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
Our best villas in Kissimmee
Check out our best villas in Kissimmee.
Premium owner
Villa to rent in Kissimmee, Florida
★★★★★(52)
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
Premium owner
Villa with private pool in Kissimmee, Florida
★★★★★(28)
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 £797 per week
Premium owner
Emerald villa to rent
★★★★★(3)
7 bedroom villa • Sleeps 14
Disney World, Orlando, Kissimmee, Four Corners, Emerald Islands, Margaritaville
From £1,111 per week
Cumbrian Lakes holiday villa rental with private pool
★★★★★(49)
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 £752 per week
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
Holiday villa in Kissimmee, Florida, with private pool
★★★★★(1)
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 £1,143 per week
Villa rental in Kissimmee, Florida, with private pool
★★★★★(23)
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 £914 per week
Villa rental in Kissimmee, Florida, with private pool
★★★★★(4)
4 bedroom villa • Sleeps 8
Beautiful 4 bedroom villa with private south facing pool and conservation lake view, just 3 miles from Disney!!
From £755 per week
Villas in Kissimmee with private pools
Enjoy the space and privacy of a villa with a private pool.
Sunset Lakes villa to rent
★★★★★(9)
4 bedroom villa • Sleeps 8
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
Windsor Hills villa to rent
★★★★★(2)
5 bedroom villa • Sleeps 10
Windsor Hills Resort- Minutes to Clubhouse
Heated private pool
From £1,056 per week
Holiday villa in Kissimmee, Florida, with private pool
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
From £1,058 per week
Villa rental in Kissimmee, Florida, with private pool
★★★★★(4)
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 £1,010 per week
Villa rental in Kissimmee, Florida, with private pool
5 bedroom villa • Sleeps 10
Escape to serenity in our luxurious 5 bed 5 bath home offering stunning sunsets, privacy with no rear neighbors and an enchanting overlook of the beautiful surroundings at Windsor Hills Resort
Heated private pool
From £1,063 per week
Reunion villa to rent
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!!!!!!
Heated private pool
From £797 per week
Indian Ridge holiday villa rental with private pool
★★★★★(2)
4 bedroom villa • Sleeps 8
Luxury 4 bedroom villa with south facing private pool, just 5 minutes from Walt Disney World
Heated private pool: 1m to 1.8m deep
From £705 per week
Villa to rent in Kissimmee, Florida
6 bedroom villa • Sleeps 12
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 £1,595 per week
Cheap villas in Kissimmee
Rent one of our cheapest villas in Kissimmee for a low cost holiday.
Kissimmee villa to rent
3 bedroom villa • Sleeps 6
This 3 bedroom villa is located in Kissimmee and sleeps 6 people. It has barbeque facilities, parking nearby and an air conditioning.
From £518 per week
Holiday villa in Kissimmee, Florida, with private pool
★★★★★(6)
4 bedroom villa • Sleeps 8
newly furnished on prestigious emerald Island resort. Airconditioned throughout incl Games room. free internet ,national and internatinal calls. close to theme parks and ammenities.
From £615 per week
Kissimmee holiday villa rental
4 bedroom villa • Sleeps 8
This 4 bedroom villa is located in Kissimmee and sleeps 8 people. It has barbeque facilities, parking nearby and an air conditioning.
From £622 per week
Villa to rent in Kissimmee, Florida
4 bedroom villa • Sleeps 8
This 4 bedroom villa is located in Kissimmee and sleeps 8 people. It has a garden, parking nearby and an air conditioning.
From £657 per week
Holiday villa in Kissimmee, Florida, with shared pool
★★★★★(10)
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 £690 per week
Villa in Kissimmee, Florida
4 bedroom villa • Sleeps 9
This 4 bedroom villa is located in Kissimmee and sleeps 9 people. It has parking nearby and an air conditioning.
From £705 per week
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 £715 per week
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 an air conditioning.
From £753 per week
Explore Kissimmee holiday lettings
- Save £100's booking your holiday lettingClickstay is a low cost holiday home rental website offering direct bookings with owners. We don't charge service fees, making it unlikely for you to find a cheaper holiday property elsewhere.
- Price comparison made easyOur owners provide links to their listings on Airbnb, Booking.com and Vrbo - making it easy for you to compare prices. You should always find the lowest price on Clickstay.
- Easy communication with ownersHave direct contact with our owners by using our messaging system. We don't filter out messages between you and the owner.
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Over 3,000 verified reviews
Lowest price pledge
Owners have the lowest prices on Clickstay
Prices and Availability
Cheapest month: September 2026 average weekly price £1,45773% of villas are available
High season: December 2026 average weekly price £2,53876% of villas are available
Most popular destination: Windsor HillsAverage weekly price £2,324
Cheapest destination: Indian RidgeAverage weekly price £779
All data is for the next 12 months and all the prices are the average weekly cost (Saturday - Saturday).
Price information for villas, Kissimmee 2026 - 2027
Average weekly price
Average weekly prices
The prices graph shows you the average weekly price for one of our villas over the next twelve months. December and June are the most expensive months where the average weekly price is £2,538 in December and £2,104 in June. The cheapest month is March where the average weekly price is £1,060 (01/03 - 08/03). The average price varies considerably between regions, distance from the nearest beach and the size of the villa.Availability for villas, Kissimmee 2026 - 2027
Average available villas
Weekly availability
The graph above shows the availability over the next twelve months. March (01/03 - 08/03) is the busiest time where only 91 of our villas are available to book. The quietest time to visit is in December (06/12 - 13/12) where 84% of our villas have availability.Prices for popular destinations, Kissimmee 2026 - 2027
Average weekly price for destination
Average weekly prices
This graph shows the average weekly prices for villas in our most popular destinations in Kissimmee. Our cheapest popular destination is in Indian Ridge where the average weekly rental price is £779. In comparison, Windsor Hills costs an average of £2,324 per week and Emerald Island £1,862 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.
7 Best Bars In Kissimmee
You're there for a good time, not a long time. Why not go out in Kissimmee, Florida?
What To Do In Kissimmee For Free
Wondering what to do in Kissimmee for free? Well it turns out there's plenty of fun and fabulous things you can do with the family that won't cost you a penny!
Best Restaurants In Kissimmee
Where to eat like a local during your Kissimmee holiday.
Cheap Places To Stay In Kissimmee
Need a cheap holiday villa in Kissimmee? Here's 7 of the most popular that are fantastic value for money!
