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Kissimmee Vacation Rentals

(201 rentals)
Kissimmee Villa
Sleeps 12, 6 bedrooms, 3.5 bathrooms
1 review

Key Amenities

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

About this property

Bring your family to this stunning 6BR 3.5BA in the luxurious gated community just minutes from the world-famous Disney World. Have hours of fun in the game room and scenic pool backyard, or set out to explore local theme parks, golf clubs, restaurants, shops, and more!6 Comfy Bedrooms (2 Themed) ...

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Featured review

"Wonderful Stay!"

The house was lovely and had everything we needed for my family of 6 week long stay. Kitchen was well stocked with everything we needed, house and pool were clean, and the beds were comfortable. The 80s...

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$245
avg per night
Kissimmee House
Sleeps 10, 4 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Pet friendly
  • Pool
  • WiFi

About this property

This is a NON SMOKING HOME *Community: Storey Lake Floors: 2 Floor, 4 Bedrooms on one level.Pets: Pets acceptable. limit 2.Minimum Stay: 2 nightsRooms: 4 Bedrooms, 2 Bath rooms. En-suite in Master bedroom.Bed Configuration:Bedroom 1: King size bed with en-suite Bedroom...

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Featured review

"Vacation"

Comoda con todas las facilidades serca todo limpio Volveria nuevamente. Excelente espacio para ir en familia. La piscina limpia y organizada.

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$150
avg per night
Kissimmee House
Sleeps 8, 4 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

This stunning Disney area pool villa offers your family comfortable and convenient accommodations that will make your next Florida vacation a memorable one.Ideal for your next family vacation, this attractive 4 bedroom, 2 bath Disney area vacation home is conveniently located just 10 minutes to the...

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$170
avg per night
Kissimmee House
Sleeps 16, 8 bedrooms, 6 bathrooms
5 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Located on Windsor Island Resort, an exclusive gated community in Kissimmee, this privately owned vacation villa is perfect for you and your family. 8 good-sized bedrooms, 2 lounge areas, an air-conditioned games room area and a private pool and spa with no rear overlooking neighbours.The resort...

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Featured review

"Rental home"

The home felt like home away from home. House was clean and the host was very attentive and friendly.

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$275
avg per night
Kissimmee Villa
Sleeps 10, 5 bedrooms, 3 bathrooms
11 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

This fantastic 5 bedroom, 4 bath Vacation Villa offers all of the conveniences of home and everything you need for a fun family vacation including a Private Screened-In Pool, Outdoor Spa, Games Room, Fully Equipped Kitchen, Free Wireless High-Speed Internet, Full Size Washer/Dryer, Coffee Maker and Microwave....

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Featured review

"Amazing Villa and location"

Stayed at Emerald Island Resort in July. Villa was in an excellent location and was gorgeous, massive, real good value and helped made a holiday of a lifetime!

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$205
avg per night

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Kissimmee House
Sleeps 15, 5 bedrooms, 5 bathrooms
10 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Enjoy this family friendly, five bedroom Orlando vacation home that sleeps 15 people and features a private pool, a Super Mario game and movie room, and themed rooms for the kids including a Beauty and The Beast castle room and Transformers! The entire interior of this home is brand new, so you'll...

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$243
avg per night
Kissimmee Villa
Sleeps 12, 5 bedrooms, 3 bathrooms
16 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

This villa is a stunning 5 Bed 3 Bath villa that can comfortably sleep 12 guests.A stunning, larger than average, 5 Bed 3 Bathroom villa with a fantastic private pool. All rooms in the villa are spacious. The villa is furnished and maintained to a very high standard.The villa is spaciously arranged...

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Featured review

"Our great vacation"

My family and I have stayed at this home twice and it has been great. The home is clean and very comfortable. We love to cook and the kitchen was well stocked with cooking utensils. Rent here you will...

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$130
avg per night
Kissimmee Villa
Sleeps 6, 3 bedrooms, 2 bathrooms
18 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

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.Full air con and hi-speed WiFi throughout.The spacious sitting room has a Queen sofa sleeper bed so...

