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Winter Park rentals, vacation homes direct from the owners

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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₱29249* week
Contact
direct by owners
Night₱4527*
from ₱4178/Night*
See the rates
Up to-36%
Depending on the season
102 requests already received
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 180m² 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 >50km
  • 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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₱6630* Night
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direct by owners
from ₱6630/Night*
See the rates
Up to-30%
Depending on the season
72 requests already received
Advert 52637
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Westridge House 220m² 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 2,5km
  • 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
Advert 21027
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Vista Cay Resort Penthouse 200m² 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
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₱55712* week
Contact
direct by owners
from ₱8009/Night*
See the rates
Up to-11%
Depending on the season
42 requests already received
Advert 32199
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Crescent Lakes Luxury Villa 280m² 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 4km
  • 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
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₱40843* week
Contact
direct by owners
from ₱5835/Night*
See the rates
Up to-13%
Depending on the season
43 requests already received
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 den
  • 2 Bathroom
  • Living room
  • Sitting room
  • American style kitchen
  • Dining area
Advantages
  • Countryside vacation
  • Ideal for all age groups
  • Kids welcome
  • Setting : Luxuriant, Exclusive
  • 18 hole golf course at 2km
  • Golf
3 bedrooms Villa for rent for 8 people
Luxury Villa in Orlando - Advert 50836
Pool view, Luxury Villa in Orlando - Advert 50836
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₱8328* Night
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direct by owners
from ₱8328/Night*
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19 requests already received
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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₱57922* week
Contact
direct by owners
from ₱8275/Night*
See the rates
Up to-26%
Depending on the season
33 requests already received
Advert 21999
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OSPREY VIEW Villa 250m² 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
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₱10608* Night
Contact
direct by owners
from ₱10608/Night*
See the rates
Up to-50%
Depending on the season
37 requests already received
Advert 26315PDF
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Come and relax in this family friendly home close to the Disney Parks. The house features 7 bedrooms, 4.5 Bathrooms, with televisions and DVD players. Relax on the sun deck and in the pool without out being overlooked.

Emerald Island Resort Villa 280m² in a resort. unobscured, not overlooked, swimming pool, fantastic sunset view

There are 2 King Bedrooms, 2 Queen Bedrooms, 2 Twin Bedrooms and one bunk bedroom with two sets of bunks. The house also includes a Highchair, Stroller's and 2 cots/cribs for the itty-bitty travelers. The house has a large living area and a fully equipped kitchen, perfect for family and friends to relax together. The fabulous pool with a child safety fence backs onto a conservation area for those quiet... Villa Rental in Kissimmee #26315 >

Swimming poolTennisParking
Interior facilities
  • 5 Bathroom
  • 4 Shower room
  • Living room
  • Sitting room
  • Separate kitchen
  • Dining room
Advantages
  • City vacation
  • Ideal for all age groups and large families
  • Kids welcome
  • Setting : Luxurious, Pleasant
  • Heated swimming pool at 100m
7 bedrooms Villa for rent from 2 to 16 people
View from the swimming pool, Villa in Kissimmee - Advert 26315
Dining area, Villa in Kissimmee - Advert 26315
Living room, Villa in Kissimmee - Advert 26315
Kitchen, Villa in Kissimmee - Advert 26315
Kitchen Area, Villa in Kissimmee - Advert 26315
Living room, Villa in Kissimmee - Advert 26315
View the advert

₱4721* Weekend
Contact
direct by owners
Night₱4190*
week₱26521*
2 weeks₱47738*
Month₱100780*
from ₱2387/Night*
See the rates
Up to-44%
Depending on the season
24 requests already received
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 120m² 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 7,5km
  • Golf, Horse riding, Fishing
4 bedrooms Apartment-Flat for rent from 1 to 10 people
Single family home, Apartment-Flat in Kissimmee - Advert 6229
The apartment house/building, Apartment-Flat in Kissimmee - Advert 6229
Single family home, Apartment-Flat in Kissimmee - Advert 6229
Heated swimming pool, Apartment-Flat in Kissimmee - Advert 6229
The property, Apartment-Flat in Kissimmee - Advert 6229
King-size bed(s), Apartment-Flat in Kissimmee - Advert 6229
View the advert

