Villas near to Chatham Park

Search for your perfect Florida holiday villa by availability, number of bedrooms, location and specific requirements. All villas are within a 30-minute drive of Walt Disney World Resort. Where you find suitable villas or want to compare villa amenities, location and price, simply Save to Shortlist.
Listing Villas in:
★ Communal pool and sports courts available
★ Straightforward route to Walt Disney World Resort, Seaworld and Premium Outlets via SR535
★ Straightforward route to Universal Studios via Interstate 4
★ Walmart and Publix supermarkets nearby on SR535
★ Varied selection of restaurants nearby on US192 and SR535
Where you have searched on specific dates and prices are available, then an estimated price for your dates will be shown. Where no dates are selected, then the lowest nightly rate will be shown. These prices are for renting the villa (not per person) and will include local Florida taxes but will exclude any discounts or optional extras e.g. pool heating.
Sort Villas:
Villas per Page:
Villas near to Chatham Park
These villas are located near to Chatham Park, so you will still have the same familiar local shops, restaurants and routes to the attractions.

#393  Luxury 3 bedroom, 2 bathroom villa with private south facing lakeside pool

3 Bedrooms, sleeps 6
• 2 Bathrooms
• Private Pool
• Wi-Fi
• Barbecue
• Lake Views
• Disney Springs 7.6 miles
Private Pool Wi-Fi Internet Barbecue Grill Wheelchair Accessible Shops Nearby Restaurants Nearby Payment accepted in Sterling
Book this villa
From £86 per night
Lakeside Dream is a luxury, very secluded villa with heated pool and large south facing deck area in a prime position on the charming and tranquil Windward Cay development. The villa is on a sizeable plot set back from the lake which is very private. It is a perfect short-term holiday home which is ideal for couples or for an average sized family with older children.

This spacious villa has a large open plan living/dining and kitchen area. It is fully air conditioned, there is a 24/7 monitored alarm system for your additional security and a safe to guard your valuables....

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

4 Bedrooms, sleeps 10
• 1 Ensuite, 1 Double and 2 Twin
• 2 Bathrooms
• Private Pool
• Wi-Fi
• Barbecue
• Games Room
• Disney Springs 7.6 miles
Private Pool Wi-Fi Internet Games Room Barbecue Grill Cot and Stroller Shops Nearby Restaurants Nearby Payment accepted in Sterling
Book this villa
From £78 per night
We are looking forward to welcoming you to our Villa...

Let us tell you about
Windward Cay and our 4 bed villa with South facing pool that can accommodate between 10 and 12 guest depending on how sleeping arrangements are made, allowing two familys to share a Florida vacation together..


The surounding area.
Windward Cay is located Just off the Highway 192 at Mile ‘Marker 14’ Windward Cay is nearby to all of the major Orlando attractions, Walt Disney World, Universal Studios to Sea World and so much more!

We are close to local Restaurants and Shopping...

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

3 Bedrooms, sleeps 6
• 1 Ensuite, 1 Double and 1 Twin
• 2 Bathrooms
• Private Pool with Spa / Hot Tub
• Wi-Fi
• Barbecue
• Games Room
• Lake Views
• Disney Springs 7.6 miles
Private Pool Spa / Hot Tub 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 £78 per night
Our homely and beautiful fully air conditioned private villa with fabulous lakeside views is located on a fantastic large plot in the beautiful and peaceful community of Windward Cay ’the hidden jewel of Kissimmee’ situated less than half a mile from the 192 with all the shops and restaurants you could wish for. With the excitement and thrill of the Disney Parks just seven miles away, Sea World only ten miles and Universal only thirteen miles the location could not be better. Free hi-speed internet and TV package.

Copy 28.308213, -81.472160 and search...

#234  Attractive 3Bed Vacation Home 36’ SOUTH facing Pool

3 Bedrooms, sleeps 8
• 1 Ensuite, 1 Double and 1 Twin
• 2 Bathrooms
• Private Pool with Spa / Hot Tub
• Wi-Fi
• Lake Views
• Disney Springs 7.6 miles
Private Pool Spa / Hot Tub Wi-Fi Internet Cot and Stroller Shops Nearby Restaurants Nearby Payment accepted in Sterling
Book this villa
From £79 per night
Windward Cay Kissimmee - Hidden Jewel Of Kissimmee

This Stunning 3-bedroom, 2-bathroom vacation home in the heart of Kissimmee is the perfect vacation home for your family to enjoy a wonderful holiday in the Florida sunshine, and explore the many attractions and theme parks in and around Orlando.

