List your home
Apply filters
£ to

50 Holiday homes near Windsor Hills Resort

Reset search

Show results on map

Filter your search

Price per night

Price per night

£ to per night

Bedrooms

Location

  • United States Clear
  • Florida Clear
  • Central Florida Clear
  • Kissimmee Clear
  • Clear

Location

  • All locations

more +

less -

Activities

more +

less -

Suitability

more +

less -

Facilities

more +

less -

Filters applied: House (0)

To book this holiday home you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more
50 Results   |  

More results near Windsor Hills Resort

from £113 / night

£791 - £1302 / week

View

18 Photos

Distance approx 0.07 miles from Windsor Hills Resort   |  Show on Map

Holiday home rental

Central Florida / Kissimmee

House / 6 Bedrooms / sleeps 14

Min stay varies

Add to shortlist

from £113 / night

£791 - £1302 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
Internet Access Heated Pool Private Pool VCR DVD Player Television  …see more

from £89 / night

£623 - £1092 / week

View

18 Photos

Distance approx 0.18 miles from Windsor Hills Resort   |  Show on Map

Holiday home rental

Central Florida / Kissimmee

House / 6 Bedrooms / sleeps 14

Min stay varies

Add to shortlist

from £89 / night

£623 - £1092 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
Internet Access Heated Pool Private Pool Television Satellite or cable TV DVD Player  …see more

from £154 / night

£1074 - £1610 / week

View

21 Photos

Distance approx 0.25 miles from Windsor Hills Resort   |  Show on Map

Holiday home with shared pool in Kissimmee

Central Florida / Kissimmee

House / 5 Bedrooms / sleeps 10

1 night min stay

Add to shortlist

from £154 / night

£1074 - £1610 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
This beautiful 5 Bed/ 3 Bath home comfortably sleeps 10 guests  …see more

Featured properties

from £213 / night

£1487 - £2067 / week

View

16 Photos

Distance approx 0.47 miles from Windsor Hills Resort   |  Show on Map

Kissimmee holiday home rental

Kissimmee / Sunset Lakes

House / 4 Bedrooms / sleeps 8

3 Nights min stay

Add to shortlist

from £213 / night

£1487 - £2067 / week

View

Key info:

  • Great for children of all ages
  • No pets allowed
Gorgeous executive home in the gated community of Formosa Gardens. Villa features 4 bedrooms, 3 baths, 2 Living Rooms and conveniently located within 5 minutes of shopping and Walt Disney World. King and Queen master bedroom along with 2 twin bedrooms. Beautiful lake view with accompanying pool and  …see more

from £429 / night

£3000 - £3580 / week

View

21 Photos

Distance approx 0.5 miles from Windsor Hills Resort   |  Show on Map

Kissimmee holiday home rental

Kissimmee / Sunset Lakes

House / 7 Bedrooms / sleeps 15

3 Nights min stay

Add to shortlist

from £429 / night

£3000 - £3580 / week

View

Key info:

  • Great for children of all ages
  • No pets allowed
Can you say wow what a house!! 7 bedroom/7 bath pool home located in the luxurious, gated community of Formosa Gardens. Pool & spa face the lake for the ultimate privacy. Bedding consists of 2 King master bedrooms, 2 double bedrooms, 2 twin bedroom and 1 bunk bedroom. Gameroom in the garage  …see more

from £332 / night

£2320 - £2420 / week

View

20 Photos

Distance approx 0.5 miles from Windsor Hills Resort   |  Show on Map

Home rental in Kissimmee

Kissimmee / Sunset Lakes

House / 6 Bedrooms / sleeps 15

3 Nights min stay

Add to shortlist

from £332 / night

£2320 - £2420 / week

View

Key info:

