Villas in Kissimmee

Rent a villa in Kissimmee and get the most out of your holiday. Browse over 100 villas and narrow down your search by filtering on the number of bedrooms, bathrooms and other facilities

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Lowest price pledge

Owners have the lowest prices on Clickstay

Clickstay logo
5%*
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14 - 18%
Booking dot com logo
15 - 25%
Vrbo logo
15%
*5% paid by the owner.

Our 10 best villas in Kissimmee

Rent a great villa in Kissimmee for a wonderful holiday.
  • Villa in Emerald, Florida
    Premium owner

    Villa with private pool in Kissimmee, Florida

    (26)
    4 bedroom villa • Sleeps 8

    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
  • Villa in Emerald, Florida
    Premium owner

    Villa to rent in Kissimmee, Florida

    (1)
    7 bedroom villa • Sleeps 14

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

    From £1,240 per week
  • Villa in Reunion, Florida
    Premium owner

    Villa rental in Kissimmee, Florida, with private pool

    7 bedroom villa • Sleeps 18

    Experience all the magic at this fully decorated themed Villa. This 7 bedroom 7 bath (plus game room) home has been designer decorated and includes themed rooms. Located just 6 miles from Disney!!!!!!

    Lowest price pledge
    From £1,186 per week
  • Villa in Eagle Pointe, Florida

    Villa to rent in Kissimmee, Florida

    (45)
    3 bedroom villa • Sleeps 6

    «««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
  • Villa in Cumbrian Lakes, Florida

    Cumbrian Lakes holiday villa rental with private pool

    (40)
    4 bedroom villa • Sleeps 8

    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
  • Villa in Windsor Hills, Florida: Windsor Hills Retreat

    Windsor Hills villa to rent

    (64)
    6 bedroom villa • Sleeps 12

    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.

    Lowest price pledge
    From £1,694 per week
  • Villa in Emerald, Florida: Felicitys Villa

    Villa with private pool in Kissimmee, Florida

    (31)
    6 bedroom villa • Sleeps 14

    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
  • Villa in Indian Creek, Florida

    Holiday villa in Kissimmee, Florida, with private pool

    (3)
    5 bedroom villa • Sleeps 10

    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.

    From £1,024 per week
  • Villa in Emerald, Florida: South facing private pool with outstanding lake and conservation view

    Holiday villa in Kissimmee, Florida, with private pool

    7 bedroom villa • Sleeps 20

    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 Lakeside, Florida

    Villa rental in Kissimmee, Florida, with private pool

    (17)
    4 bedroom villa • Sleeps 9

    Luxurious holiday home, which sleeps 9, situated in quiet lakeside residential area, 15 minutes from Orlando Airport and only 30 minutes from Disney.

    From £790 per week

Villas in Kissimmee with private pools

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

    Holiday villa in Kissimmee, Florida, with private pool

    (2)
    4 bedroom villa • Sleeps 8

    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
  • Villa in Windsor Palms, Florida

    Villa with private pool in Kissimmee, Florida

    (1)
    6 bedroom villa • Sleeps 12

    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 Emerald, Florida

    Emerald holiday villa rental with private pool

    (1)
    7 bedroom villa • Sleeps 10

    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
  • Villa in Lake Berkley, Florida

    Villa to rent in Kissimmee, Florida

    7 bedroom villa • Sleeps 14

    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 £1,305 per week
  • Villa in Emerald, Florida

    Villa to rent in Kissimmee, Florida

    4 bedroom villa • Sleeps 8

    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 Rolling Hills, Florida: View over lanai to pool and lake beyond

    Villa with private pool in Kissimmee, Florida

    (13)
    4 bedroom villa • Sleeps 8

    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
  • Villa in Windsor Hills, Florida

    Holiday villa in Kissimmee, Florida, with private pool

    (1)
    5 bedroom villa • Sleeps 10

    Windsor Hills Resort- Minutes to Clubhouse

    Heated private pool
    Lowest price pledge
    From £1,271 per week
  • Villa in Oak, Florida