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Featured review

"We absolutely loved the villa."

The villa was perfect for our family. It was extremely spacious and well equipped. It had everything we needed.The pool was perfect for enjoying lazy mornings and there were lots of pool toys for the...

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$135
avg per night
Kissimmee Apartment
Sleeps 4, 1 bedroom, 1 bathroom

Distance to park: 11 miles to Castaway Cove Adventure Park

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Welcome to this charming fully furnished one bedroom one bathroom apartment located in Heritage Key Villas, Kissimmee, Florida. This apartment is the epitome of convenience and comfort, offering a flexible lease term ranging from one month to twelve months, with a minimum stay of just 30 days, making...

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$106
avg per night
Kissimmee Villa
Sleeps 8, 4 bedrooms, 3 bathrooms
5 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Ideal for your next family vacation, this striking 4-bedroom, 3 bath Disney area vacation home is conveniently located just 10 minutes to the Walt Disney World Resort, 15-20 minutes from Universal Studios Florida and SeaWorld Orlando. Florida’s famous beaches are just a quick 45 minutes away. ...

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Featured review

"Very comfortable villa with a great pond view and beautiful sunsets!"

We stayed in this villa for 20 nights. Upon arrival the house was spotless and we found the furniture to be very comfortable. We used the hot tub and pool a lot and were glad that we could find shade...

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$170
avg per night
Kissimmee House
Sleeps 13, 6 bedrooms, 5 bathrooms
3 reviews

About this property

Spacious 6 bed, 5 bath, sleeps thirteen Fully screened South facing pool with relaxing spa Formal, informal and outside dining options Upstairs TV lounge with a further two living areas downstairs Pool table in the games room Located on gated resort of Solterra with excellent amenities

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Featured review

"Loved it.."

We had a wonderful time can't wait to visit again. I believe the kids favorite part was the pool. They did not want to leave..

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$297
avg per night
Kissimmee Villa
Sleeps 8, 4 bedrooms, 3 bathrooms
15 reviews

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Your villa is located in an upscale gated community located just 8 miles from Walt Disney World. Terra Verde Resort is one of the most desired resorts in the Orlando area. Only a 25-minute drive from the Orlando International Airport and is situated central to all of Orlando’s famous attractions....

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Featured review

"Fantastic-Excellent."

IWe visited Orlando a lots of time,We are familiar with Lake Berkley.We had always very good impresion of staying in Lake Berkley.This time we stayed in Lake berkley drive 929.We arrived at almost 03;00...

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$155
avg per night
Kissimmee Townhome
Sleeps 8, 4 bedrooms, 3 bathrooms

Distance to park: 4 miles to Disney Parks

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • Rentals by owner
  • WiFi

About this property

Looking for the Perfect Vacation spot near the Magic? Our 4 Bedroom, 3 Bathroom Disney-Themed Condo in Kissimmee, FL is your Dream Getaway! ️ Sleeps up to 8 Only 4 miles from Disney Park Entrance Lakefront views for serene Mornings & Magical Evenings Fully equipped Kitchen – Perfect...

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$122
avg per night
Kissimmee House
Sleeps 8, 4 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

This unique 4-bedroom, 3-bathroom luxury Town home is situated on the new community of Tuscan Hills. Tuscan Hills is a new secure gated community, with extensive oak landscaping, located in Davenport on highway 27, close to highway 192, and only minutes from interstate 4.The town house is on over...

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$110
avg per night
Kissimmee House
Sleeps 16, 8 bedrooms, 5 bathrooms
17 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

This spacious home is designed to impress with top-tier amenities and elegant touches, making it ideal for families or groups craving an unforgettable escape. Enjoy the ultimate blend of comfort and excitement ensuring your stay is spectacular.Bedroom 1: (3) Twin Beds, Bathroom Attached Bedroom 2:...

