Kissimmee Villas

Kissimmee Villas

Listing Villas in:

#502  4 Bed / 3 Bath, Sleeps 8 - South Facing Private Pool - Games Room

Kissimmee Creekside
4 Bedrooms, sleeps 8
• 1 Ensuite, 2 Double and 1 Twin
• 2 Bathrooms
• Private Pool
• Barbecue
• Games Room
Villa Facilities & Amenities
Private Pool Ownership Verified Wi-Fi Internet Computer or Laptop Games Room Barbecue Grill Cot and Stroller Shops Nearby Restaurants Nearby Payment accepted in Sterling
Book this villa
From £129 per night

#472  Luxury 4 Bedroom Villa with Private Pool and Lake View

Kissimmee Eagle Pointe
4 Bedrooms, sleeps 8
• 1 Ensuite, 2 Double and 1 Twin
• 2 Bathrooms
• Private Pool
• Games Room
• Lake Views
Villa Facilities & Amenities
Private Pool Ownership Verified Wi-Fi Internet Games Room Cot and Stroller Shops Nearby Payment accepted in Sterling Payment accepted in US Dollars
Book this villa
From £123 / US$152 per night

#234  Attractive 3 Bed Vacation Home - '36ft' SOUTH facing Pool with Lake view.

Kissimmee Windward Cay
10 July 2026 - 18 September 2026 — FREE Welcome Pack
3 Bedrooms, sleeps 8
• 1 Ensuite, 1 Double and 1 Twin
• 2 Bathrooms
• Private Pool with Spa / Hot Tub
• Lake Views
Villa Facilities & Amenities
Private Pool Spa / Hot Tub Ownership Verified Wi-Fi Internet Cot and Stroller Shops Nearby Restaurants Nearby Payment accepted in Sterling
Book this villa
From £111 per night

#160  SOUTH FACING STUNNING LAKE VIEW EXECUTIVE VILLA ON A GATED COMMUNITY, KISSIMMEE

Kissimmee Lake Berkley Resort
16 April 2025 - 9 May 2026  ★  FREE Pool Heating  ★  LATE DEAL  ★
5 Bedrooms, sleeps 12
• 1 Ensuite, 3 Double and 1 Twin
• 3 Bathrooms
• Private Pool with Spa / Hot Tub
• Games Room
• Lake Views
• Community Clubhouse
Villa Facilities & Amenities
Private Pool Spa / Hot Tub Ownership Verified Wi-Fi Internet Games Room Cot and Stroller Shops Nearby Restaurants Nearby Community / Resort Pool Clubhouse Tennis / Sports Courts Gated Community Payment accepted in Sterling Payment accepted in US Dollars
Book this villa
From £185 / US$233 per night

#101  Shops, Bars, Outlets, Disney all within 5 mins - Very Private Pool Area

Kissimmee Indian Wells
11 - 21 April 2026  ★  Discount for 7 Nights or more  ★  LATE DEAL  ★
3 Bedrooms, sleeps 6
• 1 Ensuite, 1 Double and 1 Twin
• 2 Bathrooms
• Private Pool
• Barbecue
Villa Facilities & Amenities
Private Pool Ownership Verified Wi-Fi Internet Barbecue Grill Cot and Stroller Wheelchair Accessible Shops Nearby Restaurants Nearby Community / Resort Pool Tennis / Sports Courts Payment accepted in Sterling Payment accepted in US Dollars
Book this villa
From £106 / US$170 per night

#102  40ft Pool with Spa * Lakeside Views * Local Bars and Shops

Kissimmee Indian Wells
3 Bedrooms, sleeps 6
• 1 Ensuite, 1 Double and 1 Twin
• 2 Bathrooms
• Private Pool with Spa / Hot Tub
• Lake Views
Villa Facilities & Amenities
Private Pool Spa / Hot Tub Ownership Verified Wi-Fi Internet Cot and Stroller Wheelchair Accessible Shops Nearby Restaurants Nearby Community / Resort Pool Tennis / Sports Courts Payment accepted in Sterling Payment accepted in US Dollars
Book this villa
From £106 / US$170 per night

