Villas in Kissimmee
Book a villa in Kissimmee for a relaxing holiday: we have over 100 villas in Kissimmee for you to rent from cheap villas to luxurious villas with private pools
Our best villas in Kissimmee
Rent a great villa in Kissimmee for a wonderful holiday.
Premium owner
Sunchaser Villa On Eagle Pointe
★★★★★(54)
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 £680 per week
Premium owner
Skc Villa Close To Disney
★★★★★(29)
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 £788 per week
Premium owner
Margaritavilla At Emerald Islands
★★★★★(3)
7 bedroom villa • Sleeps 14
Disney World, Orlando, Kissimmee, Four Corners, Emerald Islands, Margaritaville
From £1,151 per week
Villa Serena At Cumbrian Lakes
★★★★★(52)
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 £725 per week
Dreams Come True Villa
★★★★★(3)
5 bedroom villa • Sleeps 10
Windsor Hills Resort- Minutes to Clubhouse
From £1,089 per week
Felicity's Villa Usd
★★★★★(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 £1,280 per week
Buenaventura Lakes Sector
★★★★★(25)
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 £875 per week
Paradise Castle Near Disney
★★★★★(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 £1,130 per week
Villas in Kissimmee with private pools
Enjoy the space and privacy of a villa with a private pool.
Encore Resort 6br/games/bbq Free/private Pool
★★★★★(1)
6 bedroom villa • Sleeps 12
Encore Resort 6BR/Games/BBQ free/Private Pool
Private pool
From £1,204 per week
Pri's Disney Villa In Emerald Island Resort
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 £951 per week
Lakeside Retreat
★★★★★(4)
4 bedroom villa • Sleeps 8
Beautiful 4 bedroom villa with private south facing pool and conservation lake view, just 3 miles from Disney!!
Heated private pool: 0.4m to 2m deep
From £710 per week
Magical Mickey Villa
★★★★★(1)
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 £1,089 per week
Rising Star At Sunset Lakes
★★★★★(10)
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 £1,050 per week
Flagstone Villa
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 £1,577 per week
Superb 4 Bed Villa With Lake View, Private Pool. (ref 04)
4 bedroom villa • Sleeps 8
Luxury villa right on lake edge. Free fishing on 3 lakes. Gated Resort. Our 4 Bed, 2 Bath villa is furnished to a very high standard and benefits from a perfect lake view position.
Private pool
From £920 per week
Mufasa's Pride - Tax Included (us $)
★★★★★(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.
Heated private pool: 1.2m to 2m deep
From £707 per week
Cheap villas in Kissimmee
Rent one of our cheapest villas in Kissimmee for a low cost holiday.
Relaxing 3br Haven For 8 At Seven Dwarfs
3 bedroom villa • Sleeps 6
This 3 bedroom villa is located in Kissimmee and sleeps 6 people. It has a garden, barbeque facilities and parking nearby.
From £526 per week
Smart Stay, 3br At Amazing Orlando Location
3 bedroom villa • Sleeps 8
This 3 bedroom villa with swimming pool is located in Kissimmee and sleeps 8 people. It has parking nearby and an air conditioning.
From £581 per week
Welcoming 4 Br Sleeps 10 Guests
4 bedroom villa • Sleeps 8
This 4 bedroom villa is located in Kissimmee and sleeps 8 people. It has a garden, barbeque facilities and parking nearby.
From £601 per week
Pet Friendly 4 Br With Hot Tub
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 £615 per week
4bd/3ba,renovated,executive Villa With Spa,must See,10 Min Disney
4 bedroom villa • Sleeps 8
Located in the quiet gated community of Cumbrian Lakes. Exclusive 4 bedrooms and 3 full bathrooms, including en-suite in the master bedroom. Can accommodate groups sleeping 8 guests. The master bed
From £934 per week
Remodeled Gem - Comfort And Location
4 bedroom villa • Sleeps 8
This 4 bedroom villa with swimming pool is located in Kissimmee and sleeps 8 people. It has a garden, parking nearby and an air conditioning.
