Villas in Kissimmee

Our 10 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 £876 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 £1,162 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
★★★★★(42)
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
Windsor Hills villa to rent
★★★★★(64)
6 bedroom villa • Sleeps 12
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.
Lowest price pledge
From £1,669 per week
Villa rental 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
Windsor Palms villa to rent
★★★★★(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.
From £1,110 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 £1,256 per week
Holiday villa 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.
From £1,110 per week

Villas in Kissimmee with private pools

Enjoy the space and privacy of a villa with a private pool.

Villa rental in Kissimmee, Florida, with private pool
★★★★★(19)
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
Windsor Hills villa to rent
★★★★★(2)
5 bedroom villa • Sleeps 10
Windsor Hills Resort- Minutes to Clubhouse
Heated private pool
Lowest price pledge
From £1,252 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.
Heated private pool
From £784 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
Lowest price pledge
From £888 per week
Emerald holiday villa rental with private pool
★★★★★(1)
7 bedroom villa • Sleeps 10
South Facing pool and hot tub Spa.Huge 3900 sq ft of living and playing space.7 Bed 5.5 bath Disney in 10 minutes.
Heated private pool: 10m x 5m and 0.1m to 1.8m deep
From £985 per week
Villa rental 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
Lowest price pledge
From £1,162 per week
Emerald holiday villa rental 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.
Private pool
From £876 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 £1,460 per week
Windsor Hills holiday villa rental 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
Lowest price pledge
From £1,314 per week
Sunset Lakes villa to rent
★★★★★(7)
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

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 with shared pool is located in Kissimmee and sleeps 6 people. It has parking nearby and an air conditioning.
From £636 per week
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 £653 per week
Villa rental in Kissimmee, Florida, with private pool
3 bedroom villa • Sleeps 6
This 3 bedroom villa with private pool is located in Kissimmee and sleeps 6 people. It has parking nearby and an air conditioning.
From £671 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 £674 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 £785 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 £828 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 £870 per week
Villa rental in Kissimmee, Florida, with swimming pool
4 bedroom villa • Sleeps 11
This 4 bedroom villa with swimming pool is located in Kissimmee and sleeps 11 people. It has parking nearby and an air conditioning.
From £873 per week
Villa with swimming pool in Kissimmee, Florida
4 bedroom villa • Sleeps 10
This 4 bedroom villa with swimming pool is located in Kissimmee and sleeps 10 people. It has parking nearby and an air conditioning.
From £873 per week
Villa with swimming pool in Kissimmee, Florida
4 bedroom villa • Sleeps 10
This 4 bedroom villa with swimming pool is located in Kissimmee and sleeps 10 people. It has parking nearby and an air conditioning.
From £873 per week

Prices and Availability for villas in Kissimmee

Cheapest month: September 2025 average weekly price £1,55079% of villas are available

High season: December 2025 average weekly price £2,37414% of villas are available

Most popular destination: Windsor HillsAverage weekly price £2,402

Cheapest destination: Indian RidgeAverage weekly price £783

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 (2025)

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 April are the most expensive months to rent a villa in Kissimmee where the average price is £2,374 in December and £2,201 in April. The cheapest month to rent a villa is in September where the average weekly price is £1,526 (20/09 - 27/09). 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 (2025)

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. December (28/12 - 04/01) is the busiest time to rent a villa in Kissimmee where only 86 of our villas are available to book. The quietest time to visit Kissimmee at the moment is in November (08/11 - 15/11) where 83% of our villas have availability.

Prices for top villa destinations in Kissimmee (2025)

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 £783. In comparison, Windsor Hills costs an average of £2,402 per week and Emerald Island £1,854 per week.

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.

Rated highly on Feefo

Lowest price pledge

Key holiday destinations in Kissimmee

Windsor Hills

Emerald Island

Lake Berkley

Our 10 best villas in Kissimmee

Villa to rent in Kissimmee, Florida

Villa with private pool in Kissimmee, Florida

Villa rental in Kissimmee, Florida, with private pool

Villa with private pool in Kissimmee, Florida

Cumbrian Lakes holiday villa rental with private pool

Windsor Hills villa to rent

Villa rental in Kissimmee, Florida, with private pool

Windsor Palms villa to rent

Holiday villa in Kissimmee, Florida, with private pool

Holiday villa in Kissimmee, Florida, with private pool