HOLIDAY LETTINGS book direct with the owners The time of a holiday
IHA Holiday lettings
531390
+Share your most beautiful photos!

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!
108 Results
Sort the results by
Indifferent
Reviews - +
Reviews + -
Price - +
Price + -
Person(s) - +
Person(s) + -
Bedroom(s) - +
Bedroom(s) + -
Town A - Z
Town Z - A
Updated - +
Updated + -
Lodgings A - Z
Lodgings Z - A

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)

£399 week
Contact
book direct with the owners
from £57/Night*
See the rates
Up to-32%
Depending on the season
34 requests already received
Advert 44232
Display the map
Villa in a private road. swimming pool view
Villa Rental in Kissimmee #44232 >Swimming poolParking
Interior facilities
  • 3 Bathroom
  • Living room
  • Separate kitchen
  • Dining area
  • Games room
  • Patio
Advantages
  • City holidays
  • Ideal for all age groups
  • Children welcome
  • Setting : Luxuriant, Peaceful
  • Public swimming pool at <165'
  • Golf
4 bedrooms Villa for rent from 1 to 10 people
Villa in Kissimmee - Advert 44232
Villa in Kissimmee - Advert 44232
View the advert

£142* Night
Contact
book direct with the owners
from £142/Night*
See the rates
Up to-28%
Depending on the season
1 request already received
Advert 41333
Display the map
House 3,000 Sq.ft. in a private property. swimming pool, lake view
House Rental in Kissimmee #41333 >Swimming poolParkingBaby chair
Interior facilities
  • 3 Bathroom
  • 3 Shower room
  • 1 WC
  • Living room
  • Sitting room
  • Separate kitchen
Advantages
  • City holidays
  • Children welcome
  • Setting : Lakeside
  • Golf, Spa, Fishing
5 bedrooms House for rent from 1 to 12 people
House in Kissimmee - Advert 41333
View the advert

Contact
book direct with the owners
16 requests already received
Advert 28259
Display the map
Luxury Villa 3,000 Sq.ft. in a luxury property. swimming pool, lake, street/avenue view
Villa Rental in Kissimmee #28259 >Swimming poolParkingBaby chair
Interior facilities
  • Sleeping area
  • 3 Bathroom
  • 3 Shower room
  • 3 WC
  • Living room
  • Sitting room
Advantages
  • Countryside holidays
  • Children welcome
  • Setting : Lakeside
  • Golf, Horse riding, Fishing
5 bedrooms Villa for rent for 12 people
King-size bed(s), Luxury Villa in Kissimmee - Advert 28259
View from the dining-room, Luxury Villa in Kissimmee - Advert 28259
View the advert

£76* Weekend
Contact
book direct with the owners
Night£76*
week£535*
2 weeks£1069*
Month£1528*
from £38/Night*
See the rates
Up to-33%
Depending on the season
7 requests already received
Advert 2189
Display the map
Indian Ridge Oaks House 1,300 Sq.ft. in a private property. swimming pool, garden/park, street/avenue view
House Rental in Kissimmee #2189 >Swimming poolTennisParking
Interior facilities
  • 2 Bathroom
  • 2 Shower room
  • Living room 110 Sq.ft.
  • American style kitchen
  • Dining area
  • Dressing room
Advantages
  • Countryside holidays
  • Ideal for all age groups and family
  • Children welcome
  • Setting : Peaceful, Suitable for a relaxing break
  • 18 hole golf course at 1.25mi.
  • Family Holiday Destinations
  • Golf, Culture
3 bedrooms House for rent from 1 to 6 people
Heated swimming pool, House in Kissimmee - Advert 2189
Bedroom, House in Kissimmee - Advert 2189
View the advert


£611* week
Contact
book direct with the owners
Night£92*
from £88/Night*
See the rates
Up to-24%
Depending on the season
3 requests already received
Advert 59305
Display the map
Indian Oaks Trial House 1,300 Sq.ft. in a private property. swimming pool, garden/park, fantastic sunset view
House Rental in Kissimmee #59305 >Swimming poolTennisParking
Interior facilities
  • 1 Super king-size bed(s)
  • 1 Sofa bed(s) 2 pers
  • 4 Single bed(s)
  • 1 Baby cot(s)
  • T.V.
  • Home cinema
Advantages
  • Countryside holidays
  • Ideal for all age groups
  • Children welcome
  • Setting : Tranquil, Suitable for a relaxing break
  • Golf, Festival
3 bedrooms House for rent from 1 to 8 people
Kitchen Area, House in Kissimmee - Advert 59305
House in Kissimmee - Advert 59305
View the advert