  • Great for children of all ages
  • No pets allowed
Imagine watching a movie in your very own 10 seater theater!! Well imagine no more as this amazing home has a theater and much, much more. Enjoy a swim in this huge pool facing the lake and play pool in your gameroom. Exercise bike in the corner for your peace and quiet while burning the vacation  …see more

from £199 / night

£1387 - £1790 / week

View

24 Photos

Distance approx 0.5 miles from Windsor Hills Resort   |  Show on Map

Holiday home in Kissimmee

Kissimmee / Kissimmee City

House / 5 Bedrooms / sleeps 12

3 Nights min stay

Add to shortlist

from £199 / night

£1387 - £1790 / week

View

Key info:

  • Great for children of all ages
  • No pets allowed
Located in the prestigious gated community of Formosa Gardens this ultimate five bedroom, 4 bathroom Orlando vacation home is has everything you're looking for and more. This property has a fun games room for the entire family to enjoy! Amenities Pool heat available Community clubhouse VCR Stereo  …see more

from £231 / night

£1614 - £2194 / week

View

24 Photos

Distance approx 0.51 miles from Windsor Hills Resort   |  Show on Map

Kissimmee holiday home rental

Kissimmee / Kissimmee City

House / 5 Bedrooms / sleeps 10

3 Nights min stay

Add to shortlist

from £231 / night

£1614 - £2194 / week

View

Key info:

  • Great for children of all ages
  • No pets allowed
Executive, 5 bdrm Gameroom in the gated community of Formosa Gardens. Enjoy two, comfortable King master bedrooms, double bedroom and 2 twin bdrms. Gameroom with pool table in garage. Pool and spa face the lake which gives you a feeling of serenity. Amenities Pool heat available VCR Private Pool  …see more

from £246 / night

£1718 - £2660 / week

View

Excellent 5/5 

27 Photos

Distance approx 0.58 miles from Windsor Hills Resort   |  Show on Map

Kissimmee holiday home rental

Kissimmee / Formosa Gardens

House / 6 Bedrooms / sleeps 12

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £246 / night

£1718 - £2660 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Spacious 3400 ft, 6 bedoomed home, non smoking, sleeps 12, free wifi,games room,south facing swimming pool,secluded large corner plot. Free wifi, 6 bedrooms,south facing pool, secluded large corner plot , very comfortable home, games room.  …see more

from £93 / night

£647 - £1134 / week

View

Very Good 4/5 

21 Photos

Distance approx 0.59 miles from Windsor Hills Resort   |  Show on Map

Holiday home in Kissimmee

Kissimmee / Formosa Gardens

House / 5 Bedrooms / sleeps 10

Very Good 4/5 

4 Nights min stay

Add to shortlist

from £93 / night

£647 - £1134 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
Conveniently located near the Disneyland, this spacious and comfortable house has its own swimming pool and is ideal for a family holiday. We'll do our best to accommodate your requests. Book now!  …see more

from £213 / night

£1487 - £2067 / week

View

15 Photos

Distance approx 0.59 miles from Windsor Hills Resort   |  Show on Map

Holiday home in Kissimmee

Kissimmee / Sunset Lakes

House / 4 Bedrooms / sleeps 8

3 Nights min stay

Add to shortlist

from £213 / night

£1487 - £2067 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
Here the beautiful, Lake view 4 bedroom in gated community of Formosa Gardens. located in Formosa Gardens, a must see top notch beautiful home with many upgrades and professionally decorated with high quality furnishings, with a pool, spa, game room and much more. just 3 miles from disney,Has two  …see more

from £429 / night

£3000 - £3580 / week

View

12 Photos

Distance approx 0.61 miles from Windsor Hills Resort   |  Show on Map

Holiday home in Kissimmee

Kissimmee / Sunset Lakes

House / 7 Bedrooms / sleeps 14

3 Nights min stay

Add to shortlist

from £429 / night

£3000 - £3580 / week

View

Key info:

