HOLIDAY LETTINGS book direct with the owners The time of a holiday
IHA Holiday lettings
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Winter Park rentals, holiday lettings direct from the owners

You will find many studios, flats, houses and villas for your holiday in Winter Park. 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 Park with absolute confidence!
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£126* Night
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book direct with the owners
from £126/Night*
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18 requests already received
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Advert 53363
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Flat-Apartments in a golf/resort. panoramic, unobscured, swimming pool, garden/park view
Flat-Apartments Rental in Orlando #53363 >Swimming poolTennisParking
Interior facilities
  • Sitting room
  • Separate kitchen
  • Dining room
  • Tv room
  • Fitness room
  • Laundry room
Advantages
  • City holidays
  • Ideal for all age groups and family
  • Children welcome
  • Setting : Urban, Heavenly
  • Meublés de Tourisme : 5 stars
  • Golf
2 bedrooms Flat-Apartments for rent for 4 people

£395 week
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book direct with the owners
from £57/Night*
See the rates
Up to-25%
Depending on the season
86 requests already received
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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

£2722* Month
Contact
book direct with the owners
Night£120*
week£729*
2 weeks£1457*
from £91/Night*
See the rates
Up to-21%
Depending on the season
16 requests already received
see details
Advert 14516
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Our home is only 5 miles from Disney property which makes coming back for a bit of peace and quiet and a rest mid-day easy. The garden area has fruit trees and you are welcome to help yourself - fresh lemons fir your drinks.

Lindfields Villa 1,600 Sq.ft. in an estate. not overlooked, swimming pool, garden/park, fantastic sunset view

The house is well furnished, here are TV's in each bedroom and as well as full air conditioning all rooms have overhead fans, including outside on the lanai. The kitchen is fully fitted with dishwasher, huge fridge/freezer, microwave, stove and table and chairs situated in the bay window. There is a lovely glass dining table for more formal dining. The Master bedroom has a large (6ft) King bed and... Villa Rental in Kissimmee #14516 >

Swimming poolParkingBaby chair
Interior facilities
  • 2 Bathroom
  • Living room
  • Large american style kitchen
  • Dining area
  • Cosy nook
  • Loggia
Advantages
  • City holidays
  • Ideal for all age groups and couples
  • Children welcome
  • Setting : Peaceful, Suitable for a relaxing break
  • 18 hole golf course at 3mi.
  • Golf
3 bedrooms Villa for rent for 6 people
Heated swimming pool, Villa in Kissimmee - Advert 14516
Pool view, Villa in Kissimmee - Advert 14516

£116* Night
Contact
book direct with the owners
week£813*
from £116/Night*
See the rates
Up to-12%
Depending on the season
3 requests already received
see details
Advert 57637PDF
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Live the American dream in your very own Florida holiday home located in the quiet gated community of The Hamlets, just off highway 192 in Kissimmee.

Villa Linton Villa 2,370 Sq.ft in an estate. not overlooked, swimming pool, street/avenue view

Our Florida villa is a tastefully decorated & beautifully co-ordinated home. Our home has 5 bedrooms, including King & Queen master suites, 3 bedrooms themed with children in mind - Winnie the Pooh Queen room, Mickey & Minnie twin room and Scooby Doo twin room with unique Mystery Machine bed and giant Scooby Doo and 3 bathrooms. We have a TV Lounge and formal dining area plus fully equipped kitchen... Villa Rental in Kissimmee #57637 >

Swimming poolParkingBaby chair
Interior facilities
  • 3 Bathroom
  • Living room
  • Sitting room
  • American style kitchen
  • Dining room
  • Dining area
Advantages
  • Countryside holidays
  • Ideal for all age groups and family groups
  • Children welcome
  • Setting : Quiet
  • Stretch of water at 1.25mi.
  • Golf, Horse riding, Fishing
5 bedrooms Villa for rent from 2 to 10 people
Pool view, Villa in Kissimmee - Advert 57637
Tv room, Villa in Kissimmee - Advert 57637
Dining room, Villa in Kissimmee - Advert 57637
Kitchen Area, Villa in Kissimmee - Advert 57637
Master bedroom, Villa in Kissimmee - Advert 57637
Bathroom, Villa in Kissimmee - Advert 57637