#191  Spacious Villa with Private Pool in Disney Area

Kissimmee Lake Berkley Resort
4 Bedrooms, sleeps 8
• 2 Ensuite, 1 Double and 1 Twin
• 3 Bathrooms
• Private Pool
• Games Room
• Community Clubhouse
Villa Facilities & Amenities
Private Pool Ownership Verified Wi-Fi Internet Games Room Shops Nearby Restaurants Nearby Community / Resort Pool Clubhouse Tennis / Sports Courts Gated Community Payment accepted in Sterling
Book this villa
From £115 per night

#321  Windward Cay 'Another Attractive 3 bed Villa with Large Pool Deck Area'.

Kissimmee Windward Cay
10 July 2026 - 10 September 2026 — FREE Welcome Pack
3 Bedrooms, sleeps 6
• 1 Ensuite, 1 Double and 1 Twin
• 2 Bathrooms
• Private Pool
Villa Facilities & Amenities
Private Pool Ownership Verified Wi-Fi Internet Cot and Stroller Shops Nearby Restaurants Nearby Payment accepted in Sterling
Book this villa
From £114 per night

#113  Splendid 3 Bed Villa On Windward Cay

Kissimmee Windward Cay
9 July 2026 - 9 September 2026 — FREE Welcome Pack
3 Bedrooms, sleeps 6
• 1 Ensuite, 1 Double and 1 Twin
• 2 Bathrooms
• Private Pool
Villa Facilities & Amenities
Private Pool Ownership Verified Wi-Fi Internet Cot and Stroller Shops Nearby Restaurants Nearby Payment accepted in Sterling
Book this villa
From £114 per night

#141  The Willows Villa at Cumbrian Lakes

Kissimmee Cumbrian Lakes
3 Bedrooms, sleeps 6
• 1 Ensuite, 1 Double and 1 Twin
• 2 Bathrooms
• Private Pool
• Games Room
Villa Facilities & Amenities
Private Pool Ownership Verified Wi-Fi Internet Games Room Shops Nearby Community / Resort Pool Gated Community Payment accepted in Sterling
Book this villa
From £114 per night

#186  Florida Lets A Dream! With WIFI

Kissimmee Windward Cay
3 Bedrooms, sleeps 8
• 1 Ensuite, 1 Double and 1 Twin
• 2 Bathrooms
• Private Pool
Villa Facilities & Amenities
Private Pool Ownership Verified Wi-Fi Internet Cot and Stroller Shops Nearby Restaurants Nearby Payment accepted in Sterling
Book this villa
From £111 per night

#482  4 bed villa with 'South' facing pool in Windward Cay & WIFI

Kissimmee Windward Cay
10 July 2026 - 1 September 2026 — School Holidays Deal
4 Bedrooms, sleeps 10
• 1 Ensuite, 1 Double and 2 Twin
• 2 Bathrooms
• Private Pool
Villa Facilities & Amenities
Private Pool Ownership Verified Wi-Fi Internet Cot and Stroller Shops Nearby Restaurants Nearby Payment accepted in Sterling
Book this villa
From £114 per night

#153  Beautiful Florida holiday home with private south facing pool & spa

Kissimmee The Hamlets
5 Bedrooms, sleeps 10
• 2 Ensuite, 1 Double and 2 Twin
• 3 Bathrooms
• Private Pool with Spa / Hot Tub
• Games Room
Villa Facilities & Amenities
Private Pool Spa / Hot Tub Ownership Verified Wi-Fi Internet Games Room Cot and Stroller Wheelchair Accessible Shops Nearby Restaurants Nearby Gated Community Payment accepted in Sterling Payment accepted in US Dollars
Book this villa
From £136 / US$207 per night

#440  Disney Lake View Villa 5 bedroom luxury modern Villa, Stunning lake views close to parks restaurants shopping free Wi-Fi

