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Kissimmee Luxury Holiday Homes

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    Travellers to Kissimmee are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    755 Matching Rentals in KissimmeeView all 5,032 rentals
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    New Opening 8br/6ba pool villa from $260/nt ,Close to Disney1 / 66
    (7)Very good
    8 Bedrooms, 6 Bathrooms, Sleeps 18 Quick View
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    New Opening 9 Br/6 Ba luxurious Pool House from $300/nt, Close To Disney1 / 63
    (4)Excellent
    9 Bedrooms, 6 Bathrooms, Sleeps 20 Quick View
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    Grand Opening! luxury Disney Villa for large group1 / 90
    (1)Excellent
    9 Bedrooms, 6 Bathrooms, Sleeps 22 Quick View
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    Brand New 8br/6ba pool villa from $260/nt ,Close to Disney1 / 64
    (12)Very good
    8 Bedrooms, 6 Bathrooms, Sleeps 18 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Sauna
    • Wi-Fi
    • Children's Pool
    • DVD Player
    • Housekeeping Included
    • Air Conditioning
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 November 2018
    We loved this house! It was perfect for our party of 14. There were minor issues, but I've never seen a rental house that didn't have a few kinks. The layout was so nice we're...
    Reviewed 25 August 2018
    This was the first time our family rented a home in Orlando area. I would definitely do it again. The size and style/decor was perfect for our family which included...
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    About this property
    Windsor at Westside Resort is one of the newest and most luxurious resort communities in the Orlando/Kissimmee,Developed by one of the nation's largest developer , the Pulte Homes. Just 8 miles from Disney, and within easy reach to all the attractions, shopping, and dining in the Disney area, this...
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    Kissimmee, Central Florida 34747
    Holiday Rental House - 8 Bedrooms, 6 Bathrooms, Sleeps 18
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    New Vacation - Near Disney 6BE/5BA1 / 41
    (5)Excellent
    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Grill
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • DVD Player
    • Patio
    • Private Indoor Pool
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 August 2017
    The owner of this home was very professional! He made sure that we had a great stay and also even got us a good deal at Walt Disney World which was awesome! The house was...
    Reviewed 2 August 2017
    We were 3 families and 12 people in total. The house was perfect and beatiful.  Everything was neat and clean. The kids enjoyed the pool and game room. We all enjoyed the space...
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    About this property
    This spacious home-away-from-home offers a luxurious and well-designed living space – with professionally furnished and decorated rooms and decor. This terrific home offers 6 bedrooms to sleep up to 14 guests, and the private, screened pool has a crystal clear pool to enjoy, as well as a...
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    Kissimmee, Central Florida 34746
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 14
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    BEAUTIFUL 7 Bedroom 5 Bathroom Solara  Resort Vill1 / 147
    (2)Very good
    7 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Parking
    • Private Outdoor Pool (Unheated)
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 May 2019
    Nice comfortable house, a few minor problems addressed well by owners. Window blinds could have been better. Fairly close to Disney parks.
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    About this property
    We invite you to enjoy our wonderful home on your next trip to Orlando. Absolutely perfect for multi-family groups, or golf groups, this property features all the comforts of home and more! Book your vacation now at this beautiful home with pool and spa located in the gorgeous Solaora Resort. Plus...
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    Kissimmee, Central Florida 34746
    Holiday Rental House - 7 Bedrooms, 5 Bathrooms, Sleeps 14
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    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Wi-Fi
    • DVD Player
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    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This six bedroom beautifully decorated home features an east facing pool and has all the comforts of a perfect vacation home for your enjoyment in Trafalgar Village Resort, which offers a unique Resort experience. Located about 15 minutes from the Disney theme park area, this is an ideal location...
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    Kissimmee, Central Florida 34758
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    8 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
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    About this property
    Located just minutes from Disney, this beautiful two-story 8-bedroom, 6-bathroom Windsor Westside vacation home has all the comforts of home and everything you need for your vacation. Enjoy the home’s convenient location to Disney attractions and its luxury features and amenities including 3...
