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Winter Haven rentals, vacation homes direct from the owners

You will find many studios, apartments, houses and villas for your vacations in Winter Haven. 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 Haven with absolute confidence!
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1 ReviewFantastic house with all amenities located near to the theme parks01/01/2017

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direct by owners
29 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 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 1.25mi.
  • Golf
3 bedrooms Villa for rent from 1 to 6 people
Villa, Villa in Kissimmee - Advert 10141
Southerly view, Villa in Kissimmee - Advert 10141

$2600 Month
Contact
direct by owners
Night$110
week$730
2 weeks$1400
from $87/Night*
See the rates
Up to-10%
Depending on the season
8 requests already received
see details
Advert 28407
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Sunset Ridge Villa in a private estate. not overlooked, swimming pool view
Villa Rental in Davenport #28407 >Swimming poolParking
Interior facilities
  • 2 Bathroom
  • 2 Toilets
  • Living room
  • Sitting room
  • American style kitchen
  • Dining area
Advantages
  • Countryside vacation
  • Ideal for all age groups and family groups
  • Kids welcome
  • Setting : Peaceful, Suitable for a relaxing break
  • 18 hole golf course at 1.25mi.
  • Golf
4 bedrooms Villa for rent for 8 people
The property, Villa in Davenport - Advert 28407
Sitting room, Villa in Davenport - Advert 28407

$125 Night
Contact
direct by owners
from $125/Night*
See the rates
Up to-22%
Depending on the season
9 requests already received
see details
Advert 25703
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Coupe DeVille Villa 1,940 Sq.ft. in an estate. unobscured, not overlooked, country side, swimming pool view
Villa Rental in Davenport #25703 >Swimming poolTennisParking
Interior facilities
  • 3 Bathroom
  • 1 Toilets
  • Living room
  • American style kitchen
  • Dining area
  • Walk-in closet
Advantages
  • Countryside vacation
  • Ideal for all age groups and family groups
  • Kids welcome
  • Setting : Calm, Picturesque
  • Lake at 6mi.
  • Golf
4 bedrooms Villa for rent from 1 to 8 people
South-westerly view, Villa in Davenport - Advert 25703
View from the patio, Villa in Davenport - Advert 25703

$89 Weekend
Contact
direct by owners
Night$79
week$500
2 weeks$900
Month$1900
from $45/Night*
See the rates
Up to-44%
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

$2500 Month
Contact
direct by owners
Night$100
week$650
2 weeks$1300
from $84/Night*
See the rates
Up to-30%
Depending on the season
8 requests already received
see details
Advert 26229PDF
Show map
House 1,940 Sq.ft. in a private property. not overlooked, swimming pool, fantastic sunset view
House Rental in Davenport #26229 >Swimming poolParkingHigh chair
Interior facilities
  • 3 Bathroom
  • Living room 215 Sq.ft.
  • Separate kitchen
  • Dining room
  • Cosy nook
  • Games room
Advantages
  • Countryside vacation
  • Ideal for all age groups and large families
  • Kids welcome
  • Setting : Calm, Suitable for a relaxing break
  • 9 hole golf course at 2.5mi.
  • Golf
4 bedrooms House for rent from 2 to 8 people
Heated swimming pool, House in Davenport - Advert 26229
Living room, House in Davenport - Advert 26229
Kitchen, House in Davenport - Advert 26229
Master bedroom, House in Davenport - Advert 26229

$2500 Month
Contact
direct by owners
week$800
2 weeks$1550
Night$125
from $84/Night*
See the rates
Up to-20%
Depending on the season
2 requests already received
see details
Advert 72463PDF
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There are 4 bedrooms sleeping 9 people (2 master suites) and there are 2 cots One of the master suites is in the garage conversion allowing privacy from the main house ideal for grandparents.

