Kissimmee Vacation Rentals, Villas, & More

1-50 of 625 Kissimmee Rentals

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Kissimmee Florida Vacation Rentals - Home
1 / 24

Kissimmee Home
6 Bedrooms / 4 Bathrooms / Sleeps 14

from

$170

/ night

Email Owner
Bedrooms:6
Bathrooms:4
Sleeps:14
Type:Home
Per night:$170 - $290
Per month:$5,100 - $8,700
Pets allowed:No
Internet:Yes

A great option for your next Disney vacation. Enjoy all the comforts of home while on vacation, a heated, south facing pool & spa, large deck, big screen TV, CD, DVD, BBQ, video games (PS2 and XBOX! ), TV & cable in all rooms, FREE phone calls within United States, broadband...

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Kissimmee Florida Vacation Rentals - Townhouse
1 / 16

Kissimmee Townhouse
3 Bedrooms / 2 Bathrooms / Sleeps 8

“ Excellent ”7 Reviews

from

$75

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:8
Type:Townhouse
Per night:$75
Per week:$525 - $650
Pets allowed:Yes
Internet:No

Venetian Bay Villages is a community full of white picket fences, friendly sidewalk trails, numerous pools and a clubhouse that rivals any major resort. It is located only minutes away from the restaurants and attractions on the 192 Highway. The resort style pools and clubhouse...

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Relax after a busy day

“ Excellent ”
September 23, 2013
Nice place, very comfortable. Felt very homey with plenty of pots, pans and dishes to cook a meal at 'home.' Pool just around the corner within walking distance felt very private. Seemed like there were quite a few people who live in the complex, but they seemed nice- Just watch out for the three little kids who live a couple buildings over. They do not pay attention when riding their bikes and almost got hit by cars a couple times. Security at front gate was nice to know that not just anyone was coming and going. Plenty of sidewalks around the complex to go for walks or jogs and outside the complex along the main road there are sidewalks if you want to go for a longer run. I had a pleasant stay Anne Marie, Thank you.
Kristen Hand, Portland, Oregon

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Kissimmee Florida Vacation Rentals - Condo
1 / 22
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Condo
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:Yes

Our Canadian- owned vacation condo located near Formosa Gardens Boulevard and Silk Road in Kissimmee, FL is available for rent! This lovely 1500 sq. ft condo is spacious enough to house 6 people comfortably with it's 3 bedrooms and 2 bathrooms. It is newly and completely furnished...

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Very nice place!

“ Excellent ”
September 28, 2014
My experience in this place was awesome...,nice and clean 5 points recommend.
Silvia Lobaton, Pennsylvania

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1 / 29

Kissimmee Home
7 Bedrooms / 7.5 Bathrooms / Sleeps 12

from

$720

/ night

Email Owner
Bedrooms:7
Bathrooms:7.5
Sleeps:12
Type:Home
Per night:$720 - $1,050
Per week:$5,040 - $7,350
Pets allowed:No
Internet:Yes

Property Ref: RVH_001 . This unique, one of a kind, beautiful, private custom Estate Home features over 8, 200 sq/ft of luxury accommodation and balconies. This ‘WOW! ’ factor home is private, quiet and not overlooked. Soak up the Florida sun on the biggest rear deck...

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Your home in the sunshine
1 / 26

Kissimmee Townhouse
3 Bedrooms / 3 Bathrooms / Sleeps 8

from

$68

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:8
Type:Townhouse
Per night:$68 - $115
Per week:$480 - $800
Pets allowed:No
Internet:Yes

The Trafalgar Village community is centred around a luxurious club house (a 2 minute stroll from the property) with amenities that include a man made beach and lagoon, lakes (stocked for fishing), a pool and games arcade room, a 48 seat movie theatre, a fitness room, a business...

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Kissimmee Florida Vacation Rentals - Villa
1 / 24

Kissimmee Villa
4 Bedrooms / 4 Bathrooms / Sleeps 8

from

$170

/ night

Email Owner
Bedrooms:4
Bathrooms:4
Sleeps:8
Type:Villa
Per night:$170 - $234
Per month:$5,100 - $7,020
Pets allowed:No
Internet:Yes

Holiday Paradise Villa is a comfortable and convenient 4 bedroom, 4 bathroom privately owned villa located in the world famous 5 star Windsor Hills Resort. The beautifully decorated 1824 square foot home features four bedrooms each with its our private en suite bathroom. The ...

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Front
1 / 22

Kissimmee Home
4 Bedrooms / 3 Bathrooms / Sleeps 10

“ Excellent ”6 Reviews

from

$99

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:10
Type:Home
Per night:$99 - $149
Per week:$699 - $990
Pets allowed:No
Internet:Yes

This brand new 4 bedroom vacation hosue has it ALL. It can fit two families (8- 10 people) This model features a spacious single story open floor plan, and a screened- in private pool With beautiful ceramic tile throughout the home and soft carpeting in each of the bedrooms, this...

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Great vacation home for a family

“ Excellent ”
November 11, 2013
It is a great home for our whole family to stay for one week. Everyone loved the stay in this home. It has ample room and bed for 10 people. The house. bed, linen etc are very clean and of good quality. To our surprise, it eve has all sets of cooking ware. It made us feeling live moving to a brand new house. My son gave it a super five star rating. He rarely gave high rating to hotels we visited. But this vacation home is truly exceptional. This excellent vacation home made our Orlando trip perfect! Kids enjoyed theme parks and adult enjoyed the comfortable home.
David Ye, New Jersey

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King Bedroom
1 / 13

Kissimmee Townhouse
3 Bedrooms / 3 Bathrooms / Sleeps 8

“ Excellent ”93 Reviews

from

$49

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:8
Type:Townhouse
Per night:$49 - $75
Per week:$380 - $525
Pets allowed:No
Internet:Yes

Welcome to 1 of my 2 gorgeous vacation houses located on the same site, couple steps from each other. They are located on the quiet and beautiful Crestwynd Bay in Kissimmee, which has the definition of “convenience”. Whether traveling to the theme parks or heading to play a ...