£79* Night
Contact
book direct with the owners
from £79/Night*
See the rates
Up to-29%
Depending on the season
8 requests already received
see details
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

£55* Night
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book direct with the owners
from £55/Night*
See the rates
Up to-50%
Depending on the season
24 requests already received
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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

£2600 Month
Contact
book direct with the owners
Night£95
week£665
2 weeks£1330
from £87/Night*
See the rates
Up to-30%
Depending on the season
54 requests already received
see details
Advert 20316PDF
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Oak Island Dream Villa 3,000 Sq.ft. in a luxury property. not overlooked, swimming pool, street/avenue view
Villa Rental in Kissimmee #20316 >Swimming poolParkingBaby chair
Interior facilities
  • Sleeping area
  • 4 Bathroom
  • 1 Shower room
  • 1 WC
  • Living room 750 Sq.ft.
  • Sitting room 700 Sq.ft.
Advantages
  • City holidays
  • Ideal for all age groups and large families
  • Children welcome
  • Setting : Rural, Tropical
  • Bus stop / bus station at 0.3mi.
  • Golf, Horse riding, Culture, Fishing
6 bedrooms Villa for rent from 4 to 12 people
View from the sitting-room, Villa in Kissimmee - Advert 20316
The property, Villa in Kissimmee - Advert 20316
Living room, Villa in Kissimmee - Advert 20316
Sitting room, Villa in Kissimmee - Advert 20316

£1521* Month
Contact
book direct with the owners
Night£72*
from £51/Night*
See the rates
Up to-14%
Depending on the season
58 requests already received
see details
Advert 28601
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House. not overlooked view
House Rental in Kissimmee #28601 >Swimming poolParking
Interior facilities
  • 2 Bathroom
  • Kitchen Area
  • Dining room
  • Dining area
  • Laundry room
  • 1 King-size bed(s)
Advantages
  • City holidays
  • Children welcome
  • Setting : Pleasant
3 bedrooms House for rent from 1 to 6 people
House in Kissimmee - Advert 28601
House in Kissimmee - Advert 28601

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book direct with the owners
26 requests already received
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Advert 10141
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Located 3 miles south of Disney main entrance. South facing solar heated pool with 6ft high. Privacy fences and forested area to the rear.

Orlando Villa 1,940 Sq.ft. in a luxury property. not overlooked, country side, swimming pool, forest view

Five HDTVs, Wi-fi, two dvd players and 70+ dvds. Hi-fi and music. Monitored security system, safe, smoke and co2 alarms. Large family room, separate front room, dining room, master bedroom with ensuite. Two other bedrooms have twin beds and are located on the other side of the house next to the second bedroom. Double garage with electric door lift. Mature gardens front and rear. Villa Rental in Kissimmee #10141 >

Swimming poolParkingBaby chair
Interior facilities
  • 2 Bathroom
  • 2 WC
  • Living room
  • Sitting room
  • American style kitchen
  • Dining room
Advantages
  • Countryside holidays
  • Ideal for all age groups
  • Children welcome
  • Setting : Country setting
  • 18 hole golf course at 1.25mi.
  • Golf
3 bedrooms Villa for rent from 1 to 6 people
Villa in Kissimmee - Advert 10141
Villa, Villa in Kissimmee - Advert 10141

£800 week
Contact
book direct with the owners
from £115/Night*
See the rates
Up to-11%
Depending on the season
42 requests already received
see details
Advert 32199
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Crescent Lakes Luxury Villa 3,000 Sq.ft. in a luxury property. swimming pool, lake view
Villa Rental in Orlando #32199 >Swimming poolParkingBaby chair
Interior facilities
  • Sleeping area
  • Living room
  • Separate kitchen
  • Dining area
  • Tv room
  • Games room
Advantages
  • Countryside holidays
  • Ideal for all age groups and large families
  • Children welcome
  • Setting : Lakeside, Luxuriant
  • Town centre at 2.5mi.
  • Golf, Horse riding, Fishing
6 bedrooms Villa for rent for 14 people
Games room, Luxury Villa in Orlando - Advert 32199
Games room, Luxury Villa in Orlando - Advert 32199

