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Vacation Rentals & House Rentals in Kissimmee

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497 house rentals

New Opening 9 Br/6 Ba luxurious Pool House from $300/nt, Close To Disney

Kissimmee house

9 bedrooms / 6 bathrooms / sleeps 18

“Great time!” House was a perfect fit for my family. We had a great time and plan on making this a yearly trip. Central to everything, but far enough away you didn’t feel trapped. Would highly recommend it!

Responds fast! avg. 32 minutes

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Price per night from

$401

Disney World 2 Miles

Kissimmee condo

2 bedrooms / 2 bathrooms / sleeps 5

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Price per night from

$101

NEW LISTING! 3-Bedroom Resort Villa

Kissimmee villa

3 bedrooms / 2 bathrooms / sleeps 10

“Beautiful Resort” The unit was absolutely spacious. Chris was very helpful in booking the unit. He told me that the unit number was assigned by the resort and it would be look identical to the pictures. The unit that was assigned to us was exactly as shown in the pictures. We were located on the third floor and it had a balcony with a great view of the pond. Plenty of kitchen space and bathrooms. The master suite that i stayed in had a jacuzzi and own bathroom. I only wish I had more time to check out the resorts amenities, but since I traveled from VA my family and I went to all the major Orlando attractions. But even with that said you can't go wrong staying at Star Island resort. I would love to go back.

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Price per night from

$182

New Opening 8br/6ba pool villa from $260/nt ,Close to Disney

Kissimmee house

8 bedrooms / 6 bathrooms / sleeps 18

“Family vacation” This by far was the best we went to. There is something for everyone to do down to the kids, the house was beautiful.

Responds fast! avg. 32 minutes

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Price per night from

$297

Caribe Cove Resort - 2 BR * Unit Top floor * New Mattress - WiFi/Parking free

Kissimmee apartment

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$149

From $100/NT,1.5 Mile to Disney ,1808 sq ft 4br/3ba townhome with lake view

Kissimmee apartment

4 bedrooms / 3 bathrooms / sleeps 8

“Great location” We had great times in Oakwater, all was perfect! The house is fully equipped, all is clean, new and works perfect!It is an ideal location, close to everything. Near the home are so many great restaurants such as: Bonefish, Longhorn, Golden Corral, Ihop, Bahama Breeze, Buffalo Wild Wings, Flippers Pizza*, Red Lobster and lots more! The super target is within 2 min as well as the Publix.It is also located in very quiet area. There are great sports facilities, tennis court, and the pool area itself is fantastic. We enjoyed it very much and the pool s huge and warm !!! We loved it and will definitely recommend to our friends and family!

Responds fast! avg. 32 minutes

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Price per night from

$115

Brand New 8br/6ba pool villa from $260/nt ,Close to Disney

Kissimmee house

8 bedrooms / 6 bathrooms / sleeps 18

“Mrs” Me and my family really enjoyed staying at the property rental it was ever thing we need in a vaction rental.

Responds fast! avg. 32 minutes

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$308

⭐Great Value Villa w/ Private Pool - Nearby Disney Resort⭐

Kissimmee villa

7 bedrooms / 5 bathrooms / sleeps 18

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$242

5 Star Rated Disney Adventure Villa at Windsor Hills Luxury Villa New Water Park

Kissimmee villa

6 bedrooms / 4 bathrooms / sleeps 16

“Perfect localtion and great house with a perfect pool.” I'm a rookie at time sharing, but the owner helped me all the way. We saved money by staying here instead of inside Disney. The location was only 10 to 15 minutes for all of the Parks.

Responds fast! avg. 2 hours 58 minutes

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Price per night from

$228

New 9br/6ba pool villa from $280/nt,Close to Disney

Kissimmee house

9 bedrooms / 6 bathrooms / sleeps 20

“Nice house for large family” The house itself is very attractive. The bedrooms were very well appointed. There were sufficient towels and plates, silverware, glassware, etc., for our party. Our major problem was the parking. It is a very over-crowded community and we had five cars (to be expected in a six master-bedroom house that fits 18+), and we often had trouble parking near the house. My only other complaint (if you could call it that) was the trash. We had one large trash can and it got picked up on Monday morning. We were there for six full days with 13 people, so we easily refilled it up and then had multiple loose bags with nowhere to put them through the end of our stay. No recyclable can was available, either, so recyclables had to go in trash bags. Owner was easy to work with. Thanks for a very nice home!

