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Holiday Rentals in Kissimmee, FL

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    All 3,244 Rentals in Kissimmee
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    Travellers to Kissimmee are booking June dates now. Secure your holiday rental today, and have the perfect trip.
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    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    4 Bedrooms / 4 Bathrooms / Sleeps 10
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    3 Bedrooms / 3 Bathrooms / Sleeps 6
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    3 Bedrooms / 3 Bathrooms / Sleeps 6
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    About this property
    Welcome to Our 5 Star Luxury Florida Home We welcome you to stay in our luxury Seven Eagles fully air conditioned 3 bed en-suite Town Villa in the 5 Star luxury Reunion Resort and Club in Orlando, Florida. We are just minutes away from the holiday 'World of Entertainment': Disney World... View all property information
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    1 / 22
    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    About this property
    This superbly located home is on the prestigious 5 Star Gated Resort of Windsor Palms, located less than 3 miles from Disneyworld. Enjoy a spacious, luxury home with large deck, SW facing pool, spa and conservation views. Watch the sun go down whilst enjoying a glass of wine or dinner on the patio.... View all property information
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    1 / 26
    5 Bedrooms / 5 Bathrooms / Sleeps 10
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    About this property
    Reunion is stunning resort community and this beautiful 5 bedroom, 4.5 bathroom vacation rental is sure to make your next stay exceptional in the sunshine state. The entire unit is exquisitely decorated and features a high-end furniture package, three 42-inch flat screen TV's along with each well... View all property information
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    $139
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    1 / 24
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    This large 3 bedroom 2 baths house is beautifully furnished and offers anything a traveler will need. Has up to date appliances and a full kitchen. To start you up you will find toilet paper, paper towels, dish washer tablets, laundry detergent, bottles of water in the fridge and complimentary... View all property information
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    6 Bedrooms / 4 Bathrooms / Sleeps 13
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    About this property
    Floor Plan (Brentwood) 2,812 sq ft. 2 story home with pool and spa (South-West facing pool) We invite you to enjoy our luxurious Villa on your next trip to Orlando. Absolutely stunning, this professionally decorated and furnished property features all the comforts of home and more! This 6 bedroom,... View all property information
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    1 / 36
    6 Bedrooms / 4 Bathrooms / Sleeps 12
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    About this property
    ***PRICE INCLUDES FREE POOL AND SPA HEAT & WI-FI*** Beds: 6 Baths: 4 Sleeps: 12 King: 1 (Master) Queen: 3 (1 Master) Twin: 2 Free Wireless High Speed Internet Pool and Spa Fully Screened-in Pool Deck privately enclosed Games Room Air Conditioning Laundry TV/DVD in every room Superb Resort Amenities... View all property information
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    $114
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    1 / 31
    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    About this property
    All of your needs and desires in a vacation home will be easily fulfilled when you visit us at Coral Cay Resort. The popularity of this amazing leisure community remains unmatched by other vacation destinations in the area. Fun filled days of sunshine, adventure and relaxation await you, so don't... View all property information
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    $192
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    4 Bedrooms / 3 Bathrooms / Sleeps 10
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    About this property
    Our beautiful luxury villa is situated in Cumbrian Lakes Resort, a 24 hours gated community in a quiet location, next to 120 acres of conservation area and backing on to a lovely lake. Its ideal situation only four minutes from Highway 192 and 10 minutes from Disney, means it is perfectly located... View all property information
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    1 / 27
    6 Bedrooms / 4 Bathrooms / Sleeps 12
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    About this property
    Situated in gated and fully guarded resort community of the Windsor Hills, about 2miles distance from Disney. The privately owned 6bedrooms and 3.5baths vacation villa offers 2master size suites, south facing pool and spa, about 2-3minutes short walking distance to the community club house and... View all property information
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    1 / 13
    4 Bedrooms / 2 Bathrooms / Sleeps 10
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    About this property
    Villa Betty Boo is on the prestigious Hampton Lakes Community which has a swimming pool, basketball, volleyball and tennis courts for your free use. Hampton Lakes is beautifully landscaped and is a very secure community. Villa Betty Boo has 4 spacious bedrooms and can sleep 8 - 9 people + infants... View all property information
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    $338
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    1 / 16
    6 Bedrooms / 10 Bathrooms / Sleeps 13
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    • Balcony
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    • Mountain Views
    • Pool Table
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    • x
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    About this property
    3 Master Suites : Queen Suite On Ground Floor : Lake View : Large Private Pool & Spa : Free High Speed Wifi : Free International Calls: Luxury Games Rooms Welcome to our outstanding Windsor Hills Perfect Hideaway Villa where the magic starts minutes from Disney World theme parks and many major... View all property information
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    $236
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    1 / 38
    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    • x
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    About this property
    Welcome to Sun Palm Disney Villa ! Located less than a 10 minute drive from Walt Disney World in Orlando, Florida and within the fabulous Windsor Palms Resort community. Sun Palm Disney Villa has everything! ESCAPE, RELAX and ENJOY the private wooded conservation view with no rear neighbors and... View all property information
