Kissimmee Vacation Rentals

(416 rentals)
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9 BR | 8 BA | Sleeps 18 | Quick View

1

Distance to park: 3 miles to Disney Animal Kingdom

$523

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

We’ve fallen in love with our new vacation villa, and we think you will too. Located just minutes from Disney (Animal kingdom is a 6 minute drive!) plus Margaritaville with its Water Park and many restaurants, Hartley House is the perfect home for your next family vacation. You’ll be so close ...

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Property Type

Kissimmee Villa

"Hartley House family gathering"

We have just returned from a great family holiday in Florida we took all our family away for our fiftieth wedding anniversary ,three years late .We stayed at Hartley House ,we have never stayed in a american ...

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$115

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool
  • Rentals by owner

About this property

Come relax in this 4 bedroom, 3 bathroom home. Sit on the screened in pool deck and just watch the wildlife , eat meals, have a cup of coffee and just relax. You are on vacation. Two king beds, queen and 2 twin beds . possibility of 3 bedrooms having the use of their own TV. - towels, linens, ...

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Property Type

Kissimmee House

"South facing pool with wildlife made for a great stay!"

We loved everything about this house! It had everything we wanted and needed. The communication and interaction with Diane was wonderful. She was very attentive and responsive to my questions.If ...

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5 BR | 5 BA | Sleeps 12 | Quick View

7

Distance to park: 3 miles to Disney's Animal Kingdom

$268

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

Lumiere's Lodge is just 2.5 miles from Disney's Animal Kingdom; easy access to all Orlando attractions. This is your own private home with 5 bedrooms, 5 baths, private pool and hot tub, everything you could want for a great stay near Disney!This wonderful updated home is very close to Disney World ...

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Property Type

Kissimmee Villa

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4 BR | 4 BA | Sleeps 8 | Quick View

10

Distance to park: 2 miles to Disney

$258

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool
  • Rentals by owner

About this property

Wonderfully Themed villa in the beautiful gated community of Windsor Hills, just two miles from Disney. Enjoy complimentary pool & spa heat, themed rooms, and a fun games room in the garage (air hockey, ping ping, foosball)! This is one of very few 4-bedroom units on the resort. We're nice and close ...

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Property Type

Kissimmee Villa

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Pool
  • Rentals by owner

About this property

Hello, Our vacation home is located in a gated community with a large swimming pool, playground for the children, shuffle board, pool table and a workout room. It’s a duplex with its own separate driveway. There are three bedrooms and two full baths. The kitchen was just fully remodeled in 2022 ...

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Property Type

Kissimmee Villa

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$389

avg/night

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Key Amenities

  • Private pool

About this property

Bring the whole family to this great place with lots of room for fun. You will love it

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Property Type

Kissimmee House

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4 BR | 4 BA | Sleeps 10 | Quick View

$267

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Our vacation home has been professionally furnished to the highest of standards. This 4 bedroom pool home has an ample 2400 square feet of living space conveniently located all on one level.The rich standing ornaments and wall decor compliment the furniture throughout the villa. Watch your favourite ...

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Property Type

Kissimmee Villa

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Property Reference RVH_088RRThe Legends Villa at Reunion Vacation HomesSpend your next vacation in comfort at Villa Tuscana. This five-bedroom, Tuscany-inspired home, provides guests with some of the best views in Reunion Resort. As soon as you exit your car in the driveway, you are greeted with ...

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Property Type

Kissimmee House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

The main spaces of the home:- 3 BEDROOMS & 2 BATHROOMS to accommodate 8 guests as such: (All bedrooms have flat-screen SMART TVs.)BEDROOM 1: 1 King bed (master suite 1st floor) BEDROOM 2: 1 King bed (2nd floor) BEDROOM 3: 2 Full beds (2nd floor)- MAIN LIVING ROOM features plush ...

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Property Type

Kissimmee Townhome

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8 BR | 6 BA | Sleeps 16 | Quick View

4.9 rating on other travel sites

$380

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

"Private, peaceful, comfortable, and FUN!! Incredible movie theater inside. Awesome movie theater poolside. And, a really cool Star Wars themed game room. The pool and spa are very private. The home is beautiful, and it is a very short walk to the clubhouse and water park." Keith C.LOOKING ...