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    Kissimmee, Central Florida 34747
    Holiday Rental House - 8 Bedrooms, 6 Bathrooms, Sleeps 16
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    10 bedroom new home beautifully decorated1 / 36
    (2)Very good
    10 Bedrooms, 8 Bathrooms, Sleeps 20 Quick View
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    • Private Outdoor Pool (Unheated)
    • Parking
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Be ready for an amazing vacation when staying in this beautiful home. Located in the exclusive gated community of Sonoma Resort, a brand-new vacation rental resort located next to 'The Loop', a premier shopping and entertainment mecca, jut 10 minutes from Disney parks, as upscale brand outlets,...
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    Kissimmee, Central Florida 34741
    Condo/Apartment - 10 Bedrooms, 8 Bathrooms, Sleeps 20
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    Brand New 9br/6ba pool villa from $300/nt,Close to Disney1 / 71
    (13)Very good
    9 Bedrooms, 6 Bathrooms, Sleeps 20 Quick View
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    • Sauna
    • Children's Pool
    • DVD Player
    • Hot Tub
    • Air Conditioning
    • Housekeeping Included
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 June 2017
    We booked this house for our beach wedding. The owner was amazing to deal with and never had an issue. When we go to Florida again we will definitely book with this owner.
    Reviewed 17 November 2016
    We enjoyed our stay at this spacious, well furnished house. Initial issues with the pump in the pool and with domestic cleaning were quickly resolved by the owners' representative
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    About this property
    Windsor at Westside Resort is one of the newest and most luxurious resort communities in the Orlando/Kissimmee,Developed by one of the nation's largest developer , the Pulte Homes. Just 8 miles from Disney, and within easy reach to all the attractions, shopping, and dining in the Disney area, this...
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    Kissimmee, Central Florida 34747
    Holiday Rental House - 9 Bedrooms, 6 Bathrooms, Sleeps 20
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    10 Bedrooms, 8 Bathrooms, Sleeps 20 Quick View
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    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Parking
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sonoma Resort is a brand new vacation rental resort located next to 'The Loop', a premier shopping and entertainment mecca, jut 10 minutes from Disney parks, as upscale brand outlets, malls and numerous championship golf courses. The resort offers Sonoma offers exceptional amenities to include a...
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    Kissimmee, Central Florida 34741
    Condo/Apartment - 10 Bedrooms, 8 Bathrooms, Sleeps 20
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    Beautiful luxurious home close to Disney, Kissimmee1 / 140
    (12)Excellent
    8 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    • Cable/satellite TV
    • Housekeeping Included
    • Hot Tub
    • Children's Pool
    • Patio
    • Washer
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 March 2019
    This house was exactly as pictured - accommodated all 12 of us - was well equipped with kitchen essentials and lots of towels and bedding etc. No complaints at all - would...
    Reviewed 22 January 2019
    Beautiful clean home. Plenty of room for my children, grandchildren and myself. Loved everything from the well stocked kitchen to the comfy mattresses. The pool/hot tub in the...
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    About this property
    Our. Wonderful holiday home, On Windsor at Westside, a gated community. Minutes from Disney . Our home has a large private South East facing pool and spa. The screened patio / lanai has been extended to give more room to sunbath. Or to lounge and relax. The largest on the community. Guests also...
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    Kissimmee, Central Florida 34747
    Holiday Rental House - 8 Bedrooms, 6 Bathrooms, Sleeps 16
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    7 Bedrooms, 8 Bathrooms, Sleeps 17 Quick View
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    • Grill
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    When you've exhausted yourselves at the parks - take a day relaxing by your private, crystal clear pool. In the evenings, have fun with the family in the games room, or take some time to explore the clubhouse at the fabulous Sonoma Resort. Luxury Orlando vacation rental!Our fully furnished...