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    1 / 19
    4 Bedrooms / 4 Bathrooms / Sleeps 8
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    • x
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    About this property
    Emerald Island Resort is a prestigious gated & guarded community located on Disney's doorstep. Surrounded by a Conservation Area, it encompasses over 300 acres with 11 heavily wooded acres right in the middle of the community. Once inside, you feel as if you have entered a special preserve. Owners... View all property information
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    Located in one of the most private community, our place is like a island of happiness in the middle of a ocean. You'll love it and enjoyed it. Our pool is boarded by a conservation area and make your stay at home and around the pool more enjoyable. Villa Inge and Michael is fully furnished and... View all property information
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    1 / 28
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
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    • Gym
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    About this property
    A 3 bedroom home, with 2 bathrooms, High Hopes is a third story unit, and is extremely well furnished with your comfort in mind. It sleeps 6-8 people comfortably, but we restrict occupancy to 6 to preserve the condition of the home. The bedrooms in High Hopes consist of 2 luxurious Masters, one... View all property information
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    3 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Suitable for children
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    About this property
    Property Ref: RVH_067 This fantastic 2,000 sq. ft town home has amazing views over the Arnold Palmer Legacy Golf Course. Enjoy beautiful sunsets from your own Private Patio. Close by are two heritage crossing communal pools and hot tub to choose from. This three-bedroom town home, features a... View all property information
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    1 / 20
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Hot Tub
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    • Washer
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
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    • x
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    About this property
    The only thing missing from Disney’s Beach House is the sand between your toes! Local artists were called in to paint incredible murals on the walls, transforming the living room into your own private beach! The living room has a 50” flat screen TV, Wii game system and DVD player. This open floor... View all property information
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    1 / 21
    3 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Air Conditioning
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    About this property
    Property Ref RVH_127 Second Floor Condo With Stunning Golf Views - Spacious 3 Bed 3 Bath Luxury Condo Located in the upscale Reunion Resort community The Villas North and overlooking the The Independence golf course by Tom Watson, this wonderful second floor 3 bedroom vacation condo is close to... View all property information
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    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    About this property
    4 Bedroom/2 bathroom villa less than 4 miles from Disney and within 5 mins of the I4 corridor for all other attractions, Family room with sliding patio door leading to pool area, flat screen 52'LCD, HD cable TV & VCR/DVD player, ceiling fan, high speed wireless internet access * separate lounge... View all property information
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    1 / 16
    3 Bedrooms / 2 Bathrooms / Sleeps 10
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    About this property
    Near all theme parks, esp. Disney. Luxury townhouse in a gated community available for rent. Minimum 3 nights. Clubhouse, community pool, playgrounds for your use. Located in a quiet area in Kissimmee. Restaurants, shopping nearby. Beds: 1 Queen Bed, 4 Twin Beds, 1 Sofa Bed View all property information
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    1 / 24
    4 Bedrooms / 4 Bathrooms / Sleeps 8
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    About this property
    This villa is situated in the exclusive Calabay Parc at Tower lake. Only 15 minutes from Walt Disney World and all the major Orlando attractions. Great, Yeah! The villa is in a gated community with A PRIVATE POOL, Spa, Games room, majestic views over Tower lake and shops only 2mins away. TV.S IN... View all property information
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    $190
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    1 / 19
    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    • x
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    About this property
    There is a full kitchen which opens to the dining and living areas so no one misses out on those important family conversations. Dining and Living areas comfortably decorated. Enjoy your favorite show on the large screen HD TV in the living area and settle back on the sofa or comfortable chair.... View all property information
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    1 / 13
    5 Bedrooms / 4 Bathrooms / Sleeps 10
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    • Air Conditioning
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    • Fireplace
    • Hot Tub
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    About this property
    This newly upgraded Mickeys Magical Vacation Home this 5-bedroom 4 baths resort home is located in the popular Resort Community in Indian Creek only 2.5 miles to Walt Disney World Entrance in Kissimmee, Florida and is perfectly placed for the shops, restaurants, fun and attractions that... View all property information
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    1 / 9
    4 Bedrooms / 3 Bathrooms / Sleeps 10
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    • x
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    About this property
    Make the best of your Vacation with a private home that sleeps up to 10. This 1-story, 4 bedroom/3 bath home is only 30 mins from Disney. It provides lots of room to spread out & for kids to play, but is a relaxing sanctuary after a long day at the Parks. Fully furnished w/ linens, towels, dishes &... View all property information
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    2 Bedrooms / 2 Bathrooms / Sleeps 8
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    • ?