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Property Type

Kissimmee House

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$301

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

About this property

Luxury vacation 5 bedroom home with a private pool. Wi-Fi, Swimming Pool . Relax in your resort-style vacation home in Windsor at Westside Mediterranean-themed community and enjoy resort-style amenities such as outside fireplace, resort-style pool, cover patio, lazy river, water playground, private cabanas, ...

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Property Type

Kissimmee Villa

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5 BR | 5.5 BA | Sleeps 13 | Quick View

3

Distance to park: 12 miles to Disney's Magic Kingdom Park

$392

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool
  • Rentals by owner

About this property

Welcome to Westside Villa! -20 minute drive to all Disney Parks -Private, heated pool; gas grill; EV charger on-site -Modern arcade: racing simulators, virtual reality, arcade deck -3 king size suites with smart TVs -2 uniquely themed bunk rooms (Star Wars and Fairy Tale) -All bedrooms have ensuite ...

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Property Type

Kissimmee House

"Home away from home."

My family and I thouroly enjoyed our vacation in Kissimmee. The home we stayed in had lots of entertainment for everyone. The pool was in constant use and the games room was awesome. We would definitely ...

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6 BR | 4 BA | Sleeps 14 | Quick View

5.0 rating on other travel sites

$310

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

"We have stayed in many Windsor hills homes and this is THE one to stay in! Beautifully decorated, fun and so comfortable!" Beth MARE YOU LOOKING for a very special vacation home? This is it . . . Totally renovated by a professional decorator and includes an incredible game room, a private ...

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Property Type

Kissimmee House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Pool
  • Private pool
  • Rentals by owner

About this property

Guests have private access to the entire home including all outdoor areas, the private, sparkling heated pool and spa as well as the in house laundry and fun game room. Also included with your stay is full use of the amazing Veranda Palms Resort amenities on offer including: Gated entrance with 24-hour ...

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Property Type

Kissimmee Villa

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9 BR | 6 BA | Sleeps 24 | Quick View

11

Distance to park: 2 miles to Sunday's Grill

$319

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Pool
  • Private pool

About this property

For last minute rentals or longer extended rentals, please inquiry about our discounted rates.This luxury vacation home is located in the Windsor at Westside upscale resort community - A perfect destination for DISNEY WORLD (10 minutes away), golf, and relaxing and celebrating with family and friends. ...

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Property Type

Kissimmee Villa

"Great Trip"

The house was wonderful and very immaculate. There was plenty of room for everyone. Great communication.

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

This is a beautiful professionally decorated and furnished 3 Bed, 2 Bath Villa located at Lake Berkley Resort. Have your vacation here in comfort and relaxation with air conditioning throughout.The spacious sitting room has a Queen sofa sleeper bed so the villa can easily accommodate 8 persons. This ...

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Property Type

Kissimmee Villa

"The Holiday of a lifetime"

Our first time coming to Florida and we could not have dreamed for a better location or accommodation for our trip. The Villa is roomy, very clean and perfectly positioned for the parks, the old town and ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool
  • Rentals by owner

About this property

Stay in our Massive, single family home located 10 minutes from Disney! Large 4,800 square foot home in a fantastic location House sleeps up to 26 people in our 16 total beds 10 Minutes to Disney 10 Bathrooms Cable TV at the home Fast WiFi - ideal for working remotely Beautiful Pool and ...

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Property Type

Kissimmee House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

"Kids and adults will love the indoor Star Wars movie theater, poolside theater, and huge Harry Potter game room. The virtual reality room is really cool. The pool, spa and lanai offer a lot of fun as well plus it's a perfect area to relax. The home has something for everyone." Chris S.Looking ...

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Property Type

Kissimmee House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool
  • Rentals by owner

About this property

Our luxury Kissimmee vacation villa will comfortably sleep 10 people. It is fully air-conditioned for your comfort, and has a very roomy and spacious floor plan. It has 2 lounge areas (one with 2 full sofas, and a ceiling fan, the other with a love seat and a sofa bed), both have cable T.V. The kitchen ...

