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Winter Park rentals, vacation homes direct from the owners

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You will find many studios, apartments, houses and villas for your vacations in Winter Park. Contact the owners directly on the IHA site and enjoy the best rental rates, promotions and last minute deals that meet your budget. Visit the photo gallery on private rentals for a break with family or friends. All vacation listings on IHA are verified, plan your trip to Winter Park with absolute confidence!
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87 Results
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$125 Night
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direct by owners
from $125/Night*
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Up to-30%
Depending on the season
68 requests already received
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Advert 52637
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Westridge House 2,370 Sq.ft in a luxury property. swimming pool view
House Rental in Orlando #52637 >Swimming poolParking
Interior facilities
  • Sleeping den
  • 3 Bathroom
  • Living room
  • Sitting room
  • Separate kitchen
  • Dining room
Advantages
  • City vacation
  • Ideal for all age groups and large families
  • Kids welcome
  • Setting : Luxurious, Peaceful
  • 18 hole golf course at 1.5mi.
  • Golf, Fishing
5 bedrooms House for rent for 10 people
Single family home, House in Orlando - Advert 52637
Living room, House in Orlando - Advert 52637

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direct by owners
15 requests already received
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Advert 21027
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Vista Cay Resort Penthouse 2,150 Sq.ft. in a residence. lake view
Apartment-Flat Rental in Orlando #21027 >Swimming poolParking
Interior facilities
  • Sleeping den
  • 2 Bathroom
  • 2 Shower room
  • Living room
  • Sitting room
  • Separate kitchen
Advantages
  • City vacation
  • Ideal for all age groups and family
  • Kids welcome
  • Setting : City, Picturesque
  • Ecotourism
3 bedrooms Apartment-Flat for rent for 8 people

$99 Night
Contact
direct by owners
from $99/Night*
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Up to-43%
Depending on the season
5 requests already received
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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 vacation
  • Ideal for all age groups and family
  • Kids welcome
  • Setting : Pleasant, Lively
  • Downtown 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

$157 Night
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direct by owners
from $157/Night*
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18 requests already received
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Advert 53363
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Apartment-Flat in a golf/resort. panoramic, unobscured, swimming pool, garden/park view
Apartment-Flat Rental in Orlando #53363 >Swimming poolTennisParking
Interior facilities
  • Sitting room
  • Separate kitchen
  • Dining room
  • Tv den
  • Fitness room
  • Laundry room
Advantages
  • City vacation
  • Ideal for all age groups and family
  • Kids welcome
  • Setting : Urban, Heavenly
  • Meublés de Tourisme : 5 stars
  • Golf
2 bedrooms Apartment-Flat for rent for 4 people

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direct by owners
3 requests already received
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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 Toilets
  • Living room 205 Sq.ft.
  • Sitting room 150 Sq.ft.
  • Large american style kitchen
Advantages
  • City vacation
  • Ideal for large families and family groups
  • Kids welcome
  • Setting : Lakeside, Quiet
4 bedrooms House for rent from 1 to 10 people

$493* week
Contact
direct by owners
from $71/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 poolParkingHigh chair
Interior facilities
  • 2 Bathroom
  • Living room
  • Sitting room
  • Separate kitchen
  • Dining room
  • Dining area
Advantages
  • Countryside vacation
  • Ideal for family groups and senior(s)
  • Kids welcome
  • Setting : Lakeside, Luxuriant
  • Downtown 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

$3247* Month
Contact
direct by owners
Night$119*
week$831*
2 weeks$1661*
from $109/Night*
See the rates
Up to-30%
Depending on the season
54 requests already received
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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 poolParkingHigh chair
Interior facilities
  • Sleeping den
  • 4 Bathroom
  • 1 Shower room
  • 1 Toilets
  • Living room 750 Sq.ft.
  • Sitting room 700 Sq.ft.
Advantages
  • City vacation
  • Ideal for all age groups and large families
  • Kids 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

$999* week
Contact
direct by owners
from $144/Night*
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Up to-11%
Depending on the season
42 requests already received
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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 poolParkingHigh chair
Interior facilities
  • Sleeping den
  • Living room
  • Separate kitchen
  • Dining area
  • Tv den
  • Games room
Advantages
  • Countryside vacation
  • Ideal for all age groups and large families
  • Kids welcome
  • Setting : Lakeside, Luxuriant
  • Downtown 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

$145 Night
Contact
direct by owners
week$1015
from $145/Night*
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Up to-12%
Depending on the season
3 requests already received
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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 poolParkingHigh chair
Interior facilities
  • 3 Bathroom
  • Living room
  • Sitting room
  • American style kitchen
  • Dining room
  • Dining area
Advantages
  • Countryside vacation
  • Ideal for all age groups and family groups
  • Kids 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 den, 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

$3400 Month
Contact
direct by owners
Night$150
week$910
2 weeks$1820
from $114/Night*
See the rates
Up to-21%
Depending on the season
16 requests already received
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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 poolParkingHigh chair
Interior facilities
  • 2 Bathroom
  • Living room
  • Large american style kitchen
  • Dining area
  • Cosy nook
  • Loggia
Advantages
  • City vacation
  • Ideal for all age groups and couples
  • Kids 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

$89 Weekend
Contact
direct by owners
Night$79
week$500
2 weeks$900
Month$1900
from $45/Night*
See the rates
Up to-36%
Depending on the season
20 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 Apartment-Flat 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... Apartment-Flat Rental in Kissimmee #6229 >

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

$99 Night
Contact
direct by owners
from $99/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 den
  • 3 Bathroom
  • 3 Shower room
  • Living room
  • Separate kitchen
  • Dining room
Advantages
  • City vacation
  • Ideal for all age groups and large families
  • Kids 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

$1249* Month
Contact
direct by owners
week$437*
2 weeks$749*
from $42/Night*
See the rates
28 requests already received
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Advert 13980
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House in a charming property.
House Rental in Kissimmee #13980 >Swimming poolTennisParking
Interior facilities
  • 2 Bathroom
  • 2 Toilets
  • Living room
  • American style kitchen
  • Dining area
  • Laundry room
Advantages
  • City vacation
  • Ideal for all age groups and honeymoon
  • Kids welcome
  • Setting : Suitable for a relaxing break, Condusive to shopping
  • Golf
3 bedrooms House for rent from 2 to 6 people
Single family home, House in Kissimmee - Advert 13980
House in Kissimmee - Advert 13980

$1092 week
Contact
direct by owners
from $156/Night*
See the rates
Up to-26%
Depending on the season
31 requests already received
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Advert 21999
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OSPREY VIEW Villa 2,700 Sq.ft. in a charming property.
Villa Rental in Orlando #21999 >
Interior facilities
  • 3 Bathroom
  • Living room
  • Sitting room
  • Separate kitchen
  • Dining room
  • Dining area
Advantages
  • City vacation
  • Ideal for all age groups
  • Kids welcome
  • Setting : Peaceful, Exclusive
4 bedrooms Villa for rent for 8 people
Living room, Villa in Orlando - Advert 21999
Living room, Villa in Orlando - Advert 21999


$525* week
Contact
direct by owners
Night$81*
from $75/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 vacation
  • Ideal for all age groups and family groups
  • Kids 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
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