    • x
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    About this property
    Rooms open to furnished balconies or patios. The air-conditioned guestrooms at Vacation Village at Parkway include safes and coffee/tea makers. Wireless high-speed Internet access (surcharge) is provided. Televisions are equipped with DVD players. All accommodations provide phones along with free... View all property information
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    1 / 24
    7 Bedrooms / 5 Bathrooms / Sleeps 16
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    • x
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    About this property
    Thank you for visiting Tinkerbells Retreat Choosing the right villa for your holiday is very important, when you go on holiday you need to have all the information you need to make the right decision for you and your family. We trust our web site will provide you with all the information in order... View all property information
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    1 / 24
    3 Bedrooms / 3 Bathrooms / Sleeps 6
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    • Air Conditioning
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    • Internet Access
    • Ping Pong Table
    • Pool Table
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    • x
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    About this property
    Located in southeast Kissimmee on the shores of Lake Marion and 20 min from Legoland, this private ground floor end unit is totally renovated and fully decorated and has a screened lanai, 2 king beds, 2 twin beds which can be converted into a third King, playpen/crib, 2 strollers and high chair.... View all property information
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    1 Bedroom / 1 Bathroom / Sleeps 4
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    About this property
    I own unit 262 at the Heritage Park Inn. The unit has two queen beds, small refrigerator and microwave. There is free wifi and breakfast included. The property has a restaurant and laundry facilities on site. Small pets are allowed. This is a NON SMOKING room. This property is essentially a... View all property information
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    1 / 16
    6 Bedrooms / 6 Bathrooms / Sleeps 16
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    About this property
    Spacious Executive home in a 24 hour guard gated community. All the amenities for you to enjoy including Wi-Fi, Large Pool/Spa & Game Room. This 2 storey home has a Master Bedroom with ensuite on the first level, 2 additional Master Bedrooms with an ensuite and 3 Twin Bedrooms on the second floor.... View all property information
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    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    • x
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    About this property
    This single family home is located in Crescent Lakes, a well-established, mature, well landscaped, sub-division in Kissimmee just minutes from local shopping. Crescent Lakes has a children's park, basketball hoops and many lakes available for fishing, stocked with bass and catfish. You are just a... View all property information
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    5 Bedrooms / 5 Bathrooms / Sleeps 10
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    • Air Conditioning
    • Balcony
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    • Grill
    • Hot Tub
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    • Private Outdoor...
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    • Pets allowed
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    • x
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    About this property
    *Waterpark and Golf not included in rental rate. Best Home Best Location!!! Fabulous Luxury 5 Bedroom, Front Line Golf View Pool Home set on the Watson Signature Golf Course #4 hole #5 Tee. Remember - Not all Reunion homes are created equal. This is one of the finest homes on all Reunion.... View all property information
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    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Air Conditioning
    • Balcony
    • Dryer
    • Grill
    • Gym
    • Hot Tub
    • Internet Access
    • Private Outdoor...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    PARADISE PALMS RESORT ORLANDO - YOU SHOULD BE HERE NOW! ---- YOU CAN BOOK THIS PROPERTY ONLINE - www.apexvacationhomes.com ------- or call 407-749-6373 Located in a gated community with 24 hour manned security, 7 miles from Walt Disney World ®Resort and 12 miles from the Universal Studios - Very... View all property information
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    5 Bedrooms / 4 Bathrooms / Sleeps 12
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Wi-Fi
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    The Property: Luxurius 5 bedroom vacation home located in one of the best areas in Orlando, less than 4 miles to Disney World Main Gate and close to Sea World, Universal Studios, Islands of Adventure and the rest of the attractions that proposes this beautiful city. It is ideal for your dream... View all property information
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    2 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Gym
    • Hot Tub
    • Ping Pong Table
    • Safe
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    two bedroom villa sleeps up to 8 with 1,552 square feet of living space. The master bedroom includes a king bed with adjoining master bath featuring a whirlpool tub, dual vanity and separate shower. The guest bedroom includes two queen beds and an adjacent full-sized bath. The open living area... View all property information
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    2 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Balcony
    • Dishwasher
    • Dryer
    • Hot Tub
    • Housekeeping...