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Property Type

Kissimmee Villa

"Excellent villa"

Very clean and central to all theme parks, it was well cleaned for our arrival and the pool was cleaned twice a week during our stay. Would highly recommend this villa

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

This home is thoughtfully furnished. Recently upgraded with a Tempur-Pedic contour supreme king size mattress, LED TV in every bedroom, Frozen themed and Mickey themed twin rooms. This four bedroom luxury home is specifically set up for vacationing guests. The house, just three miles from Disney, is located ...

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Property Type

Kissimmee House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Rentals by owner

About this property

A beautiful vacation condo located in a prestigious gated and guarded community, for you to relax and spend time with your family and friends. With the prime location in Kissimmee near Disney World, major parks and restaurants, shops and so much more, this 3BD/2BA condo unit is designed for your best ...

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Property Type

Kissimmee Villa

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9 BR | 5 BA | Sleeps 18 | Quick View

$471

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

Be sure to visit our website to check availability on all our homes! Save our page for future vacations to the Orlando area!Visit us at lostinthemagic . comThe Retreat at Champions Gate - Kissimmee, Florida is a new upscale gated resort community located just 12 miles from Walt Disney World. ...

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Property Type

Kissimmee House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

This fabulous 4 Bed Villa is located in secure gated Lake Berkley ResortThis fabulous 4 Bed Villa is located in a peaceful corner of Lake Berkley Resort with beautiful views to the Conservation Area and one on the lakes at Lake Berkley.The villa is fully equipped with everything you will need ...

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Property Type

Kissimmee Villa

"Great company to use"

This is our 3rd visit to Orlando in 7 years. We used Stephen and VIP Villa on all occasions and have stayed at different Villas each time. The location of the lake Berkley resort is perfect for the theme ...

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7 BR | 7 BA | Sleeps 14 | Quick View

$396

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

Be sure to visit our website to check availability on all our homes! Save our page for future vacations to the Orlando area!Visit us at lostinthemagic . comReunion Resort -Kissimmee, Florida is only 15 minutes to the area's main attraction... Walt Disney World. This gated luxury resort sits nestled ...

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Property Type

Kissimmee House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Pool
  • Private pool
  • Rentals by owner

About this property

KEY FEATURES 7 Spacious, themed bedrooms; 4 kings, 2 queens, 2 doubles + 2 sofa beds 4.5 Large bathrooms; 3 full ensuites, 1 shared full, 1 half Modern kitchen; dining area and kitchen island seating Two separate lounge areas, each with a Smart TV and comfortable seating High-speed WiFi throughout ...

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Property Type

Kissimmee House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Private pool

About this property

Beautiful south facing Villa with private pool and hot tub overlooking a peaceful lake.This private gated community is 20 minutes to Disney’s Magic Kingdom and 20 minutes to Universal Studio and 45minutes to the gorgeous Daytona beach where you can actually drive your car onto this huge beach.A ...

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Property Type

Kissimmee House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Bring the whole family to this great place with lots of room for fun. This home has 9 bedrooms that comfortably sleeps 19 guest. This home has a equipped kitchen and only 10-15 minutes from Disney.

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Property Type

Kissimmee House

"Excelllent"

What helps the most is having a management company that is readily available. And they were amazing.

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6 BR | 3.5 BA | Sleeps 14 | Quick View

4.8 rating on other travel sites

$379

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

"Something for everyone - fun, beauty, and comfort. There's so much to love! Everyone will love the incredible Avengers game room; it is like no other. Plus, all will love the heated pool and spa. Kids will love the themed bedrooms. And, adults will love the professionally decorated beauty of the ...

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Property Type

Kissimmee House

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7 BR | 5.5 BA | Sleeps 14 | Quick View

2

Distance to park: 5 miles to Disney World

$244

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Pool
  • Private pool
  • Rentals by owner

About this property

Excellent Private Detached Family Vacation home/Villa located in prestigious man gated Vacation Resort of EMERALD ISLAND RESORTS. SPECIAL DISCOUNTS !!! ! 25% OFF FOR WEEKLY AND 30% OFF FOR MONTHLY BOOKINGS. SPECIAL RATES FROM JANUARY TO MARCH monthly bookings. Weekly $1706 Monthly $5900.00 ...

