Villas in Kissimmee

Book a villa in Kissimmee for a relaxing holiday: we have over 90 villas in Kissimmee for you to rent from cheap villas to luxurious villas with private pools

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 £1,541 per week
    (53)
  • 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 £627 per week
    (26)
  • 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 £156 per week
    (25)
  • 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
    (30)
  • 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.

    From £721 per week
    (5)
  • 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 £823 per week
    (9)
  • 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 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 Sunset Lakes, Florida
    4 bedroom villa • Sleeps 8

    Sunset Lakes holiday villa rental with private pool

    Luxury 4 bedroom, 3 bathroom villa, in quiet gated community, yet only 5 mins from Disney! Private screened south facing pool with stunning lake view!! Games room+AC..new TV /DVD combos all bedrooms!

    From £732 per week
    (13)
  • 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 £684 per week
    (4)

Villas in Kissimmee with private pools

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

    Holiday villa 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 £2,127 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 £1,078 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.

    Private pool
    From £664 per week
    (4)
  • Villa in Lake Berkley, Florida
    4 bedroom villa • Sleeps 8

    Holiday villa 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 £917 per week
  • Villa in Reunion, Florida
    10 bedroom villa • Sleeps 20

    Villa to rent in Kissimmee, Florida

    This modern masterpiece at Reunion is a 8,320 sq. ft., pool villa offering lavish views of the golf course. This home's modern custom-built design and endless space for up to 28 guests features 9 luxu

    Heated private pool
    57m x 25m and 1.8m deep
    From £10,382 per week
  • Villa in Cumbrian Lakes, Florida
    4 bedroom villa • Sleeps 8

    Cumbrian Lakes villa to rent

    This stunning Disney area pool vila offers your family comfortable and convenient accommodations that will make your next Florida vacation a memorable one.

    Private pool
    From £1,078 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.

    Heated private pool
    From £1,348 per week
    (32)
  • Villa in Emerald, Florida
    7 bedroom villa • Sleeps 14

    Emerald holiday villa rental with private pool

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

    Heated private pool
    From £1,127 per week
  • 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 Cumbrian Lakes, Florida: Front View
    10 bedroom villa • Sleeps 16

    Holiday villa in Kissimmee, Florida, with private pool

    This is a beautiful 7 bedrooms / 5 full and 2 half bathrooms. The home is perfectly located in the quiet gated community of Cumbrian Lakes. The home has a fabulous view of one of the lakes in the comm

    Heated private pool
    From £1,279 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 £460 per week
    (6)
  • 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 £490 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 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 £521 per week
  • Villa in Venetian Bay, Florida
    3 bedroom villa • Sleeps 8

    Venetian Bay holiday villa rental 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 £534 per week
    (1)
  • 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 Kissimmee, Florida
    4 bedroom villa • Sleeps 8

    Kissimmee holiday villa rental with swimming pool

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

    From £601 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 £608 per week
  • Villa in Kissimmee, Florida
    4 bedroom villa • Sleeps 12

    Kissimmee villa to rent

    This 4 bedroom villa with shared pool is located in Kissimmee and sleeps 12 people. It has WiFi, parking nearby and air conditioning.

    From £614 per week

Explore Kissimmee holiday lettings

Villa rentals

Prices and Availability for villas in Kissimmee

Cheapest monthJanuary 2023 average weekly price £1,45728% of villas are available
High seasonDecember 2022 average weekly price £2,15958% of villas are available
Most popular destinationWindsor HillsAverage weekly price £2,253
Cheapest destinationIndian RidgeAverage weekly price £654

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 (2022 - 2023)

£0£2,783£2,087£1,392£696JanuaryFebruaryMarchAprilMayJuneJulyAugustSeptemberOctoberNovemberDecember
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 £2,159 in December and £2,042 in March. The cheapest month to rent a villa is in January where the average weekly price is £1,207 (01/01 - 08/01). 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 (2022 - 2023)

0%100%75%50%25%JanuaryFebruaryMarchAprilMayJuneJulyAugustSeptemberOctoberNovemberDecember
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. January (01/01 - 08/01) is the busiest time to rent a villa in Kissimmee where only 119 of our villas are available to book. The quietest time to visit Kissimmee at the moment is in December (03/12 - 10/12) where 67% of our villas have availability.

Prices for top villa destinations in Kissimmee (2022 - 2023)

£0£2,253£1,689£1,126£563EmeraldIslandIndianCreekIndianRidgeLakeBerkleySunsetLakesWindsorHills
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 £654. In comparison, Windsor Hills costs an average of £2,253 per week and Emerald Island £2,166 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.