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Holiday Rentals in Kissimmee

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    Travellers to Kissimmee are booking July dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 48
    5 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    6 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    Studio, 3 Bathrooms, Sleeps 8 | Quick View
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    INTERNAL CODE: AV4SDA3B08G-4 The Property: This stunning 3 bedrooms vacation apartment located in the city of Kissimmee, in the best touristic zone of the Greater Orlando, offers the amenities and services of one of the best 4 star resorts, like a beautiful swimming pool. This holiday rental... View all property information
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    Kissimmee, Central Florida 34744
    1 / 22
    5 of 5 bubbles (5) Excellent
    6 Bedrooms, 5 Bathrooms, Sleeps 13 | Quick View
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    6 Bedroom 4.5 Bath Vacation Home "Penny Lane" is perfectly located on the exclusive Emerald Island gated resort community, less than 3 miles from Walt Disney World in Kissimmee, Florida. With 6 bedrooms and 4.5 bathrooms, this fully air-conditioned, elegant and spacious Orlando vacation home is... View all property information
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    Kissimmee, Central Florida 34747
    1 / 35
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Welcome to the Sunny Isles where you have a sparkling pool waiting for the splashing or the relaxing to begin. Lots of space to run and have fun out back for the kids to run that energy off. A beautiful open concept flow with a fully equipped kitchen. Spacious bedrooms and large bathrooms with a... View all property information
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    Kissimmee, Central Florida 34746
    1 / 36
    8 Bedrooms, 6 Bathrooms, Sleeps 16 | Quick View
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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 Windsor at Wesside... View all property information
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    Kissimmee, Central Florida 34747
    1 / 37
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Welcome to Florida! If you are looking for a vacation home near Disney, we are here to help! We have over 200 beautiful homes, from 1 bedroom condos to 10 bedroom pool villas, all just minutes away from Walt Disney World! <BR><BR>This Crestwynd 3 Bedroom Vacation Townhome Includes The Following... View all property information
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    Kissimmee, Central Florida 34747
    1 / 42
    4 of 5 bubbles (1) Very good
    6 Bedrooms, 4 Bathrooms, Sleeps 15 | Quick View
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    About this property
    Totally Brand NEW furnished Windsor Hills Palm at Windsor Hills Resort Manned gated resort, 3 miles away from Disney World, Close to shopping, restaurants, Windsor Hills is a 5 star resort which benefits from amenities of an exceptionally high standard. The all inclusive amenities includes * A... View all property information
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    Kissimmee, Central Florida 34747
    1 / 16
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Welcome Home to this wonderful second story condo on the gated community of Villas at Islands Club, Kissimmee, Florida. Once you enter the gates you know you are entering somewhere special and this is where you will make some wonderful memories to last a lifetime! With 2 pools to enjoy , tennis,... View all property information
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    Kissimmee, Central Florida 34747
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    1 / 24
    5 of 5 bubbles (1) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Brand new 2 level 4 bed/3.5 bath townhouse, modern appliances, cable TV, free Wi-Fi, 2 complementary parking spaces. Private terrace facing lake. Access to community pool, playgrounds, picnic areas. 10 min to Disney, 20 to Universal. 4 bedrooms and 3.5 baths 1st bedroom: Master suite with a King... View all property information
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    Kissimmee, Central Florida 34746
    1 / 24
    4.5 of 5 bubbles (12) Very good
    5 Bedrooms, 6 Bathrooms, Sleeps 10 | Quick View
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    • Waterfront
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    About this property
    Premier, 2 storey, south facing villa with wonderful, private, lake & conservation views. BEST LOCATION in CUMBRIAN LAKES with an extra large lanai pool/spa area, 5 bedrooms & 3.5 bathrooms in the fabulous secure gated community of Cumbrian Lakes with free Wi Fi + 55" flatscreen TV.. Only 12 mins... View all property information
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    Kissimmee, Central Florida FL 34746
    1 / 17
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    This one story single family pool home is fully equipped with all your vacation needs that makes it a perfect home away from home. Featuring three bedrooms and two bathrooms. Fully loaded with cable, TV's, wireless internet throughout the home, fresh linens, fully equipped kitchen, and a gorgeous... View all property information
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    Kissimmee, Central Florida 34746
    1 / 23
    8 Bedrooms, 5 Bathrooms, Sleeps 20 | Quick View
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    About this property
    Newly owned 8 bedroom 5 bath 20 sleeper luxury villa for multi-family vacation stays, sports team stays, family reunions, golfing trips... 8 br/5 bath/private pool, spa and games room, free wifi, wii, private games room with air hockey and pool table. Magic destination 2736 is a luxury villa of... View all property information
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    Kissimmee, Central Florida 34747
    1 / 22
