
    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 30 minutes from Disney.

    From £695 per week
    (16)
  • Villa in Kissimmee, Florida
    4 bedroom villa • Sleeps 8

    Kissimmee villa to rent

    This 4 bedroom villa with private pool is located in Kissimmee and sleeps 8 people. It has barbeque facilities and air conditioning.

    From £705 per week
  • Villa in Kissimmee, Florida
    3 bedroom villa • Sleeps 6

    Villa rental in Kissimmee, Florida, with private pool

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

    From £711 per week
  • Villa in Kissimmee, Florida
    4 bedroom villa • Sleeps 8

    Kissimmee villa to rent

    This 4 bedroom villa with private pool is located in Four Corners and sleeps 8 people. It has parking nearby and air conditioning.

    From £725 per week
  • Villa in Kissimmee, Florida
    4 bedroom villa • Sleeps 8

    Villa rental in Kissimmee, Florida, with private pool

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

    From £725 per week
  • Villa in Indian Creek, Florida: Minnie Heaven
    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.

    From £730 per week
    (5)

Explore Kissimmee holiday lettings

Villa rentals

Prices and Availability for villas in Kissimmee

Cheapest monthNovember 2024 average weekly price £1,65548% of villas are available
High seasonMarch 2024 average weekly price £2,22931% of villas are available
Most popular destinationWindsor HillsAverage weekly price £2,342
Cheapest destinationIndian RidgeAverage weekly price £726

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 (2024)

£0£2,445£1,834£1,223£611DecemberJanuaryFebruaryMarchAprilMayJuneJulyAugustSeptemberOctoberNovember
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. March and July are the most expensive months to rent a villa in Kissimmee where the average price is £2,229 in March and £2,186 in July. The cheapest month to rent a villa is in December where the average weekly price is £1,493 (02/12 - 09/12). 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 (2024)

0%100%75%50%25%DecemberJanuaryFebruaryMarchAprilMayJuneJulyAugustSeptemberOctoberNovember
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. December (23/12 - 30/12) is the busiest time to rent a villa in Kissimmee where only 118 of our villas are available to book. The quietest time to visit Kissimmee at the moment is in November (23/11 - 30/11) where 89% of our villas have availability.

Prices for top villa destinations in Kissimmee (2024)

£0£2,342£1,756£1,171£585EmeraldIslandIndianCreekIndianRidgeLakeBerkleySunsetLakesWindsorHills
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 Indian Ridge where the average weekly rental price is £726. In comparison, Windsor Hills costs an average of £2,342 per week and Emerald Island £1,920 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.