Villas in Kissimmee
Rent your perfect holiday villa: choose from over 90 villas in Kissimmee including villas with private pools and cheap villas
Our best villas in Kissimmee
Check out our best villas in Kissimmee.
Premium owner
Villa to rent in Kissimmee, Florida
★★★★★(48)
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
★★★★★(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 £848 per week
Premium owner
Villa rental in Kissimmee, Florida, with private pool
★★★★★(2)
7 bedroom villa • Sleeps 14
Disney World, Orlando, Kissimmee, Four Corners, Emerald Islands, Margaritaville
From £1,239 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
Cumbrian Lakes holiday villa rental with private pool
★★★★★(43)
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 £732 per week
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
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 £1,216 per week
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.
From £784 per week
Villas in Kissimmee with private pools
Enjoy the space and privacy of a villa with a private pool.
Windsor Hills holiday villa rental with private pool
★★★★★(2)
5 bedroom villa • Sleeps 10
Windsor Hills Resort- Minutes to Clubhouse
Heated private pool
From £1,131 per week
Villa rental in Kissimmee, Florida, with private pool
★★★★★(20)
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.
Heated private pool
From £790 per week
Villa with private pool in Kissimmee, Florida
★★★★★(2)
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 £1,075 per week
Villa rental in Kissimmee, Florida, with private pool
★★★★★(3)
4 bedroom villa • Sleeps 8
Beautiful 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 £860 per week
Villa rental 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 £1,075 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 £1,125 per week
Reunion holiday villa rental 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!!!!!!
Heated private pool
From £848 per week
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 £1,414 per week
Cheap villas in Kissimmee
Rent one of our cheapest villas in Kissimmee for a low cost holiday.
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 £669 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
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 £760 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 £801 per week
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 £843 per week
Holiday villa in Kissimmee, Florida, with private pool
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 £848 per week
Villa rental in Kissimmee, Florida, with private pool
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.
From £848 per week
Villa to rent in Kissimmee, Florida
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 £868 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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Owners have the lowest prices on Clickstay
Prices and Availability
Cheapest month: September 2025 average weekly price £1,45773% of villas are available
High season: December 2025 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 2025 - 2026
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 2025 - 2026
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 2025 - 2026
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!