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$420
avg per night
Kissimmee House
Sleeps 12, 6 bedrooms, 6 bathrooms
8 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Our 6 Bedrooms 6 Bathroom, luxury villa ideal for you and your families / friend’s vacation.As you enter the home you are greeted with a large living room area. Towards the back of the villa there is an open plan living/dining/kitchen area. There are tri-sliding doors to the pool area where...

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Featured review

"Stunning villa"

Let me start by saying location was Ok.South of I-4 not so good. Traffic very bad to theme park near I-4. Gated community nice. Guards were very nice and pleasant. Now for the Villa. Villa was beautiful.Entry...

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$185
avg per night
Kissimmee House
Sleeps 12, 6 bedrooms, 3 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Situated on the very popular well maintained and long-established peaceful golfing Highlands Reserve community on the US27 in Davenport is this beautiful, well-presented villa with 6 bedrooms and 3 bathrooms. It can accommodate up to 12 guests very comfortably.The spacious open-plan villa is a great...

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Featured review

"Great location"

We very much enjoyed our stay. Villa was clean, well equipped and close to Disney. Management company was quick to respond to any questions.

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$220
avg per night
Kissimmee House
Sleeps 10, 5 bedrooms, 4 bathrooms
12 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to our stunning spacious 5 bedroom, 4 bath home located in the much sought after community of Tuscan Hills near DisneyThis beautiful home offers 2 masters en-suite bedrooms and 3 sitting rooms.Full air con and hi-speed WiFi throughout.The villa uniquely has 3 sitting rooms, two of...

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Featured review

"Amazing villa"

My family and I stayed at this wonderful villa for 5 nights. The house is very spacious,.clean and in a secured gated community. Watersong community is the best area for villa rentals close to Disney. We...

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$165
avg per night
Kissimmee House
Sleeps 16, 8 bedrooms, 6 bathrooms
6 reviews

Distance to park: 8 miles to Disney Animal Kingdom

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

Windsor at Westside Resort is one of the newest and most luxurious resort communities in the Orlando/Kissimmee, Developed by one of the nation's largest developer , the Pulte Homes. Just 8 miles from Disney, and within easy reach to all the attractions, shopping, and dining in the Disney area, this...

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Featured review

"Awesome"

Verry nice villa, warm jacuzzi. It was awesome. Bathrooms and bedrooms were good. Everthing was clean when we arrived. Great

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$360
avg per night
Kissimmee Villa
Sleeps 8, 3 bedrooms, 2 bathrooms
5 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Pool
  • Rentals by owner
  • WiFi

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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Featured review

"Clean and quiet retreat"

Nice, clean, and has all of the amenities necessary! I have enjoyed my stay in this quiet and peaceful vacation rental. Beautiful view of pond right outside of screened lanai. The home was clean, and Randy...

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$100
avg per night
Kissimmee House
Sleeps 14, 7 bedrooms, 6 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Enchanted Oasis at EmeraldOnly 15 minutes to Disney! Private Pool & Spa with heating available at the perfect vacation retreat in this stunning 7-bedroom, 6-bathroom home, located in the sought-after Emerald Island Resort. Designed for unforgettable stays, this property features covered poolside...

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$349
avg per night
Kissimmee House
Sleeps 12, 6 bedrooms, 3.5 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Step into sheer Luxury and experience gated resort style vacationing at its finest. at our Windsor Palms, 6 bedroom pool home, the special touches will leave every family member with a smile. This gorgeous home has two king bedrooms, two queen bedrooms and two rooms with 2 twin beds. With 4 bathrooms...

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Featured review

"Caaa vacasional"

Hola estoy muy interesado en rentar su casa de vacaciones la fecha es junio 26a julio 10 con mi familia somos 12

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$250
avg per night
Kissimmee House
Sleeps 16, 8 bedrooms, 5 bathrooms
7 reviews

Distance to park: 6 miles to Disney world

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Welcome to our luxury finished 3600 Sq ft 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 and the Convention Center...