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Winter home

“ Excellent ”
March 3, 2015
We stayed at One of Sophia Sun's properties for the month of Jan and Feb 2015. My first impression of the townhouse was how immaculate everything was. The special touches the house keepers provided were enjoyable. It was convenient to location of our family and friends. Plus close to many attractions in the area. Sophia was a joy to communicate to if we needed to ask her a question. We would recommend her prosperity to our friends in the North. Of course this was the perfect winter to be in FL seeing that the first snow storm up North dumped 6 feet of snow. Thank you Sophia and Vacationhomerentals for everything.
Alice Setler, Cape Cod MA USA

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Kissimmee Florida Vacation Rentals - Home
1 / 8

Kissimmee Home
3 Bedrooms / 2 Bathrooms / Sleeps 6

from

$85

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$85 - $102
Per month:$2,550 - $3,060
Pets allowed:No
Internet:Yes

Suray is our Jewel. A gift from the Orient. A beautiful air conditioned 3 bed 2 bath villa with a west facing screened solar heated pool and deck overlooking a lake. The bedrooms comprise a King bed in the master, Queen bed in the guest and Twin beds in the third Bedroom. The villa...

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Kissimmee Florida Vacation Rentals - Villa
1 / 39

Kissimmee Villa
8 Bedrooms / 5 Bathrooms / Sleeps 18

“ Excellent ”1 Review

from

$199

/ night

Email Owner
Bedrooms:8
Bathrooms:5
Sleeps:18
Type:Villa
Per night:$199 - $459
Per month:$5,970 - $13,770
Pets allowed:No
Internet:Yes

Welcome to our brand new luxury finished 3600 Sqft pool home at beautiful Crystal Cove Resort. It is conveniently located close to shopping and dining (less than 1 mile away). Disney is only 6 miles away. Just minutes from major attractions like Sea World, Universal Studios, Aquatica...

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Perfect place to stay!!!

“ Excellent ”
August 23, 2014
The home was actually even better than expected!!! It was really spacious, clean and well decorated. The kids loved the Wii, board games and of course the games room. The fully stocked kitchen gave us the chance to prepare the feast for the big group. Another thing I have to mention is the amazing swimming pool with the hot tub. It was nice, clean and refreshing. We all had a really good time ! I highly recommend this beautiful villa to everyone!
AnDong Pan, Vancouver, Canada

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Kissimmee Florida Vacation Rentals - Condo
1 / 18

Kissimmee Condo
3 Bedrooms / 3 Bathrooms / Sleeps 8

“ Excellent ”2 Reviews

from

$115

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:8
Type:Condo
Per night:$115 - $185
Per month:$3,450 - $5,550
Pets allowed:No
Internet:Yes

Property Ref: RVH_138 This large 1, 630 sq. ft 3 bed, 3 bath condo is located in The Villas South at Cabana Court close to the heart of Reunion Resort. Located on the third floor and only 150 yards from the Cabana Court pool! This condo is located in Building C. If you are...

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Great place to stay

“ Excellent ”
July 1, 2014
All was perfect
Lino Rojas, Colombia

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Kissimmee Florida Vacation Rentals - Apartment
1 / 35

Kissimmee Apartment
3 Bedrooms / 2 Bathrooms / Sleeps 6

from

$79

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Apartment
Per night:$79 - $145
Per week:$553 - $1,015
Pets allowed:No
Internet:Yes

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...

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Tropical Pool at Legacy Dunes with gently shelving entry ideal for little ones!
1 / 30

Kissimmee Condo
2 Bedrooms / 2 Bathrooms / Sleeps 6

“ Very Good ”1 Review

from

$69

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Condo
Per night:$69 - $99
Per week:$400 - $690
Pets allowed:No
Internet:Yes

Fantastic place for a family or group vacation in Orlando! near all the attractions. 2 double bedroom condo 4 miles from Disney World. Literally 10 minutes from everywhere Disney, Epcot, Animal Kingdom, Hollywood Studios, Celebration, Sea World, Universal Studios. Busch...

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Average Condo

“ Very Good ”
March 16, 2015
The area is in a great location. The unit spacious but a little dated. Master bed definitely needs to be changed. Mattress was awful. cabinetry peeling and patio could use a cleaning and paint job.
Thelma Noble, Bear Creek Twp, PA

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1 / 34

Kissimmee Home
4 Bedrooms / 3 Bathrooms / Sleeps 8

“ Excellent ”37 Reviews

from

$125

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:8
Type:Home
Per night:$125 - $179
Per week:$983
Pets allowed:No
Internet:Yes

Ideally located just minutes from Disney many great golf courses near by. Why stay in a cramped hotel room when you can stay at Debbie’s Florida Retreat a beautifully decorated, Luxury Pool Home with 4 bedrooms, 3 full bathrooms, a gourmet kitchen and screened- in private...

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Florida Retreat

“ Excellent ”
January 5, 2015
Debbie's Florida Retreat was a great vacation home for our family. The house was very clean and well maintained upon our arrival and the pool and hot tub were a great added amenity. The house is also conveniently located within 20 minutes of all the Orlando attractions. I highly recommend this house if you are staying in the Orlando area for both the amenities and the value for the price.
Robert Fenn, Oak Park, MI

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Kissimmee Florida Vacation Rentals - Villa
1 / 11

Kissimmee Villa
4 Bedrooms / 2 Bathrooms / Sleeps 8

“ Excellent ”2 Reviews

from

$100

/ night

Email Owner
Bedrooms:4
Bathrooms:2
Sleeps:8
Type:Villa
Per night:$100 - $110
Per month:$3,000 - $3,300
Pets allowed:No
Internet:No

During the stay, if our guests would like to retain the bit of independence, than a stay in private Villa is ideal way to make it possible. Beautiful Disney Area Villa features private swimming pool, our guests can escape all thrills and spill down the roads and have ultimate family...

