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Winter Garden rentals, holiday lettings direct from the owners

You will find many studios, flats, houses and villas for your holiday in Winter Garden. Contact the owners directly on the IHA site and enjoy the best rental prices, promotions and last minute deals that meet your budget. Visit the picture gallery on private lettings for a break with family or friends. All holiday listings on IHA are verified, plan your journey to Winter Garden with absolute confidence!
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Towns close to : Winter Garden
Clermont - Holidays in Clermont
at 11mi.
3 advert(s)
Orlando
at 13mi.
7 advert(s)
at 15mi.
1 advert(s)
at 17mi.
1 advert(s)
at 17mi.
2 advert(s)
Kissimmee - Lake Kissimmee
at 22mi.
59 advert(s)
at 22mi.
2 advert(s)
Davenport - Golfing in Davenport
at 28mi.
19 advert(s)

£91* Night
Contact
book direct with the owners
from £91/Night*
See the rates
25 requests already received
Advert 74164
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5 Minutes to Disney. 4 bedrooms, 3 bathrooms private pool and hot tub. Pool table in garage.

House 1,300 Sq.ft. in a private property. not overlooked, swimming pool view

Lake view. Close to shopping and many restaurants. Two king size master suites and two twin bedrooms with 2 beds in each bedroom. Fully equipped house. All towels and linens supplied. House Rental in Kissimmee #74164 >

Swimming poolTennisParking
Interior facilities
  • 2 Bathroom
  • 2 Shower room
  • Living room
  • Sitting room
  • Separate kitchen
  • Dining area
Advantages
  • City holidays
  • Ideal for all age groups and family groups
  • Children welcome
  • Setting : Quiet
  • Golf
4 bedrooms House for rent from 1 to 8 people
House in Kissimmee - Advert 74164
House in Kissimmee - Advert 74164
View the advert

£76* Weekend
Contact
book direct with the owners
Night£69*
week£481*
2 weeks£962*
Month£1636*
from £38/Night*
See the rates
Up to-31%
Depending on the season
31 requests already received
Advert 23419
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Family owned villa in gated community 4 Bedrooms sleeps 8, 3 bathrooms large family / dining area. Private Pool screened lanai in garden. Games Room

Magic Landings Villa 2,700 Sq.ft. in an estate. country side, swimming pool, garden/park, lake view

Our magnificent Florida Villa provides spacious accommodation of 2 double bedrooms with queen beds and en suite bathrooms with walk-in closets; 2 twin bedrooms and further bathroom; open plan family room with patio doors onto the pool area, dining area, breakfast bar, fully equipped kitchen; laundry room; games room; fully air conditioned; beautifully furnished throughout to create a cosy home from... Villa Rental in Kissimmee #23419 >

Swimming poolParking
Interior facilities
  • 3 Bathroom
  • Living room
  • American style kitchen
  • Dining area
  • Games room
  • Dressing room
Advantages
  • City holidays
  • Ideal for all age groups
  • Children welcome
  • Setting : Lakeside, Pleasant
  • Golf, Horse riding, Culture, Fishing
4 bedrooms Villa for rent from 2 to 8 people
Living room, Villa in Kissimmee - Advert 23419
Kitchen Area, Villa in Kissimmee - Advert 23419
View the advert

£381* Weekend
Contact
book direct with the owners
Night£305*
week£1520*
from £191/Night*
See the rates
Up to-67%
Depending on the season
27 requests already received
Advert 69693
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14 Room Disney Area Golf Resort Villa with FREE Tennis, Discount Golf & SPA (Disney Estate)

Villa 4,300 Sq.ft. in a golf/resort. country side, swimming pool, garden/park, forest view

Why rent hotel rooms?! When you can get a private Disney Golf & Tennis Resort Villa Estate with “the best location” only about 10 minutes from Disney World's Animal Kingdom! 14 Room Disney Area Golf Resort Villa with FREE Tennis, Discount Golf & SPA (Disney Estate) Approximately 4500sf (about 3500sf interior & about 1000sf pool patio). The Estate is a great vacation paradise with its private pool and... Villa Rental in Kissimmee #69693 >

Swimming poolTennisParking
Interior facilities
  • Sleeping area
  • 5 Bathroom
  • 5 Shower room
  • 1 WC
  • Living room
  • Sitting room
Advantages
  • City holidays
  • Children welcome
  • Setting : Enchanting
  • Village centre at 0.5mi.
  • Naturism
  • Charmance
  • Golf, Spa, Culture
12 bedrooms Villa for rent from 1 to 28 people
General, Villa in Kissimmee - Advert 69693
Villa, Villa in Kissimmee - Advert 69693
View the advert