Responds fast! avg. 32 minutes

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$355

Located in Emerald Island Resort Beautiful 7 Bed 4.5 Bath Villa Close 2 Disney

Kissimmee villa

7 bedrooms / 7 bathrooms / sleeps 16

“great house!” very nice and spacious home. My family and I enjoyed our long weekend at the pool. The movie room/ game room is a great bonus for the adults and kids. Definitely will be back.

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Price per night from

$150

Windsor at Westside Disney Villa 8bed 6bath SW pool 25 minutes from Disney

Kissimmee villa

8 bedrooms / 6 bathrooms / sleeps 16

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Price per night from

$366

*CLEAN - Afforable Townhome - 5 Miles from Disney*

Kissimmee townhouse

3 bedrooms / 2 bathrooms / sleeps 6

“Exceptional” This place was beautiful... I’ve always booked hotel rooms when I go on vacations but never again will I book a hotel... this place had everything I could ask for and more my family and I were very pleased and satisfied.

Responds fast! avg. 3 hours 48 minutes

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Price per night from

$109

Bella Vida New Phase 6 bedroom Modern Home

Kissimmee house

6 bedrooms / 7 bathrooms / sleeps 12

Responds fast! avg. 1 hour 21 minutes

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Price per night from

$309

Still time to book !

Kissimmee house

3 bedrooms / 3 bathrooms / sleeps 8

“Fantastic rental” Great location, safe neighborhood, very clean house, and a great price. Will definitely stay again!!

Responds fast! avg. 16 minutes

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Price per night from

$112

Wonderful 4 bed, 3 bath home in Paradise Palms!

Kissimmee house

4 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 12 minutes

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Price per night from

$138

Your new Vacation Home? - Paradise Palms Resort

Kissimmee townhouse

4 bedrooms / 3 bathrooms / sleeps 9

“Already ready to come back !” The house was amazing!We bring the kiddies every year for Spring Break & I’m so happy we decided to switch houses this year! It was so modern and updated. The house had everything you can imagine even a stroller! Mr. Frode was nice throughout the whole process. Can’t wait to come back again.

Responds fast! avg. 2 hours 10 minutes

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Price per night from

$155

Legacy Dunes Condo, Kissimmee, Orlando

Kissimmee apartment

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$113

Beautiful Lake Marion 2-bed in Palm Tree Paradise

Kissimmee villa

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$88

To Infinity & Beyond - Wonderful family vacation home just 1.5 miles to Disney!!

Kissimmee townhouse

3 bedrooms / 3 bathrooms / sleeps 8

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Price per night from

$103

New 9Br/6Ba luxurious Pool House from $300/nt, Close To Disney

Kissimmee house

9 bedrooms / 6 bathrooms / sleeps 18

Responds fast! avg. 32 minutes

Match: Table tennis

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Price per night from

$401

Executive 4 Bedroom / 3 Bathroom Lake View Home in Gated Resort Community

Kissimmee house

4 bedrooms / 3 bathrooms / sleeps 8

“Love that house!” Second time we rented this house and we just loved! Amazing house, clean, very spacious and very safe community! We recommended!!!!

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Price per night from

$136

Windsor Palms - Luxury Villa with SW Facing Pool

Kissimmee villa

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 29 minutes

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Price per night from

$206

Unique 5 Star Home - Private Pool, Free SOLAR Pool heat, WIFI, BBQ, Disney

Kissimmee house

3 bedrooms / 2 bathrooms / sleeps 7

“Violet lane” Home was clean and charming.We enjoyed the pool and privacy greatly. Owner thought of most anything we may need, except one; toilet paper. This was our first time staying in a private home rather than a hotel so perhaps it isn’t a given but if we had known, it would have saved us an immediate trip to store. I cannot speak for other guests but felt that not starting laundry, despite stating was not mandatory, not doing so may affect my deposit. A few other minor issues: missing ping pong table, “key?” to working slot machines, how, or if, the ice maker worked and where the garage door opener was located(we did find on the furnace in the garage the day before we left), and whether the swinging chair was safe to use, despite the crack, may have been problems easily remedied with a phone call but ultimately not important enough to bother owner and take time away from us. Not meant to be a negative review, it is not. Overall, we had a lovely time and would stay again. However, it seemed important to be honest in regard to our experience.