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Wonderful Home!

“ Excellent ”
March 3, 2015
We recently stayed at this home with my brother, mother and my two children (8 and 4). There was a perfect amount of space to allow for privacy and family gatherings. My children enjoyed the pool immensely and the amentities are perfect for a family looking to stretch out a little with all the comforts of home. Since this experience, there is no way we could ever be happy with just a hotel room again. The house was conveniently located, very clean and comfortable. Everything we needed was right there. Great place!
Mary-Lee Armstrong, Montreal, Quebec

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Kissimmee Florida Vacation Rentals - Home
1 / 18

Kissimmee Home
4 Bedrooms / 3 Bathrooms / Sleeps 8

“ Excellent ”6 Reviews

from

$150

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:8
Type:Home
Per night:$150
Per month:$4,500
Pets allowed:No
Internet:Yes

Newly Renovated! 4 Bedrooms including: 2 Master bedrooms with King size beds and en suites 1 bedroom with Queen size bed 1 bedroom with double twin beds Games room with pool table and fos All rooms include cable programming with LCD TVs Screened Pool with Hot...

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home review

“ Excellent ”
March 9, 2015
This home was very nice; spacious, clean, comfortable. The internet service wasnt great but we managed ok. Quiet neighborhood, good for walking. Close to parks and stores. The ants were a bit of a pain but not impossible to deal with.
Rose Sheehan, peacham, vt

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Royal Palm Bay is a great place for a wonderful vacation!
1 / 16

Kissimmee Condo
2 Bedrooms / 2.5 Bathrooms / Sleeps 6

from

$85

/ night

Email Owner
Bedrooms:2
Bathrooms:2.5
Sleeps:6
Type:Condo
Per night:$85 - $125
Per week:$595 - $875
Pets allowed:No
Internet:Yes

This spacious second floor unit features 2 Bedrooms, 2 Baths, Living Room, Dining Room and a Brand New Kitchen. Ceramic tile throughout, new carpeting, new furniture throughout and Wi- FI High Speed Internet! Living Room has 27" Flat Panel TV with DVD Player, Master bedroom...

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Kissimmee Florida Vacation Rentals - Condo
1 / 20

Kissimmee Condo
3 Bedrooms / 2 Bathrooms / Sleeps 8

“ Excellent ”6 Reviews

from

$109

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:8
Type:Condo
Per night:$109 - $139
Per month:$3,270 - $4,170
Pets allowed:No
Internet:Yes

MEET THE NEW "SIMBA'S PRIDE! " Disney World area home - the most exciting, vacation home in the Disney World/Orlando area! At less than the cost of many small hotel rooms in the area, and 400%- 500% less than staying "on property" this home is almost a "too good to be true" value....

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Very nice place

“ Excellent ”
February 12, 2015
Clean accommodation's, large rooms & bedrooms. Great place over all!
Heather Kowaleski, Harbor Beach MI

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Kissimmee Florida Vacation Rentals - Home
1 / 16

Kissimmee Home
5 Bedrooms / 4 Bathrooms / Sleeps 12

“ Excellent ”16 Reviews

from

$160

/ night

Email Owner
Bedrooms:5
Bathrooms:4
Sleeps:12
Type:Home
Per night:$160 - $179
Per month:$4,800 - $5,370
Pets allowed:No
Internet:Yes

Dopey's Delight is a Disney vacation rental that is nestled in the popular Indian Creek community, less than 3 miles from Disney's doorstep in Kissimmee, Florida and is perfectly placed for the shops, restaurants, fun and attractions that Orlando has to offer. With 5 bedrooms ...

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Best vacation ever!

“ Excellent ”
December 1, 2014
Wonderful home. Great floor plan . Plenty of room for all 9 of us. Fantastic privacy with 3 split bedroom with their own baths on opposite ends of home and 2 bedrooms that shared a bath. Plenty of dishes and cooking supplies very conducive for home cooked meals. The kitchen was a dream to work in. Easy drive to all Disney attractions and convenient to shops and restaurants. We all had a fantastic time. Home was clean and bright. Would definitely recommend to multi generational families. The space was very easy to share. Would stay again in the future. Only issue was no garbage pickup on Thursday due to thanksgiving holiday which was an issue due to raccoons trying to get into trash. Wish I would have known earlier so I could have talked to owner about an alternative.
Maggie Hendler, Elk Grove Village, Il. USA

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Kissimmee Florida Vacation Rentals - Condo
1 / 30

Kissimmee Condo
3 Bedrooms / 2 Bathrooms / Sleeps 8

“ Excellent ”11 Reviews

from

$43

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:8
Type:Condo
Per night:$43
Per week:$299
Pets allowed:No
Internet:Yes

3 Bedroom 2 Bath Condo For Rent At Windsor Hills! Best Price Guarantee. Closest To Disney - Be On Property In Two Minutes. Full Use Of All Windsor Hills Amenities - king Master Bed - free Wireless Internet - flat Screen Hdtv And Dvd Players Every Room - electronic...