Lindfields Villa 2,150 Sq.ft.. not overlooked, swimming pool, garden/park, city view

With one family bathroom and 2 full ensuites, there is a kitchen, family room, dining room, living/games room and laundry room there's plenty of space. Our villa is fully air conditioned with ceiling fans throughout, cable TV in all bedrooms & a 55 TV, DVD and video in family room, large heated pool (15x30) with extended pool deck full sized screened pool enclosure (will not affect your suntan!) luxuriously... Villa Rental in Four Corners - Kissimmee #72463 >

Swimming poolParkingHigh chair
Interior facilities
  • 2 Bathroom
  • 1 Shower room
  • Living room 150 Sq.ft.
  • Sitting room 150 Sq.ft.
  • Separate kitchen
  • Dining room
Advantages
  • City vacation
  • Ideal for all age groups and couples with baby
  • Setting : Peaceful, Luxurious
  • Bus stop / bus station at 1.85mi.
4 bedrooms Villa for rent from 1 to 9 people
Kitchen, Villa in Four Corners - Advert 72463
Villa in Four Corners - Advert 72463
Swimming pool, Villa in Four Corners - Advert 72463
Master bedroom, Villa in Four Corners - Advert 72463
Equipment at the guest's disposal, Villa in Four Corners - Advert 72463
Twin bed(s), Villa in Four Corners - Advert 72463

$1611* Month
Contact
direct by owners
week$376*
from $54/Night*
See the rates
Up to-52%
Depending on the season
20 requests already received
see details
Advert 59422
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Villa. unobscured, garden/park, street/avenue view
Villa Rental in Haines City #59422 >Swimming poolTennisParking
Interior facilities
  • Sleeping den
  • 1 Bathroom
  • 1 Shower room
  • 2 Toilets
  • Dining room
  • Bar area
Advantages
  • Countryside vacation
  • Ideal for family and senior(s)
  • Kids welcome
  • Setting : Bucolic, Tranquil
  • Meublés de Tourisme
  • Golf, Culture, Fishing
3 bedrooms Villa for rent for 8 people
Surroundings, Villa in Haines City - Advert 59422
Interior, Villa in Haines City - Advert 59422

$2180 Month
Contact
direct by owners
Night$100
week$725
2 weeks$1165
from $73/Night*
See the rates
Up to-43%
Depending on the season
24 requests already received
see details
Advert 50449PDF
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Tupelo Honey Villa 1,940 Sq.ft. in a luxury property. unobscured, not overlooked, swimming pool, garden/park view
Villa Rental in Davenport #50449 >Swimming poolParkingHigh chair
Interior facilities
  • 3 Bathroom
  • Living room
  • Large american style kitchen
  • Dining area
  • Games room
  • Walk-in closet
Advantages
  • Countryside vacation
  • Ideal for family and all age groups
  • Kids welcome
  • Setting : Luxurious, Suitable for a relaxing break
  • 9 hole golf course at 2.5mi.
  • Golf
4 bedrooms Villa for rent for 8 people
Heated swimming pool, Villa in Davenport - Advert 50449
Heated swimming pool, Villa in Davenport - Advert 50449
South-westerly view, Villa in Davenport - Advert 50449
Outside furniture, Villa in Davenport - Advert 50449

$2100 Month
Contact
direct by owners
Night$105
week$700
2 weeks$1600
from $70/Night*
See the rates
Up to-22%
Depending on the season
Theme break
Golf
2 requests already received
see details
Advert 44741
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This freshly decorated upscale villa is located on the grounds of the property, a gated community with 24 hour manned security. The home features a private, south facing swimming pool.

Southern Dunes House 1,600 Sq.ft. in a charming property. swimming pool view
1 Theme break

His 1600 sq. ft. single story villa is comprised of 2 gorgeous master suites; one having direct access to the private pool deck, with king size bed, an en-suite bathroom and large walk in closet. At the front of the home you will find the second master bedroom with queen bed, private en-suite bathroom and large closet. Both of these master bedrooms are equipped with new 24” HD LCD TV’s. Two twin bedrooms,... House Rental in Haines City #44741 >

Swimming poolTennisParking
Interior facilities
  • 3 Bathroom
  • 3 Shower room
  • 3 Toilets
  • Living room
  • Separate kitchen
  • Dining room
Advantages
  • City vacation
  • Ideal for all age groups and family
  • Kids welcome
  • Setting : Isolated, Sporty
  • 18 hole golf course at <165'
  • Golf, Fishing
4 bedrooms House for rent from 1 to 8 people
House in Haines City - Advert 44741
House in Haines City - Advert 44741