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Featured review

"Pleasant Stay in Crystal Cove"

Large and spacious home in Kissimmee. Close to many attractions and restaurants. Bedrooms, kitchen and bathrooms. Pleasant and easy to maintain for extended stay. Washer and Dryer on site make vacation...

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$298
avg per night
Kissimmee House
Sleeps 8, 4 bedrooms, 3 bathrooms
6 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Bring your family and stay at this beautiful vacation home in the Emerald Island Resort community. You will be just minutes away from Walt Disney World® Resort, and all of the nearby theme parks and attractions of Orlando, Florida. This home has 1 King en-suite, 1 queen en-suite and 2 sets of twins.This...

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Featured review

"Great stay at a lovely villa"

We are just back from 2 weeks here, we had a fabulous time making use of the games room and the pool. Thank you

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$165
avg per night
Kissimmee Villa
Sleeps 14, 6 bedrooms, 5.5 bathrooms
2 reviews

Distance to park: 3 miles to Disney World

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

About this property

This "Tropical Magic" villa is proudly offered to you by "Emerald Island Rentals"Air Conditioning • Free Wi-Fi • Free Internet • Outdoor Grill • Parking Included • Pool • SMART TVs through-out • Full-size laundry facilities • Children Welcome...

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Featured review

"Excellent vacation & house"

we were a family of 10 staying in this beautiful house was well equipt with everything we needed room was a big hit ..The heated pool was sure a big catcher the 4 children loved it so did the adults.....

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$297
avg per night
Kissimmee House
Sleeps 18, 9 bedrooms, 6 bathrooms
6 reviews

Distance to park: 8 miles to Disney World

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Windsor at Westside Resort is one of the newest and most luxurious resort communities in the Orlando/Kissimmee,Developed by one of the nation's largest developer , the Pulte Homes. Just 8 miles from Disney, and within easy reach to all the attractions, shopping, and dining in the Disney area, this...

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Featured review

"Great property!!"

What a great property! It was perfect for our family. Very spacious and clean. Definitely staying there again on our next stay in Florida.

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$417
avg per night
Kissimmee House
Sleeps 16, 6 bedrooms, 5 bathrooms
14 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Welcome to The Minions Mansion, a family fun, six bedroom resort vacation home that features a private pool, four KING bedrooms, a Minions themed bedroom, Star Wars themed arcade & movie theater, a billiards pool lounge with air hockey, a Super Mario gaming loft, and more! Located only minutes from...

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$310
avg per night
Kissimmee Condo
Sleeps 8, 4 bedrooms, 3 bathrooms
8 reviews

Distance to park: 2 miles to Disney’s Animal Kingdom Park

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Welcome to the Sun Lake Resort. We have 4 identical 1650 sqft units with 4 bedrooms and 3 bathrooms. The beautiful condo faces to sun lake and it has a spacious screened patio. It only takes 1 minute walk to a plaza for shopping and restaurants which is very convenient! More importantly, you are only...

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Featured review

"Awesome stay"

Beautiful resort and room was great. Great location and staff was very helpful. Would highly recommend this property.

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$145
avg per night
Kissimmee Villa
Sleeps 14, 7 bedrooms, 4.5 bathrooms
16 reviews

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

This luxury villa is perfectly located on the exclusive Emerald Island Resort community less than 3 miles from Walt Disney World, Florida. The property has 7 bedrooms two of which are master bedrooms with en suite bathrooms and a further two and a half bathrooms.This stunning elegant and spacious...

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Featured review

"Great stay"

Great stay at this villa in Emerald Island, location is perfect for all the parks as well as going to the beaches. Katrina was very responsive12 in our party, 4 of which were children, the property...

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$144
avg per night
Kissimmee House
Sleeps 16, 7 bedrooms, 4 bathrooms
11 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Relax in the comfort of this luxurious, family friendly, seven bedroom, resort vacation home that sleeps 16-18 people. Featuring a private pool, Avengers movie room, themed rooms for the kids including Star Wars, Harry Potter and Pirates themes, and resort amenities included at the exclusive Terra Verde...