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Price per night from

$149

AMAZING POOL HOME,GAME ROOM, 10 MIN. FROM DISNEY!!

Kissimmee house

4 bedrooms / 3 bathrooms / sleeps 10

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Price per night from

$172

***NEWLY RENOVATED 2020 - Private Pool - Gated Resort - Free WIFI - Near DISNEY!

Kissimmee house

4 bedrooms / 3 bathrooms / sleeps 10

“Great family rental with plenty of space!” Great rental! Lots of space for our family to spread out and our kids loved the private pool! We will never stay in a hotel again!! We stayed during Hurricane Matthew and felt very safe! Super close to any store/restaurant you could ever want and less than 10 minutes to Disney! The owner Manuel was super easy to work with and very accommodating! I can't say enough about him! My only "negative" comments would be we were not aware toilet paper, garbage bags and paper towel were not unlimited. We ran out during Hurricane Matthew when stores were closed but with a quick email to Manuel, the Clubhouse had some on our doorstep in 10 minutes! Also, the pack n play at the home for our son was not quite as sturdy as what we have at home. But again, after speaking to Manuel I was told he has an actual crib to rent as well.

Responds fast! avg. 1 hour 43 minutes

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Price per night from

$181

Luxury 3-bdr house next to Disney

Kissimmee townhouse

3 bedrooms / 6 bathrooms / sleeps 8

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Price per night from

$195

Beautiful 1 Bedroom 5-Star Resort Villa Close To Disney

Kissimmee villa

1 bedroom / 1 bathroom / sleeps 4

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Price per night from

$183

One of the closest communities to Disney!

Kissimmee villa

4 bedrooms / 2 bathrooms / sleeps 8

“Fantastic villa so close to Disney” Stayed twice now at Mickeys Den. So close to Disney. Tracey the owner was super helpful providing lots,of,info,before,we,even got there. She also phoned us whilst there to check all was ok which was a really nice touch. Alan the manager was also just a call away and was a great help. Villa is spacious, spotlessly clean and well equipped. The pool area is great too. Can't find any fault with this villa. It really has been perfect for our holiday needs. Having stayed previously at a villa supposedly close to Disney ( was a 30 min drive ) this really was close! Perfect location. Lots of shops and restaurants a short drive away too. Excellent location. Highly recommend it.

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Price per night from

$138

Splended Bed 3 Villa on Windward Cay

Kissimmee villa

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$137

Beautiful House, Lake View with 5 Bedrooms Disney

Kissimmee house

5 bedrooms / 5 bathrooms / sleeps 12

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Price per night from

$263

Bella Vida 4 Bedroom Townhome

Kissimmee townhouse

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 22 minutes

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Price per night from

$159

5BR Beautiful Disney Villa

Kissimmee house

5 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 1 hour 46 minutes

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Price per night from

$189

Remodelled 2021 Windsor Hills 2-Bedroom Condominium 2 Miles 2 Disney - Gated

Kissimmee condo

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$143

CONDO FOR RENT AT WESTGATE TOWN CENTER ORLANDO FLO

Kissimmee condo

2 bedrooms / 3 bathrooms / sleeps 8

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Price per night from

$217

SUPER Close To Disney, Gameroom, Private Backyard, Lake, Free WiFi, Pool, Spa

Kissimmee house

7 bedrooms / 5 bathrooms / sleeps 17

“Very welcoming and worth it !” Me and my family absolutely loved this vacation house everything was so welcoming and near perfect ! This house is definitely something we will never forget and hopefully when we come back we will be able to rent from kim molnar again ! Everything was to a T ! Thank you so much kim !

Responds fast! avg. 2 hours 5 minutes

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Price per night from

$262

Beautiful townhouse near Disney World 3BR 2BA

Kissimmee townhouse

3 bedrooms / 2 bathrooms / sleeps 8

“Everything was as promised” This unit was clean, reasonably priced, and exactly as pictured in the listing. The owners were quick to respond to my questions and exceedingly helpful. I cannot recommend this place highly enough.

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Price per night from

$97

MINUTES TO WALT DISNEY WORLD'S FRONT GATE

Kissimmee condo

3 bedrooms / 2 bathrooms / sleeps 8

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Price per night from

$125

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