$119* Night
Contact
direct by owners
from $119/Night*
See the rates
WEEKEND IDEAS
$119* Night
see details
Advert 31183
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1 SPECIAL OFFER
Weekend ideas
$119* Night8 persBOOK NOW
Villa in a luxury property. not overlooked, swimming pool, garden/park, lake view
Villa Rental in Davenport #31183 >Swimming poolParkingHigh chair
Interior facilities
  • 2 Bathroom
  • 1 Shower room
  • 4 Toilets
  • Living room
  • Games room
  • Laundry room
Advantages
  • City vacation
  • Ideal for all age groups and family
  • Kids welcome
  • Setting : Condusive to shopping, Lakeside
  • High class retailers at 12.5mi.
4 bedrooms Villa for rent from 1 to 8 people
Pool view, Villa in Davenport - Advert 31183
Interior, Villa in Davenport - Advert 31183
Outside setting, Villa in Davenport - Advert 31183
Games room, Villa in Davenport - Advert 31183

$350 Night
Contact
direct by owners
from $350/Night*
See the rates
Up to-42%
Depending on the season
1 request already received
see details
Advert 44506
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House in a private property. village, fantastic sunset view
House Rental in Davenport #44506 >Swimming poolTennis
Interior facilities
  • Sleeping den
  • 5 Bathroom
  • 5 Shower room
  • Living room
  • Sitting room
  • American style kitchen
Advantages
  • City vacation
  • Ideal for all age groups and family groups
  • Kids welcome
  • Setting : Pleasant, Picturesque
  • Golf, Festival, Culture
8 bedrooms House for rent from 2 to 16 people
Interior layout, House in Davenport - Advert 44506
Bedroom, House in Davenport - Advert 44506

Contact
direct by owners
12 requests already received
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Advert 9762
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Tuscan Hills Luxury Villa 1,940 Sq.ft. in a private property. swimming pool view
Villa Rental in Davenport #9762 >Swimming poolTennisParking
Interior facilities
  • 3 Bathroom
  • 1 Toilets
  • Living room
  • Separate kitchen
  • Dining room
  • Games room
Advantages
  • Countryside vacation
  • Ideal for all age groups
  • Kids welcome
  • Setting : Natural, Peaceful
  • Lake at 2.5mi.
  • Golf, Fishing
4 bedrooms Villa for rent from 1 to 8 people
Façade, Luxury Villa in Davenport - Advert 9762
Private swimming pool, Luxury Villa in Davenport - Advert 9762

$179 Night
Contact
direct by owners
from $179/Night*
See the rates
Up to-14%
Depending on the season
8 requests already received
see details
Advert 70627
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The Retreat at Legacy Park Villa 3,800 Sq.ft. in a luxury property. panoramic, country side, swimming pool, garden/park view
Villa Rental in Davenport #70627 >Swimming poolParkingHigh chair
Interior facilities
  • Sleeping den
  • 4 Bathroom
  • Living room
  • Sitting room
  • Large american style kitchen
  • Dining room
Advantages
  • Countryside vacation
  • Ideal for all age groups and family groups
  • Kids welcome
  • Setting : Luxurious, Condusive to shopping
  • Forest at 330'
  • Gay friendly
  • Golf, Culture
5 bedrooms Villa for rent for 12 people

$125* 2 weeks
Contact
direct by owners
Night$71*
Weekend$205*
week$500*
Month$1998*
from $9/Night*
See the rates
Up to-88%
Depending on the season
58 requests already received
see details
Advert 13916
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Bridgewater crossing Villa 1,940 Sq.ft. in a luxury property. not overlooked, swimming pool, lake view
Villa Rental in Davenport #13916 >Swimming poolTennisParking
Interior facilities
  • 3 Bathroom
  • 3 Shower room
  • Living room
  • Sitting room
  • American style kitchen
  • Dining room
Advantages
  • Countryside vacation
  • Ideal for all age groups and family
  • Kids welcome
  • Setting : Suitable for a relaxing break, Luxurious
  • Lake at 4.5mi.
  • Golf, Horse riding, Fishing
4 bedrooms Villa for rent for 8 people
Villa in Davenport - Advert 13916
Villa in Davenport - Advert 13916


$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
see details
Advert 20316PDF
Show map
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