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Kissimmee Vacation Rentals

(201 rentals)
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 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 Condo
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

This is a NON SMOKING condo *Community: Sweetwater Club VillasFloors: First Floor CondoPets: PLEASE ASK ABOUT OUR PET POLICY.Rooms: 3 Bedrooms, 2 Bath rooms. En-suite in Master bedroom.Bed Configuration: King bed (1) Queen bed (1), Two Twin Beds (2). Sleeps 6.Flooring: Ceramic...

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$250
avg per night
Kissimmee Villa
Sleeps 8, 4 bedrooms, 3 bathrooms
7 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to our fabulous 4-bedroom, 3-bathroom family villa, located in the highly sought-after community of Orange Tree in Clermont, just off Highway 27.This spacious and fully air-conditioned home is ideal for families or groups of up to 8 guests. With two living areas, a fully equipped kitchen,...

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Featured review

"AWESOME!!!!"

This home is just as described. It is clean, well kept, beautifully decorated and spacious with plenty of kitchen utensils. The game room was so much fun. We had a few hiccups but the property management...

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$140
avg per night
Kissimmee House
Sleeps 8, 3 bedrooms, 2 bathrooms
4 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

This beautiful home is a 3-bedroom, 2-bathroom with its own private screened pool. The home is located in Lindfields; a peaceful subdivision situated approximately 10 minutes from the Walt Disney World entrance and is conveniently located for the other attractions. It is an ideal location with easy access...

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Featured review

"Cheap and cheerful"

Villa was easy to find, near plenty of shops and restaurants. Villa was nice and clean, could have done either a bit of tlc. Ad we entered the villa there were lots of bushes protruding over the path A...

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$130
avg per night

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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 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 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 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 Townhome
Sleeps 10, 5 bedrooms, 3 bathrooms
2 reviews

Distance to park: 6 miles to Disney kingdom

Key Amenities

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

About this property

Welcome to Coral Cay Resort! Coral Cay resort Situated 6 miles from Disney World, 1 mile to Walmart and target. 0.5 mile off highway 192.Seaworld and Convention Center are 8 miles away.Just minutes from Orlando's vast array of theme parks, fabulous dining options and world-class shopping.Our...

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Featured review

"Vacation was beautiful!"

We had an awesome week in Florida! The house was amazing! The owners were awesome!!!!’ 6 stars! My family and myself will book again very soon!!

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$153
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 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 Villa
Sleeps 10, 5 bedrooms, 4 bathrooms
22 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to our stunning, larger than average, 5 Bed 4 Bathroom villa with a beautiful view of the conservation area at the rear as background of our private pool. All rooms in the villa are spacious. The villa is furnished and maintained to a very high standard.The villa is located just off US 192...

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Featured review

"Fabulous Villa on Bellavida Resort"

All I can say is fabulous, the villa was everything you promised and more, absolutely superb. Cleaning was done to a high standard throughout. Pool was enjoyed by all, multi coloured pool light at night...

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$160
avg per night
Kissimmee Villa
Sleeps 6, 3 bedrooms, 2 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to our stunning 3 bed, 2 bath villa perfectly located just off Highway 27 in Davenport and is only 15 minutes from Disney main gate.It has an open, inviting floorplan with its own pool and gorgeous private pool, deck and spa; as well as a games room.This home is beautiful fresh and very...

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Featured review

"Great place to stay."

The villa is very convenient for shops and eating places - Walmart, Aldi and a large number of restaurants are less than 10 minutes away. The villa is also easily accessible to all the theme parks and shopping...

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$135
avg per night
Kissimmee House
Sleeps 12, 4 bedrooms, 3 bathrooms
17 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • WiFi

About this property

This 4 bedroom Themed Orlando vacation home sleeps 12, and features a Ratatouille themed living area, two master suites, a Guardians of the Galaxy themed room, a Toy Story themed room, and a Star Wars themed room! Located only minutes from Walt Disney World, Universal Studios, and all Orlando attractions!The...

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$233
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 Townhome
Sleeps 8, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Modern 3-Bedroom Townhome – Near Disney!Enjoy the best of Orlando in this spacious and cozy home just minutes from Disney! Located in a gated community right next to the new Dollar Tree in Kissimmee, our home comfortably sleeps up to 8 guests.Bedrooms:Suite 1: King bed + private bathroomSuite...