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Amazing Home

“ Excellent ”
February 26, 2015
We stayed in a 4 bedroom home 8 minutes from Disney. The kids lived the pool and all the free space. They home was clean and spacious. I will definitely stay again.
Savitrie Ramsahai, Queens. New York

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Kissimmee Florida Vacation Rentals - Villa
1 / 48

Kissimmee Villa
5 Bedrooms / 3.5 Bathrooms / Sleeps 12

“ Excellent ”2 Reviews

from

$140

/ night

Email Owner
Bedrooms:5
Bathrooms:3.5
Sleeps:12
Type:Villa
Per night:$140
Per week:$975
Pets allowed:No
Internet:Yes

A WARM & INVITING WELCOME awaits you at our idyllic LAKESIDE family home ... THE PRESIDENTIAL LODGE. As the name suggests, we've spared no expense in creating a luxurious yet comfortable home where you and your family can enjoy a memorable vacation at DISNEY WORLD ORLANDO. Our...

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Golf trip with the wives

“ Excellent ”
March 9, 2015
We took our annual trip to Kissimee with our wives to play golf (three couples). We always rent a house for at least a week. The Presidential Lodge was our best lodging to date. The house was as clean as you would keep your home. The furnishings were attractive, and functional. The house has all the amenities of home. We entertained our friends from the area almost every night in the well equipped and spacious kitchen/family room. Beautiful warm evenings were spent on the patio by the pool and a lot laughs and bad pool playing were had in the game room. The wives enjoyed the many malls and outlets and we all visited our favorites restaurants. What a great break in the action from our New England weather. Everyone is talking about next year"s trip already.
Cornell Lewis, New England

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Bedrooms:5
Bathrooms:5
Sleeps:12
Type:Villa
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:Yes

Executive 4000 sq. ft. 5 bedroom, 5 bathroom, Lakeside Villa with 30' Pool and Spa. High- Speed wireless Internet and computer. Perfect for that Orlando, Holiday Parks, Family Vacation, Reunion, Golf Holiday, or just a weeks relaxing in the sun by the pool. Our luxuriously ...

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What an Oasis!

“ Excellent ”
January 24, 2015
We stayed 9 days in this lovely home in January and absolutely loved it. It's situated on a nice quiet street in a gated community and backs on to a lovely lake that was always the centrepiece of our bird watching. The pictures say it all and it was more beautiful in real life. Our highlights were the pool, the hot tub, the covered barbecue area, the location on the lake, the roominess of the whole house, and overall, just how much it just felt like coming "home" to peace and quiet after the chaotic days at Disney and Universal. We picked this place also because of how much privacy it offered in comparison to others in the area and we were not disappointed. We also had the added bonus of always seeing the beautiful sunrises and sunsets...not too mention a view of the moon from our nightly swims. We would definitely recommend this villa to those looking for a very comfortable home away from home while being a close driving distance to the attractions. David was very helpful and was always available for any questions. We would not hesitate to stay here again. We understand they are doing a few renovations which we will certainly want to see on a return visit.Many thanks for the use of your villa.
Mitch and Judith, Ottawa

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Kissimmee Florida Vacation Rentals - Villa
1 / 24

Kissimmee Villa
8 Bedrooms / 4.5 Bathrooms / Sleeps 20

“ Excellent ”5 Reviews

from

$199

/ night

Email Owner
Bedrooms:8
Bathrooms:4.5
Sleeps:20
Type:Villa
Per night:$199 - $799
Per month:$5,970 - $23,970
Pets allowed:No
Internet:Yes

Please email us to check availability of this home or other homes we have! Home is fully air conditioned and completely non smoking. Furnished 8bedrooms and 5baths luxurious home is perfectly located in enclave area. There are two king sized master suites, two king sized bedrooms,...

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great vacation

“ Excellent ”
July 4, 2014
My family stay at this villa and had a wonderful time.Ms.Lili was great help us the whole time,I never met her but I count her as one of my friend. Thank you so much!!!!
jerome snoddy, Washington,D.C.

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Kissimmee Florida Vacation Rentals - Townhouse
1 / 13

Kissimmee Townhouse
4 Bedrooms / 3 Bathrooms / Sleeps 10

“ Excellent ”5 Reviews

Bedrooms:4
Bathrooms:3
Sleeps:10
Type:Townhouse
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:Yes

Beautifully decorated large vacation home in a gated community, with new furniture and 4 flat screen tv's. This home has 4 bedrooms. 3 upstairs with 2 full baths, and 1 on the main floor with another full bath. Offers full kitchen, with all the amenities of home, the pool, hot...

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Great rental

“ Excellent ”
January 9, 2015
After being scammed with another rental property, I was extremely worried this would be the same thing. Totally not the case as the description is completely accurate. Close to theme parks, grocery stores, restaurants, and more. Comes stocked with basics such as pots/pans, dinnerware, and flatware. Great location and owners are very nice. Highly recommend.
Maria Ellis, Las Vegas, NV

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Kissimmee Florida Vacation Rentals - Home
1 / 34

Kissimmee Home
7 Bedrooms / 4.5 Bathrooms / Sleeps 16

from

$240

/ night

Email Owner
Bedrooms:7
Bathrooms:4.5
Sleeps:16
Type:Home
Per night:$240 - $290
Per week:$1,680 - $2,030
Pets allowed:No
Internet:Yes

Excecutive 7 Bedroom Pool home in the Prestigious Emerald Isle Resort Community! Oversized covered lanai overlooks the screen enclosed pool and whirlpool Game room with a pool table and airhocky table Internet service is provided free of charge TV's with DVD players in all the...

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Pool Area with separate hot tub for 12 people
1 / 13

Kissimmee Villa
4 Bedrooms / 3.5 Bathrooms / Sleeps 8

“ Excellent ”6 Reviews

from

$89

/ night

Email Owner
Bedrooms:4
Bathrooms:3.5
Sleeps:8
Type:Villa
Per night:$89 - $139
Per week:$623 - $973
Pets allowed:No
Internet:Yes

Perfect Jacuzzi Tub and shower for 2 people... Beautiful and well furnished Villa situated in the Venetian Bay Villages has all the amenities required for a relaxing and fun vacation. Rental villa provides Linens, Washer & Dryer, Microwave, Dishwasher, and much more. Stay ...

