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Winter Park rentals, holiday lettings direct from the owners

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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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£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

£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

£877* week
Contact
book direct with the owners
from £126/Night*
See the rates
Up to-23%
Depending on the season
10 requests already received
see details
Advert 16912
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We have Two 5 bedrooms, 4 Bathromes homes just one mile from Hwy 192 and Walmart, and 7 miles from Disney Property. This home has a large pool and Hot Tub and has Free Wi-Fi and Free Worldwide Phone calls and Games Room. Two King Masters.

Indian Point Villa 2,370 Sq.ft in a luxury property. swimming pool view

5 Bed 4 Bath Home with Pool and Hot Tub. The home has a fully fitted Kitchen, Games Room with Pool Table; Commercial Grade Washer and Dryer; Full Air Con as well as fans in most rooms for added comfort. Large Lounge and Dining Area as well as Breakfast Nook off the Kitchen. Bedrooms are 2 King Size and 1 Queen, + 1 Twin bedroom and 1 Bunk bed room that sleeps 3. There is also a roll away bed for a... Villa Rental in Kissimmee #16912 >

Swimming poolTennisParking
Interior facilities
  • 4 Bathroom
  • Living room
  • Sitting room
  • Separate kitchen
  • Dining room
  • Cosy nook
Advantages
  • Countryside holidays
  • Ideal for large families and all age groups
  • Children welcome
  • Setting : Quiet, Peaceful
  • Lake at 4.5mi.
  • Golf, Horse riding, Fishing
5 bedrooms Villa for rent for 12 people
View from the living room, Villa in Kissimmee - Advert 16912
Super king-size bed(s), Villa in Kissimmee - Advert 16912
Super king-size bed(s), Villa in Kissimmee - Advert 16912
Bedroom, Villa in Kissimmee - Advert 16912
Child's room, Villa in Kissimmee - Advert 16912
Guest bedroom, Villa in Kissimmee - Advert 16912

£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

£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

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

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

£420 week
Contact
book direct with the owners
from £60/Night*
See the rates
Up to-28%
Depending on the season
23 requests already received
see details
Advert 38905
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Villa > 0.25 acre in a private property. not overlooked, swimming pool, forest, fantastic sunset view
Villa Rental in Kissimmee #38905 >Swimming poolParkingBaby chair
Interior facilities
  • 2 Bathroom
  • Shower room
  • WC
  • Living room 860 Sq.ft.
  • Sitting room
  • Separate kitchen
Advantages
  • City holidays
  • Setting : Peaceful, Quiet
  • Golf, Horse riding, Fishing
3 bedrooms Villa for rent from 1 to 8 people
North-easterly view, Villa in Kissimmee - Advert 38905
Villa, Villa in Kissimmee - Advert 38905

£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

£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

£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

£420 week
Contact
book direct with the owners
Night£65
from £60/Night*
See the rates
Up to-36%
Depending on the season
77 requests already received
see details
Advert 5295
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Welcome to our beautiful home in Florida. We offer the utmost in luxury and convenience just few minutes from Disney World.

Sunset Lodge - Glenbrook Villa 1,940 Sq.ft. in an estate. not overlooked view

Our executive villa is fully air-conditioned and features two master bedrooms each with an en-suite bathroom and two further twin bedrooms which share the third bathroom. All bedrooms have a TV. With a sofa bed in the family room, the villa is suitable for up to 10 people. The family room has a 46-inch HD TV with a DVD player and Playstation 2, and gives direct access to the patio area with its outdoor... Villa Rental in Orlando #5295 >

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 and family groups
  • Children welcome
  • Setting : Peaceful, Luxuriant
  • Sandy beach at >31mi.
  • Golf
4 bedrooms Villa for rent for 10 people
Heated swimming pool, Villa in Orlando - Advert 5295
Living room, Villa in Orlando - Advert 5295

£126* Night
Contact
book direct with the owners
from £126/Night*
See the rates
18 requests already received
see details
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

£79* Night
Contact
book direct with the owners
from £79/Night*
See the rates
Up to-43%
Depending on the season
5 requests already received
see details
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


£72* Weekend
Contact
book direct with the owners
Night£64*
week£440*
from £36/Night*
See the rates
Up to-39%
Depending on the season
81 requests already received
see details
Advert 46191
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Disney Lakeside Villa, 4 Bed / 2 Bath overlooking lake and conservation area. With Private south-facing pool and patio. Only 10 mins from Disney.

Villa in a charming property. country side, swimming pool, garden/park, lake view

This fully A/C, 4 Bed / 2 Bath very spacious villa, sleeps 8, has been furnished to a very high standard. With Formal Living Room, Dining Room, fully-fitted Kitchen, Breakfast area and Family Room. Plus laundry Area and Games Room. Master Bedroom with Ensuite, Queen Double, 2 Twin Bedrooms, one which is Disney-themed and Family Bathroom. Cable TV’s and DVD’s in Family Room and bedrooms, Hi Fi System... Villa Rental in Kissimmee #46191 >

Swimming poolParkingBaby chair
Interior facilities
  • Living room
  • Sitting room
  • Separate kitchen
  • Dining room
  • Dining area
  • Games room
Advantages
  • Countryside holidays
  • Ideal for all age groups
  • Children welcome
  • Setting : Luxuriant, Peaceful
  • Lake at <165'
  • Golf, Horse riding, Fishing
4 bedrooms Villa for rent from 1 to 8 people
Villa, Villa in Kissimmee - Advert 46191
View from the living room, Villa in Kissimmee - Advert 46191
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