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$321
avg per night
Kissimmee House
Sleeps 12, 6 bedrooms, 4 bathrooms
7 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Our fabulous 6-bedroom, 4.5-bathroom luxury vacation villa is set in the tranquil location of beautiful Watersong and the property overlooks a conservation area at the rear.The villa sleeps 12 guests and boasts a private pool as well as a games room.Situated at the front of the house as you enter,...

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Featured review

"Family vacation/daughter celebration"

My family and i had a wonderful time at this home. Everything was great, the pool was wonderful and the property manager was amazing the wholw time. Will book again.

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$185
avg per night
Kissimmee Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Pool
  • WiFi

About this property

This is a NON SMOKING condo *Community: Secret LakeFloors: Ground Floor Condo.Pets: Pets OK.Rooms: 2 Bed rooms, 2 Bath rooms. En-suite in Master bedroom.Bed Configuration: King (1), Two Queen Beds (2). Sleeps 6Flooring: Carpet throughout with tile in bath and kitchen.General:...

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$120
avg per night
Kissimmee Townhome
Sleeps 8, 4 bedrooms, 3 bathrooms
1 review

Distance to park: 5 miles to Disney,Seworld

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Welcome to our new opening 4 Bedroom/3 bathroom Townhouse in CLUB CORTILE,This gated-community is close to every major Orlando attraction: Disney's Magic Kingdom, Epcot, Animal Kingdom, Universal Studios (Harry Potter), Sea World, and many more. Club Cortile is also conveniently close to WalMart,...

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Featured review

"Well located safe townhouse on a lake with good club facilities"

We are a pensioned couple from the Netherlands and in Florida to play golf in the sunshine. We have rented from the owner on several occasions over the last 15 years. This was our first time in the Club...

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$142
avg per night
Kissimmee Villa
Sleeps 8, 4 bedrooms, 3 bathrooms
17 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

A stunning, larger than average 4 Bed 3 Bathroom villa.There are 2 sitting rooms both with lots of comfortable seating. Both rooms have large screen TVs, ideal for when the adults want to watch the latest sports programme whilst the kids enjoy the latest Disney film. Netflix subscription is also included...

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Featured review

"Highly recommend this villa"

We have just returned home after spending two great weeks at this amazing villa.It was spacious,spotlessly clean, with very comfortable beds and all the amenities you need for a relaxing, enjoyable holiday. The...

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$120
avg per night
Kissimmee House
Sleeps 8, 4 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Want to enjoy a stay at a vacation home for you and your family? Our house offers a direct escape to a vacation paradise just for you! It offers 4 bedrooms and 2 bathrooms, and accommodates with a cozy living room. In the garage, there is also a game room for you or children to relax and have some fun....

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$165
avg per night
Kissimmee Villa
Sleeps 14, 7 bedrooms, 7.5 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

This lake home is one of the larger homes on Lake Berkley and boasts 7 bedrooms 7.5 bathrooms. This really is the perfect place to unwind after a busy day visiting central Florida's attractions or just enjoying the home for everything it has to offer.This home is perfect for the larger families...

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Featured review

"Great pool!"

We stayed at the home for a week In March. Our kids loved the pool! Paying for the pool heating was a great decision.The home is big with lots of room for the kids to run around. It is close to the...

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$250
avg per night
Kissimmee Villa
Sleeps 10, 5 bedrooms, 4 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Our fabulous 5-bedroom, 4-bathroom luxury vacation villa is set in the tranquil location of beautiful Watersong, with no rear neighbours the property overlooks a conservation area at the rear.The villa sleeps 10 guests and boasts a private south facing pool/spa as well as a games room.At the rear...

