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Kissimmee Vacation Rentals

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    Travellers to Kissimmee are booking July dates now. Secure your vacation rental today, and have the perfect trip.
    16 Matching Rentals in KissimmeeView all 5,074 rentals
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    Close to Disney World 6 Bedroom luxury villa/ pool1 / 22
    (6)Excellent
    6 Bedrooms, 5 Bathrooms, Sleeps 13 Quick View
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    Secret Key Villa1 / 19
    (18)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    The Emerald Dolphin, Kissimmee Rental with WiFi, Hot Tub and Pool1 / 79
    (6)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Luxury 7 Bed Villa, 4.5 bathrooms, close to Disney World1 / 34
    (17)Excellent
    7 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    Amenities & Details
    • Washer
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • Grill
    • DVD Player
    • Sauna
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 24, 2018
    We've been lucky to have numerous wonderful vacations to the Orlando area with our extended family and this one was one of the best. A few minor hiccups to start with were...
    Reviewed July 30, 2017
    This House had everything that we need more than enough room for everyone, The game room and pool was awesome. Caroline and Simone H. answer any questions I had quick...
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    About this property
    Come and relax in this family friendly home in the beautiful Emerald Island Resort close to the Disney Parks. The house features 7 bedrooms, 4.5 Bathrooms, with televisions and DVD players in each bedroom. There are 2 King Bedrooms, 2 Queen Bedrooms, 2 Twin Bedrooms and one bunk bedroom with two...
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    Kissimmee, Central Florida 34747
    Holiday Rental House - 7 Bedrooms, 5 Bathrooms, Sleeps 16
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    Fun, Disney Themed 7 BR home in Disney/Orlando1 / 32
    (15)Excellent
    7 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    Amenities & Details
    • Air Conditioning
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Internet Access
    • Washer
    • Hot Tub
    • Patio
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 26, 2015
    lovely home,everything provided,lovely house will stay here again,location central to everything, the only thing that disappointed us was that the coffee machine did not work,
    Reviewed August 3, 2015
    This was the first time booking through VRBO. Everything about the experience was great. The house was very clean and had plenty of room for our 15 party group. The owners...
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    About this property
    ANNOUNCING NEW AND COMING ATTRACTIONS: In June of 2018 a NEW A/C UNIT in the game room, NEW POOL FURNITURE and a FOOSBALL TABLE have been added. Starting in September of 2018 we will be updating the GAME ROOM with NEW CARPET, a NEW PAINT SCHEME AND A NEW POOL TABLE! ABOUT THE HOME: All in all,...
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    Kissimmee, Central Florida 34747
    Holiday Rental House - 7 Bedrooms, 5 Bathrooms, Sleeps 16
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    Emerald Magic Villa by Emerald Island Rentals1 / 48
    (7)Excellent
    6 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • Hot Tub
    • DVD Player
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Grill
    • Children's Pool
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 31, 2016
    we had a great time, and the house was everything we expected, we will recomended to all our friends and for furthert trios it will be our number one choice.
    Reviewed August 2, 2015
    I cannot begin to say how pleased we were with the home. The beds were great, the rooms large, every possible accessory that could be thought of was provided. The pool was...
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    About this property
    A 6 bed/5.5 bath villa in Emerald Island Resort offering outstanding amenities such as an air-conditioned game room and a south-facing pool/spa. With 4 king master suites and 2 themed kids rooms, this villa can accommodate up to 14 in sheer luxury. The large pool and spa area with a south facing...
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    Kissimmee, Central Florida 34747
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 14
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    Goofys Getaway Townhome @ Emerald Island Resort1 / 25
    (45)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Washer
    • Hot Tub
    • Patio
    • Sauna
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    Well this is the nicest villa I have ever rented in Orlando. There is not one thing that I could wish for. The location is perfect. Privacy, quiet and very secure. It is...
    Reviewed January 9, 2018
    My family and I stayed at this house for 5 days. We arrived at 6:00 am and despite the early time Andrew was able to accommodate us. I am very grateful for that. The House was...