£55* Weekend
Contact
book direct with the owners
Night£55*
week£381*
2 weeks£710*
Month£1031*
from £27/Night*
See the rates
Up to-30%
Depending on the season
31 requests already received
Advert 22351
Display the map
Island Club Charming Triplex 1,300 Sq.ft. in a town house. panoramic, sea/ocean, garden/park, lake view
Flat-Apartments Rental in Kissimmee #22351 >Swimming poolTennisParking
Interior facilities
  • 1 Bathroom
  • 1 Shower room
  • Living room
  • Separate kitchen
  • Dining area
  • Dressing room
Advantages
  • Seaside holidays
  • Ideal for all age groups and family groups
  • Children welcome
  • Setting : Seaside, City
  • Sandy beach at 31mi.
  • Golf, Festival, Spa, Horse riding, Culture, Fishing
3 bedrooms Flat-Apartments for rent for 8 people
View from the garden/park, Charming Triplex in Kissimmee - Advert 22351
Living room, Charming Triplex in Kissimmee - Advert 22351
View the advert

Contact
book direct with the owners
2 requests already received
Advert 66150
Display the map
Crescent Lakes House 2,700 Sq.ft. in a private property. not overlooked, swimming pool, garden/park, forest view
House Rental in Kissimmee #66150 >Swimming poolTennisParking
Interior facilities
  • 3 Bathroom
  • 2 Shower room
  • 1 WC
  • Living room
  • Separate kitchen
  • Dining area
Advantages
  • Countryside holidays
  • Ideal for all age groups
  • Children welcome
  • Setting : Tropical, Peaceful
  • Horse riding, Culture, Fishing
5 bedrooms House for rent from 1 to 12 people
Private swimming-pool, House in Kissimmee - Advert 66150
House in Kissimmee - Advert 66150
View the advert

£470 week
Contact
book direct with the owners
from £68/Night*
See the rates
38 requests already received
Advert 71179
Display the map
Villa in a private property. not overlooked, swimming pool, garden/park view
Villa Rental in Kissimmee #71179 >Swimming poolTennisParking
Interior facilities
  • Living room
  • Sitting room
  • Dining room
  • Dining area
  • Games room
  • Laundry room
Advantages
  • City holidays
  • Ideal for all age groups and family groups
  • Children welcome
  • Setting : Tranquil
4 bedrooms Villa for rent for 10 people
Private swimming-pool, Villa in Kissimmee - Advert 71179
Sitting room, Villa in Kissimmee - Advert 71179
View the advert

£390 week
Contact
book direct with the owners
from £56/Night*
See the rates
Up to-35%
Depending on the season
15 requests already received
Advert 75628
Display the map
Cumbrian Lakes Villa 860 Sq.ft. in a private road. swimming pool, garden/park, forest, lake view
Villa Rental in Kissimmee #75628 >Swimming poolParkingBaby chair
Interior facilities
  • 3 Bathroom
  • 3 Shower room
  • 4 WC
  • Living room
  • American style kitchen
  • Dining room
Advantages
  • City holidays
  • Children welcome
  • Setting : Suitable for a relaxing break, Picturesque
  • Town centre at 3mi.
  • Family Holiday Destinations
  • Golf, Horse riding, Fishing
4 bedrooms Villa for rent from 2 to 8 people
Living room, Villa in Kissimmee - Advert 75628
Living room, Villa in Kissimmee - Advert 75628
View the advert

£662* week
Contact
book direct with the owners
Night£116*
from £95/Night*
See the rates
Up to-23%
Depending on the season
16 requests already received
Advert 45157
Display the map
Luxury Villa in a luxury property. unobscured, not overlooked, swimming pool, lake view
Villa Rental in Kissimmee #45157 >Swimming poolParkingBaby chair
Interior facilities
  • 3 Bathroom
  • 1 Shower room
  • 4 WC
  • Living room
  • Sitting room
  • Separate kitchen
Advantages
  • Seaside holidays
  • Children welcome
  • Setting : Tranquil, Pleasant
  • Sandy beach at >31mi.
  • Meublés de Tourisme
  • Golf, Festival, Horse riding, Fishing
5 bedrooms Villa for rent for 12 people
Large bedroom, Luxury Villa in Kissimmee - Advert 45157
Heated swimming pool, Luxury Villa in Kissimmee - Advert 45157
View the advert

