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

Rent a great villa in Kissimmee for a wonderful holiday.
  • 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 £1,414 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 £155 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 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

    From £376 per week
    (28)
  • Villa in Sunset Lakes, Florida
    4 bedroom villa • Sleeps 8

    Sunset Lakes villa to rent

    Sunset Lakes, 4 Bed, 3.5 Bath, Pool & Spa overlooking lake. Master Bedroom & Ensuite. Double room & Ensuite. Two Twins (one themed). Seperate Bathroom. Lounge. Dining Area. Wi-Fi & Cable. A/C. Garage.

    From £888 per week
  • 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.

    From £1,070 per week
    (32)
  • 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
    (7)
  • Villa in Emerald, Florida
    6 bedroom villa • Sleeps 13

    Villa rental 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!

    From £776 per week
  • 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 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 £694 per week
    (2)

Villas in Kissimmee with private pools

Enjoy the space and privacy of a villa with a private pool.
  • 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 Reunion, Florida
    7 bedroom villa • Sleeps 14

    Villa rental in Kissimmee, Florida, with private pool

    Situated a short drive away from Disney, this impressive 7-bedroom, 7.5-bathroom mansion has enough space to sleep up to 14 guests.

    Heated private pool
    From £2,110 per week
  • Villa in Emerald, Florida
    7 bedroom villa • Sleeps 14

    Villa rental in Kissimmee, Florida, with private pool

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

    Heated private pool
    From £1,118 per week
  • 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 £1,337 per week
  • Villa in Emerald, Florida
    4 bedroom villa • Sleeps 8

    Villa with private pool in Kissimmee, Florida

    2 Master Suites! This fantastic 4 bedroom, 3 bath Vacation Villa offers all of the conveniences of home and everything you need for a fun family vacation.

    Heated private pool
    From £877 per week
  • Villa in Lake Berkley, Florida
    4 bedroom villa • Sleeps 8

    Villa rental in Kissimmee, Florida, with private pool

    A stunning, larger than average 4 Bed 3 Bathroom villa that had a major refurbishment in 2018

    Heated private pool
    From £808 per week
  • 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 £1,579 per week
  • 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.

    Heated private pool
    7.5m x 4.3m and 1m to 1.4m deep
    From £792 per week
    (9)
  • Villa in Lake Berkley, Florida
    4 bedroom villa • Sleeps 8

    Villa with private pool in Kissimmee, Florida

    This stunning 4 Bed Villa is located in a peaceful corner of Lake Berkley Resort with beautiful views to the Conservation Area and one on the lakes at Lake Berkley, as well as your own swimming pool.

    Private pool
    From £738 per week
  • Villa in Lake Berkley, Florida
    4 bedroom villa • Sleeps 8

    Lake Berkley villa to rent

    Luxury villa right on lake edge. Free fishing on 3 lakes. Gated Resort. Our 4 Bed, 2 Bath villa is furnished to a very high standard and benefits from a perfect lake view position.

    Private pool
    From £808 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 £486 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 £486 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 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.

    From £517 per week
    (15)
  • 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 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)
  • Villa in Venetian Bay, Florida
    3 bedroom villa • Sleeps 8

    Holiday villa 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 £583 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 £584 per week
  • Villa in Kissimmee, Florida
    4 bedroom villa • Sleeps 8

    Kissimmee villa to rent

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

    From £603 per week

Explore Kissimmee holiday lettings

Villa rentals

Prices and Availability for villas in Kissimmee

Cheapest monthSeptember 2022 average weekly price £1,73929% of villas are available
High seasonJuly 2022 average weekly price £2,55342% of villas are available
Most popular destinationWindsor HillsAverage weekly price £2,214
Cheapest destinationIndian RidgeAverage weekly price £659

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£3,092£2,319£1,546£773SeptemberOctoberNovemberDecemberJanuaryFebruaryMarchAprilMayJuneJulyAugust
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. July and December are the most expensive months to rent a villa in Kissimmee where the average price is £2,553 in July and £2,495 in December. The cheapest month to rent a villa is in September where the average weekly price is £1,730 (11/09 - 18/09). 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%SeptemberOctoberNovemberDecemberJanuaryFebruaryMarchAprilMayJuneJulyAugust
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. February (26/02 - 05/03) is the busiest time to rent a villa in Kissimmee where only 152 of our villas are available to book. The quietest time to visit Kissimmee at the moment is in June (18/06 - 25/06) where 45% of our villas have availability.

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

£0£2,214£1,661£1,107£554EmeraldIslandIndianCreekIndianRidgeLakeBerkleySunsetLakesWindsorHills
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 £659. In comparison, Windsor Hills costs an average of £2,214 per week and Emerald Island £2,054 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.