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Winter Vacation

“ Excellent ”
December 4, 2014
My experience with this rental was great. The house was nice and clean and accommodated myself and family well. I want to give a special thanks to Rob who really helped me in finding this rental. He sent me paperwork of things to do when you don't want to go to theme parks. He also answered all my questions and had such a great personality. I look forward to my winter vacation next year because I know who to call. Lol thanks again for allowing my family to enjoy Your Great property. See ya next year!!
Dena Ellis, Charlotte, NC

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Kissimmee Florida Vacation Rentals - Villa
1 / 24

Kissimmee Villa
6 Bedrooms / 4 Bathrooms / Sleeps 12

from

$300

/ night

Email Owner
Bedrooms:6
Bathrooms:4
Sleeps:12
Type:Villa
Per night:$300
Per month:$9,000
Pets allowed:No
Internet:Yes

Windsor Hills villa description Located in the 24/7 guarded and gated community of Windsor Hills, the Disney area's #1 Vacation Resort! Only 2 Miles from Disney. South facing pool/SPA for all day Sun exposure AND Extra privacy! an Exclusive feature, only few houses in Windsor...

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Kissimmee Florida Vacation Rentals - Villa
1 / 24

Kissimmee Villa
8 Bedrooms / 4.5 Bathrooms / Sleeps 20

from

$178

/ night

Email Owner
Bedrooms:8
Bathrooms:4.5
Sleeps:20
Type:Villa
Per night:$178 - $599
Per month:$5,340 - $17,970
Pets allowed:No
Internet:Yes

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. Please email us to...

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1 / 17

Kissimmee Villa
6 Bedrooms / 4 Bathrooms / Sleeps 12

“ Excellent ”1 Review

from

$207

/ night

Email Owner
Bedrooms:6
Bathrooms:4
Sleeps:12
Type:Villa
Per night:$207 - $293
Per month:$6,210 - $8,790
Pets allowed:No
Internet:Yes

Be one of the first families to stay in this 'brand new' 6 Bedrooms 4 Baths and Pool Home in the guarded gated community of Windsor Hills! This luxury Orlando vacation villa is a six bedroom, four baths, pool and spa home located in the brand new, exclusive rental community...

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A great family vacation

“ Excellent ”
March 3, 2015
Our family loved staying at this house. Owner and local property management were a pleasure to deal with. House is maintained, furnished and equipped to a very high standard! Great proxomity to parks.
Allen Guffey, Florence, SC

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Kissimmee Florida Vacation Rentals - Condo
1 / 32

Kissimmee Condo
3 Bedrooms / 2 Bathrooms / Sleeps 8

“ Excellent ”7 Reviews

from

$70

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:8
Type:Condo
Per night:$70 - $105
Per week:$490 - $735
Pets allowed:No
Internet:Yes

Condominium: It is a professionally decorated and furnished and spacious 3- bedroom/2- bathroom condominium offering space, style, luxury and privacy. It is nestled in Villas at Island Club Resort. This beautiful, gated resort community offers luxury with a unique Caribbean Island...

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Kissimmee 2014

“ Excellent ”
September 16, 2014
Excellent condominium; good location and close to theme parks. Relation rate/service is also considerated as good. We spent a wonderful Holiday, included the lodging. Visiting Orlando again we would ask the same lodging. Can be recommanded to our friends. Thank you
LORGE Nicolas, Gosseldange, Luxembourg, Europe

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Family Room
1 / 17

Kissimmee Home
7 Bedrooms / 4.5 Bathrooms / Sleeps 16

“ Excellent ”4 Reviews

from

$200

/ night

Email Owner
Bedrooms:7
Bathrooms:4.5
Sleeps:16
Type:Home
Per night:$200 - $360
Per month:$6,000 - $10,800
Pets allowed:No
Internet:Yes

Kirk Manor is a beautiful 7 bed/4. 5 bath home situated at the most prestigious vacation spot- Emerald Island Resort. Kirk Manor vacation home has a private pool and screen lanai with lots of patio furniture and is close to all the Orlando attractions in Kissimmee, Florida. Kirk...

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Vacation Perfection!

“ Excellent ”
August 12, 2014
Our family had a fabulous time staying at Kirk Manor! The home is so comfortable and conveniently located close to Disney World. The owners provided absolutely everything we needed during our stay. We all enjoyed the lovely swimming pool and hot tub and our grandchildren spent time in the game room as well. We would highly recommend this rental property!
Kathleen Humski, Wisconsin

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1 / 14

Kissimmee Townhouse
4 Bedrooms / 3 Bathrooms / Sleeps 10

“ Excellent ”13 Reviews

from

$85

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:10
Type:Townhouse
Per night:$85 - $100
Per month:$2,550 - $3,000
Pets allowed:No
Internet:Yes

Enjoy a relaxing and unforgettable vacation at our Encantada Villa. Luxuriously furnished, this 4 bedroom/3 bathroom townhome with heated- private pool, is located in the gated community of Encantada Resort. On the main floor, you will enjoy opened kitchen on the dining area ...

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What you book is what you get!

“ Excellent ”
September 24, 2014
We were please With this house. Spacious, clean, close to the Disney parks. We also had excellent service. The only downside is the lack of kitchen tools.
Martin Lavoie, Tadoussac, Canada

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Kissimmee Florida Vacation Rentals - Villa
1 / 27

Kissimmee Villa
5 Bedrooms / 3 Bathrooms / Sleeps 10

“ Excellent ”3 Reviews

from

$99

/ night

Email Owner
Bedrooms:5
Bathrooms:3
Sleeps:10
Type:Villa
Per night:$99
Per month:$2,970
Pets allowed:No
Internet:Yes

This LOVELY, almost BRAND- NEW TWO STORY EXECUTIVE FASHIONED VACATION HOME RENTAL has five- bedrooms, three- baths, and features an over- sized deck with a covered lanai, and a private swimming pool overlooking a lake. There is ceramic tile throughout the kitchen and dining...