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    Kissimmee, Central Florida 34741
    Holiday Rental House - 7 Bedrooms, 8 Bathrooms, Sleeps 17
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    W157 - 4 Bedroom Reunion Villa With Guest Suite1 / 31
    (1)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Grill
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 March 2018
    We stayed here the last week of February and the first week of March, great property, no issues, the property management company was very responsive and made a point to stop by...
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    About this property
    Located on Excitement Drive in the Liberty Bluff section of the Reunion Resort, this beautiful executive family home is Pet Friendly all year round for all durations. The gorgeous courtyard style design offers three bedrooms in the main house and a separate guest suite across the courtyard. A...
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    Kissimmee, Central Florida 34747
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Amazing 8 Bedrooms 7 bath Orlando Villa with private pool | 6 miles from Disney1 / 42
    (16)Excellent
    8 Bedrooms, 7 Bathrooms, Sleeps 18 Quick View
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    • Washer
    • DVD Player
    • Cable/satellite TV
    • Air Conditioning
    • Hot Tub
    • Patio
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 February 2019
    I looked at countless airbnb rentals and was going back and forth between wanting to stay on property at Disney or going the rental route. After reading several reviews on...
    Reviewed 8 January 2019
    Touching by Lovely host Lily invited, have the chance to visit the Paradise Florida - ‘Hawaii in Land’ by using my words. The most Americans think they should go once in their...
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    About this property
    This NEW Orlando 8-bedroom seven bath Encore Reunion luxury home is 6 miles away from Disney World. It is the perfect home for Orlando Vacation to go to Disney World, Epcot, Disney Hollywood, Universal Studio, Sea World and other theme parks. Situated in a highly sought-after Liberty Bluff...
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    Kissimmee, Central Florida 34747
    Holiday Rental House - 8 Bedrooms, 7 Bathrooms, Sleeps 18
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    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Wi-Fi
    • Parking
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This outstanding custom built three story home offers space and comfort for a multi family vacation. The imposing floor plan has been furnished with families in mind so therefore offers comfort and relaxation to its guests. The location on the Legends Corner division of the world renowned Reunion...
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    Kissimmee, Central Florida 34747
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    Stunning Family Villa with Lakeside Views - Pool & Spa - Movie Room - Games Room1 / 60
    (2)Very good
    6 Bedrooms, 7 Bathrooms, Sleeps 15 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Patio
    • Hot Tub
    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    Very spacious and comfortable villa for 2 families. Modern decor. Good, quiet location (30 mins drive to Disney World). Children particularly enjoyed the cinema room and pool...
    Reviewed 31 May 2018
    This was our second time staying in Bella Vida resort which is a fantastic location, with a huge Walmart just 10 minutes walk away and designer outlets and factory shops also...
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    About this property
    Sitting on the Bella Vida resort (gated) is this stunning, 6 bedroom vacation home, offering amazing lakeside views. The home is well decorated with a spacious pool deck, good-sized private pool with integrated spa, luxurious home theatre and an air conditioned games room. Situated just off the...
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    Kissimmee, Central Florida 34746
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 15
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    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
    • Grill
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    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Overview The 4 bedroom Blue House as this superb home is known commands an impressive position on Excitement Drive in the Homestead community of the Reunion Resort and Spa. From the first floor balcony the view of the fairway is unobstructed for the golf enthusiast. The Reunion Resort spa is...
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    Kissimmee, Central Florida 34747
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    Jungle Book Bungalow1 / 39
    (1)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Hot Tub
    • Wi-Fi
    • Air Conditioning
    • Grill
    • Shared Outdoor Pool (Unheated)
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 October 2016
    Just returned back to the UK from this townhouse and would definitely love to stay here again! The house itself is spacious, I don't think the photos do it justice. There are...
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    About this property
    This two story four bedroom three and a half bathroom townhome is located in Regal Oaks: the perfect location for your next Orlando getaway. Situated right behind Old Town with Fun Spot right next door, entertainment abounds. Take a stroll down the brick lined street of Old Town and wander into...