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Property Type

Kissimmee House

"Amazing 7 Bed rooms Villa Near Disney"

Our stay with Family and friens were superb. Cost is just a fraction of what otherwise with any Hotels. VEry large House with 7 Bedrooms and 6 Wash rooms. Own private pool and lanai . Bbq grill was provided ...

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8 BR | 6 BA | Sleeps 16 | Quick View

4.8 rating on other travel sites

$361

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

"One word - FUN!! Incredible movie theater inside. Awesome movie theater poolside. And, a really cool Star Wars themed game room with LED lighting. The home is professionally decorated. It's beautiful, yet very comfortable." Cindy C.LOOKING for an incredibly fun vacation home to rent? This ...

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Property Type

Kissimmee House

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4 BR | 3 BA | Sleeps 8 | Quick View

1

Distance to park: 2 miles to Disney's Animal Kingdom

$200

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

4 Bedroom /3 Bath / Pool & Spa Vacation HomeCONTACT US AND REQUEST A DETAILED QUOTE !! No Booking Fees - Book Direct with the HomeownerCheck our Reviews on VRBO - Property #284051

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Property Type

Kissimmee House

"Awesome"

Thank you Awesome Would do again Very close to everything Great pool sand hot tub Felt safe Thank you again

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

and enjoy all that Florida has to offer? Look no further, introducing Villa Mickey Lakeview, the spacious 8 bedroom, 6 bathroom vacation home with beautiful lake views where the entire group can make memories to last a lifetime!Enter through the front door into the inviting foyer, make your way down ...

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Property Type

Kissimmee House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

"This was our first time renting a home for a vacation. This vacation rental has changed our future vacation options forever. Everything about the home and community was A+. The kids didn't want to leave and the grown ups enjoyed the amenities more than the kids. I would recommend this home for rental ...

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Property Type

Kissimmee House

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$121

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool
  • Rentals by owner

About this property

Close to the Attractions but away from the crowds. 4 bedroom/3 bath single story home on "lake". Ducks, Sandhill Cranes, sometimes a falcon, turtles. King, king, and 4 twin beds, TV in all bedrooms, WiFi, FREE US, Canada and US Territory phone calls. Fully furnished. Not suitable for ...

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Property Type

Kissimmee House

"Relaxing stay"

It was the perfect neighborhood that was quiet and relaxing. It definitely wasn’t far from the attractions. We enjoyed our stay!!

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

Property Reference RVH_1021RBalconies, patios, and lanais are not accessible. During 2023 there may be construction occurring on the exterior of the building by the home owners association.Welcome to Seven Eagles Joy. This 3 bed, 3 bath townhome is located in the heart of Reunion Resort - Seven ...

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Property Type

Kissimmee Townhome

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4 BR | 3 BA | Sleeps 8 | Quick View

7

Distance to park: 4 miles to Disney World

$155

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool
  • Rentals by owner

About this property

Enjoy Orlando, Florida, home to Disney World, Sea World, Universal Studios, and Islands of Adventure, in style. Conveniently located on the Exclusive Emerald Island Resort. The house is spacious where family can enjoy being together and also have some alone time. Our home is within minutes of all the ...

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Property Type

Kissimmee House

"Great home and location"

We just stayed at this home for 9 nights in July and we loved it. It’s close to Disney parks, tons of places to eat nearby, beautiful resort with things to do. The house was clean, updated and roomy. ...

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$145

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool
  • Rentals by owner

About this property

Enjoy a magical vacation just 3 miles from all the Disney parks at the Pineapple Vacation Villa situated in the elegant Windsor Palms Resort. -Our holiday home offers all of the latest features in vacation rentals. With four bedrooms including two master-en-suites with private bathrooms plus two twin ...

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Property Type

Kissimmee Villa

"Home away home."

