Villas in Kissimmee

Book a villa in Kissimmee for a relaxing holiday: we have over 120 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 £1,737 per week
    (60)
  • 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
    (32)
  • Villa in Buenaventura Lakes, Florida
    4 bedroom villa • Sleeps 8

    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 £799 per week
    (5)
  • 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
    (37)
  • 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
    (9)
  • 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
    (25)
  • 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

    From £1,358 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 £512 per week
    (7)
  • Villa in Windsor Palms, Florida
    4 bedroom villa • Sleeps 8

    Windsor Palms holiday villa rental with private pool

    This is an exceptional vacation home in the much sought after Windsor Palms Resort. Come stay at this beautifully appointed 4 bedroom, 3 bath luxury home in the 24/7 Gated w/guard Windsor Palms Resort

    From £949 per week
    (1)
  • Villa in Emerald, Florida
    8 bedroom villa • Sleeps 14

    Villa rental in Kissimmee, Florida, with private pool

    Emerald Island Safari 8 Bedroom with gameroom with AC and More

    From £1,868 per week

Villas in Kissimmee with private pools

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

    Lake Berkley villa to rent

    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 £890 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 £1,008 per week
  • Villa in Lake Berkley, Florida
    7 bedroom villa • Sleeps 14

    Villa to rent in Kissimmee, Florida

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

    Heated private pool
    1m to 1.8m deep
    From £1,750 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 £1,483 per week
  • Villa in Windsor Palms, Florida
    6 bedroom villa • Sleeps 12

    Holiday villa in Kissimmee, Florida, 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 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.

    Heated private pool
    From £1,751 per week
  • Villa in Sunset Lakes, Florida: Pool terrace has shrubs to both sides for privacy
    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!

    Heated private pool
    27m x 12m and 2m to 1.8m deep
    From £836 per week
    (16)
  • Villa in Emerald, Florida
    4 bedroom villa • Sleeps 8

    Villa rental in Kissimmee, Florida, with private pool

    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 £1,186 per week
  • Villa in Emerald, Florida
    4 bedroom villa • Sleeps 8

    Emerald villa to rent

    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 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.

    Heated private pool
    8m x 3m and 1m to 1.8m deep
    From £1,338 per week
    (27)

Cheap villas in Kissimmee

Rent one of our cheapest villas in Kissimmee for a low cost holiday.
  • 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 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 £639 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 Kissimmee and sleeps 8 people. It has barbeque facilities and air conditioning.

    From £646 per week
  • Villa in Kissimmee, Florida
    4 bedroom villa • Sleeps 11

    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 £675 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 30 minutes from Disney.

    From £695 per week
    (15)
  • 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 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)
  • Villa in Kissimmee, Florida
    4 bedroom villa • Sleeps 12

    Villa with swimming pool in Kissimmee, Florida

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

    From £737 per week
  • 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 £743 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 £743 per week

Explore Kissimmee holiday lettings

Villa rentals

Prices and Availability for villas in Kissimmee

Cheapest monthOctober 2023 average weekly price £1,32662% of villas are available
High seasonDecember 2023 average weekly price £1,96051% of villas are available
Most popular destinationWindsor HillsAverage weekly price £2,343
Cheapest destinationIndian RidgeAverage weekly price £658

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 (2023 - 2024)

£0£2,550£1,912£1,275£637FebruaryMarchAprilMayJuneJulyAugustSeptemberOctoberNovemberDecemberJanuary
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 July are the most expensive months to rent a villa in Kissimmee where the average price is £1,960 in December and £1,935 in July. The cheapest month to rent a villa is in September where the average weekly price is £1,151 (16/09 - 23/09). 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 (2023 - 2024)

0%100%75%50%25%FebruaryMarchAprilMayJuneJulyAugustSeptemberOctoberNovemberDecemberJanuary
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 (18/02 - 25/02) is the busiest time to rent a villa in Kissimmee where only 108 of our villas are available to book. The quietest time to visit Kissimmee at the moment is in December (09/12 - 16/12) where 83% of our villas have availability.

Prices for top villa destinations in Kissimmee (2023 - 2024)

£0£2,343£1,757£1,172£586EmeraldIslandIndianCreekIndianRidgeLakeBerkleySunsetLakesWindsorHills
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 £658. In comparison, Windsor Hills costs an average of £2,343 per week and Emerald Island £1,950 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.