    Villa rental in Kissimmee, Florida, with private pool

    (2)
    4 bedroom villa • Sleeps 8

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

    Heated private pool: 0.4m to 2m deep
    From £842 per week
  • Villa in Emerald, Florida

    Emerald villa to rent

    6 bedroom villa • Sleeps 13

    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
    Lowest price pledge
    From £1,334 per week
  • Villa in Indian Creek, Florida

    Villa with private pool in Kissimmee, Florida

    (32)
    5 bedroom villa • Sleeps 10

    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 £1,483 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

    Holiday villa in Kissimmee, Florida, with shared pool

    (9)
    3 bedroom villa • Sleeps 6

    A large 1500+ sq ft property with 3 bedrooms, 2 bathrooms less than 5 miles from Disney. Set in a quiet, gated, speed restricted, lakeside community.

    From £523 per week
  • Villa in Kissimmee, Florida

    Kissimmee villa to rent

    3 bedroom villa • Sleeps 6

    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

    Indian Ridge holiday villa rental with private pool

    (1)
    4 bedroom villa • Sleeps 8

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

    From £674 per week
  • Villa in Indian Creek, Florida

    Villa rental in Kissimmee, Florida, with private pool

    (3)
    5 bedroom villa • Sleeps 10

    Beautifully Decorated 5 bedroom, 4 bath home just 3.5 miles from the Maingate to Walt Disney World with hi-speed internet access.

    From £797 per week
  • Villa in Kissimmee, Florida

    Villa rental in Kissimmee, Florida, with swimming pool

    4 bedroom villa • Sleeps 8

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

    From £853 per week
  • Villa in Kissimmee, Florida

    Villa rental in Kissimmee, Florida, with private pool

    3 bedroom villa • Sleeps 6

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

    From £861 per week
  • Villa in Indian Creek, Florida: Minnie Heaven

    Holiday villa in Kissimmee, Florida, with private pool

    (5)
    4 bedroom villa • Sleeps 10

    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 £884 per week
  • Villa in Cumbrian Lakes, Florida: Front Elevation

    Villa to rent in Kissimmee, Florida

    (14)
    4 bedroom villa • Sleeps 8

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

    From £888 per week
  • Villa in Lake Berkley, Florida

    Villa with private pool in Kissimmee, Florida

    4 bedroom villa • Sleeps 8

    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.

    From £890 per week
  • Villa in Kissimmee, Florida

    Villa with shared pool in Kissimmee, Florida

    5 bedroom villa • Sleeps 10

    This 5 bedroom villa with shared pool is located in Kissimmee and sleeps 10 people. It has parking nearby and air conditioning.

    From £900 per week

Explore Kissimmee holiday lettings

Villa rentals

Prices and Availability for villas in Kissimmee

Cheapest monthSeptember 2024 average weekly price £1,75141% of villas are available
High seasonDecember 2024 average weekly price £2,86739% of villas are available
Most popular destinationWindsor HillsAverage weekly price £2,347
Cheapest destinationIndian RidgeAverage weekly price £782

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 - 2025)

£0£3,682£2,762£1,841£921JulyAugustSeptemberOctoberNovemberDecemberJanuaryFebruaryMarchAprilMayJune
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 March are the most expensive months to rent a villa in Kissimmee where the average price is £2,867 in December and £2,387 in March. The cheapest month to rent a villa is in June where the average weekly price is £1,662 (07/06 - 14/06). 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 - 2025)

0%100%75%50%25%JulyAugustSeptemberOctoberNovemberDecemberJanuaryFebruaryMarchAprilMayJune
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. July (20/07 - 27/07) is the busiest time to rent a villa in Kissimmee where only 97 of our villas are available to book. The quietest time to visit Kissimmee at the moment is in June (07/06 - 14/06) where 82% of our villas have availability.

Prices for top villa destinations in Kissimmee (2024 - 2025)

£0£2,347£1,760£1,173£587EmeraldIslandIndianCreekIndianRidgeLakeBerkleySunsetLakesWindsorHills
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 £782. In comparison, Windsor Hills costs an average of £2,347 per week and Emerald Island £1,954 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.