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$139
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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$296
avg per night
Kissimmee Townhome
Sleeps 8, 4 bedrooms, 3 bathrooms
6 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 Kissimee/Orlando area for its proximity to theme parks and other major attractions. Situated 6 miles from Disney,1 mile to walmart and target, 8 miles to seaworld and convention center.This 1500 sqft...

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Featured review

"Second stay"

This is a nice place. Well kept and clean. There is 3 pools but not enough lounge chairs. The room was nice. Needed to buy a frying pan there is not enough kitchen gadgets and the cups for coffee are very...

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$146
avg per night
Kissimmee House
Sleeps 8, 4 bedrooms, 3 bathrooms
3 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

We welcome you to our beautiful professionally decorated and furnished 4 Bed, 3 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 villa has two sitting room has comfortable...

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Featured review

"Great villa"

Recently had a family vacation it was an amazing villa. Clean and great location close to everything. Will definitely rent again.

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$160
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 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 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 House
Sleeps 16, 9 bedrooms, 5 bathrooms
11 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Welcome to your 9-bedroom lakefront villa with a private pool, just minutes from Disney! Race in the Mario Kart room, sleep in a Princess Castle, explore the glowing Avatar game room, and relax in the vibrant Coco loft. Packed with luxury amenities, themed fun, and endless photo ops—this is the...

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$401
avg per night
Kissimmee Villa
Sleeps 6, 3 bedrooms, 2 bathrooms
5 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

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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Featured review

"soaring eagle lane"

tidy villa nice views our small lake ducks will come up to be fed nice size pool overall good villa games room in garage

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$140
avg per night
Kissimmee Villa
Sleeps 8, 4 bedrooms, 3 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

At Calabay near Disney- This 4 bedroom 3 bath home is well maintained and cared for. It is a perfect vacation rental getaway. The spacious foyer leads to a well equipped kitchen/dining room. The master bedroom has a king bed; master bath has double sinks, garden tub, privacy toilet & shower. A second...

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Featured review

"Perfect serene environment"

My family and I thoroughly enjoyed our stay at the villa. It’s truly one of the best private rental properties in Florida, and we would rate it over 100%!

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$155
avg per night
Kissimmee House
Sleeps 18, 9 bedrooms, 6 bathrooms
5 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 Vacation Home for Families"

We spent a great week in this home with our extended family. Tons of rooms and bathrooms and a nice big kitchen. Private pool and community water park were great for the kids. Location was convenient. We...

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$400
avg per night
Kissimmee House
Sleeps 16, 8 bedrooms, 6 bathrooms
11 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Welcome to the Epic Universe House, an 8BR resort pool home that sleeps 22, and pays tribute to the new Epic Universal park, featuring a Ministry of Magic arcade, Nintendo World gaming room, & themed rooms including How To Train Your Dragon, Zelda and more! Located only minutes from Disney World,...

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$467
avg per night
Kissimmee Villa
Sleeps 8, 4 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to our superb 4-bedroom, 2.5-bathroom villa, located in the peaceful community of Eagle Pointe in Kissimmee, just minutes from Highway 192 and a short drive to Disney and other major Orlando attractions.The villa is spacious, comfortable, and well-equipped with everything you need for a relaxing...

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$160
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
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 Villa
Sleeps 8, 4 bedrooms, 3 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Our luxury 4 bedroom home is located within the top rated community of Indian Creek. 2 of the bedrooms have ensuite bathrooms.The villa is furnished to a very high standard and is fully Air-conditioned throughout keeping the villa cool in the warm Florida weather.Full hi-speed WiFi throughout...

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Featured review

"Excellent Vacation"

Great family-friendly house with a stunning pool and wonderful hot tub. Close to all major theme parks, many restaurants & stores. Neighborhood is super quiet with walking paths & nearby park.

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$160
avg per night
Kissimmee Villa
Sleeps 8, 4 bedrooms, 3.5 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Your family will be close to everything when you stay at this centrally-located gated Summerville Resort. It’s the perfect place for a trip!! The space is modern and stylish. This 4 bedroom (townhouse is Spacious enough to sleep 8.Access to resort, amenities, pool, gym, outdoor playground,...