From £649 per week
Beautiful 4br Home W/ Modern Design
4 bedroom villa • Sleeps 11
This 4 bedroom villa is located in Kissimmee and sleeps 11 people. It has a garden, parking nearby and an air conditioning.
From £649 per week
Savvy 4bed Stay Near Orlando Attractions
4 bedroom villa • Sleeps 10
This 4 bedroom villa with swimming pool is located in Kissimmee and sleeps 10 people. It has a garden, parking nearby and an air conditioning.
From £649 per week
Reviews
We have 418 reviews from past holidaymakers.
- Fiona★★★★★Family • from Kirkcaldy, United Kingdom • October 20265 bedroom Dreams Come True VillaWe had a great stay for 16 nights and would look to come back again and recommend to friends. Windsor Hills lovely area, great location and villa was beautiful.
- Richard★★★★★Family • from Leeds, United Kingdom • July 20264 bedroom Villa Serena At Cumbrian LakesVery spacious lovely villa. Had everything we needed to enjoy our holiday. The couple of issues we had were attended to straight away by the managing agent. We were very reluctant to leave at the end of our 2 week stay.
- David★★★★★Family • from Nelson, United Kingdom • June 20264 bedroom Villa Serena At Cumbrian LakesExcellent home. Quality furniture and furnishings. Lovely beds and bedding. All you need supplied. Nice quality and plenty outside pool furniture. Great location. Recommended.
- Stuart★★★★★Couple • from Belfast, United Kingdom • September 20263 bedroom Sunchaser Villa On Eagle PointeWe recently stayed for 2 weeks in September. The villa was modern, clean, well equipped and perfect for our stay. The pool area overlooking the pond was the highlight for us, watching the wildlife coming and going. The location was excellent, only a few minutes drive from the 192 with all of our favourite restaurants and a Walmart only a quick scoot down the road. Closeness to Disney was also fantastic. Having stayed in other areas before we definitely preferred Kissammee and wouldn't hesitate to return to this villa in future. Thanks for having us!
- Neil★★★★★Family • from Tunbridge Wells, United Kingdom • June 20264 bedroom Buenaventura Lakes SectorWe had a fantastic stay in this lovely villa, 30 min form the parks maximum, easy drive and good connections to the motorways etc. Great size property with a lovely pool area, was hopeful that there was Jacuzzi in the corner but it was a seated chill area, still really nice just no bubble lol. The area was very nice and quiet with no alligators that we noted in the lake (much to the lads disappointment!). Air con was perfect and all you need for a 2 week holiday was supplied and some bits and bobs left behind ie tea bags etc. and of course we obliged and left some non perishables too. It was a great trip and lovely place to unwind after a manic high itinerary theme park fest which was appreciated. Good comm's from the host also. this was a great place if you are looking to go to Florida and want a lake view, parks access and not to far form amenities ticking all the boxes after hours of research! Thanks Raymond.
- Chris★★★★★Family • from Seaham, United Kingdom • May 20266 bedroom Encore Resort 6br/games/bbq Free/private PoolFantastic property in an ideal location for all of the parks. Prompt response from Rodrigo when we had an issue with the air conditioning unit. Sorted within 24hrs.
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.
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Prices and Availability
Cheapest month: October 2027 average weekly price £96734% of villas are available
High season: December 2026 average weekly price £1,70231% of villas are available
Most popular destination: Windsor HillsAverage weekly price £1,698
Cheapest destination: Lake BerkleyAverage weekly price £1,027
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 April are the most expensive months where the average weekly price is £1,702 in December and £1,587 in April. The cheapest month is October where the average weekly price is £938 (03/10 - 10/10). 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. October (10/10 - 17/10) is the busiest time where 19% of our villas are available to book. The quietest time to visit is in September (25/09 - 02/10) where 89% 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 Lake Berkley where the average weekly rental price is £1,027. In comparison, Windsor Hills costs an average of £1,698 per week and Cumbrian Lakes £1,347 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.
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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.