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Featured review

"Lovely stay at this villa"

Booking process very easy. Had lovely stay here with family. Villa is great location, is clean modern and well furnished/equipped. We will stay here again next visit to Micky. Stan

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$185
avg per night
Kissimmee House
Sleeps 8, 4 bedrooms, 3.5 bathrooms
10 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to our beautiful villa situated in Veranda Palms, ideally located close to US-192 and only a 10-minute drive from I-4Our home boasts peaceful water views at the back with no rear neighbours plus the front is situated across from open countryside.The villa has also been professionally decorated...

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Featured review

"Comforts of Home"

The mattresses and blankets were fantastic. Everything was very clean, and I loved the themed rooms. The pool was great too, with floats and towels for everyone. The only thing I think could have been improved...

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$185
avg per night
Kissimmee Villa
Sleeps 10, 5 bedrooms, 4 bathrooms
6 reviews

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

One of the closest possible communities to Walt Disney World (less than 3 miles away), Emerald Island is a quiet oasis in which to spend your vacation. Emerald Island is an exclusive gated community less than a mile from the world famous US Highway 192 where you will find shops, restaurants, and entertainment....

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Featured review

"Family vacation"

Our family were there for 2 1/2 weeks and everyone loved it. Location very close to parks,restaurants and stores.Grandkids loved the time in the pool. House was big enough for the family and clean.Screens...

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Kissimmee Villa
Sleeps 8, 4 bedrooms, 2 bathrooms
14 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

he villa is situated within Lake Berkley, Kissimmee, one of the most sought after locations for people wanting to rent a villa. For those visiting Disney it is just 5 miles away--approximately 10 minutes drive. All the other major theme parks are also very close by. For convenience and very cheap shopping...

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Featured review

"rental at Lake Berkeley"

We spent 2 weeks in this home and enjoyed our visit. Was easy access to areas where we wanted to go and the community was lovely. I would rent this property again.Elizabeth :)

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$155
avg per night
Kissimmee Villa
Sleeps 8, 4 bedrooms, 4 bathrooms
27 reviews

Distance to park: 2 miles to Disney

Key Amenities

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

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...

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Featured review

"Amazing rental"

This place was very clean and well put together. The themed rooms were amazing and the location to the Disney parks couldn't get any better than here. It felt safe and clean with all staff in the gated...

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$340
avg per night
Kissimmee Townhome
Sleeps 10, 5 bedrooms, 3 bathrooms
3 reviews

Distance to park: 6 miles to Disney,Seaworld

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Pool
  • Rentals by owner
  • WiFi

About this property

Welcome to the beautiful Coral Cay Resort. It is one of the most popular resort destinations in the Kissimmee/Orlando area for its proximity to the theme parks and other major attractions. Situated 6 miles from Disney World, 1 mile to Walmart and target. 8 miles to Seaworld and Convention center. Minutes...

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Featured review

"Comfortable place to stay....."

We stayed here while in Florida for my daughter's dance competition. It was so nice to come "home" after a long day of dance. I loved that the driveway was right up to the door. I also loved that it...

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$154
avg per night
Kissimmee House
Sleeps 10, 5 bedrooms, 4.5 bathrooms
3 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to our superb 5-bedroom 4.5-bathroom villa, located in the community of Solana in Davenport. It is fully gated for security.The villa is modern and very spacious with all the amenities you could want. It sleeps up to 10 guests.The villa benefits from 2 sitting rooms. One is classed as...

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Featured review

"Lovely house handy Disney andalltheattractions"

The location of this house was great for visiting all the attractions. There were 10 of us—9 adults and 1 child. We loved everything about this place. It was clean, everything we needed, pool and hot...

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$165
avg per night
Kissimmee Villa
Sleeps 8, 4 bedrooms, 3 bathrooms
3 reviews

Key Amenities

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

About this property

RECENTLY REFURBISHEDLuxurious Windsor Palms with an extra wide cul de sac lot and with a pool that is not overlooked. Our guests enjoy terrific privacy in one of the premier resorts in the Disney vicinity. We have a south facing pool with kiddy pool and stand alone hot tub. Numerous child friendly...