With generously sized bedrooms, a south-facing pool with a spa pool (Pool heat additional) and a games room, this home enjoys a tranquil woodland location on the Windward Cay development. The pool area is the perfect spot to relax in the sun or enjoy a barbecue or al...

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

5 Bedrooms, sleeps 10
• 2 Ensuite, 1 Double and 2 Twin
• 3 Bathrooms
• Private Pool with Spa / Hot Tub
• Wi-Fi
• Games Room
• Disney Springs 6.9 miles
Private Pool Spa / Hot Tub 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 £99 / US$153 per night
Beautiful Florida holiday home with private south facing 30’x18’ pool & spa, located in the quiet gated community of The Hamlets. Just off highway 192 in Kissimmee, it is only a few minutes drive to hundreds of shops, restaurants & attractions and some are even within walking distance. Our home is just a short drive to Disney Maingate & Sea World.. The villa is beautifully furnished to the highest standards with themed rooms for children.

We hold a TripAdvisor Certificate of Excellance for 2017, 2018 and 2019

#130  4 Bedroom Villa with South-Facing Private Pool and Wi-Fi

4 Bedrooms, sleeps 8
• 1 Ensuite, 1 Double and 2 Twin
• 2 Bathrooms
• Private Pool
• Wi-Fi
• Disney Springs 7.6 miles
Private Pool Wi-Fi Internet Cot and Stroller Shops Nearby Restaurants Nearby Payment accepted in Sterling
Book this villa
From £68 per night
Thank you for your interest in our Villa in Kissimmee Florida.
The villa is situated on a small, quiet residential estate just off Highway 192, with all it"s shops and restaurants. Close to Disney, Universal Studios, Seaworld and Gatorland
All linen and towels are provided. The villa is fully air conditioned.
Walmart is a few minutes away, where you can buy almost anything, including attraction tickets at a slightly reduced rate
We have a local management company on hand to help you in any way they can.
We cannot take bookings for less than 7 nights.

#101  Very Private Pool - Shops, Bars, Outlets in walking distance - Disney 5 mins - Free Wi-Fi

3 Bedrooms, sleeps 6
• 1 Ensuite, 1 Double and 1 Twin
• 2 Bathrooms
• Private Pool
• Wi-Fi
• Barbecue
• Disney Springs 4.8 miles
Private Pool 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 £78 / US$124 per night
Homely luxury, an over-sized fully-fenced private pool and FREE ultra-fast 250Mb+ Wi-Fi.

Disney 5 minutes, Seaworld 10 minutes and Universal Studios under 20 minutes. Indian Wells is the closest villa community to the parks, attractions, Premium Outlets and International Drive. There is even a WalMart within walking distance!

Set in a peaceful location on the edge of Indian Wells and overlooking woodland, our villa: Elegant is a 3 bedroom, 2 bathroom single storey vacation Florida villa. With almost 1500sqft of air-conditioned tiled living areas and carpeted...

#102  40ft Pool with Spa * Lakeside Views * Local Bars and Shops * 500Mb+ Wi-Fi * Premium Cable *

3 Bedrooms, sleeps 6
• 1 Ensuite, 1 Double and 1 Twin
• 2 Bathrooms
• Private Pool with Spa / Hot Tub
• Wi-Fi
• Lake Views
• Disney Springs 4.8 miles
Private Pool Spa / Hot Tub 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 £78 / US$124 per night
Spacious, excellently equipped, huge 40ft pool, spa and lakeside views.

Disney under 5 mins, Seaworld and International Drive 10 mins. Also, what other community boasts shops, bars, Walmart and factory outlets all within walking distance?

Located in the Lake Buena Vista area, Indian Wells is recognised as the closest rental community to the attractions and means you have more time at the parks and not sat in traffic. With the largest pool you are likely to find in any rental home and offering excellent value for money, why settle for second best.

#485  Spectacular view of Lake Berkley and Island

5 Bedrooms, sleeps 11
• 2 Ensuite, 1 Double and 2 Twin
• 4 Bathrooms
• Private Pool with Spa / Hot Tub
• Wi-Fi
• Barbecue
• Games Room
• Lake Views
• Community Clubhouse
• Disney Springs 9.3 miles
Private Pool Spa / Hot Tub Wi-Fi Internet Games Room Barbecue Grill Cot and Stroller Wheelchair Accessible Shops Nearby Restaurants Nearby Community / Resort Pool Clubhouse Tennis / Sports Courts Gated Community Payment accepted in Sterling
Book this villa
From £160 per night
It's all about 'THE VIEW'!!!