Kissimmee Lake Berkley Resort
5 Bedrooms, sleeps 10
• 1 Ensuite, 3 Double and 1 Twin
• 3 Bathrooms
• Private Pool with Spa / Hot Tub
• Barbecue
• Lake Views
• Community Clubhouse
Villa Facilities & Amenities
Private Pool Spa / Hot Tub Ownership Verified Wi-Fi Internet Barbecue Grill Wheelchair Accessible 360° Video Tour Shops Nearby Restaurants Nearby Community / Resort Pool Clubhouse Tennis / Sports Courts Gated Community Payment accepted in Sterling
Book this villa
From £221 per night

#144  BrightwaterVilla spacious lakeside home at beautiful gated / guarded Lake Berkley

Kissimmee Lake Berkley Resort
5 Bedrooms, sleeps 11
• 2 Ensuite, 1 Double and 2 Twin
• 4 Bathrooms
• Private Pool with Spa / Hot Tub
• Barbecue
• Games Room
• Lake Views
• Community Clubhouse
Villa Facilities & Amenities
Private Pool Spa / Hot Tub Ownership Verified Wi-Fi Internet Games Room Barbecue Grill Cot and Stroller Shops Nearby Restaurants Nearby Community / Resort Pool Clubhouse Tennis / Sports Courts Gated Community Payment accepted in Sterling Payment accepted in US Dollars
Book this villa
From £180 / US$249 per night

#137  Evansvilla luxury 4 Bed Villa with Private Pool/Spa

Kissimmee Terra Verde
4 Bedrooms, sleeps 10
• 2 Ensuite and 2 Twin
• 3 Bathrooms
• Private Pool with Spa / Hot Tub
• Games Room
• Community Clubhouse
Villa Facilities & Amenities
Private Pool Spa / Hot Tub Ownership Verified Wi-Fi Internet Games Room Cot and Stroller Wheelchair Accessible Shops Nearby Restaurants Nearby Community / Resort Pool Clubhouse Tennis / Sports Courts Gated Community Payment accepted in Sterling Payment accepted in US Dollars
Book this villa
From £100 / US$136 per night

#387  'Lakeside Haven' South Facing Pool, Spa and Stunning Lakeside Views

Kissimmee Windward Cay
3 Bedrooms, sleeps 6
• 1 Ensuite, 1 Double and 1 Twin
• 2 Bathrooms
• Private Pool with Spa / Hot Tub
• Barbecue
• Games Room
• Lake Views
Villa Facilities & Amenities
Private Pool Spa / Hot Tub Ownership Verified Wi-Fi Internet Games Room Barbecue Grill Cot and Stroller 360° Video Tour Shops Nearby Restaurants Nearby Payment accepted in Sterling
Book this villa
From £107 per night

#204  Resort Lifestyle with Private Villa Luxury

Kissimmee Terra Verde
4 Bedrooms, sleeps 10
• 2 Ensuite and 2 Twin
• 3 Bathrooms
• Private Pool
• Games Room
• Community Clubhouse
Villa Facilities & Amenities
Private Pool Ownership Verified Wi-Fi Internet Games Room Cot and Stroller Shops Nearby Restaurants Nearby Community / Resort Pool Clubhouse Tennis / Sports Courts Gated Community Payment accepted in Sterling Payment accepted in US Dollars
Book this villa
From £89 / US$121 per night

BOOKING A VILLA: Where you are flexible with your dates, check dates either side for potentially more villas and a better deal. Filter villas by the number of bedrooms you need and any preferences. Shortlist those villas which are ideal for your holiday, so that you can compare availability, location, amenities and price. Adding a villa to your shortlist will not contact the owners of a villa. For more information or to book a specific villa, simply enquire. You can send an enquiry to a specific villa owner, multiple villas and even to all villas to check availability. The villa owners will respond with the price for your dates and provide you more details about booking. You are under no obligation to book a villa which you enquire about.

If you have rented a Florida villa in the past five years then you will know prices have increased. Florida has seen above inflation price increases since re-opening after the US Travel Ban in 2021, which have resulted in villa owner costs increasing considerably. Such increases have seen many villas sold, so the demand for villas at peak periods now exceeds availability. However with no service fee to pay when booking through this website, you will not find the same villa cheaper on other websites. Private holiday villas still offer fantastic value and will work out cheaper than booking multiple hotel rooms. Not forgetting your private pool and privacy of your own bedroom.