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    Kissimmee, Central Florida 34746
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Elegant 8 Bedroom Private Pool/Spa Villa 3 miles to Disney1 / 100
    (11)Very good
    8 Bedrooms, 5 Bathrooms, Sleeps 19 Quick View
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    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Internet Access
    • Washer
    • Hot Tub
    • Air Conditioning
    • Sauna
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 December 2017
    Location: was ideal, attractions are easily available. Community is safe, well maintained, reception was very polite and helpful in answering questions and addressing any...
    Reviewed 3 April 2017
    Loved this place private pool and enough room! Very close to all Disney parks. All very clean nice game room also!
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    About this property
    Only 3 miles to Disney, 14 miles to SeaWorld, 17 miles from Universal Studio and easy access to all major theme parks, this lovely 8 bedroom 4.5 bath heated pool/spa villa is located on the prestigious Emerald Island Resort, a beautiful community with 24/7 guarded gate.This spacious villa can...
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    Kissimmee, Central Florida 34747
    Holiday Rental House - 8 Bedrooms, 5 Bathrooms, Sleeps 19
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    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This luxurious home is located on the prestigious Muirfield Loop within Legends Corner on Reunion Resort. The home was custom built and is extremely spacious with soaring ceilings, natural stone, grand pillars, and a dramatic gallery landing overlooking the entrance hall. All bedrooms are...
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    Kissimmee, Central Florida 34747
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    14 Bedrooms, 14 Bathrooms, Sleeps 30 Quick View
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    • Private Outdoor Pool (Heated)
    • Internet Access
    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This magnificent luxury vacation home is located in Reunion Resort Orlando Florida. Offering over 14,500 sq. ft of luxury accommodation under roof with 12,160 sq.ft heated and cooled. Family Reunion's This vacation rental home is perfect for large multi-generation family reunion's, prepare...
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    Kissimmee, Central Florida 34747
    Holiday Rental House - 14 Bedrooms, 14 Bathrooms, Sleeps 30
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    SEC84021 / 32
    (9)Excellent
    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Waterfront
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Hot Tub
    • Central Heating
    • Washer
    • Internet Access
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 June 2017
    The home is beautiful ! We had an awesome vacation. 4 master suites each with a bathroom plus 2 extra bedrooms for children and a theater room and pool made it so very...
    Reviewed 20 December 2016
    Amazing home close to Disney and various Orlando attractions!!! This home is fully equipped. The movie theater game room was fantastic!!! This home is a vacation in and of...
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    About this property
    This executive villa, “Paradise Falls,” in the stunning Emerald Island resort just entered the vacation rental market in July 2015 for the first time ever! The entire 6 bedroom 5 and a half bathroom villa was professionally decorated and refurbished top to bottom for your absolute enjoyment. You...
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    Kissimmee, Central Florida 34747
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
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    LUXURY DREAMS DISNEY HOUSE PRIVATE POOL SPA GAMEROOM1 / 23
    (3)Very good
    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Air Conditioning
    • Sauna
    • Shared Indoor Pool
    • Grill
    • Wi-Fi
    • Hot Tub
    • Cable/satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 December 2018
    We loved our stay at Encore. The house was beautiful everyone had their own room. The kids loved the pool and game room. Also they had a great time at water park. House is...
    Reviewed 20 September 2018
    I loved the house, the kitchen had everything we could possibly need. It is very comfortable within a resort. Carlos was always attentive to our needs, will be going back!!
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    About this property
    Spacious brand new house in leading rental home community in the Disney Parks area of Central Florida. With private pool and game room inhouse, this luxury gated community offers easy access to theme parks, and is around a 6 minute drive to Walt Disney World. This spacious and comfortable, modern 6...
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    Kissimmee, Central Florida 34747
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    7 Bedrooms, 6 Bathrooms, Sleeps 18 Quick View
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    • Air Conditioning
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This amazing 7-bedroom home, with 6.5 bathroom is conveniently located in Sonoma Resort, a brand-new vacation rental resort just 10 minutes from Disney parks, upscale brand outlets and more. Featuring 7 bedrooms and 6.5 bathrooms is a perfect fit for families and friends travelling together. This...