    • Safe
    • Satellite TV
    • Sauna
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    About this property
    Great value! Great Location! Great Amenities and services to the luxurious accommodation within minutes from the Walt Disney Worlds Resorts within close proximity to Universal Orlando Resort and Sea Worlkd Orlando and Disney Animal Kingdom. Don't miss it! Award Winning Orlando Vacation Villas!... View all property information
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    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Gym
    • Internet Access
    • Pool Table
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    About this property
    Spacious and luxurious 2 and 3 bedroom villas located in heart of central Florida. Enjoy the excitement of Disney World, Sea World, Universal Studios, and more, or just relax in resorts jacuzzi/ swimming pools, fishing/boating, mini-golf, dining/shopping.. (too many amenities to mention).... View all property information
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    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Housekeeping...
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Everyone can enjoy the swimming pools, tennis courts, shuffleboard, basketball courts, horseshoe, and lake stocked for fishing. Kids will love the children's pool, playground, and mushroom-shaped pool fountain. Relax in the whirlpool/hot tub and take a break at the on-site gym. Additional amenities... View all property information
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    3 Bedrooms / 4 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Balcony
    • Hot Tub
    • Shared Indoor Pool
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Beautiful 3 bedroom condo located in the very popular 5 Star gated Community of Windsor Hills. You would not find a nicer community anywhere! Windsor Hills is a unique vacation home rental community that your family will enjoy time and time again. Some of the magnificent features of this 24-hour... View all property information
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    4 Bedrooms / 3 Bathrooms / Sleeps 11
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Private Outdoor...
    • Safe
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    About this property
    Bass Lake Estates is a small, Beautifully maintained community, and is one of the closest to Orlando's main attractions. It is a mature development of detached pool homes with a Glorious large natural lake,which attract many varieties of fish and wildlife. Relaxing in the peace and tranquillity of... View all property information
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    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Gym
    • Hot Tub
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Specializing in vacation rentals located within Reunion Resort, Windsor Hills Resort and The Retreat at Champions Gate; Magical Vacation Homes offers the finest selection of privately owned, luxury rental properties that are fully furnished and exquisitely designed to provide your family with the... View all property information
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    $143
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    3 Bedrooms / 2 Bathrooms / Sleeps 8
    traveller have booked this property
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
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    • Elder access
    • ?
    About this property
    Enjoy your vacation or business trip in this tastefully, richly decorated 3 bedroom/2 bath /1 car garage condo (2nd floor Gardenia plan) of 1,475 sq ft. Feel at home in a fully equipped kitchen with brand new appliances. The condo is located in a quite part of the gated contemporary themed,... View all property information
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    2 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Air Conditioning
    • Balcony
    • Safe
    • Shared Outdoor Pool...
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • Wheelchair access
    • Elder access
    About this property
    •Decorated two bedrooms suites, three baths condo offers spaciouness for your confortable and relaxing stay in Orlando area. Can accomodate 4 to 8 guests. Featuring equiped gourmet kitchen, with dining area, living room with color TV, WiFi and private terracesL ocated one mile from Disney World... View all property information
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Dishwasher
    • Gym
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Beds: 3 Baths: 3 Sleeps: 8 King: 1 (Master) Queen: 1 (Master) Twin: 1 (Master) Free Wireless High Speed Internet Screened Balcony with Table and Chairs Larger Floorplan with 1,472 sq. ft. Air Conditioning Laundry TV/DVD Playstation 2 Very close to a host of superb Resort amenities 2.5 miles to Walt... View all property information
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    1 / 39
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Gym
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Beds: 3 Baths: 2 Sleeps: 6 King: 1 (Master) Queen: 1 Twin Beds: 1 Free Wireless High Speed Internet Very Close to all the superb Resort ameneties. Fully Screened in Balcony, Privately Enclosed. Conservation view. Air Conditioning Laundry Room TV/DVD in every room 1.5 miles to Walt Disney World... View all property information
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    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Dishwasher
    • Safe
    • Satellite TV
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    We have a timeshare available in Kissimmee, Florida (near the entrance of Disney). It's a 2 bedroom (sleeps six), 2 bathroom townhouse with private laundry, private entrance. There is a kitchen with granite counter tops and breakfast bar. Also a dining room and living room. It also has a patio.... View all property information
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    2 Bedrooms / 2 Bathrooms / Sleeps 6
    traveller have booked this property
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    About this property
    This ground floor apartment is first class. Compare staying here with staying in a Disney Hotel and you will be astonished. Half the price of a 'moderate' Disney Resort but twice as much space as a 'Deluxe' Resort. Not only will you be saving money but you will also have the benefit of two... View all property information
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Gym
    • Private Outdoor...
    • Satellite TV
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Beds: 3 Baths: 2 Sleeps: 6 King: 1 (Master) Queen: 1 Twin Beds: 1 Free Wireless High Speed Internet Very Close to all the superb Resort ameneties. Fully Screened in Balcony, Privately Enclosed. Lake view. Air Conditioning Laundry Room TV in every room 1.5 miles to Walt Disney World Oakwater is a... View all property information
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