We enjoyed 10 nights here late July. Karen is amazing to work with. Communication is number 1. Very safe and quiet within a gated community. This was just the kind of place we were looking for, cozy, ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool
  • Rentals by owner

About this property

☆☆ HIGHLIGHTS ☆☆✹ 3 fun kids’ bedrooms; Pirate room, Choo-Choo Train room + Princess room ✹ 2 master suites ✹ 8 beds; 3 kings, 1 queen + 4 twins ✹ 5 full bathrooms; essential toiletries provided ✹ Full kitchen w/ modern appliances + coffee bar ✹ Huge kitchen island ...

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Property Type

Kissimmee House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Luxury Screened-In, Lake Front, Private Pool Home! This amazing 3 bedroom, 2 bathroom, Disney Area Vacation Rental Home is located in the family-friendly residential community of Eagle Pointe. Just a few short miles from Orlando's World-Renowned Theme Parks including the Walt Disney World® Resort, ...

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Property Type

Kissimmee Villa

"Perfect setting, great location"

This part of Kissimmee is a great location for visiting the theme parks and has easy access to the I-4, a big bonus for heading to Tampa where we always go at least once. The villa itself is on a well maintained ...

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$110

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool
  • Rentals by owner

About this property

CHEERY AND BRIGHT. Just what a vacation home should be. 4 bedrooms, 2 bathrooms, great views and just minutes from all the fun. Fully furnished , just bring personal items or things you cannot live without. Located in Eagle Pointe, a well sought-after vacation home community. Just minutes from what ...

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Property Type

Kissimmee House

"Vacation"

The house was perfect for our family’s size and the location was great. We enjoyed the large pool and the kids loved it.

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool
  • Rentals by owner

About this property

Recently renovated luxury property now available for your next Orlando adventure. Two themed kids bedrooms each sleep 4 kids (or adults), five oversized bedrooms each with king size beds. All bedrooms feature en-suite bathrooms. Two bedrooms downstairs, 5 bedrooms upstairs (including the two themed bedrooms). ...

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Property Type

Kissimmee House

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6 BR | 5.5 BA | Sleeps 18 | Quick View

1

Distance to park: 4 miles to Animal Kingdom

$326

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

Pack your bags for an unforgettable trip to the happiest place on Earth at 'Minnie's Maingate Manor'! Minnie’s Maingate Manor is a 6-bedroom, 5.5-bathroom vacation rental home with themed bedrooms, sleeping accommodations for 16, and a private screened-in pool and spa. This Florida escape is perfect ...

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Property Type

Kissimmee House

"Amazing"

Such an amazing home! You want for nothing. My grandkids were in awe of the dress up clothes.They loved the games room. It was very clean. The pool was warm and they had so many beach towels and pool toys. ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

"Kids and adults love the game room. Really cool. Movie theater in the converted garage is incredible - better than being at a regular movie theater. And, maybe your biggest treat will be the poolside theater. Very pretty and comfortable home and full of fun." Keith C.LOOKING for an incredibly ...

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Property Type

Kissimmee House

"Great spot! Exactly as described!"

Terrific house. Has everything you need. All the electronics were working as they should. The theatre room and the outdoor pool/tub were the highlights. When I had question about the place while I was there, ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

Immerse yourself in this much-beloved world and find the hidden easter eggs in the room as you open the door to Potter's Place. This charming open-concept themed home is ready to make you feel revitalized. From a cleaned, well-maintained space to a fully equipped kitchen to cozy beds and pillows, your ...

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Property Type

Kissimmee Townhome

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

7 bedroom 4.5 bath waterfront home located in the highly desired Emerald Island resort close to Disney and Universal Studios. The ground floor of this villa is an open concept with a living area featuring a 65" Smart 4k tv. The granite countertop kitchen boasts all new 2022 stainless appliances. ...

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Property Type

Kissimmee Villa

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Pool
  • Private pool
  • Rentals by owner

About this property

Get ready to experience the vacation of a lifetime at Big Top Family Vacation Villa, situated in the heart of Solara Resort. This stunning villa boasts 9 spacious bedrooms and 6.5 luxurious bathrooms, providing ample space for up to 22 guests. Perfectly located just 8 miles away from Walt Disney World ...