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$150
avg per night
Kissimmee Villa
Sleeps 14, 6 bedrooms, 4 bathrooms

Key Amenities

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

About this property

****CONTACT US FOR SPECIAL RATES & DISCOUNTED QUOTES***Central Breeze Villa located in the popular Windsor Hills Resort. Just 3 miles from Disney. Cozy, quiet & filled with fun to entertain everyone. Enjoy the saltwater pool, spa tub or just lounge on your private lanai. Head inside for a...

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$392
avg per night
Kissimmee Villa
Sleeps 14, 0 bedrooms, 4.5 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

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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$277
avg per night
Kissimmee House
Sleeps 16, 7 bedrooms, 6 bathrooms
17 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Enjoy the family fun in this 7BR resort vacation home that sleeps 17 people and features 3 KING bedrooms, a private pool w/ spa, an Avatar arcade game room, a FROZEN Castle room, and more themed rooms including Star Wars, Lion King, Monsters Inc, and Moana! Located only minutes from Disney World, Universal...

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$467
avg per night
Kissimmee Villa
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to our idyllic 3 bed, 2 bath villa at Indian Ridge in the heart of Kissimmee. Because it is close to both the US192 and the I-4 it is a perfect place in which to enjoy Disney (10 minutes away) and Universal which is 20-25 minutes away.You are greeted by an airy, open plan living space creating...

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$145
avg per night
Kissimmee Villa
Sleeps 11, 4 bedrooms, 3 bathrooms
4 reviews

Key Amenities

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

About this property

Magic Lake View Villa near Disney- Totally private (no neighbors looking in either side) heated PRIVATE South pool with hot tub facing a 14 acre natural fishing lake on a prestigious Lake Berkley Resort, 24/7 Security - gated territory, 100% SAFE! Just 7.8 miles to DISNEY! The villa has everything...

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Featured review

"Lovely sunny villa in a great location."

We visited this villa for 2 weeks in October 2025. We loved the outdoor space and the villa had everything we needed. The location is perfect for visiting parks and local restaurants. Walmart is close by....

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$250
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 House
Sleeps 14, 5 bedrooms, 5 bathrooms
8 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

This lakefront resort pool home sleeps 14 and is steps from the Paradise Palms clubhouse, and only minutes from Disney World, Universal, and all Orlando attractions. Featuring 5 bedrooms with three king beds, private pool, a Tron themed game & movie room, and themed rooms for the kids including Mickey...

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$237
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, 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 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 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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$345
avg per night
Kissimmee House
Sleeps 14, 5 bedrooms, 4 bathrooms
9 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Welcome to The Marvel Mansion, a spacious five bedroom Orlando vacation home that sleeps 14 and features a large private fenced backyard with pool & spa, a Super Smash Bros movie theater & game room, TWO king bedrooms, and themed rooms for the kids and adults including Spider Man, Guardians of...

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$305
avg per night
Kissimmee House
Sleeps 16, 8 bedrooms, 6 bathrooms
5 reviews

Distance to park: 8 miles to Disney World

Key Amenities

  • Air conditioning
  • Hot tub
  • 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

"Very nice"

We really enjoyed our stay. Community was really nice and house was huge. Had some good amenities and was a real easy drive to all the parks. Pool was nice… wish we paid for heat but we didn’t. ...

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$361
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, 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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$320
avg per night
Kissimmee House
Sleeps 18, 8 bedrooms, 6 bathrooms

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Windsor at Westside Resort features a large 10,000 sq.ft. clubhouse which includes a resort-style pool, lazy river, water slide, & hot tub. Other amenities include a gym, beach volleyball, cabana rentals, basketball court, game room, tiki bar and concierge desk.Location is great with a Kissimmee...

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Kissimmee House
Sleeps 20, 10 bedrooms, 7 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Exciting NEW 10 bedroom family vacation home Offering privacy and space for everyone 4300 square feet of awesomeness 2 separate large living areas Relaxing pool with spa Covered outdoor dining and seating Games loft with pool table and foosball Windsor Island Resort offers a wide variety of world...

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Kissimmee Weather

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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

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.