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Summer Stay

“ Excellent ”
June 29, 2014
This house is absolutely gorgeous and very well maintained. Everything from the yard to the pool area was immaculate. Great neighborhood and location, beautiful scenery, very well furnished and EXCELLENT management. Definitely planning to another stay.
PM Wells, Brunswick, GA

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Kissimmee Florida Vacation Rentals - Home
1 / 21

Kissimmee Home
4 Bedrooms / 3.5 Bathrooms / Sleeps 10

from

$150

/ night

Email Owner
Bedrooms:4
Bathrooms:3.5
Sleeps:10
Type:Home
Per night:$150 - $180
Per week:$1,100 - $1,300
Pets allowed:No
Internet:Yes

$1100 per week in month of FEBRUARY- JULY 1, 2015 (Cleaning & Taxes included ) OPTIONAL POOL HEAT is $140 per WEEK or $150 a night plus one time $90 cleaning ( Taxes Included ) NO ANIMALS & NO SMOKING NO ANIMALS & NO SMOKING This Luxuriously Huge 2400 Square foot Furnished Italian...

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Kissimmee Florida Vacation Rentals - Villa
1 / 49

Kissimmee Villa
6 Bedrooms / 4 Bathrooms / Sleeps 12

“ Excellent ”27 Reviews

from

$145

/ night

Email Owner
Bedrooms:6
Bathrooms:4
Sleeps:12
Type:Villa
Per night:$145 - $200
Per month:$4,350 - $6,000
Pets allowed:No
Internet:No

1. 'RATED EXCELLENT' by Tripadvisor 2. 'Top Rental Property - Winner 2011, ' awarded by Flipkey Congratulations ! Based at exceptional guests reviews and impressive listings . Kissimmee Vacation Rentals With 3000sqft of fully air conditioned space incorporating 6 bedrooms,...

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Great Place

“ Excellent ”
December 4, 2014
We are a group of eight golfers from Ontario who venture to the Orlando area each fall for one last "golf your brains out" week before retiring from the game until the next Canadian spring allows for yet another season. We are returning renters of Jacksonvilla which in itself says something about the level of satisfaction we have with this accommodation. The house is well appointed, centrally located and fits our needs to a "tee"! The house's owner, Michael, is very accommodating to deal with as is his property management "guy" who deals with your every need on a very timely basis.Great place, great price!
Jim Young, Kingston, ON

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Kissimmee Florida Vacation Rentals - Villa
1 / 10

Kissimmee Villa
3 Bedrooms / 3 Bathrooms / Sleeps 6

from

$99

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:6
Type:Villa
Per night:$99 - $135
Per month:$2,970 - $4,050
Pets allowed:No
Internet:Yes

Welcome to your home away from home! Everything you and your family will need for your Florida vacation is provided in this lovely 3 bedroom, 3 bath townhome located in the prestigious, subdivision of Windsor Hills. This exclusive guarded/gated community is located only 2 miles...

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Kissimmee Florida Vacation Rentals - Villa
1 / 22

Kissimmee Villa
7 Bedrooms / 4.5 Bathrooms / Sleeps 16

“ Excellent ”1 Review

from

$250

/ night

Email Owner
Bedrooms:7
Bathrooms:4.5
Sleeps:16
Type:Villa
Per night:$250 - $300
Per month:$7,500 - $9,000
Pets allowed:No
Internet:Yes

The villa, an exquisitely furnished property offers 2881 s. f. of air- conditioned flexible living & play space for up to 16 people, is located in the prestigious Emerald Island Resort, the closest gated vacation community to Disney world (3 miles). it is also close to Sea World,...

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Wonderful

“ Excellent ”
October 22, 2014
great property, very well equiped, a lot of room. placed 10 min. to Disney, quit nighberhood, clean, sw pool was ok. we enjoyed out week stay there very much.
Eyal Ashkenazy Adv, Israel

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Kissimmee Florida Vacation Rentals - Apartment
1 / 27

Kissimmee Apartment
3 Bedrooms / 2 Bathrooms / Sleeps 6

from

$89

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Apartment
Per night:$89 - $145
Per week:$623 - $1,015
Pets allowed:No
Internet:Yes

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...

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Kissimmee Florida Vacation Rentals - Townhouse
1 / 18

Kissimmee Townhouse
3 Bedrooms / 2 Bathrooms / Sleeps 6

“ Excellent ”23 Reviews

from

$60

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Townhouse
Per night:$60 - $75
Per month:$1,800 - $2,250
Pets allowed:No
Internet:No

Beautiful three bedrooms two baths townhouse with amenities. Venetian Bay Villages has a beautiful village concept setting with a resort- style clubhouse that includes gym, 4 pools, business center. There are tennis courts, volleyball, basketball, picnic area, children's play...

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awesome

“ Excellent ”
March 19, 2015
The best place I have stayed in,i would rent this everytime I come to fla..loved it
Sherry Payton Brueck, michigan

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Welcome!!
1 / 24

Kissimmee Home
5 Bedrooms / 3 Bathrooms / Sleeps 12

“ Excellent ”7 Reviews

from

$100

/ night

Email Owner
Bedrooms:5
Bathrooms:3
Sleeps:12
Type:Home
Per night:$100 - $175
Per week:$700 - $1,225
Pets allowed:No
Internet:Yes

This Luxuriously appointed home is presented with upgraded furniture and fittings throughout, and fully air conditioned to create a comfortable indoor climate. With1 bedroom and bathroom located on the ground floor of the home, it is an ideal choice for groups with elderly...