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Please be advised that this home is not located in Orlando, Fl. The location of this home is in Lucaya Village near Old Town on Polynesian Isle Blvd, Kissimee, FL. Lucaya Village is a gated resort style condo that attracts thousands of tourists every year due to its prime location, excellent... View all property information
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    Kissimmee, Central Florida 34746
    1 / 16
    4.5 of 5 bubbles (7) Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    About this property
    Welcome to "Mickey's Tree House", which we have carefully selected for its excellent location and superb features! The villa has been furnished with "up-market" quality furniture, fittings, and curtains, not the usual contract furniture pack found in many rental villas, as we use the property... View all property information
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    Kissimmee, Central Florida 34746
    1 / 17
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    This lakefront four-bedroom, two-bath villa for 8 guests offers lovely water views from a screened-in pool area. And that's just the beginning. Plan your Walt Disney World excursion (just a 20-minute drive away). Stroll through the heart of downtown Orlando. Or find total relaxation back at home in... View all property information
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    Kissimmee, Central Florida 34746
    1 / 23
    3 Bedrooms, 3 Bathrooms, Sleeps 2 | Quick View
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    About this property
    Our property was chosen and built for space and comfort. Its location guarantees a peaceful, secured and comfortable stay throughout your vacation. Your home is a 3 bed/2.5 bathroom townhome in Tuscany Preserve, a gated resort community with 24 hr security on Lake Marion in Poinciana. The townhome... View all property information
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    Kissimmee, Central Florida 34759
    1 / 64
    4 of 5 bubbles (21) Very good
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    The Villas at Seven Dwarfs Lane is the #1 and newest premier resort and vacation rentals in the Orlando area, near Disney World. Its proximity to Orlando's world-renowned attractions is unrivaled. Staying in one of Townhome gives you automatic membership to all the private resort facilities, for... View all property information
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    Kissimmee, Central Florida 34746
    1 / 29
    5 of 5 bubbles (1) Excellent
    7 Bedrooms, 4 Bathrooms, Sleeps 16 | Quick View
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    • Waterfront
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    About this property
    Beautiful lake views with Huge south facing private pool. Separate heatable children's pool (1 foot depth max) 12 Person Spa/Jacuzzi and massive deck with shaded area. This house is magnificent! It is one of the largest in the Orlando Vacation Home area and ideal for large groups of people and... View all property information
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    Kissimmee, Central Florida 34758
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    1 / 23
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Windsor Hills - Kissimmee, Florida is an upscale gated community located just 2 miles from Walt Disney World. This luxury resort sits nestled just off Hwy 192 in Kissimmee, Florida and is one of the most desired resorts in the Orlando area. During your stay you will enjoy this well appointed home... View all property information
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    Kissimmee, Central Florida 34747
    1 / 35
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    Celebrate your Florida vacation in this welcoming 5 bedroom Superior level vacation home. Spread out, relax and enjoy two stories of upscale furnishings, convenient amenities and lively decor. Experience the ultimate in comfortable accommodations with five bedrooms that all include televisions and... View all property information
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    Kissimmee, Central Florida 32805
    1 / 35
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Enjoy your luxury vacation staying only 10 minutes from Disney in a modern vacation home! - Gated community - Less than 5 minutes to the grocery store - Close to Universal and outlet shopping malls - Enjoy the complimentary access to the heated resort pool / playground / clubhouse / gym /... View all property information
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    Kissimmee, Central Florida 34746
    1 / 35
    9 Bedrooms, 5 Bathrooms, Sleeps 22 | Quick View
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    About this property
    Be the envy of your friends when you tell them about your vacation in this beautiful home. Let's start with the gourmet kitchen offering Granite Counter Tops, Stainless Steel Appliances, Upgraded Small Appliances, Dinnerware, Silverware & Cookware to suit the most discriminating chef! The Formal... View all property information
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    Kissimmee, Central Florida
    1 / 18
    11 Bedrooms, 10 Bathrooms, Sleeps 22 | Quick View
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    About this property
    Top Villas does vacation rentals differently. Book with us and youll get the best homes, at the best prices, from people who really care. Best rate guarantee | Tailor-made service | 24/7 guest support Special Offer! Book today to enjoy exclusive extras unique to Top Villas! Free transfers to... View all property information
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    Kissimmee, Central Florida 34747
    1 / 13
    5 of 5 bubbles (1) Excellent
    4 Bedrooms, 8 Bathrooms, Sleeps 8 | Quick View
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    About this property
    This two storey luxury vacation home is fully air conditioned with ceiling fans in nearly every room. The house itself has just been refurbished to a high standard offering the luxury of a modernised master bedroom ensuite, three additional bedrooms, a family bathroom and kitchen with granite... View all property information
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    Kissimmee, Central Florida 34743