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    Location Information
    Kissimmee, Central Florida 34741
    Holiday Rental House - 7 Bedrooms, 6 Bathrooms, Sleeps 18
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    15 Bedrooms, 13 Bathrooms, Sleeps 30 Quick View
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    • Private Outdoor Pool (Unheated)
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sonoma Resort is conveniently located next to 'The Loop', a premier shopping and entertainment mecca. In addition, the excitement of Disney World, Universal Studios and Sea World as well as upscale brand outlets, malls and numerous championship golf courses are only minutes away. Sonoma offers...
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    Kissimmee, Central Florida 34741
    Holiday Rental House - 15 Bedrooms, 13 Bathrooms, Sleeps 30
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    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
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    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in the beautiful Golden Bear Dr area of Reunion Resort's west side, this magnificent 5 bedroom luxury pool home offers a perfect base for guests planning a family vacation in Orlando. Just 12 minutes from Disney and within easy reach of all of the theme parks, this spectacular home offers...
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    Location Information
    Kissimmee, Central Florida 34747
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    Fantastic Cumbrian Lakes Villa with Hot Tub and WiFi1 / 28
    (1)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Grill
    • Air Conditioning
    • DVD Player
    • Cable/satellite TV
    • Hot Tub
    • Washer
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 April 2014
    We shared this house with our family with age ranges from 3 to 59. The four young children wanted to stay at the "holiday house" forever!!Its in a great location and...
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    About this property
    You will feel it the moment you pass the entry gates to this beautiful new community. A sense of peace and harmony with nature. Pleasing street-scapes are lined with ancient oak trees, giving shade as well as a taste of Florida's natural beauty. Sparkling lakes provide a habitat for cranes,...
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    Location Information
    Kissimmee, Central Florida 34746 6727
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    ⭐Modern House⭐ 6BD/6.5 BA Bella Vida Resort/ PRIVATE POOL/ LAKE VIEW/NEAR DISNEY1 / 30
    (3)Very good
    6 Bedrooms, 7 Bathrooms, Sleeps 16 Quick View
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    • Air Conditioning
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    • Hot Tub
    • Sauna
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 September 2017
    Great house in a great location, large open areas for large families (we had 8 staying here). Ensuite and TV's in every bedroom kept the kids happy and a nice swimming pool out...
    Reviewed 1 November 2016
    House was gorgeous and well kept. The owner is very accommodating and helpful. I would recommend this vacation home as a great stay for any family. Thanks again Bruno.
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    About this property
    Opening on January 2016, This terrific home offers 6 bedrooms to sleep up to 16 guests, and the private, screened pool has a crystal clear pool to enjoy, as well as a sun-drenched deck. All the bedrooms come with TV so that you can enjoy your favorite shows or check out the weather for each day...
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    Kissimmee, Central Florida 34746
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 16
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    Prestige 3: New Lux Home, South Fc Lake View, Pool1 / 25
    (5)Excellent
    8 Bedrooms, 6 Bathrooms, Sleeps 20 Quick View
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    • DVD Player
    • Washer
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Patio
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 August 2018
    We had a group of 14 people on our holiday and this villa was the perfect base for us. It offered beautiful bedrooms with ample living space, we never felt that we were living...
    Reviewed 3 March 2018
    Our entire family (16 members) from parents, grown children and grand-kids aged 13 years - 6 months of age were comfortably accommodated in this fabulous rental home! The...
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    About this property
    This 4,000 sq. ft. home is in the new Windsor at Westside gated community (sister community to Windsor Hills) and just minutes from Disney. 8 bedrooms and 6 bathrooms, with 4 en-suites. Pool area with heated, SOUTH-FACING pool, IN-GROUND Jacuzzi. Game room with seating, pool table and foosball...