We extend a warm invitation to you and your family, to enjoy the delights of our luxurious 5 bedroom (2 en-suite masters), 4 Bathroom Executive Lake View home with the added bonuses of a games room, private screened pool and a lanai.

Our beautiful, spacious and inviting home has been professionally furnished and is comprehensibly equipped with everything that you would require for the perfect vacation - even down to an umbrella! Yes it does sometimes rain in Florida!

Winter Haven enjoys a prime location within Lake Berkley resort,...

#113  Splendid 3 Bed Villa On Windward Cay

28 August 2022 - 29 September 2022 — FREE Welcome Pack
3 Bedrooms, sleeps 6
• 1 Ensuite, 1 Double and 1 Twin
• 2 Bathrooms
• Private Pool
• Wi-Fi
• Disney Springs 7.6 miles
Private Pool Wi-Fi Internet Cot and Stroller Shops Nearby Restaurants Nearby Payment accepted in Sterling
Book this villa
From £78 per night
This 3-bedroom, 2-bathroom vacation home is in the heart of Kissimmee is the perfect vacation home for your family to enjoy.

Executive Villa in the quiet and prestigious Windward Cay development.

The property is fully air-conditioned and has a fully fitted kitchen recently refurbished with granite worktop.

with a ensuite with door leading from the bathroom to the pool deck, the main bedroom also has a Queen size bed and patio doors leading to the pool deck. Our villa Sleeps 6.

We offer a great home with a great service and have many repeat guests.

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

5 Bedrooms, sleeps 11
• 2 Ensuite, 1 Double and 2 Twin
• 4 Bathrooms
• Private Pool with Spa / Hot Tub
• Wi-Fi
• Barbecue
• Games Room
• Lake Views
• Community Clubhouse
• Disney Springs 9.3 miles
Private Pool Spa / Hot Tub 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 £165 / US$216 per night
BrightwaterVilla
Our spacious 5 bedroom, 4 bathroom, lakeside home in an oasis of calm off Highway 192 in Kissimmee within walking distance of Medieval Times, WalMart. 7.8 miles to Disney.

We sleep 10 in comfort. 11th guest charged at $25 / £18 per night including taxes. 11th guest is accommodated on a sofabed in upstairs open plan den; or we have 2 travel cots / cribs for infants.

We are baby and toddler friendly. Bed side guard, stair gate, 2 high chairs, 2 good quality reclining buggies / strollers with hoods.

Downstairs and upstairs lake and pool facing...

#186  Florida Lets A Dream! With Internet

3 Bedrooms, sleeps 8
• 1 Ensuite, 1 Double and 1 Twin
• 2 Bathrooms
• Private Pool
• Wi-Fi
• Disney Springs 7.6 miles
Private Pool Wi-Fi Internet Cot and Stroller Shops Nearby Restaurants Nearby Payment accepted in Sterling
Book this villa
From £78 per night
Windward Cay, Kissimmee, Orlando, Florida. Just off the 192 at 'Marker 14'

One of 3 of our superior, well appointed detached villas, all 3 bedrooms that sleep up to 8 guests. Our villas are ideally situated on a small private development a premium location, enjoying a relaxed, peaceful setting, and yet so close to the attraction packed Highway 192, with its vast choice of shops, restaurants and entertainment. (The 192 also provides easy access to Orlando’s main attractions, Disney World being a mere 15 minutes drive away)

(Our homes are 'pet free' due to own...

#160  SOUTH FACING, 5 BEDROOMS, 3 BATHROOMS, GAMESROOM, KISSIMMEE

★ LATE DEAL ★ — 26 June 2022 - 1 July 2022 — Short Break Deal
5 Bedrooms, sleeps 12
• 1 Ensuite, 3 Double and 1 Twin
• 3 Bathrooms
• Private Pool with Spa / Hot Tub
• Wi-Fi
• Games Room
• Lake Views
• Community Clubhouse
• Disney Springs 9.3 miles
Private Pool Spa / Hot Tub 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 £160 / US$233 per night
Welcome to our true south facing villa with stunning, uninterrupted views of the largest lake on Lake Berkley resort. Being one of only seven villas with this south facing view you can be assured when the sun is shining it will be on you, great to relax, enjoy and listen to nature and watch wildlife from the pool deck. If you still want to enjoy the outdoor sun but fancy some shade the lanai is ideal for alfresco dining with picturesque views. The large pool deck hosts a private pool, hot tub and lanai with sun loungers, table and chairs.
The Villa boasts over 3000 ft.²...
Shortlisting a is the easiest way to compare specific villas for availability, location, amenities and price. Saving a villa to your shortlist will not contact the owners, so for more information on renting the villa, you still need to send an enquiry.