£76* Night
Contact
book direct with the owners
from £76/Night*
See the rates
Up to-43%
Depending on the season
8 requests already received
Advert 25762
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House 1,940 Sq.ft. in a resort. swimming pool, garden/park, lake view
House Rental in Kissimmee #25762 >Swimming poolTennisParking
Interior facilities
  • 2 Bathroom
  • 1 Shower room
  • Living room
  • Sitting room
  • Kitchen Area
  • Dining room
Advantages
  • City holidays
  • Ideal for all age groups and family
  • Children welcome
  • Setting : Pleasant, Lively
  • Town centre at 6mi.
4 bedrooms House for rent from 1 to 8 people
The property, House in Kissimmee - Advert 25762
House, House in Kissimmee - Advert 25762
View the advert


£66* Night
Contact
book direct with the owners
week£460*
from £66/Night*
See the rates
Up to-31%
Depending on the season
34 requests already received
Advert 54786
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Windsor Palms Villa in a charming property. swimming pool, garden/park view
Villa Rental in Kissimmee #54786 >Swimming poolTennisParking
Interior facilities
  • Sleeping area
  • 2 Bathroom
  • Living room
  • Sitting room
  • Separate kitchen
  • Dining room
Advantages
  • Countryside holidays
  • Ideal for all age groups and family
  • Setting : Luxurious, Pleasant
  • Town centre at 1.25mi.
  • Golf, Culture
3 bedrooms Villa for rent for 8 people
Covered swimming pool, Villa in Kissimmee - Advert 54786
Living room, Villa in Kissimmee - Advert 54786
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£550 week
Contact
book direct with the owners
from £79/Night*
See the rates
Up to-15%
Depending on the season
26 requests already received
Advert 3254
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Cumbrian Lakes Villa 2,370 Sq.ft in a private property. not overlooked, swimming pool view
Villa Rental in Kissimmee #3254 >Swimming poolParking
Interior facilities
  • Sleeping area
  • 3 Bathroom
  • 3 Shower room
  • 5 WC
  • Living room
  • Sitting room
Advantages
  • City holidays
  • Children welcome
  • Setting : Condusive to shopping
  • Flying clubs at 3mi.
  • Golf, Fishing
5 bedrooms Villa for rent for 12 people
Cosy nook, Villa in Kissimmee - Advert 3254
Tv room, Villa in Kissimmee - Advert 3254
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£84* Night
Contact
book direct with the owners
week£588*
from £84/Night*
See the rates
Up to-47%
Depending on the season
9 requests already received
Advert 13433
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Remington House 2,700 Sq.ft. in an estate. not overlooked, swimming pool view
House Rental in Kissimmee #13433 >Swimming poolParking
Interior facilities
  • 3 Bathroom
  • 1 WC
  • Living room
  • Sitting room
  • Large american style kitchen
  • Dining room
Advantages
  • City holidays
  • Ideal for all age groups and family groups
  • Children welcome
  • Setting : Luxuriant, Suitable for a relaxing break
  • Bus stop / bus station at 0.5mi.
  • Golf, Culture, Fishing
4 bedrooms House for rent from 1 to 8 people
View from the swimming pool, House in Kissimmee - Advert 13433
View from the kitchen, House in Kissimmee - Advert 13433
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Contact
book direct with the owners
3 requests already received
Advert 18317
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Coral Cay Resort Town House 1,600 Sq.ft. in a luxury property. panoramic, swimming pool, garden/park, lake view
House Rental in Kissimmee #18317 >Swimming poolParking
Interior facilities
  • 3 Bathroom
  • 3 Shower room
  • 3 WC
  • Living room 205 Sq.ft.
  • Sitting room 150 Sq.ft.
  • Large american style kitchen
Advantages
  • City holidays
  • Ideal for large families and family groups
  • Children welcome
  • Setting : Lakeside, Quiet
4 bedrooms House for rent from 1 to 10 people
View the advert

