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Holiday Rentals in Kissimmee

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    Travellers to Kissimmee are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    15 Matching Rentals in KissimmeeView all 5,569 rentals
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    Kissimmee, Florida, 'Amazing Castle in the Sun with Private South Facing Pool'1 / 28
    (20)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Affordable and Luxurious Ground Floor Condo at Cane Island Resort1 / 23
    (29)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Seasons Villa,5 Bedrooms, Pool with Spa, Gameroom Sleeps 101 / 17
    (25)Very good
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Enchanting Star Lake View House with Balcony, Pool, and Jacuzzi1 / 100
    (10)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Washer
    • Grill
    • Private Indoor Pool
    • Hot Tub
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 July 2017
    Love the area the house was nice and support team helpful. my family enjoyed staying there and are hoping to visit again
    Reviewed 10 July 2017
    Looked into loads of villas before booking this one. Ticked all the boxes at the best price.located just off formosa Blvd, off the 192 so very handy for restaurants, shops...
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    About this property
    This immaculate 4 bedroom, 3 bath, family vacation villa is ideally situated only 3 miles from Disney World! The villa overlooks a tranquil lake, a home to herons and other wildlife all year round, and from here it's a short journey to all the major attractions in and around Orlando. The...
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    Location Information
    Kissimmee, Central Florida 34747
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    DORAL WOODS SECLUDED VILLA1 / 24
    (37)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Hot Tub
    • Washer
    • Private Outdoor Pool (Heated)
    • Secure Parking
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    Was expecting to have difficulty in finding it, with the title etched in my mind but with the satellite navigation, it was no problem. A spacious cul de sac and ample parking on...
    Reviewed 3 October 2017
    We have just arrived back home from spending,,,,,,, another fantastic break at Angies villa.The location is the best. When villa owners describe their pools as...
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    About this property
    AS A RESPONSIBLE OWNER, THE CALENDER FOR THIS PROPERTY IS ALWAYS KEPT UP TO DATE. See my Doral Woods video below and check out the latest updates, links & recommendations on my Doral Woods Florida Villa Facebook page. There's nothing quite like coming home to the comfort of your own luxury villa...
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    Kissimmee, Central Florida 34758
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Affordable Luxury for Your Family Next to Disney1 / 11
    (14)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    • Balcony
    • Wi-Fi
    • DVD Player
    • Hot Tub
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    Everything as advertised very clean and nice. maybe 10-15 minutes from disney parks - but remember disney hotels are 5-10 if you drive and 10-15 by bus so faster by not waiting...
    Reviewed 8 July 2017
    This condo was everything we needed and could ask for, each child had there own bed ages 3, 9, 15. We had a beautiful King to stretch out in after the day was through. We would...
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    About this property
    Windsor Hills is an oasis only a mile from Disney World. Amenities include a huge pool with a water slide, clubhouse, playgrounds, exercise room, putting green, sports area, convenience store and shuttles to major attractions. AAA gives it a 3 diamond rating and units are in high demand. Our...
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    Kissimmee, Central Florida 34747
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Cozy 3 Bedroom 2 Bath Pool home 4 miles to Disney (2157)1 / 14
    (13)Average
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Air Conditioning
    • Washer
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Parking
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 June 2013
    Wonderful location for our place. Great for the money! Yes older pool and home, but in great condition.
    Reviewed 11 June 2011
    Please bring or be prepared to buy cleaning supplies and garbage bags. There was a vacuum and broom with dust pan. You will need soap, paper towels, and tissues. There was only...
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    About this property
    This spacious Three bedroomed home is situated in a peaceful area on the popular Indian Ridge complex. Located only 3 miles for Disney World Resort area, this community features a community swimming pool, tennis courts, a children’s playground, and walking trail.The large Master bedroom has a queen...
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    Kissimmee, Central Florida 34747
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedroom Orlando Vacation Rental awesome locatio1 / 20
    (16)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Air Conditioning
    • Balcony
    • Wi-Fi
    • Patio
    • Washer
    • Grill
    • DVD Player
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 April 2017
    When my family got to Kissimmee we had a rude awakening our logging had been cancelled I just so happen to open up the site and found Jim he had just had a cancellation and a...
    Reviewed 25 April 2016
    Coming from Canada you don't know what you have rented until you arrive. We were very very pleased with the service on line to book our stay. The house, grounds & pool were...
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    About this property
    Our executive villa at island club is one of the most sought after destination resort for families visiting the Orlando area. It has earned this reputation because it boasts one of the best location with Disney World just 4 miles away. So close you can 'See the fireworks from your own back yard'....
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    Kissimmee, Central Florida 34747
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Windsor Hills 3 Bedroom Condo located just 2 minutes from Disney1 / 22
    (1)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Hot Tub
    • Internet Access
    • DVD Player
    • Grill
    • Washer
    • Cable/satellite TV
    • Air Conditioning
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 April 2017
    We rent a condo for a month every year so we have had a lot of experience,both good and bad. This was pretty good. We have stayed at Windsor Palms before so we knew the general...