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    About this property
    Goofy's Getaway is a well appointed 3 bed/2.5 bath Townhome villa located in the heart of the Emerald Island Resort gated community and only minutes from Walt Disney World. Goofy's Getaway has a spacious lounge and dining area with sumptuous, comfy sofas, dining table and chairs, 40' HDTV, Blu-ray...
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    Kissimmee, Central Florida 34747
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Luxury Townhome at Emerald Island Resort near Disney Orlando/ Kissimmee1 / 53
    (8)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Hot Tub
    • Internet Access
    • Air Conditioning
    • Washer
    • Sauna
    • Grill
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 3, 2014
    My husband,son and 5 year old grandson and I stayed here for 8 nights in June. The owner was extremely easy to communicate with. He even added some extra touches for my...
    Reviewed May 29, 2014
    Great condo close to Disney. Great condition with plenty of room. Pool close to condo in gated community and minutes from everything you need.
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    About this property
    Greetings! If you like what you see below, please go ahead and make reservation online with confidence. Located within 2.5 miles (4 kilometers) of Disney parks, this townhome is located at prestigious Emerald Island Resort and is fully furnished. It is 3 bedroom 2.5 bath unit. This centrally...
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    Kissimmee, Central Florida 34747
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Emerald Sunset Large 6 Bed 5 Bath Vacation Rental1 / 20
    (2)Very good
    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Air Conditioning
    • DVD Player
    • Hot Tub
    • Cable/satellite TV
    • Parking
    • Internet Access
    • Private Outdoor Pool (Heated)
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 7, 2015
    The home was in a perfect location, well decorated, and met our needs. Close to everything like the grocery store, theme parks, restaurants, main interstate, and shops, which...
    Reviewed April 11, 2015
    If you haven't already booked this villa book it nowThanks to Bill (villa owner) for a fabulous villa fitted out with everything we could need. From a smooth and simple booking...
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    About this property
    Emerald Island Resort Orlando Florida Be our guest at Emerald Sunset Closest Vacation Homes to Disney with private pool facing conservation lot location We cordially invite you to be our guest in our 6 bed 5.5 bath lavish Magna Bay villa, which sleeps up to12 guest comfortably Affording you you...
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    Kissimmee, Central Florida 34747
    Condo/Apartment - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    Disney Villa, Emerald Island1 / 24
    (9)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • DVD Player
    • Hot Tub
    • Patio
    • Wi-Fi
    • Air Conditioning
    • Washer
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 17, 2017
    Wonderful vacation home with great amenities! Beautiful gated community! Close to all the parks and attractions!
    Reviewed January 7, 2017
    The house was clean and everything was in order. We had an amazing vacation!!! They came and clean the pool and water it was nice and warmer!! We really enjoyed it!!!
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    About this property
    Had a major refurbishment completed, including new furniture throughout, new tile flooring throughout, granite work surfaces and new appliances in this 2005 Emerald Island Resort, Kissimmee, pool home. Located 3 miles from Disney World main gate, and easy reach of all Orlando attractions. Our...
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    Location Information
    Kissimmee, Central Florida 34747
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Washer
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Hot Tub
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Very Affordable 3 bedroom 2.5 Bath Townhouse Minutes to Disney, Restaurants and Shopping Great 3 Bedroom 2.5 Bath town home This tastefully appointed townhouse is in the beautiful gated community of Emerald Island Resort which features 2 large pools, 2 hot tubs, cyber room, concierge, exercise...
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    Kissimmee, Central Florida 34747
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Emerald Island Resort's 7 bed villa - Disney Magic1 / 39
    (29)Excellent
    7 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Patio
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    • DVD Player
    • Hot Tub
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 17, 2016
    House was exactly as advertised. Sri was helpful from start to finish. Closer to Disney than expected, only about ten minutes to the first park. One member of our group is...
    Reviewed August 23, 2015
    I would like say the house Simbas Magic was everything we needed for an excellent stay in Orlando for our extended family (15). It was well maintained and had lots for the...