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    Kissimmee, Central Florida 34747
    Holiday Rental House - 8 Bedrooms, 6 Bathrooms, Sleeps 20
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    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    PROPETY DESCRIPTION: - Single family house with 6 Bedrooms and 5.5 Baths - Accommodates up to 12 people comfortably - Private pool* - Game room - Gated community. - Free Wi-Fi. - Electronic lock. - All rooms have flat-screen high-definition TV. - A/C OVERVIEW There are three couple bedrooms, one...
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    Kissimmee, Central Florida 34746
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    Gorgeous Top Pool Home SL47301 / 60
    (1)Excellent
    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    6 Bedrooms, 5 Bathrooms, Welcome to the SINGLE FAMILY HOME of your dreams in Kissimmee!! This 6 bedroom and 5 bathroom rental home located in the Storey Lake Resort Community. The 6 bedrooms and 2 living rooms, all together with 8 LED TVs. The large kitchen is a chef’s dream to cook in, with...
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    Kissimmee, Central Florida 34746
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 14
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    6 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This gorgeous six bedroom four bathroom pool home is also known as Tinkerbell's Little Castle and is located within Windsor Hills. This beautiful home happens to be situated right in front of one of the community’s’ largest children’s playground, perfect for the little ones! This spacious...
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    Kissimmee, Central Florida 34747
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 14
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    6 Bedrooms, 6 Bathrooms, Sleeps 15 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Secure Parking
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Great Brand New Luxury Single family Home, 6 bedrooms & 6 bathrooms + Game Room with air hockey & pool table on first floor. 1 Suite downstairs and 2 Suites upstairs, cinema room upstairs, equipped kitchen, screened Private Pool & Spa. Private parking. Newly furnished & decorated. Fully Equipped,...
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    Kissimmee, Central Florida 34746
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 15
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Unheated)
    • Grill
    • DVD Player
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautiful home has exquisite features throughout it's unique floor plan and is located on Homestead overlooking the ninth hole of the Tom Watson signature golf course. With this central location within the resort all the main amenities, Reunion Grande Hotel, club house, golf pro shop and spa...
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    Kissimmee, Central Florida 34747
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    W158 - 4 Br Reunion Resort Villa - Pet Friendly1 / 46
    (1)Terrible
    4 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    • DVD Player
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Luxury 4 Bedroom Villa with Screened Pool and Private Guest Suite Pet Friendly Home year round for all durations. This beautiful custom built home is located in Homestead which is the centre of the resort and convenient for the Grand Hotel, Club House,Annika Golf Academy and several of the...
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    Location Information
    Kissimmee, Central Florida 34747
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 11
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    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Air Conditioning
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in Veranda Palms, a stunning gated community whose serenity is provided by the beautiful conservation area of Shingle Creek Regional Park and Preserve, this vacation home is convenient to all major theme parks, fine dining, shopping, and golf courses. The sandy Florida beaches and the...
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    Kissimmee, Central Florida 34746
    Condo/Apartment - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    2675CA - Sonoma Resort1 / 150
    (2)Excellent
    6 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    • Parking
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Grill
    • DVD Player
    • Wi-Fi
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 July 2019
    We had a great time staying at this home, we had a minor problem but, it was taken care of quickly. I didn’t know what to expect when we arrived. The home was just as beautiful...
    Reviewed 22 March 2019
    This is a very nice home. Nice pool walking trails quiet neighborhood. Large kitchen with breakfast bar and dining area for entertaining.
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    About this property
    Welcome to the FANTASTIC BRAND NEW SINGLE FAMILY HOME of your Dreams in Kissimmee!! This 6 bedroom and 6,5 bathroom rental home in 2 floors is located in the Sonoma Resort. Take a break and cool off in your very own pool and dine poolside at your leisure. For your convenience, this home includes a...
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    Kissimmee, Central Florida 34741
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 14
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    8 Bedrooms, 9 Bathrooms, Sleeps 20 Quick View
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    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Washer
    • Grill
    • Internet Access
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Property Reference RVH_254R Truly one of a kind custom, luxury home situated inside of the world famous Reunion Resort. The home is located within the well established Homestead community boasting spectacular views of the Independence golf course. Stepping into the grand entrance of the...