₱8487* Night
Contact
direct by owners
week₱59407*
from ₱8487/Night*
See the rates
Up to-11%
Depending on the season
3 requests already received
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 220m² 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 2km
  • 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
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₱5569* Night
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direct by owners
from ₱5569/Night*
See the rates
Up to-20%
Depending on the season
13 requests already received
Advert 2224
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Stay in our clean, safe and secure 4 bedroom townhouse in the gated community of Venetian Bay Villages, Kissimmee, FL for your visit to Florida

Venetian Bay Village Town House 150m² in a private property. swimming pool, courtyard, lake, village view

Plenty of room for your entire family, all together in one private townhouse in the gated community of Venetian Bay Villages. with 4 pools, 4 children play areas, a game room, 24 hour private security. you can feel secure your family will have a great time enjoying the Florida sun, the Disney parks, Universal and Sea World. House Rental in Kissimmee #2224 >

Swimming poolTennisParking
Interior facilities
  • 3 Bathroom
  • Living room
  • Kitchen Area
  • Dining room
  • Dining area
  • Laundry room
Advantages
  • Countryside vacation
  • Ideal for all age groups and large families
  • Kids welcome
  • Setting : Exclusive
  • Lake at 50m
  • Golf, Horse riding, Fishing
4 bedrooms House for rent from 1 to 10 people
Handicapped people welcome, Town House in Kissimmee - Advert 2224
View from the patio, Town House in Kissimmee - Advert 2224
Shared swimming pool, Town House in Kissimmee - Advert 2224
Outside setting, Town House in Kissimmee - Advert 2224
Large bedroom, Town House in Kissimmee - Advert 2224
Covered terrace, Town House in Kissimmee - Advert 2224
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45 requests already received
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 USA Villa 180m² 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 poolParkingHigh chair
Interior facilities
  • 2 Bathroom
  • 2 Toilets
  • Living room
  • Sitting room
  • American style kitchen
  • Dining room
Advantages
  • Countryside vacation
  • Ideal for all age groups
  • Kids welcome
  • Setting : Country setting
  • 18 hole golf course at 2km
  • Golf
3 bedrooms Villa for rent from 1 to 6 people
Villa, Villa in Kissimmee - Advert 10141
Southerly view, Villa in Kissimmee - Advert 10141
View the advert

₱4774* Weekend
Contact
direct by owners
Night₱4243*
week₱29173*
from ₱2387/Night*
See the rates
Up to-39%
Depending on the season
101 requests already received
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 poolParkingHigh chair
Interior facilities
  • Living room
  • Sitting room
  • Separate kitchen
  • Dining room
  • Dining area
  • Games room
Advantages
  • Countryside vacation
  • Ideal for all age groups
  • Kids welcome
  • Setting : Luxuriant, Peaceful
  • Lake at <50m
  • 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
View the advert

₱58081* week
Contact
direct by owners
from ₱8328/Night*
See the rates
Up to-23%
Depending on the season
12 requests already received
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 220m² 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 vacation
  • Ideal for large families and all age groups
  • Kids welcome
  • Setting : Quiet, Peaceful
  • Lake at 7,5km
  • Golf, Horse riding, Fishing
5 bedrooms Villa for rent from 2 to 12 people
View from the living room, Villa in Kissimmee - Advert 16912
King-size bed(s), Villa in Kissimmee - Advert 16912
View the advert


₱26468* Weekend
Contact
direct by owners
Night₱21164*
week₱105554*
from ₱13261/Night*
See the rates
Up to-67%
Depending on the season
28 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 400m² 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 den
  • 5 Bathroom
  • 5 Shower room
  • 1 Toilets
  • Living room
  • Sitting room
Advantages
  • City vacation
  • Kids welcome
  • Setting : Enchanting
  • Village center at 800m
  • 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