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Property Type

Kissimmee Villa

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3 BR | 2 BA | Sleeps 8 | Quick View

12

Distance to park: 12 miles to All Disney Theme Park

$111

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

If you will be visiting Orlando Florida for all of the great attractions including Walt Disney World, Universal Studios, Sea World theme parks, and all of the other major attractions? You can stay in our beautifully decorated 3 bedroom private villa, which boasts it's own private pool for less than it ...

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Property Type

Kissimmee Villa

"Lovely villa close to parks"

Great location close to the airport, Disney parks and outlets. Spacious villa that was really comfortable with a lovely pool. So many 'extras' provided such as pool toys, on demand family friendly films ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

Property Reference #RVH_1009RWelcome to Radiant View! This gorgeous 5 bedroom, 5 bath pool home is located in Reunion Resort in the Homestead neighborhood of the exclusive Reunion Resort. A truly beautiful place with world-class amenities such as infinity pools, a full-service spa, scenic walking ...

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Property Type

Kissimmee House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool
  • Rentals by owner

About this property

Welcome to Islands of Magic at Emerald Island Resort - only 5 miles to Walt Disney World theme parks!Get an exact quote right now! Scroll down to see our website link. APPLY PROMO CODE: IOM100FORMAL SEATING & DINING AREASWhen you enter the house, you will see the formal seating area and ...

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Property Type

Kissimmee House

"Best Vacation Home"

Renting this beautiful house was a breeze!! We were very happy that after checking out at least a dozen houses, we all agreed on this one!! We wanted a big house with lots of bedrooms/bathrooms! We got ...

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3 BR | 2 BA | Sleeps 6 | Quick View

13

Distance to park: 2 miles to Disney World

$138

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Rentals by owner

About this property

Welcome to Escape by KLMJ Sunshine! This is a completely renovated 3-bedroom condo in the beautiful gated community of Windsor Hills, just two miles from Disney. Enjoy the massive heated pool, brand new water park, large playground, tennis and basketball courts, mini-golf, arcade, movie theatre, fitness ...

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Kissimmee Condo

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Kissimmee Vacation Rentals

Kissimmee Weather

 | 

7222°  489°
JANUARY
7323°  499°
FEBRUARY
7725°  5312°
MARCH
8228°  5814°
APRIL
8731°  6418°
MAY
9032°  7021°
JUNE
9233°  7222°
JULY
9233°  7222°
AUGUST
9032°  7122°
SEPTEMBER
8429°  6518°
OCTOBER
7926°  5714°
NOVEMBER
7323°  5010°
DECEMBER

Soak up the Sun on Your Next Trip to Kissimmee Vacation Rentals


There’s nothing quite like a vacation to sunny Florida, a unique and inviting state with a huge variety of distinctive cities and natural areas to explore. One popular vacation destination in Florida is Kissimmee, a charming city with plenty to see and do just south of the Orlando metropolitan area. 

Kissimmee has a lot more to offer visitors than just excellent weather year-round. With a huge variety of scenic nature, shopping opportunities, and outdoor activities, Kissimmee itself has lots to offer every member of the family, not to mention its extremely close proximity to some of Orlando’s biggest amusement parks. 

You could stay in a busy hotel during your trip to Kissimmee, but then you wouldn’t be able to get a truly immersive experience of local city life. Kissimmee vacation rentals allow you to enjoy Kissimmee from inside its authentic residential neighborhoods. Additionally, having your own home to live in rather than a jam-packed hotel will provide some much-needed peace and quiet during your vacation. It will also offer plenty of space for the whole family to spread out.  

Top Tips for Traveling to Kissimmee Rentals


Like most other Florida cities, Kissimmee enjoys sunshine and clear skies throughout the majority of the year. However, the tropical climate of the state means that bouts of rain can occur throughout the seasons, particularly during the summer months, peaking in August. 

In addition to a higher likelihood of rain, the summer season in Kissimmee tends to be the most humid time of year. That’s why most vacationers choose mid to late spring or early autumn to make their trip to the city. At those times of the year, vacationers can enjoy great weather and lots of outdoor activities. 