    1 / 25
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Vacation Village at Parkway accommodations are 1,500 square feet of combined living space featuring a common foyer with separate controlled access for each suite. The spacious two bedroom accommodations are designed for the guest’s maximum comfort. Kitchen, living and dining room in each suite are... View all property information
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    Kissimmee, Central Florida 34747
    1 / 21
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    FREE cancellation up to 32 days before check in(*). No security deposit required at check in(*) Our second story condo can accommodate your entire family and comes completely furnished with everything you could possibly need to make your stay enjoyable. Our kitchen is fully furnished for you to... View all property information
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    Kissimmee, Central Florida 34747
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Our 3 bedroom, 2 bathroom, 1455 sq. ft. 2nd floor Condo sleeps 8 comfortably. It has been completely repainted, carpets cleaned and all new furniture, new beds (1 king size, l queen size, 2 twins, and pull out couch.), new linens, new dishes, new cutlery, new everything. There are 4 new flat screen... View all property information
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    Kissimmee, Central Florida 34747
    1 / 13
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Private Outdoor...
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    About this property
    A stunning, larger than average, 5-Bed 4-Bath villa with a beautiful view of the conservation area at the rear as backdrop to our private pool. The villa is furnished and maintained to a very high standard and all rooms in the villa are spacious. The villa is split over two floors which makes it... View all property information
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    Kissimmee, Central Florida 34746
    1 / 32
    5 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Make our home your home on your next trip to Orlando. Just three miles from Disney World, this house is absolutely perfect for family groups. Relax and enjoy the warm Florida sun with a south-facing pool and in-ground spa. Your vacation home features all the comforts you want and more! No detail... View all property information
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    Kissimmee, Central Florida 34747
    1 / 14
    3 of 5 bubbles (1) Average
    Studio, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Guests vacationing at our Kensington townhome in Terra Verde Resort will take advantage of the private full sized pool and great Resort amenities. This home rests safely within a guard-gated community. Family and friends can sprawl out amongst the 1650 square feet of vacation living space... View all property information
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    Kissimmee, Central Florida 34746
    1 / 52
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Kissimmee, Central Florida 34741
    1 / 38
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Villa Majorca is a newly constructed home in the sought-after, gated community of Windsor at Westside. This professionally decorated home features five bedrooms, four-1/2 bathrooms, two separate living areas, a laundry room and a fully equipped kitchen. The first floor features an open concept... View all property information
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    Kissimmee, Central Florida 34747
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    This wonderful Orlando Florida vacation home, features a nautical theme through out the home. It has a game room with pool table with a ping pong top and a private screened in pool and patio. You will not want to miss this lovely vacation home at the doorsteps of local shopping areas and close to... View all property information
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    Kissimmee, Central Florida 34746
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    1 of 5 bubbles (1) Terrible
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Calling all the game room families this is a house to love... It has basketball, air hockey and of course the favorite pool!! And not to mention SpiderMan themed bedroom. Each room including the living room has a TV. The home is fully furnished and has a fully equipped kitchen to cook in... The 4... View all property information
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    Kissimmee, Central Florida 34746
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    10 Bedrooms, 10 Bathrooms, Sleeps 22 | Quick View
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    About this property
    This luxurious two-story house with 10 bedrooms and 10 full baths is a perfect place to call home while on your Orlando vacation. It offers a gourmet kitchen, fully equipped with all of the utensils, dishes, cookware, and appliances you should need during your stay. The eating area boasts ample... View all property information
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    Kissimmee, Central Florida 34747
    1 / 18
    6 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    About this property
    "Imagine Renting This Stunning Villa In One Of Orlando`s Most Prestigious Resorts, Windsor Hills" This villa is situated in the exclusive resort of Windsor Hills. Only 1.5 miles from Walt Disney World and all the major Orlando attractions. Great, Yeah! The villa has every luxury with A PRIVATE... View all property information
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    Kissimmee, Central Florida
    1 / 56
    4.5 of 5 bubbles (13) Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Pet-friendly
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    About this property
    Find Kissimmee Vacation Rentals on FlipKeyThis fantastic townhouse is an ideal home-away-from-home for your next vacation! Located in the Regal Oak resort just behind Old Town and “Fun Spot” USA off Hwy 192 and I-4, this vacation house is a perfect place to relax and unwind. The resort is situated... View all property information