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    Location Information
    Kissimmee, Central Florida 34747
    Holiday Rental House - 8 Bedrooms, 9 Bathrooms, Sleeps 20
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    8 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    • Air Conditioning
    • Wi-Fi
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    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sonoma Resort is conveniently located next to 'The Loop', a premier shopping and entertainment mecca. In addition, the excitement of Disney World, Universal Studios and Sea World as well as upscale brand outlets, malls and numerous championship golf courses are only minutes away. Sonoma offers...
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    Location Information
    Kissimmee, Central Florida 34747
    Holiday Rental House - 8 Bedrooms, 6 Bathrooms, Sleeps 16
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    8 Bedrooms, 9 Bathrooms, Sleeps 16 Quick View
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    • Cable/satellite TV
    • Hot Tub
    • Patio
    • Private Outdoor Pool (Heated)
    • Washer
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Overview With over 4500 sq. ft. of living space, my place is close to Disney, Universal, Sea World and other theme parks. The resort offers FREE SHUTTLE SERVICE TO DISNEY & UNIVERSAL STUDIOS. You have easy access to great restaurants & dining, nightlife and other family-friendly activities. You’ll...
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    Kissimmee, Central Florida 34747
    Holiday Rental House - 8 Bedrooms, 9 Bathrooms, Sleeps 16
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    10 Bedrooms, 10 Bathrooms, Sleeps 22 Quick View
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    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in the Encore Club at Reunion, this incredible multi family vacation home is perfect for you and your family and friends to share a dream stay, just minutes from Walt Disney World! With a private pool and spa, plus lots of spacious living area, you will never want to stay in a hotel room...
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    Kissimmee, Central Florida 34747
    Holiday Rental House - 10 Bedrooms, 10 Bathrooms, Sleeps 22
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    Lovely 8 Bedroom Private Pool/Spa Villa Near Disney1 / 100
    (4)Average
    8 Bedrooms, 5 Bathrooms, Sleeps 17 Quick View
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    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
    • Sauna
    • Hot Tub
    • Internet Access
    • Washer
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 March 2014
    The pool and hot tube were perfect and the family loved them. The living areas were very nice and accommodated the family very well. Loved the ability to be together so...
    Reviewed 5 January 2014
    We rented this property at Emerald Island and was an incredible experience, the owner answered all our questions at the time of the rental, and when we arrive there, the house...
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    About this property
    Only 3 miles away from Disney and easy access to all major theme parks, this lovely 8 bedroom 4.5 bath pool/spa villa is located on the prestigious Emerald Island Resort, a beautiful community with 24/7 guarded gate.This spacious villa can comfortably sleep up to 19 guests, perfect for large group...
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    Kissimmee, Central Florida 34747
    Holiday Rental House - 8 Bedrooms, 5 Bathrooms, Sleeps 17
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    Luxury 10 Bed 10 Bath in Encore1 / 28
    (2)Excellent
    10 Bedrooms, 10 Bathrooms, Sleeps 25 Quick View
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    • Grill
    • Patio
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 June 2017
    This beautiful rental was awesome!!! I look forward to booking this rental again. The resort was also awesome!! The washer and dryer on both floors was excellent. Plenty of room...
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    About this property
    Just minutes from Disney, and easy access to many great restaurants of the Formosa area of Kissimmee, Encore Club at Reunion provides best amenities including water park, clubhouse, sports and fitness center, grand open on March 1st 2006. This fully equipped 10 bedroom luxury vacation villa will...
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    Kissimmee, Central Florida 34747
    Holiday Rental House - 10 Bedrooms, 10 Bathrooms, Sleeps 25
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    $299/nite to Sept 28   Harry Potter/Star Wars/Moana/Cinderella. Disney 5-10 min!1 / 36
    (10)Excellent
    8 Bedrooms, 5 Bathrooms, Sleeps 24 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Hot Tub
    • Patio
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 December 2018
    What a wonderful gift! This house was so well thought out. The kids had a different costume on everytime we turned around. That includes my 40 something kid's! We were in the...