Though the Kissimmee Gateway Airport is located centrally within the city, most vacationers taking commercial flights will fly into Orlando International Airport. It is located roughly 17 miles northeast of the city center, about halfway between Kissimmee and Orlando. Vacationers coming in from elsewhere in Florida can access Kissimmee by road using U.S. Route 192 and U.S. Route 441.

Things to Do Nearby Kissimmee House Rentals


Some of the most popular natural areas around Kissimmee are the swamps, which are located in major local bodies of water like Lake Tohopekaliga (known around town as Lake Toho). At Boggy Creek Airboat Adventures, you can experience the swamps from the water and get the thrill of a lifetime on an airboat driven by a local wetlands expert. Get up-close views of gator ponds, discover precious gemstones, and then grab a delicious lunch with the family at Boggy Bottom BBQ! 
Looking to explore a piece of history during your trip to Kissimmee? Medieval Times Dinner & Tournament allows visitors to step into the 11th century for an evening of authentic feasting, jousting, and sword fighting in true medieval style! Enjoy a delicious four-course meal, incredible performances, and a truly unforgettable experience for the entire family. 
Any vacation to Kissimmee isn’t complete without a trip or two to Old Town, a popular outdoor attraction with opportunities for shopping, dining, and family fun. Old Town is made up of an 18-acre stretch of classic city attractions, including the Old Town Ferris Wheel, the Great Magic Hall, and Mortem Manor, a year-round haunted house that is open for visitors to explore.

Kissimmee Annual Events


Kissimmee is a vibrant area with lots of annual festivals and events to enjoy in and around the city throughout the year. Kissimmee locals and visitors alike flock to the Ford Cuban Sandwich Festival each May near downtown Kissimmee, which celebrates the colorful history of Cuban cuisine in the area. Watch as local dining professionals attempt to build the world’s biggest Cuban sandwich during the event! 
The Ford Taste of Latino Festival is another local opportunity to celebrate and experience the best in authentic Latin cuisines in Kissimmee. The event features a contest to find the Top Latino Chef as well as plenty of live music and dance performances to enjoy as you taste a variety of Latin dishes. 
Not sure if you’ll be in town for any of Kissimmee’s larger annual events? You can enjoy Show Car Saturday Nights every Saturday night in the city on Margaritaville Boulevard. Check out the city’s best classic cars from a variety of eras and enjoy the plethora of delicious eateries and exciting shops located along the boulevard.

Wining and Dining in Kissimmee  


Between your outdoor activities and trips to local amusement parks while in Kissimmee, you’re sure to need some satisfying food and refreshing drinks to complete your perfect day. Luckily, Kissimmee is home to some of the best restaurants that Florida has to offer, combining authentic local flavors with worldly cuisine. 

To start your day off right with a delicious and hearty breakfast, look no further than Woodsby’s Countryside Café. This spot has authentic, cozy diner vibes to spare, not to mention a stacked menu of classic breakfast favorites, coffee bar items, and unique dishes you won’t want to miss out on. 

Tarantino’s Italian Restaurant is a great choice for a vacation date night or simply a nice dinner out with the family. A hearty Italian meal is a great way to finish a fun day of activities, and you’re sure to get that and more at Tarantino’s. If you bring the family along, you can take advantage of the takeout dinner special, which feeds four and includes a massive entrée, salad, and garlic bread.


FAQ

How many vacation rentals are there in/around Kissimmee?

There are 416 Kissimmee vacation rentals available on FloridaRentals.com. From house rentals to villa rentals and beyond, find a unique vacation rental for you to enjoy a memorable vacation in Florida.

How much does it cost to rent a vacation rental in Kissimmee?

There are vacation rentals available in Kissimmee for as low as $88 per night with an average price per night of $226.

Can I rent a house in Kissimmee?

Yes, you can find house rentals in Kissimmee close to Lakefront Park, Monument of States, and Old Town. Don't forget to stop in to Shingle Creek Park or the nearby theme parks!

Do any vacation rentals in Kissimmee have a pool?

Yes, there are 342 vacation rentals in Kissimmee with a pool on FloridaRentals.com. Search using our filters and book one for your next vacation!