  • Great for children of all ages
  • Air conditioning
  • No pets allowed
Gorgeous ultimate home in the gated community of Formosa Gardens. Villa features 7 bedrooms, 6 baths, 2 Living Rooms and conveniently located within 5 minutes of shopping and Walt Disney World. Beautiful lake view with accompanying pool and spa. Additional amenities: Pool heat available, VCR,  …see more

from £247 / night

£1727 - £2240 / week

View

34 Photos

Distance approx 0.64 miles from Windsor Hills Resort   |  Show on Map

Holiday home with golf nearby in Kissimmee

Central Florida / Kissimmee

House / 5 Bedrooms / sleeps 10

5 Nights min stay

Add to shortlist

from £247 / night

£1727 - £2240 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Beautiful 5 Bedroom Orlando Vacation Home just 4 miles from Disney. Loaded with upgrades and enhancements, including totally private pool, amazing children's theme rooms, air conditioned game room, large screen TVs in all rooms and terrific service.  …see more

from £247 / night

£1727 - £2240 / week

View

24 Photos

Distance approx 0.72 miles from Windsor Hills Resort   |  Show on Map

Holiday home with golf nearby in Kissimmee

Kissimmee / Indian Creek

House / 5 Bedrooms / sleeps 12

1 night min stay

Add to shortlist

from £247 / night

£1727 - £2240 / week

View

Key info:

  • Nearest beach 60 km
  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
From the moment you meet us online, we are with you every step of the way to help make the planning of your dream vacation as easy as possible. We offer our guests a welcome as warm as the sun and the utmost in personal attention.  …see more

from £93 / night

£650 - £900 / week

View

Excellent 5/5 

23 Photos

Distance approx 0.91 miles from Windsor Hills Resort   |  Show on Map

Kissimmee holiday home rental

Kissimmee / Windsor Palms

House / 4 Bedrooms / sleeps 10

Excellent 5/5 

Min stay varies

Add to shortlist

from £93 / night

£650 - £900 / week

View

Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
Welcome to Mickey's Clubhouse. Our beautiful 4 bed 3 bath villa is located on the gated 5 * community of Windsor Palms, only three miles from Disney. It has all the comforts you could wish for including a private south facing pool. Complimentary use of Windsor Palms amenities including: Cinema, Spa, Gym, Olympic size pool & Playground.  …see more

from £148 / night

£1034 - £1260 / week

View

11 Photos

Distance approx 0.98 miles from Windsor Hills Resort   |  Show on Map

Holiday home with shared pool in Kissimmee

Kissimmee / Crestwynd Bay

House / 4 Bedrooms / sleeps 8

3 Nights min stay

Add to shortlist

from £148 / night

£1034 - £1260 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
Lovely 4 Bedroom/ Bathroom private pool home located in the gated community of Windsor Palms. The bedding consists: King and Queen Master Bedroom, 1 twin bedroom and bunkbed room. Pool and spa great for swimming. Windsor Palms has a nice community clubhouse with sundry shop, basketball and tennis  …see more

from £148 / night

£1034 - £1260 / week

View

24 Photos

Distance approx 1 miles from Windsor Hills Resort   |  Show on Map

Kissimmee holiday home rental

Kissimmee / Kissimmee City

House / 4 Bedrooms / sleeps 8

3 Nights min stay

Add to shortlist

from £148 / night

£1034 - £1260 / week

View

Key info:

  • Great for children of all ages
  • No pets allowed
This delightful 4 bedroom home is located in the highly coveted Indian Creek community. Only 4 miles to the Disney parks and walking distance to shopping and restaurants. Indian Creek also has many childrens playgrounds, baseball field and soccer area with nets. The home features large living areas  …see more

from £79 / night

£550 - £700 / week

View

Excellent 5/5 

23 Photos

Distance approx 1.05 miles from Windsor Hills Resort   |  Show on Map

Holiday home with swimming pool in Kissimmee

Kissimmee / Oak Island Cove

House / 5 Bedrooms / sleeps 10

Excellent 5/5 

1 night min stay

Add to shortlist

from £79 / night

£550 - £700 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
This villa cater'd for everything we needed a large pool ,hot tub and very close to all the theme parks (only 2.8 miles from blizzard beach) and very close to many different restaurants and shops yet in a nice quiet area to relax in away from all the hustle and bustle. For a truly memorable stay look no further than our beautiful Family friendly home!  …see more