£1314* week
Contact
book direct with the owners
from £188/Night*
See the rates
Up to-31%
Depending on the season
12 requests already received
Advert 27494
Display the map
Luxury Villa 2,700 Sq.ft. in a private property. panoramic, swimming pool, lake, fantastic sunset view
Villa Rental in Kissimmee #27494 >Swimming poolParkingBaby chair
Interior facilities
  • 4 Bathroom
  • Living room
  • Separate kitchen
  • Dining room
  • Dining area
  • Tv room
Advantages
  • Countryside holidays
  • Ideal for family groups and all age groups
  • Children welcome
  • Setting : Luxuriant, Lakeside
  • Golf, Horse riding, Fishing
7 bedrooms Villa for rent for 16 people
Luxury Villa in Kissimmee - Advert 27494
Luxury Villa in Kissimmee - Advert 27494
View the advert

£69* Night
Contact
book direct with the owners
from £69/Night*
See the rates
Up to-24%
Depending on the season
21 requests already received
Advert 12459
Display the map
Villas at Island Club Villa 1,300 Sq.ft. in a resort. swimming pool, lake, street/avenue view
Villa Rental in Kissimmee #12459 >Swimming poolTennisParking
Interior facilities
  • 1 Bathroom
  • 1 Shower room
  • Living room
  • Sitting room
  • American style kitchen
  • Dining room
Advantages
  • City holidays
  • Ideal for all age groups and family groups
  • Children welcome
  • Setting : Pleasant, Quiet
  • Bus stop / bus station at 0.5mi.
  • Golf, Fishing
3 bedrooms Villa for rent for 8 people
Swimming pool, Villa in Kissimmee - Advert 12459
Pool house, Villa in Kissimmee - Advert 12459
View the advert

Contact
book direct with the owners
28 requests already received
Advert 8646
Display the map
Cumbrian lakes Villa in a private estate. swimming pool, lake, town, fantastic sunset view
Villa Rental in Kissimmee #8646 >Swimming pool
Interior facilities
  • Bathroom
  • Shower room
  • WC
  • Living room
  • Sitting room
  • Separate kitchen
Advantages
  • City holidays
  • Ideal for family groups and family
  • Children welcome
  • Setting : Lakeside, Luxurious
  • Eurogîtes, La clef verte
5 bedrooms Villa for rent for 12 people
Villa in Kissimmee - Advert 8646
Villa in Kissimmee - Advert 8646
View the advert

£420* week
Contact
book direct with the owners
Night£152*
Weekend£152*
from £60/Night*
See the rates
Up to-80%
Depending on the season
16 requests already received
Advert 33614
Display the map
Villa < 118 Sq.ft. in a golf/resort. sea/ocean, swimming pool, garden/park, village view
Villa Rental in Kissimmee #33614 >Swimming poolTennisParking
Interior facilities
  • 1 Bathroom
  • 1 Shower room
  • Living room < 100 Sq.ft
  • Kitchen Area
  • Dining room
  • 1 Double bed(s)
Advantages
  • City holidays
  • Ideal for all age groups and family
  • Children welcome
  • Setting : Calm, Tropical
  • Sandy beach at <165'
  • Naturism
  • Charmance
  • Golf
  • Pets accepted
2 bedrooms Villa for rent from 4 to 8 people
Outside, Villa in Kissimmee - Advert 33614
Bedroom, Villa in Kissimmee - Advert 33614
View the advert

Contact
book direct with the owners
15 requests already received
Advert 17896
Display the map
Sunset Lakes Villa 1,940 Sq.ft. in a housing estate. panoramic, not overlooked, country side, swimming pool view
Villa Rental in Kissimmee #17896 >Swimming poolParkingBaby chair
Interior facilities
  • 3 Bathroom
  • 3 Shower room
  • 1 WC
  • Living room
  • Sitting room
  • Separate kitchen
Advantages
  • Countryside holidays
  • Ideal for all age groups and seminar
  • Setting : Luxurious, Tranquil
  • High class retailers at 0.93mi.
  • Golf, Festival, Spa, Horse riding, Fishing
4 bedrooms Villa for rent for 10 people
Villa in Kissimmee - Advert 17896
Villa in Kissimmee - Advert 17896
View the advert