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Featured review

"Awesome vacation"

Everything was perfect from start to finish. House was better than we expected, owner was great to deal with and will for sure book this house again and have already referred friends to book this property...

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$217
avg per night
Kissimmee Villa
Sleeps 6, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Located in the prestigious, gated Windsor Palms resort community in Kissimmee, this privately owned 3-bedroom, 3-bathroom vacation villa comfortably sleeps up to 6 guests. Featuring a private south-facing splash pool with full privacy, spacious en-suite bedrooms, and just a 4-minute walk from world-class...

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$120
avg per night
Kissimmee Townhome
Sleeps 8, 4 bedrooms, 3 bathrooms
1 review

Distance to park: 2 miles to Disney

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Pool
  • Rentals by owner
  • WiFi

About this property

Welcome to Oakwater resort (the nearest 4 stars Resort from Disney) which is only 5 minutes drive from Disney World! It is also close to many other fine shops and restaurants. No traffic congestion! This resort is adjacent to an outdoor 24 hours Walmart super market( 2 minutes walking distance) Our sweet...

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Featured review

"Great property"

we were there for work in Universal Studios Epic Park, it was a great place and very accommodating, plenty of room and very clean, we will be staying again for the next round of work

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$146
avg per night
Kissimmee House
Sleeps 20, 9 bedrooms, 6 bathrooms
3 reviews

Distance to park: 2 miles to Disney’s Animal Kingdom Park

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

Windsor at Westside Resort is one of the newest and most luxurious resort communities in the Orlando/Kissimmee,Developed by one of the nation's largest developer. Just 8 miles from Disney, and within easy reach to all the attractions, shopping, and dining in the Disney area, This 24 hour guard gated...

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Featured review

"Very comfortable"

I went with my family, very comfortable. Beds 6 out of 10. Pool 7 out of 10. Rest of amenities 10 out of 10.

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$395
avg per night
Kissimmee House
Sleeps 16, 8 bedrooms, 6 bathrooms
8 reviews

Distance to park: 8 miles to Disney World

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

Windsor at Westside Resort is one of the newest and most luxurious resort communities in the Orlando/Kissimmee,Developed by one of the nation's largest developer , the Pulte Homes. Just 8 miles from Disney, and within easy reach to all the attractions, shopping, and dining in the Disney area, this...

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Featured review

"GREAT"

Great home for large family .. home is located close to shops … it’s a great location to be at! Very nice

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$366
avg per night
Kissimmee Villa
Sleeps 16, 7 bedrooms, 4.5 bathrooms
12 reviews

Distance to park: 3 miles to Disney world

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Pool
  • WiFi

About this property

Newly furnished luxurious 2-story Villa home opens its door to welcome you! This villa is furnished with two master suite and one large bedroom with upscale King-size beds; two bedrooms with queen-size beds; and two bedrooms with two twin-beds each. All bedding and mattresses are Brand New with top quality...

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Featured review

"Once Again a Wonderful Vacation"

This is the third time we have rented a vacation home from Ann and Gary at Emerald Island Resort. The 7 bedroom home was perfect for our family of 12 people. Everyone commented how comfortable the beds...

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Kissimmee Villa
Sleeps 8, 4 bedrooms, 2 bathrooms
11 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

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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Featured review

"2 week family vacation"

Our family had an amazing trip. It was as comfortable as being at home. Great communications with owner and management group if we had an issues or questions. Thank you.

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$120
avg per night
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FAQ

Proximity to Attractions

How close are Kissimmee rentals to the main entrance of Walt Disney World versus Orlando rentals?

Some Kissimmee vacation rentals are only 12 miles from Walt Disney World. Orlando rentals are a little further away from the amusement park at around 20 miles.

What is the average drive time from Kissimmee to Universal Studios or SeaWorld?

The average drive time from Kissimmee to Universal Studios is 23 minutes, while the average drive to SeaWorld takes 25 minutes.

Are there Kissimmee communities that offer shuttle services to the theme parks?