from £225 / night

£1570 - £1984 / week

View

24 Photos

Distance approx 1.05 miles from Windsor Hills Resort   |  Show on Map

Orlando holiday home rental

Central Florida / Orlando

House / 5 Bedrooms / sleeps 12

1 night min stay

Add to shortlist

from £225 / night

£1570 - £1984 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Pets welcome
  • Private garden
5 Bedroom Pool & Spa home 4 miles to Disney, lots of upgrades, WiFI, game room, 2 kings, 1 queen, 2 Children's Theme Rooms.  …see more

from £230 / night

£1610 - £1984 / week

View

44 Photos

Distance approx 1.08 miles from Windsor Hills Resort   |  Show on Map

Holiday home with golf nearby in Orlando

Central Florida / Orlando

House / 5 Bedrooms / sleeps 12

3 Nights min stay

Add to shortlist

from £230 / night

£1610 - £1984 / week

View

Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • Pets welcome
  • Private garden
Gorgeous Home with Lots of Disney Flair. 3 Kings, 2 Great Kids Theme Rooms, Private Pool, Spa, WiFi, Large Screen TV, Game Room, Wii Game System, Full Gourmet Kitchen and lots of upgrades to enhance your stay.  …see more

from £163 / night

£1137 - £1310 / week

View

24 Photos

Distance approx 1.09 miles from Windsor Hills Resort   |  Show on Map

Holiday home in Kissimmee

Kissimmee / Kissimmee City

House / 5 Bedrooms / sleeps 10

3 Nights min stay

Add to shortlist

from £163 / night

£1137 - £1310 / week

View

Key info:

  • Great for children of all ages
  • No pets allowed
amenities pool heat available vcr private pool covered lanai dvd gameroom conservation view microwave dishwasher washer/dryer bbq grills multiple tv's it is like coming home in a dream. The only thing to do is to take a dip in to the pool and relax. We also recommend for you to request that  …see more

from £89 / night

£623 - £875 / week

View

13 Photos

Distance approx 1.14 miles from Windsor Hills Resort   |  Show on Map

Holiday home with shared pool in Kissimmee

Central Florida / Kissimmee

House / 4 Bedrooms / sleeps 8

Min stay varies

Add to shortlist

from £89 / night

£623 - £875 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
Internet Access Private Pool Heated Pool Shared outdoor pool (unheated) VCR DVD Player Television Satellite or cable TV  …see more

from £164 / night

£1144 - £1428 / week

View

Excellent 5/5 

24 Photos

Distance approx 1.16 miles from Windsor Hills Resort   |  Show on Map

Holiday home in Kissimmee

Kissimmee / Oak Island Harbor

House / 6 Bedrooms / sleeps 13

Excellent 5/5 

4 Nights min stay

Add to shortlist

from £164 / night

£1144 - £1428 / week

View

Key info:

  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
This home is spotlessly presented and is decorated beautifully with exquisitive furniture.  …see more

from £71 / night

£497 - £784 / week

View

11 Photos

Distance approx 1.32 miles from Windsor Hills Resort   |  Show on Map

Holiday home with swimming pool in Celebration

Florida / Celebration

House / 3 Bedrooms / sleeps 8

Min stay varies

Add to shortlist

from £71 / night

£497 - £784 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
Internet Access Private Pool Television DVD Player Satellite or cable TV  …see more

from £78 / night

£546 - £1755 / week

View

19 Photos

Distance approx 1.36 miles from Windsor Hills Resort   |  Show on Map

Kissimmee holiday home rental

Central Florida / Kissimmee

House / 3 Bedrooms / sleeps 6

1 night min stay

Add to shortlist

from £78 / night

£546 - £1755 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
This 3 Bed and 2.5 Bath vacation home rental accommodates up to 6 people comfortably  …see more