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    About this property
    BEST Priced Condo at Five Star Windsor Hills! Luxury 3 Bedroom Condo, KING MASTER BED, FREE WIRELESS INTERNET in the Condo, FLAT SCREEN HDTV's ALL ROOMS, DVD PLAYERS, Private Washer/Dryer BEST Priced Condo at Five Star Windsor Hills! Luxury 3 Bedroom Condo, KING MASTER BED, FREE WIRELESS INTERNET...
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    Location Information
    Kissimmee, Central Florida 34747
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Big Pool Villa with a Hot Tub -  September Dates - Christmas1 / 46
    (29)Excellent
    6 Bedrooms, 5 Bathrooms, Sleeps 13 Quick View
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    Amenities & Details
    • Wi-Fi
    • Housekeeping Included
    • Hot Tub
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Cable/satellite TV
    • Air Conditioning
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 August 2017
    I cannot say enough about the Big Pool Villa. The location of the villa was perfect; very close to the parks. The area has plenty of restaurants, souvenir shops, convenience...
    Reviewed 13 August 2017
    Owner very good to deal with and always attentive. Had major issues with wifi with it not working for most of out trip. I contacted Jean and she was always on hand to help. It...
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    About this property
    & Christmas 17 dates available now. Welcome! Our 6 bed 4.2 bath villa is where you want to be only 2 miles from Disney in the prestigious Rolling Hills at Formosa Gardens Estate on a QUIET street. Our villa is in the area known to locals as the Golden Mile. This villa has a stunning 40 foot...
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    Location Information
    Kissimmee, Central Florida 34747
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 13
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    Stunning Lake View 7 bdrms 5.5 baths(4 suites)1 / 40
    (30)Excellent
    7 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    Amenities & Details
    • Waterfront
    • Grill
    • Patio
    • Washer
    • DVD Player
    • Internet Access
    • Hot Tub
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 September 2017
    We stayed at this beautiful and hosted a small party for my mothers 60th birthday. The villa was filled with everything we would possibly need plus more. It's in the most...
    Reviewed 2 March 2017
    Brilliant house. Had a fantastic time while at the property. Very clean and tidy. The instructions from the owner were very clear and helpful
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    About this property
    Lake view private swimming pool and 6 miles away from Disney with excellent access to all of Orlando's Disney theme parks and golf courses, Harmony Villa is the perfect place for your vacation in Florida. Located on the peaceful and exclusive Seasons community in Kissimmee, our brand new furnished...
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    Location Information
    Kissimmee, Central Florida 34746
    Holiday Rental House - 7 Bedrooms, 6 Bathrooms, Sleeps 16
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    Regal Oaks, Old Town, Kissimmee1 / 20
    (36)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • DVD Player
    • Patio
    • Wi-Fi
    • Balcony
    • Hot Tub
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 July 2017
    This house was everything we hoped for and more. It was my special birthday and the owner arranged for a bottle of champagne and a birthday card to be left really nice touch on...
    Reviewed 20 April 2017
    Just back from an amazing 3 week stay at Regal Oaks. It's the perfect location for the theme parks,shops bars and restaurants all within a few minutes walk. It's the first time...
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    About this property
    Our very well equipped, self catering, townhouse is located on the exclusive four star Regal Oaks, a fully managed resort with office and tourist information centre, at Old Town Kissimmee. Ideal for families or groups of up to 8 people. Regal Oaks is now a gated community and a resort offering a...
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    Location Information
    Kissimmee, Central Florida FL34746
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    4 Bedroom Pool Home & Spa - Orlando vacation rental1 / 20
    (1)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Air Conditioning
    • DVD Player
    • Internet Access
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 August 2014
    We spent more than two months last year in Seasons Blvd and it was a great experience. Jim was very helpful in every issue and solved problems promptly.. House was also great...
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    About this property
    Orlando vacation home with private pools located in select community of Seasons. This vacation homes are 'the best option' for families that have 4-10 members, need a little privacy, and enjoy a private pool, garage, spacious patio areas in your own back yard. Looking to get away from the cold...
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    Location Information
    Kissimmee, Central Florida 34746
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bed 3 Bath Townhouse - Windsor Hills Resort1 / 32
    (18)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Balcony
    • Terrace
    • Air Conditioning
    • Internet Access
    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 December 2016
    We recently stayed in this wonderful 3 bed 3 bath Townhouse on Windsor Hill Resort. We had an amazing holiday and the Townhouse was beautiful, very homely and very well...
    Reviewed 13 November 2016
    So glad we chose this townhouse, it was absolutely perfect. Everything we needed was at hand. Very spacious and only a couple of minutes walk to the clubhouse and main pool...
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    About this property
    3 Bed 3 Bath Townhouse. Fabulous 3 bedroom, 3 bathroom townhouse on Windsor Hills Resort. This home is extremely close to the fantstic resort lagoon style zero entry pool and clubhouse with all of its amenities including movie theatre and general store. With our own west facing splash pool...
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    Location Information
    Kissimmee, Central Florida 34747
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Air Conditioning
    • Washer
    • Internet Access
    • Parking
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lindfields has been a firm favorite amongst the neighborhoods along the Disney World Resort area. Within 5 miles of Disney World, its popularity boasts many facets including easy access to shops, restaurants and attractions. A quick hop over to I-4 will take you over to many more attractions that...
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    Location Information
    Kissimmee, Central Florida 34747
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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