    Reviewed 26 August 2016
    This was one of the most fun vacations that we as a family have taken to Florida. We go at least once a year and Happily Ever After made it even more special and fun. We usually...
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    About this property
    ********LAST MINUTE DEAL OF $100 OFF PER NIGHT IS AS SHOWN IN RATES/QUOTES. WAS $489/NIGHT; NOW $389 PER NIGHT SUMMER 2018!!!********** As a recent guest described it, we 'have the best homes for kids in Orlando'!!! (Yes, your many hours of hunting down the perfect vacation property are finally...
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    Kissimmee, Central Florida 34747
    Holiday Rental House - 8 Bedrooms, 5 Bathrooms, Sleeps 24
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Parking
    • Wi-Fi
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This fabulous home is nestled on a quiet spot just inside the Liberty Bluff section of the Reunion Resort commanding a spectacular view across the Arnold Palmer course, one of three PGA courses Reunion is home offers to the Reunion Grande Hotel. A custom built courtyard style home featuring many...
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    Kissimmee, Central Florida 34747
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Luxury 8 Bedroom Pool/Spa Resort Villa Near Disney1 / 200
    (4)Very good
    8 Bedrooms, 5 Bathrooms, Sleeps 19 Quick View
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    • Washer
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Cable/satellite TV
    • Sauna
    • Internet Access
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 July 2016
    Stayed here with extended family. Accessibility to parks good. However needs attention to detail with cleanliness (dust under beds) .I found a pill under one bed.No ironing...
    Reviewed 6 January 2014
    We rented this property at Emerald Island and was an incredible experience, the owner answered all our questions at the time of the rental, and when we arrive there, the house...
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    About this property
    Only 3 miles to Disney, 15 miles to SeaWorld, 17 miles from Universal Studio and easy access to all major theme parks, shipping center, restaurants, this lovely 8 bedroom 4.5 bath heated pool/spa villa is located on the prestigious Emerald Island Resort, a beautiful community with 24/7 guarded...
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    Kissimmee, Central Florida 34747
    Holiday Rental House - 8 Bedrooms, 5 Bathrooms, Sleeps 19
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    4707 Sleepy Hollow Drive1 / 80
    (1)Excellent
    6 Bedrooms, 5 Bathrooms, Sleeps 15 Quick View
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    • Patio
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    Pet friendly
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    Smoking allowed
    Reviewed 21 February 2019
    Our stay at the Story Lake Resort, 4707 Sleepy Hollow was truly a wonderful experience. The home was beautifully decorated and the floor plan was truly wonderful. Their where...
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    About this property
    Get ready for the most amazing days of your life! Located in the Storey Lake Resort, this home has plenty of space and fun to offer. This villa features 6 bedrooms and 5 bathrooms and 3,291 sq ft. The open floor concept allows everyone to hangout in the same space while enjoying dinner or watching...
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    Kissimmee, Central Florida 34746
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 15
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    11 Bedrooms, 12 Bathrooms, Sleeps 30 Quick View
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    • Grill
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
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    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Overview This dream home is situated on the Estates area of the Reunion Resort which boasts the largest home sites available. Designed and constructed by one of Reunion's leading custom builders, this 11 bedroom home boasting 14000 sq ft of living space has incorporated all the elements required to...
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    Location Information
    Kissimmee, Central Florida 34747
    Holiday Rental House - 11 Bedrooms, 12 Bathrooms, Sleeps 30
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    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Air Conditioning
    • Grill
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This contemporary style 5 bedroom villa is located at the end of Watson Court next to a conservation area in Reunion Resort. It provides privacy and is comfortably furnished, sleeping up to twelve guests. Complete with a private pool deck and spillover spa, this home is the perfect place to catch...
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    Location Information
    Kissimmee, Central Florida 34747
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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