from £71 / night

£497 - £784 / week

View

11 Photos

Distance approx 1.56 miles from Windsor Hills Resort   |  Show on Map

Holiday home rental

Central Florida / Kissimmee

House / 3 Bedrooms / sleeps 6

Min stay varies

Add to shortlist

from £71 / night

£497 - £784 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
Internet Access Private Pool Shared outdoor pool (unheated) Heated Pool VCR Satellite or cable TV Television DVD Player  …see more

from £67 / night

£467 - £817 / week

View

Excellent 5/5 

24 Photos

Distance approx 1.6 miles from Windsor Hills Resort   |  Show on Map

Home rental in Kissimmee with indoor pool

Kissimmee / Emerald Isle Kissimmee

House / 4 Bedrooms / sleeps 8

Excellent 5/5 

5 Nights min stay

Add to shortlist

from £67 / night

£467 - £817 / week

View

Key info:

  • Nearest beach 96 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
COMFORTABLE 4 BED/ 3 BATH HOUSE WITH HEATED POOL AND SPA, GAMES ROOM WITH AIRHOCKEY E GAMES ARCADE, 3 MILES TO PARKS, FREE WI-FI, CABLE TV AND A FULL RESORT WITH SWIMMING POOL, TIKI BAR, FITNESS ROOM, COMPUTERS WITH WI-FI, TENNIS COURT, TRAILS AND BEAUTIFUL GARDENS. PAY LESS THAN A HOTEL AND HAVE MORE COMFORT AND PRIVACE WITH A BIG HOUSE, RENEWED IN NOV. WITH WOODEN FLOOR.  …see more

from £96 / night

£670 - £990 / week

View

Excellent 5/5 

24 Photos

Distance approx 1.67 miles from Windsor Hills Resort   |  Show on Map

Holiday home in Kissimmee

Kissimmee / Emerald Isle Kissimmee

House / 4 Bedrooms / sleeps 8

Excellent 5/5 

1 night min stay

Add to shortlist

from £96 / night

£670 - £990 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 130 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
Located 3 miles from Disney World main gate, and easy reach of all Orlando attractions. Sleeps 8; comprising of 4 bedrooms, (2 en-suites) and 3 full bathrooms. . Private south facing heated pool and spa + games room and free Wi-Fi, Flat screen TV's in all bedrooms.  …see more

from £170 / night

£1190 - £2100 / week

View

Excellent 5/5 

24 Photos

Distance approx 1.77 miles from Windsor Hills Resort   |  Show on Map

Holiday home rental

Kissimmee / Emerald Isle Kissimmee

House / 7 Bedrooms / sleeps 16

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £170 / night

£1190 - £2100 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 50 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Theater room, lake view, South facing pool & spa, pool table, free internet, free local calls. Luxurious 5 star, 7 bedroom home has it all. Professionally decorated to a very high standard, the perfect vacation home. One of the best. 2 luxury master suites, 2 designer Queen bedrooms, 3 kids rooms, Cars, Disney Fairies & Mickey Mouse .  …see more

from £170 / night

£1190 - £2100 / week

View

Excellent 5/5 

20 Photos

Distance approx 1.77 miles from Windsor Hills Resort   |  Show on Map

Kissimmee holiday home let

Kissimmee / Emerald Isle Kissimmee

House / 7 Bedrooms / sleeps 16

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £170 / night

£1190 - £2100 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 50 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Theater room, lake view, South facing pool & spa, pool table, free internet, free local calls. Our luxurious 5star, 7 bedroom home has it all. Professionally decorated to a very high standard,the perfect vacation home. One of the best. 2 luxury master suites, 2 designer Queen bedrooms, 3 kids rooms, Toy Story, Disney Princess & Mickey Mouse .  …see more