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    About this property
    For those looking for the ultimate vacation rental experience, this is the right villa! Located in the tropical grounds of Emerald Island Resort near Disney World, this huge 7 bed villa villa offers outstanding amenities at affordable prices for parties of up to 16 guests. This luxury villa with...
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    Location Information
    Kissimmee, Central Florida 34747
    Holiday Rental House - 7 Bedrooms, 5 Bathrooms, Sleeps 16
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    8606 Sunrise Key Drive1 / 22
    (18)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Hot Tub
    • Internet Access
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed December 5, 2013
    My family love this home. They had a very good time stay in this home. I hope to get this home once again next year
    Reviewed September 12, 2013
    The service we received from lowery's was faultless, they were very helpful and we wouldn't hesitate in using them again. The villa was immaculate, extremely comfortable and...
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    About this property
    4 Night Minimum Required to Secure a Booking. This nicely appointed and spacious pool home is situated in the lush and beautifully maintained resort of Emerald Island. The community is security gated and sits in 300 acres of natural woodland, it offers guests the use of many facilities. It is a...
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    Location Information
    Kissimmee, Central Florida 34747
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Awarded Game Room,Pool,Spa, 65 4KTV,4/3, Great Reviews below1 / 27
    (82)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • DVD Player
    • Housekeeping Included
    • Hot Tub
    • Air Conditioning
    • Washer
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 15, 2018
    This was the perfect vacation home for our family. We truly enjoyed the pool and game room while we had some "down" time from Disney. Would love to stay here again...
    Reviewed April 21, 2018
    This our second time staying with Tropical Retreat expect our family grew it was kid friendly for us extra strollers and booster seats! Love the pool and privacy compared to a...
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    About this property
    We are proud to offer our guests one of the best and well-equipped homes in the area. Our game room is great, but lets not overshadow the quality and size of beds, the home theater with DirecTV, Bose, 65'4k TV, 100mbps secured internet, PC and printer, and a great kitchen with updated appliances...
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    Location Information
    Kissimmee, Central Florida 34747
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    EMERALD ISLAND (2727SK) - 3BR 2.5BA townhome, gated Resort, tons of amenities1 / 27
    (1)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Sauna
    • Air Conditioning
    • Wi-Fi
    • Parking
    • Private Outdoor Pool (Heated)
    • Balcony
    • Patio
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 18, 2014
    House was perfect. There were 4 adults and 2 children in our group, and the house provided comfort and privacy that we all desired! Disney World was about 10 minutes away and...
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    About this property
    Fantastic 3BR 2.5BA 'Emerald Island Resort' Town Home - Your home away from home for the entire family whilst on vacation, without having the added expense of a pool. NEW 39' FLATSCREEN TV in LIVING ROOM! NEW LAMINATE FLOORS IN ALL BEDROOMS! NEW MATTRESSES IN ALL BEDROOMS for a Good Night Sleep!...
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    Location Information
    Kissimmee, Central Florida 34747 2262
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    6BR/5.5Bath/4Miles to Disney/$99 per night/FreeSpa/Lanai1 / 38
    (58)Excellent
    6 Bedrooms, 6 Bathrooms, Sleeps 19 Quick View
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    Amenities & Details
    • DVD Player
    • Washer
    • Patio
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Hot Tub
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 25, 2018
    Diamond on the island is in the emerald island resort kissimmie fl. Johns home is very nice with new furniture. very close to restaurants and stores. also 5 min. to Disney.I...
    Reviewed January 5, 2017
    Very cosy and spacious living space with updated amenities for a large group. Stayed for 5 days with 15 members ranging age groups 7yrs to 50 years. Kids enjoyed the spacious...
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    About this property
    Fill my Calendar Special Prices. From August 18 to 25 just $139 per night and from Sep 8 to Oct 6 only $119 per night. The Diamond on the Island is a home built and furnished for the traveler who demands the highest standards. It is located in the exclusive gated resort of Emerald Island which is...
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    Location Information
    Kissimmee, Central Florida 34747
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 19
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