£616* week
Contact
book direct with the owners
from £88/Night*
See the rates
Up to-13%
Depending on the season
39 requests already received
see details
Advert 50836
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Bonner Villa Luxury Villa in a luxury property. not overlooked, swimming pool, nightlights view
Villa Rental in Orlando #50836 >Swimming poolTennisParking
Interior facilities
  • Sleeping area
  • 2 Bathroom
  • Living room
  • Sitting room
  • American style kitchen
  • Dining area
Advantages
  • Countryside holidays
  • Ideal for all age groups
  • Children welcome
  • Setting : Luxuriant, Exclusive
  • 18 hole golf course at 1.25mi.
  • Golf
3 bedrooms Villa for rent for 8 people
Luxury Villa in Orlando - Advert 50836
Pool view, Luxury Villa in Orlando - Advert 50836

£71* Weekend
Contact
book direct with the owners
Night£63*
week£400*
2 weeks£721*
Month£1521*
from £36/Night*
See the rates
Up to-36%
Depending on the season
19 requests already received
see details
Advert 6229PDF
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The complex is in a quiet location so you can relax before venturing out and about. The accommodation is clean and well kept with a lovely view over the lake. It is in easy reach of all facilities and parks. Tropical Pool.

Legacy Dunes Flat-Apartments 1,300 Sq.ft. in a resort. not overlooked, garden/park, lake view

Newly refurbished 4 bedroom condo for rent, 5 miles from Disney World. 10 minutes from all the Orlando attractions. An ideal base for your Orlando vacation.1400 sq feet condo - spacious and fully equipped. Full kitchen with all equipment. Home from Home. Award winning Resort. Amenities include a tropical style swimming pool with fountains, a further swimming pool a few steps away from our condo (both... Flat-Apartments Rental in Kissimmee #6229 >

Swimming poolTennisParking
Interior facilities
  • 2 Bathroom
  • Living room
  • Sitting room
  • American style kitchen
  • Dining area
  • Bar area
Advantages
  • City holidays
  • Ideal for all age groups and family
  • Children welcome
  • Setting : Tropical, Spiritual
  • Town centre at 4.5mi.
  • Golf, Horse riding, Fishing
4 bedrooms Flat-Apartments for rent from 1 to 10 people
Heated swimming pool, Flat-Apartments in Kissimmee - Advert 6229
Heated swimming pool, Flat-Apartments in Kissimmee - Advert 6229
Original swimming pool, Flat-Apartments in Kissimmee - Advert 6229
Heated swimming pool, Flat-Apartments in Kissimmee - Advert 6229
Resort, Flat-Apartments in Kissimmee - Advert 6229
Interior layout and facilities, Flat-Apartments in Kissimmee - Advert 6229

£88* Night
Contact
book direct with the owners
week£616*
from £88/Night*
See the rates
Up to-47%
Depending on the season
6 requests already received
see details
Advert 13433PDF
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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
Living room, House in Kissimmee - Advert 13433
Sitting room, House in Kissimmee - Advert 13433

£95 Weekend
Contact
book direct with the owners
Night£95
week£665
2 weeks£1264
from £48/Night*
See the rates
Up to-24%
Depending on the season
30 requests already received
see details
Advert 12822PDF
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Cumbrian Lakes Villa 2,700 Sq.ft. in an estate. unobscured, lake, street/avenue, fantastic sunset view
Villa Rental in Kissimmee #12822 >Swimming poolParkingBaby chair
Interior facilities
  • 4 Bathroom
  • 4 Shower room
  • 1 WC
  • Living room
  • Sitting room
  • American style kitchen
Advantages
  • Countryside holidays
  • Ideal for all age groups and family groups
  • Children welcome
  • Setting : Country setting, Tranquil
  • Lake at <165'
5 bedrooms Villa for rent from 6 to 10 people
Living room, Villa in Kissimmee - Advert 12822
South-westerly view, Villa in Kissimmee - Advert 12822
Games room, Villa in Kissimmee - Advert 12822
Sitting room, Villa in Kissimmee - Advert 12822


£80* Weekend
Contact
book direct with the owners
Night£72*
week£504*
2 weeks£1009*
Month£1715*
from £40/Night*
See the rates
Up to-31%
Depending on the season
30 requests already received
see details
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
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