from £264 / night

£1844 - £2310 / week

View

22 Photos

Distance approx 1.78 miles from Windsor Hills Resort   |  Show on Map

Home rental in Davenport with golf nearby

Davenport / Champions Gate

House / 7 Bedrooms / sleeps 16

2 Nights min stay

Add to shortlist

from £264 / night

£1844 - £2310 / week

View

Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Stay in Orlando's hottest new resort, The Retreat at Championsgate.  …see more

from £163 / night

£1137 - £1310 / week

View

11 Photos

Distance approx 1.84 miles from Windsor Hills Resort   |  Show on Map

Holiday home in Kissimmee

Kissimmee / Sunset Lakes

House / 5 Bedrooms / sleeps 10

3 Nights min stay

Add to shortlist

from £163 / night

£1137 - £1310 / week

View

Key info:

  • Great for children of all ages
  • No pets allowed
Three King master bedrooms!! Gameroom in the garage including air hockey and pool table. Single story 5 bedroom/4 bath with pool and spa with extended pool deck! TV and DVD in every room Amenities: pool heat available gas vcr stereo/cd private pool sw golf nearby putt covered lanai dvd gameroom  …see more

from £148 / night

£1034 - £1260 / week

View

15 Photos

Distance approx 1.84 miles from Windsor Hills Resort   |  Show on Map

Home rental in Kissimmee

Kissimmee / Sunset Lakes

House / 4 Bedrooms / sleeps 8

3 Nights min stay

Add to shortlist

from £148 / night

£1034 - £1260 / week

View

Key info:

  • Great for children of all ages
  • Air conditioning
  • No pets allowed
Beautiful Luxury 4 Bedroom, 3 Bathroom Vacation Home only 5 minutes from World Renowned Disney Attractions, Restaurants, Shopping and World Class Golfing within minutes. Conservation and Lake view from the Lanai. In the evening relax by the pool or enjoy the spa while viewing Magic Kingdom  …see more

from £134 / night

£934 / week

View

8 Photos

Distance approx 1.84 miles from Windsor Hills Resort   |  Show on Map

Holiday home in Kissimmee

Kissimmee / Emerald Isle Kissimmee

House / 5 Bedrooms / sleeps 12

3 Nights min stay

Add to shortlist

from £134 / night

£934 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
Bedding Summary: Bedroom #1: King Bed Bedroom #2: King Bed Bedroom #3: King Bed Bedroom #4: Queen Bed Bedroom #5: (2) Double Beds  …see more

from £124 / night

£864 - £1214 / week

View

Excellent 5/5 

17 Photos

Distance approx 1.84 miles from Windsor Hills Resort   |  Show on Map

Home rental in Kissimmee

Kissimmee / Oak Island Harbor

House / 4 Bedrooms / sleeps 8

Excellent 5/5 

4 Nights min stay

Add to shortlist

from £124 / night

£864 - £1214 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
This luxury 4 bedroom and 3 bathroom villa is located in the established community of Oak Island Cove. This location is probably one of the closest to Disney World's' main gate and within walking distance ( 5 mins) to shopping and the many great restaurants situated on  …see more

from £148 / night

£1034 - £1260 / week

View

24 Photos

Distance approx 1.84 miles from Windsor Hills Resort   |  Show on Map

Holiday home in Kissimmee

Kissimmee / Kissimmee City

House / 4 Bedrooms / sleeps 8

3 Nights min stay

Add to shortlist

from £148 / night

£1034 - £1260 / week

View

Key info:

  • Great for children of all ages
  • No pets allowed
pool heat available community clubhouse stereo/cd private pool covered lanai dvd gameroom pool table air hockey foosball microwave dishwasher washer/dryer garage multiple tv's fan 2 kings 4 twins weekday weekend weekly location kissimmee weekday weekend weekly accommodations 8 4 2 full 2 4 yes  …see more

from £429 / night

£3000 - £3580 / week

View

19 Photos

Distance approx 1.86 miles from Windsor Hills Resort   |  Show on Map

Kissimmee holiday home rental

Kissimmee / Paradise Palms

House / 7 Bedrooms / sleeps 14

3 Nights min stay

Add to shortlist

from £429 / night

£3000 - £3580 / week

View

Key info:

  • Great for children of all ages
  • No pets allowed
Gorgeous 7bedroom/6 bath in the upscale resort community Emerald Island. Pool and spa is southeast facing for your tanning pleasure. Games room includes pool table. Emerald Island is a resort community which features clubhouse with pool, spa with hot tub, sauna, steam room and gym. The beautifully  …see more

from £100 / night

£700 - £850 / week

View

Very Good 4.5/5 

24 Photos

Distance approx 1.88 miles from Windsor Hills Resort   |  Show on Map

Holiday home with indoor pool, golf nearby in Kissimmee

Kissimmee / Sunset Lakes

House / 6 Bedrooms / sleeps 12

Very Good 4.5/5 

3 Nights min stay

Add to shortlist

from £100 / night

£700 - £850 / week

View

Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
Large spacious well equipped house which is ideally sited in a rpivate gated community 5 minutes from Disney  …see more

from £79 / night

£550 - £750 / week

View

10 Photos

Distance approx 1.92 miles from Windsor Hills Resort   |  Show on Map

Kissimmee holiday home rental

Kissimmee / Emerald Isle Kissimmee

House / 4 Bedrooms / sleeps 10

2 Nights min stay

Add to shortlist

from £79 / night

£550 - £750 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Emerald Island Resort, Kissimmee. This prestigious, 5 star, 24 hour manned, gated community, set in 11 acres on a conservation area. Resort community amenities: gated entryway, community pools and spa, sauna, game room, snack bar, cyber cafe with internet access, sand c  …see more

from £133 / night

£929 / week

View

26 Photos

Distance approx 1.92 miles from Windsor Hills Resort   |  Show on Map

Kissimmee holiday home rental

Central Florida / Kissimmee

House / 5 Bedrooms / sleeps 12

3 Nights min stay

Add to shortlist

from £133 / night

£929 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
Bedrooms Double Bed Full Bed King Bed Queen Bed Sofa Bed Communications Internet Connection Telephone Entertainment Cable/Satellite DVD Multiple TV's TV VCR Included Services Dryer DVD or VCR DVD Player DVD/VCR COMBI Golf Nearby H.S. Internet  …see more

from £122 / night

£850 - £1200 / week

View

Excellent 5/5 

24 Photos

Distance approx 1.95 miles from Windsor Hills Resort   |  Show on Map

Holiday home in Kissimmee

Kissimmee / Emerald Isle Kissimmee

House / 6 Bedrooms / sleeps 12

Excellent 5/5 

5 Nights min stay

Add to shortlist

from £122 / night

£850 - £1200 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
This beautifully furnished, air-conditioned executive home is at Emerald Island Resort, the nearest gated community to Disney. With 6 bedrooms, all with TVs, 4 masters with en suites, and 5.5 bathrooms will sleep up to 12 people in spacious, elegantly furnished style. Close to shops and many restaurants  …see more

from £113 / night

£789 - £1265 / week

View

20 Photos

Distance approx 1.98 miles from Windsor Hills Resort   |  Show on Map

Holiday home in Kissimmee

Central Florida / Kissimmee

House / 5 Bedrooms / sleeps 11

1 night min stay

Add to shortlist

from £113 / night

£789 - £1265 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
Sunset Lakes is a picturesque sub division based in Kissimmee  …see more

from £148 / night

£1032 - £1648 / week

View

24 Photos

Distance approx 2.01 miles from Windsor Hills Resort   |  Show on Map

Home rental in Kissimmee with shared pool, golf nearby

Central Florida / Kissimmee

House / 6 Bedrooms / sleeps 12

3 Nights min stay

Add to shortlist

from £148 / night

£1032 - £1648 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
Night Life -Double Bed - King Bed - Queen Bed - Internet Connection - Telephone - Cable/Satellite - Multiple TV's - Gaming Console - Internet Connection - Linens Provided - Non Smoking - Coffeemaker - Gas Grill- Patio - Coffeemaker - Gas Grill Living Area: 2,890 SqFt - - Lot Size: 4,250 SqFt  …see more