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Perfect Vacation

“ Excellent ”
April 2, 2013
We were a little nervous renting a house for the first time, but Marilyn made us feel very comfortable. The management company was very professional. They were in contact with us throughout the process. When we arrived, the house was very clean. It looked just like the photos. There was plenty of room for two families. We used the pool and hot tub every day. Thank you for making our vacation more relaxing then ever!
Traci Genz Knudtson, Sheboygan, WI USA

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Kissimmee Florida Vacation Rentals - Condo
1 / 25

Kissimmee Condo
3 Bedrooms / 2 Bathrooms / Sleeps 8

“ Excellent ”67 Reviews

from

$43

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:8
Type:Condo
Per night:$43
Per week:$299
Pets allowed:No
Internet:Yes

Best Priced 3 Bedroom Condo For Rent At Windsor Hills. Disney Fireworks View Building - Watch Disney Fireworks, Never Leave Building. Closest To Disney - Be On Property In Two Minutes. - king Master Bed - free Wireless Internet - flat Screen Hdtv And Dvd Players...

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Awesome accomodations

“ Excellent ”
December 4, 2013
I loved this property!!! It was close enough to the parks for a quick drive yet far enough from the hustle and bustle of everything! It felt like a home away from home and would stay there again in a heart beat!
Melissa Marlein, Windsor, Ontario canada

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Kissimmee Florida Vacation Rentals - Villa
1 / 28

Kissimmee Villa
8 Bedrooms / 4.5 Bathrooms / Sleeps 19

“ Excellent ”5 Reviews

from

$199

/ night

Email Owner
Bedrooms:8
Bathrooms:4.5
Sleeps:19
Type:Villa
Per night:$199 - $299
Per week:$1,699
Pets allowed:No
Internet:Yes

Only 3 miles away from Disney parks and with its beautiful landscape and architectual design, the prestigious Emerald Island Resort is the most popular in Orlando area. Our 8 bedroom Villa is fully furnished and equipped, will provide you a private, spacious, luxury, and comfortable...

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Great Vacation with family

“ Excellent ”
June 5, 2014
We rented this home the last week in May, 2014 so we could spend some time in Florida with family. It is a lovely house with plenty of room. There were 9 of us and we all had plenty of bedrooms and bathrooms. The kids loved swimming in the private pool and playing ping pong, air hockey and pool in the game room at the house every day. The kitchen was well equipped and had plenty of storage for groceries. We loved being able to watch the Magic Kingdom fireworks, Wishes, every night from the upstairs balcony window. It was great not having to fight crowds at the parks after they were done. We had breakfast reservations at Animal Kingdom Lodge at Boma one morning and it only took us about 5 minutes to get there. The resort is a short drive to Disney which was great. Emerald Island Resort is lovely and we felt very safe there. It is a very nice neighborhood and everyone was friendly. The resort is very close to Publix, Super Target, Walmart and a lot of other places to shop. There are tons of restaurants very close so there are plenty of choices for eating out. Helen is very quick to respond to emails when booking or if you have any questions at all. Thank you, Helen, for the use of your lovely home. We would definitely rent it again from you in the future. L. Shaw
Lisa Shaw, NC, USA

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Kissimmee Florida Vacation Rentals - Villa
1 / 11

Kissimmee Villa
4 Bedrooms / 4 Bathrooms / Sleeps 8

from

$171

/ night

Email Owner
Bedrooms:4
Bathrooms:4
Sleeps:8
Type:Villa
Per night:$171 - $235
Per month:$5,130 - $7,050
Pets allowed:No
Internet:Yes

Be one of the first families to stay in this 'brand new' 4 Bedrooms 4 Baths and Pool Home in the guarded gated community of Windsor Hills! This luxury Orlando vacation villa is a four bedroom, four baths, pool and spa home located in the brand new, exclusive rental community...

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Kissimmee Florida Vacation Rentals - Home
1 / 10

Kissimmee Home
3 Bedrooms / 3 Bathrooms / Sleeps 8

from

$79

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:8
Type:Home
Per night:$79 - $105
Per week:$499 - $693
Pets allowed:No
Internet:Yes

This is a nice three bedroom homes personally decorated, furnished and maintained well. It is located in Crestwynd Bay a gated community which is peaceful and safe as well as closest to shopping, Disney and restaurants. The home consists of 1 KING bed with attached bathroom, 1 ...

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Kissimmee Florida Vacation Rentals - Villa
1 / 35

Kissimmee Villa
3 Bedrooms / 3 Bathrooms / Sleeps 6

from

$109

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:6
Type:Villa
Per night:$109 - $165
Per week:$763 - $1,155
Pets allowed:No
Internet:Yes

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...

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Kissimmee Florida Vacation Rentals - Villa
1 / 40

Kissimmee Villa
3 Bedrooms / 3 Bathrooms / Sleeps 8

from

$114

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:8
Type:Villa
Per night:$114 - $128
Per week:$795 - $895
Pets allowed:Yes
Internet:Yes

This 3 bedroom pet friendly vacation rental home welcomes families travelling with their beloved pets. This pet friendly holiday home rental is located in Chatham Park and includes a private screened in pool and sundeck. This pet friendly vacation home rental has a fully furnished...

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Kissimmee Florida Vacation Rentals - Villa
1 / 14

Kissimmee Villa
5 Bedrooms / 5.5 Bathrooms / Sleeps 10

“ Excellent ”9 Reviews

from

$199

/ night

Email Owner
Bedrooms:5
Bathrooms:5.5
Sleeps:10
Type:Villa
Per night:$199 - $299
Per week:$1,393 - $2,093
Pets allowed:No
Internet:Yes

Our exclusive vacation villa offers a private pool and 5 bedrooms that allow up to 10 guests comfortable accommodations. This luxury vacation home is equipped with all the amenities to make you stay relaxing and pleasurable. A fully equipped kitchen, 5 full bathrooms and modern...