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    Kissimmee, Central Florida 34746
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Enjoy your luxury vacation staying only 10 minutes from Disney in a modern vacation home! - Gated community - Less than 5 minutes to the grocery store - Close to Universal and outlet shopping malls - Enjoy the complimentary access to the heated resort pool / playground / clubhouse / gym /... View all property information
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    Kissimmee, Central Florida 34746
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    GetDescriptionsPlainText: Error - The description is blank Additional amenities include: foosball, games, game room, communal gym, free calls, TV in every bedroom, paved parking, large extended pool deck with private pool and spa, packn play, crib, great games room, has spa, five bedroom, three... View all property information
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    Kissimmee, Central Florida
    1 / 15
    4 of 5 bubbles (4) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Lake Berkley is just off HWY 192, in Kissimmee, Florida and is perfectly placed for the shops, restaurants, fun and attractions that Orlando has to offer. Lake Berkley is ideally located as a "home base" for other Florida activities including the Space Coast or the Gulf Coast. Completely Renovated... View all property information
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    Kissimmee, Central Florida 34746
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Plan for that next exciting Florida family vacation at this pristine, two-level townhouse with full kitchen, furnished balcony, and several Oakwater amenities including a swimming pool, hot tub, fitness center, and fun-filled game room. This two-bedroom rental in Kissimmee is just a mile-and-a-half... View all property information
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    Kissimmee, Central Florida 34747
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    This 3 bedroom 2 bathroom Condo is located in the gated Oakwater Resort, conveniently located just 1.5 miles from Disney. Within the resort you will also find a 4,000 sq. Clubhouse featuring a lagoon-style pool, tennis courts, volleyball courts and basketball courts. Condo consists of one... View all property information
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    Kissimmee, Central Florida 34746
    1 / 13
    3.5 of 5 bubbles (8) Average
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • ?
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    • ?
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    Tastefully appointed home in quite neighborhood with wedgwood motif having 3 bedrooms, 2 full baths and a cathedral style split floor plan allowing open view of optional heated pool. Master bedroom with TV, queen size bed, garden size tub and walk in shower stall. Remaining bedrooms each have 2... View all property information
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    Kissimmee, Central Florida 34747
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
    About this property
    Turn your dreams into reality in our Luxury Holiday Villa just a short distance from the Orlando theme parks.<BR><BR>This is Mickey's Retreat, our 3 Bedroom, 2 Bathroom Villa in Kissimmee, Florida. Mickey's Retreat is conveniently situated just a short ten minute drive away from Disney World and... View all property information
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    Kissimmee, Central Florida 34746
    1 / 25
    5 of 5 bubbles (1) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Pet-friendly
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    • x
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    • Smoking allowed
    • ?
    About this property
    Enjoy your luxury vacation staying only 10 minutes from Disney in a modern vacation home! - Gated community - Less than 5 minutes to the grocery store - Close to Universal and outlet shopping malls - Enjoy the complimentary access to the heated resort pool / playground / clubhouse / gym /... View all property information
    Location Information
    Kissimmee, Central Florida 34746
    1 / 16
    5 of 5 bubbles (19) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
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    • Patio
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    • Outdoor Dining Area
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    located just off Hwy 192 and is within 3 miles to Disney. It is a gated resort with a large pool and sun terrace area, along with children's playground The home, located less than a minute's walk from the pool area, has 1 King master, 1 Queen room and one themed twin room. There are ceiling fans... View all property information
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    Kissimmee, Central Florida 34747
    1 / 31
    4.5 of 5 bubbles (2) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Shared Outdoor Pool...
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    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • ?
    About this property
    This 3 bedroom condo is located on the third floor of a beautiful and safe resort community, just minutes from Disney. The master suite has a King size bed and large private bathroom The second bedroom has a Queen bed The third bedroom has two twin beds All of the bedrooms have cable TV! This condo... View all property information
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    Kissimmee, Central Florida 34747
    1 / 45
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Children's Pool
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    • Wi-Fi
    • Sauna
    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This wonderful property is located in the beautiful Paradise Palms Resort! This is a 4 bedroom townhouse close to the clubhouse ! This home has been recently decorated so be the first to use this home! This home offers a full service kitchen, private pool, grill, and much more! The upgraded... View all property information
    Location Information
    Kissimmee, Central Florida 34747