from £125 / night

£873 - £1312 / week

View

24 Photos

Distance approx 2.02 miles from Windsor Hills Resort   |  Show on Map

Holiday home with shared pool in Kissimmee

Central Florida / Kissimmee

House / 4 Bedrooms / sleeps 12

1 night min stay

Add to shortlist

from £125 / night

£873 - £1312 / week

View

Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning
  • No pets allowed
This home is Sunset Lakes pride and joy. Beautiful home with 4 nice size bedrooms, two of them are master suites with master baths, both have lake views.  …see more

from £77 / night

£539 - £826 / week

View

12 Photos

Distance approx 2.13 miles from Windsor Hills Resort   |  Show on Map

Holiday home in Kissimmee

Central Florida / Kissimmee

House / 4 Bedrooms / sleeps 10

Min stay varies

Add to shortlist

from £77 / night

£539 - £826 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
Sunset Lakes is a small gated community located right in the heart of Disneys most desirable area  …see more

from £113 / night

£789 - £1265 / week

View

24 Photos

Distance approx 2.18 miles from Windsor Hills Resort   |  Show on Map

Home rental in Kissimmee

Central Florida / Kissimmee

House / 4 Bedrooms / sleeps 8

3 Nights min stay

Add to shortlist

from £113 / night

£789 - £1265 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
Internet Connection – Telephone - Cable/Satellite - Multiple TV's - Linens Provided – Coffeemaker - Gas Grill Living Area: 1,940 SqFt -Lot Size: 2,365 SqFt  …see more

from £77 / night

£539 - £826 / week

View

11 Photos

Distance approx 2.25 miles from Windsor Hills Resort   |  Show on Map

Holiday home in Kissimmee

Central Florida / Kissimmee

House / 4 Bedrooms / sleeps 10

Min stay varies

Add to shortlist

from £77 / night

£539 - £826 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
Internet Access Private Pool Heated Pool Stereo or CD player Television Satellite or cable TV  …see more

from £61 / night

£425 - £500 / week

View

Excellent 5/5 

24 Photos

Distance approx 2.3 miles from Windsor Hills Resort   |  Show on Map

Kissimmee holiday home rental

Kissimmee / Lindfields

House / 4 Bedrooms / sleeps 8

Excellent 5/5 

Short stays welcome

Add to shortlist

from £61 / night

£425 - £500 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Our beautiful villa is located on a small exclusive development with landscaped surroundings and small lakes set in a wooded conservation area. Perfect for the person wanting to relax in quiet idyllic comfort and just 4 miles from Disney World. We maintain our villa to a very high standard inside and out, it really is home from home.  …see more

from £120 / night

£840 / week

View

7 Photos

Distance approx 2.33 miles from Windsor Hills Resort   |  Show on Map

Home letting in Kissimmee

Kissimmee / Paradise Palms

House / 4 Bedrooms / sleeps 10

5 Nights min stay

Add to shortlist

from £120 / night

£840 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
  • Private garden
4 Star 4 bedroom 3 bathroom holiday home in the heart of the Disney district with private splash pool  …see more

from £71 / night

£497 - £777 / week

View

14 Photos

Distance approx 2.53 miles from Windsor Hills Resort   |  Show on Map

Holiday home in Kissimmee

Central Florida / Kissimmee

House / 3 Bedrooms / sleeps 6

Min stay varies

Add to shortlist

from £71 / night

£497 - £777 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
Internet Access Private Pool Satellite or cable TV DVD Player Television VCR  …see more

Don’t let an old browser slow down your holiday

Your browser is out of date and might not work well with our website. Download the latest version to speed up your hunt for the perfect holiday home.

Just click on the icons to get to the download page