£76* Night
Contact
book direct with the owners
from £76/Night*
See the rates
Up to-29%
Depending on the season
8 requests already received
Advert 23242
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Villa 1,600 Sq.ft. in a resort. panoramic, swimming pool, garden/park, courtyard view
Villa Rental in Kissimmee #23242 >Swimming poolTennisParking
Interior facilities
  • Sleeping area
  • 3 Bathroom
  • 3 Shower room
  • Living room
  • Separate kitchen
  • Dining room
Advantages
  • City holidays
  • Ideal for all age groups and large families
  • Children welcome
  • Setting : Luxurious
  • 18 hole golf course at 0.3mi.
  • Golf, Festival
3 bedrooms Villa for rent from 1 to 8 people
Dining room, Villa in Kissimmee - Advert 23242
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£53* Night
Contact
book direct with the owners
from £53/Night*
See the rates
Up to-50%
Depending on the season
29 requests already received
Advert 18353
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Hamilton Reserve Villa 1,300 Sq.ft. in a property. swimming pool view
Villa Rental in Kissimmee #18353 >Swimming pool
Interior facilities
  • 1 Bathroom
  • 1 Shower room
  • Living room
  • Separate kitchen
  • Dining room
  • Dining area
Advantages
  • City holidays
  • Children welcome
  • Setting : City
  • Eurogîtes, Clé vacances : 3 keys
  • Golf, Spa, Culture
3 bedrooms Villa for rent for 6 people
Interior layout, Villa in Kissimmee - Advert 18353
Kitchen, Villa in Kissimmee - Advert 18353
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£149* Night
Contact
book direct with the owners
from £149/Night*
See the rates
Up to-15%
Depending on the season
34 requests already received
Advert 12431
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Calla Lily Villa Luxury House 2,700 Sq.ft. in a luxury property. panoramic, unobscured, not overlooked, swimming pool view
House Rental in Kissimmee #12431 >Swimming poolTennisParking
Interior facilities
  • 3 Bathroom
  • Living room
  • Sitting room
  • Large separate kitchen
  • Dining room
  • Dining area
Advantages
  • City holidays
  • Ideal for all age groups and family groups
  • Children welcome
  • Setting : Luxurious, Lakeside
  • Public tennis court at 3mi.
5 bedrooms House for rent from 1 to 12 people
Luxury House in Kissimmee - Advert 12431
Luxury House in Kissimmee - Advert 12431
View the advert

£1680* Month
Contact
book direct with the owners
Night£76*
Weekend£191*
week£535*
2 weeks£993*
from £57/Night*
See the rates
Up to-33%
Depending on the season
34 requests already received
Advert 64503
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Indian Point House 1,600 Sq.ft. in a private property. swimming pool, garden/park, meadow, lake view
House Rental in Kissimmee #64503 >Swimming poolTennisParking
Interior facilities
  • 2 Bathroom
  • 1 Shower room
  • Living room
  • Separate kitchen
  • Dining area
  • Dressing room
Advantages
  • City holidays
  • Ideal for all age groups and family
  • Children welcome
  • Setting : Luxurious, Quiet
  • Bus stop / bus station at 1.25mi.
  • Gay friendly
  • Handicap tourisme
  • Golf, Thalasso, Festival, Horse riding, Culture
3 bedrooms House for rent from 1 to 8 people
Living room, House in Kissimmee - Advert 64503
Dining area, House in Kissimmee - Advert 64503
View the advert

£395 week
Contact
book direct with the owners
from £57/Night*
See the rates
Up to-25%
Depending on the season
88 requests already received
Advert 11501
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Eagle Pointe Villa 1,940 Sq.ft. in a private property. panoramic, not overlooked, country side, swimming pool view
Villa Rental in Kissimmee #11501 >Swimming poolParkingBaby chair
Interior facilities
  • 2 Bathroom
  • Living room
  • Sitting room
  • Separate kitchen
  • Dining room
  • Dining area
Advantages
  • Countryside holidays
  • Ideal for family groups and retired people
  • Children welcome
  • Setting : Lakeside, Luxuriant
  • Town centre at 4.5mi.
4 bedrooms Villa for rent from 2 to 8 people
Outside furniture, Villa in Kissimmee - Advert 11501
Pool view, Villa in Kissimmee - Advert 11501
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£481* 2 weeks
Contact
book direct with the owners
week£504*
from £32/Night*
See the rates
Up to-10%
Depending on the season
61 requests already received
Advert 17770
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Country Crossings Villa 1,300 Sq.ft. in an estate. not overlooked, swimming pool view
Villa Rental in Kissimmee #17770 >Swimming poolBaby chairPlaypen
Interior facilities
  • 2 Bathroom
  • Living room 380 Sq.ft.
  • American style kitchen
  • Dining area
  • Dressing room
  • Patio
Advantages
  • Countryside holidays
  • Ideal for family and couples
  • Children welcome
  • Setting : Luxurious, Tropical
  • Lake at 2.5mi.
  • Golf, Fishing
3 bedrooms Villa for rent from 1 to 8 people
The property, Villa in Kissimmee - Advert 17770
Heated swimming pool, Villa in Kissimmee - Advert 17770
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£726* week
Contact
book direct with the owners
Night£118*
from £104/Night*
See the rates
Up to-29%
Depending on the season
15 requests already received
Advert 36007
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Villa 2,370 Sq.ft in a luxury property.
Villa Rental in Kissimmee #36007 >Swimming poolTennisParking
Interior facilities
  • 3 Bathroom
  • Living room
  • Sitting room
  • American style kitchen
  • Dining area
  • Games room
Advantages
  • City holidays
  • Ideal for all age groups
  • Children welcome
  • Setting : Lively
  • Golf, Spa
5 bedrooms Villa for rent for 12 people
Villa in Kissimmee - Advert 36007
Villa in Kissimmee - Advert 36007
View the advert