Yes. Encore Resort Condo, Wyndham Bonnet Creek Resort Condo, and Champions Gate Condo are some of Kissimmee’s vacation rentals offering shuttle service to Walt Disney World, Universal Studios, SeaWorld, and other attractions.

How bad is the traffic on US-192 or I-4 when driving from Kissimmee to the parks?

Both US-192 and I-4 are busy roadways leading to the parks. Traffic is heavier or lighter depending on the day of the week and the time of day. Weekday mornings, early evenings, and Saturdays are especially crowded.

Property Type & Communities

What are the most popular resort communities in Kissimmee (e.g., Reunion, ChampionsGate, Windsor Hills)?

Champions Gate, Reunion, Emerald Island, Windsor Hills, and Indian Creek are all popular resort communities in Kissimmee.

What kind of exclusive amenities do these large resort communities offer?

Some exclusive amenities include a clubhouse, tennis courts, a fitness center, a movie theater, a sauna, and a marketplace to purchase food.

Is it better to stay in a large resort or a smaller, non-gated community in Kissimmee?

The answer depends on your preferences. A smaller, non-gated community in Kissimmee offers fewer amenities than a large resort but still has a collection of fun activities nearby.

What are the main differences between staying in Kissimmee versus staying in Orlando?

Orlando is a large, bustling city full of restaurants, shops, and attractions, while Kissimmee is less crowded with a more family-friendly atmosphere. Though both cities are close to the major parks, Kissimmee is closer to Disney World, whereas Orlando is closer to Universal Studios.

Amenities & Features

What size homes are typically available for rent in Kissimmee?

The typical Kissimmee vacation home has four bedrooms and ranges from 1,980 to 2,000 square feet.

Do most house rentals come with a private, screened-in pool and lanai?

Though most house rentals come with a private, screened-in swimming pool, not all of them have a lanai.

Are multi-generational homes with multiple master suites common?

Yes, multiple master suites are common in Kissimmee vacation homes for rent.

What are some unique amenities to look for in Kissimmee homes, like private movie theaters or elaborate game rooms?

Check listings for unique amenities in Kissimmee house rentals such as EV chargers, gardens, balconies, ping pong tables, pool tables, game rooms, and heated pools.

Booking & Cost

Is it generally more affordable to rent a large house in Kissimmee compared to a similar one in Orlando?

Yes, when comparing similar homes in these two Florida cities, Kissimmee house rentals are the more affordable option.

What are the typical resort fees or community access fees I should budget for?

The typical resort fee is around $40 per day.

Are there any "hidden costs" associated with Kissimmee rentals, like pool heating or BBQ grill rental?

Studying the “Fees” section of a Kissimmee rental’s listing can help you avoid any surprise costs. Some owners list fees for services like pool heating, damage protection, and pets.

What is the best time of year to find deals on Kissimmee vacation homes?

September and October are the best times to find deals on Kissimmee vacation homes because fewer people are booking rentals.

Kissimmee Specifics

What attractions are there to see in Kissimmee itself, outside of the major theme parks?

Boggy Creek Airboat Adventures, Gatorland, Shingle Creek Regional Park, Congo River Golf, and Lake Tohopekaliga (Lake Taho) are all unique attractions in Kissimmee.

What are the best places for shopping and dining in the Kissimmee area?

The Promenade at Sunset Walk, The Crosslands, and Universal CityWalk are some of the best places for shopping, dining, or both.

How does the vibe of Kissimmee differ from the International Drive area in Orlando?

Orlando’s International Drive has a high-energy vibe with dozens of shops, restaurants, shows, spas, and other attractions. While Kissimmee has its own collection of shops, eateries, and attractions, the city’s vibe is more laid-back.

Are there any good nature-based activities, like airboat tours, that are easily accessible from Kissimmee?

Yes. Wild Florida Adventure Park, Gatorland Bird Rookery, and horseback riding sessions at Lazy H Ranch give visitors the opportunity to admire Kissimmee’s natural environment.