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.
Villa in Eagle Pointe, Florida
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
Villa in Emerald, Florida
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 £884 per week
Villa in Emerald, Florida
Premium owner

Villa with private pool in Kissimmee, Florida

(2)
7 bedroom villa • Sleeps 14

Disney World, Orlando, Kissimmee, Four Corners, Emerald Islands, Margaritaville

From £1,290 per week
Villa in Cumbrian Lakes, Florida

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
Villa in Emerald, Florida: Felicitys Villa

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
Villa in Indian Creek, Florida

Indian Creek holiday villa rental 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
Villa in Lakeside, Florida

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.

From £790 per week
Villa in Emerald, Florida: South facing private pool with outstanding lake and conservation view

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 £1,267 per week

Villas in Kissimmee with private pools

Enjoy the space and privacy of a villa with a private pool.
Villa in Windsor Palms, Florida

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 £1,119 per week
Villa in Rolling Hills, Florida: View over lanai to pool and lake beyond

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 in Windsor Palms, Florida

Windsor Palms holiday villa rental 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 £1,119 per week
Villa in Windsor Hills, Florida

Villa rental in Kissimmee, Florida, with private pool

(2)
5 bedroom villa • Sleeps 10

Windsor Hills Resort- Minutes to Clubhouse

Heated private pool
From £1,178 per week
Villa in Oak, Florida

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 £895 per week
Villa in Emerald, Florida

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 £993 per week
Villa in Emerald, Florida

Emerald holiday villa rental 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 £1,172 per week
Villa in Indian Creek, Florida

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 £1,473 per week

Cheap villas in Kissimmee

Rent one of our cheapest villas in Kissimmee for a low cost holiday.
Villa in Kissimmee, Florida

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 £642 per week
Villa in Vista Del Lago, Florida: Orlando Dreams your home from home

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 in Indian Ridge, Florida

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 in Kissimmee, Florida

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 £706 per week
Villa in Indian Creek, Florida

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 £792 per week
Villa in Kissimmee, Florida

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 £835 per week
Villa in Indian Creek, Florida: Minnie Heaven

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 £878 per week
Villa in Kissimmee, Florida

Kissimmee villa to rent

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 £881 per week

Explore Kissimmee holiday lettings

Villa rentals

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Owners have the lowest prices on Clickstay

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5%*
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*5% paid by the owner.

Prices and Availability

Cheapest monthSeptember 2025 average weekly price £1,52178% of villas are available
High seasonDecember 2025 average weekly price £2,45950% of villas are available
Most popular destinationWindsor HillsAverage weekly price £2,428
Cheapest destinationIndian 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, Kissimmee 2025 - 2026

£0£3,138£2,354£1,569£785JanuaryFebruaryMarchAprilMayJuneJulyAugustSeptemberOctoberNovemberDecember
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 £2,459 in December and £2,181 in April. The cheapest month is September where the average weekly price is £1,508 (20/09 - 27/09). The average price varies considerably between regions, distance from the nearest beach and the size of the villa.

Availability for villas, Kissimmee 2025 - 2026

0%100%75%50%25%JanuaryFebruaryMarchAprilMayJuneJulyAugustSeptemberOctoberNovemberDecember
Average available villas

Weekly availability

The graph above shows the availability over the next twelve months. January (18/01 - 25/01) is the busiest time where only 73 of our villas are available to book. The quietest time to visit is in December (06/12 - 13/12) where 89% of our villas have availability.

Prices for popular destinations, Kissimmee 2025 - 2026

£0£2,428£1,821£1,214£607EmeraldIslandIndianCreekIndianRidgeLakeBerkleySunsetLakesWindsorHills
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 £783. In comparison, Windsor Hills costs an average of £2,428 per week and Emerald Island £1,835 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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