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Terra verde resort

“ Excellent ”
December 26, 2014
Its a really nice resort.
Eric Flores, mcallen,Tx USA

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Bedrooms:5
Bathrooms:3
Sleeps:12
Type:Villa
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:Yes

Fully Furnished – Two Master Size Sites – Pool/Spa – High Speed Wi Fi – 6 TV’s –Games Area –Gated Resort . Villa Beaulieu, the luxurious house in top rated Solana Resort features 5BR (2 Masters) including two King sized, one queen sized, two twin beddings along...

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Excellent stay!

“ Excellent ”
March 4, 2015
Great place, great location. Home needs some work to stay updated and competitive with the rest.
Amma Jane, Ontario , Canada

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Kissimmee Florida Vacation Rentals - Townhouse
1 / 28

Kissimmee Townhouse
5 Bedrooms / 5 Bathrooms / Sleeps 14

from

$195

/ night

Email Owner
Bedrooms:5
Bathrooms:5
Sleeps:14
Type:Townhouse
Per night:$195 - $350
Per week:$1,365 - $2,450
Pets allowed:No
Internet:Yes

This beautiful unit is located in Paradise Palms Resort one of Florida's Premier Resorts only 5 minutes from Disney! ! and within a couple miles to restaurants, grocery stores and shopping. Stay in the lap of luxury when you book our professionally decorated unit inParadise....

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private heated swimming pool
1 / 61

Kissimmee Villa
7 Bedrooms / 4.5 Bathrooms / Sleeps 16

from

$169

/ night

Email Owner
Bedrooms:7
Bathrooms:4.5
Sleeps:16
Type:Villa
Per night:$169 - $329
Per week:$899 - $2,499
Pets allowed:No
Internet:No

Welcome to our 7BR/4. 5BA Fantasia Villa! Sleeps up to 16 guests comfortably on beds. Location & the community: Located in the guarded resort community of Terra Verde, our home is only 8 miles from Disney (map is included in the photo link below) and offers over 2800 sq....

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Kissimmee, Florida Travel Tips

Located only moments from Orlando, the beautiful resort town of Kissimmee offers the best that Florida has to offer. Families looking for vacation rentals in Kissimmee, FL have many accommodations to choose from, but renting a home is the best bang for your buck while on a Kissimmee vacation. Rentals by owner offer much more space and privacy than a hotel room, and renting by owner ensures that homes are very well maintained and updated. Keep reading to learn more tips about how to have a memorable Florida vacation in Kissimmee.
Beaches and Parks
Because it is such a popular tourist destination, there is an abundance of available vacation homes in Kissimmee. Families interested in spending time at the beach can easily find great accommodations, but hurry! Beach houses for rent in Kissimmee, FL are quickly snapped up. Make sure to reserve your spot online well in advance to save time and money.
St. Cloud Lakefront Park and Beach offers a fishing pier, splash pad, family picnic area, volleyball court, and playground. Located along the breathtaking Lake Tohopekaliga, this park is a great place to spend a relaxing afternoon.
Cocoa Beach, located just an hour's drive from Kissimmee, features beautiful weather, whale watching, fine dining, and golf.
Things to Do
A great feature of Kissimmee vacation homes is their central location to a number of popular attractions. Theme parks, outdoor activities, and fun things for the kids can all be found within a short drive. Read on to find out more about the variety of activities waiting for you in the Kissimmee area.
Theme Parks
What probably comes to mind when looking for houses for rent in Kissimmee, FL is the town's close proximity to world-famous theme parks. The magic of Disney World, Universal Orlando, and SeaWorld are only a short drive away while staying at this delightful vacation spot.
Walt Disney World needs no introduction. As the most visited entertainment complex in the world, this beloved attraction boasts four theme parks and two water parks.
Universal Orlando consists of Universal Studios, Islands of Adventure, and Wet N' Wild Orlando. Visitors can enjoy a variety of shows, dining, and events right within the borders of the park.
SeaWorld is another favorite of those visiting the Orlando area. With tons of shows, exhibits, dining, and shopping, there is surely to be something for everyone to enjoy. Kids will adore seeing killer whales, dolphins, manatees, sharks, polar bears, flamingoes, and penguins up close.
Outdoor Adventures
Airboat Tours are available via Aquatic Adventures Airboat Tours . Go bird watching, look out for alligators, or take a combination hiking tour/boat ride and learn all about the wildlife of the Florida wetlands.
Golf is a popular sport in Florida because of its year-round sunny weather. If you're a seasoned pro looking for challenging courses or just want to play mini-golf with the kids, Kissimmee has you covered.
Hot Air Balloon Rides are a great way to top off your Kissimmee vacation. Take a sunrise balloon ride over Central Florida's beautiful landscape and check out the wildlife from high above.
Fun With Kids
The kids will have no shortage of things to do while enjoying their time in Kissimmee vacation homes. Kids and parents will have all the comforts of home while having a blast exploring the nearby attractions. In addition to the great outdoors and amazing theme parks, the Kissimmee area also features lots of relaxing, family-friendly activities.
Medieval Times Dinner & Tournament is guaranteed to always be a fun time. Have dinner while being entertained by a live-action jousting tournament.
Osceola County Pioneer Village and Museum features many exhibits depicting life in the 19th century. Located in northwestern Osceola County, the Pioneer Village has a general store, blacksmith shop, one room schoolhouse, and nature preserve.
Green Meadows Petting Farm , located just minutes from Orlando, teaches kids about a variety of farm animals and even allows them to milk a cow. The farm also has a train ride and offers pony rides.
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