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Kissimmee Vacation Rentals

(229 rentals)
Kissimmee House
Sleeps 8, 4 bedrooms, 3 bathrooms
1 review

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

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

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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Featured review

"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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$200
avg per night
Kissimmee House
Sleeps 7, 3 bedrooms, 2 bathrooms
12 reviews

Distance to park: 6 miles to Disney - Animal Kingdom

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

This private, lakefront with nature reserve, pool home offers a fusion of luxury, comfort, and convenience. This spacious 3 bedroom and 2 bath home has cathedral ceilings and an open floorplan, with a living room, breakfast nook, and formal dining area. The kitchen is fully outfitted with all the appliances ...

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Featured review

"Great Area"

Location was quiet. Home was beautiful and well maintained. My only comment would be to have a casserole dish to be able to bake something in the oven. Also a pizza pan. Besides these items it is well stocked. ...

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$127
avg per night
Kissimmee House
Sleeps 16, 7 bedrooms, 5.5 bathrooms
5 reviews

Distance to park: 8 miles to Disney World

Key Amenities

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

About this property

Waiting to welcome you is this 7 bedroom, 5.5 bathroom, 3300 sq/ft villa - perfect for large families or multigenerational gatherings comfortably sleeping up to 16 people.With Star Wars, Spiderman, Harry Potter, Avengers, and Mickey & Minnie theming, everyone is bound to find somthing they'll ...

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$373
avg per night
Kissimmee Villa
Sleeps 20, 9 bedrooms, 5 bathrooms
62 reviews

Distance to park: 7 miles to Disneyworld

Key Amenities

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

About this property

SCAN QR CODE for a VIRTUAL TOUR. Experience luxury and entertainment in this 9-bedroom villa that has 7 different themed rooms, a private pool/hot tub, and unobstructed lake views. Enjoy our Avengers movie room, Star Wars game room, Harry Potter, Frozen, Toy Story, Moana, Mickey bedrooms and 2 exclusive ...

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$501
avg per night
Special Offer
Kissimmee Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
4 reviews

Distance to park: 5 miles to Disney World

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Our lakeside condo is on the ground floor and has a screened lanai seating area for your enjoyment. The living room is quite spacious and has a flat screen television, a DVD player, a queen sleeper sofa bed, and has seating for up to six guests. The dining area also has seating for six. Save money by ...

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Featured review

"Very Comfortable and Quiet Long Term Stay"

We spent 6 weeks in Mary's Ground Floor 4 Bedroom Condo at Legacy Dunes. The condo is spacious and tastefully decorated, it is very clean and well equipped with all we needed for a comfortable long term ...

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$104
avg per night

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Kissimmee House
Sleeps 10, 4 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Charming brand new 4 br, 3 bath townhouse with pool. Located in the desirable Storey Lake Resort, in the new quiet Preserve Area, It has capacity for 12 guests. Storey Lake has a resort-style clubhouse full of amenities and fun for families, including a business center, basketball court, ping pong table, ...

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$174
avg per night
Kissimmee Condo
Sleeps 7, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

This condo is one of our most highly sought-after Orlando vacation rentals, and for a good reason. This beautiful property is equipped for up to seven guests between its three bedrooms and two bathrooms. Those who stay in this rental will be able to take full advantage of every amenity and feature that ...

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$135
avg per night
Kissimmee House
Sleeps 7, 3 bedrooms, 2 bathrooms
5 reviews

Distance to park: 6 miles to Disney - Animal Kingdom

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

The "Sweet Retreat" is just 6 miles to Disney! This "Sweet" Villa has 3 Bedrooms, 2 Baths and sparkling Sunny private pool... Perfect for families & "Sweet" on your feet with all tile in the main rooms & carpet in the bedrooms.The living room feels bright and ...

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Featured review

"Very nice villa"

Had a 2 week stay at this very nice villa. Clean, comfortable and great pool area. Good locaction. We highly recommend.

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$127
avg per night
Kissimmee Apartment
Sleeps 5, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

2bd/2ba with the Best View in the amazing community of Storey Lake. Located 10 minutes from Disney Come in and enjoy a unique experience. There is a beautiful waterpark in the community center for you to enjoy. It is the perfect place to relax, have a good time and enjoy all that Orlando has to offer. This ...

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Featured review

"2024 vacation"

The house was lovely.. lots of room, clean, bright The resort pool was absolutely beautiful.. my grandson loved his time in the pool .. lot of room to sit around and food at the pool area was really good

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$145
avg per night
Kissimmee Villa
Sleeps 12, 5 bedrooms, 5 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Name Of Home: Live Your Adventure Family VillaLocation: Encore Resort (Gated community - Disney World only mins away!)Home Highlights: XBox, Private Pool, Marvel Themed Games RoomProperty Type: Single Family Home, Two Story (2,570 SF)Bedrooms: 5 Total - 2 w/ King Beds, 1 w/ Queen Bed, ...

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$254
avg per night
Kissimmee Townhome
Sleeps 6, 3 bedrooms, 2 bathrooms
3 reviews

Distance to park: 2 miles to Fun Spot America Theme Parks

Key Amenities

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

About this property

Your family will be close to everything when you stay at this centrally-located place.This property it is fully renovated; first-floor unit with a laminate floor, high ceiling in the living room, open floor plan. The kitchen and bathrooms have been upgraded. The whole community was recently replumbed.Nice ...

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Featured review

"Great Vacation Home"

We found the townhouse to be nicely decorated with cute little touches, updated, very clean and equipped with all the necessities for a fabulous experience. It's a very safe, quiet, peaceful location, ...

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$119
avg per night
Kissimmee House
Sleeps 10, 4 bedrooms, 4 bathrooms

Key Amenities

  • Air conditioning
  • WiFi

About this property

If you’re searching for Orlando vacation rentals and want something unique, this home fits the bill! As soon as you pull up, you’ll notice the incredible Mediterranean design, which makes this house stand out from all the others on the block. Inside, you’ll have access to all kinds of ...

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$212
avg per night
Kissimmee House
Sleeps 16, 9 bedrooms, 7 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Located in the exclusive Encore community. This beautiful and luxurious vacation home is a 2-story home with 9 bedrooms, 7 bathrooms, a laundry room, game room, and a pool with hotube. It is completely fenced. The house has a capacity for 18 guests. This stylish place to stay is perfect for group trips. Charming ...

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$323
avg per night
Kissimmee Villa
Sleeps 11, 5 bedrooms, 3 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Now taking bookings for 2026/27. Welcome to “Hibiscus on the Lake” with a true south facing pool/spa. The villa has stunning, uninterrupted views of the largest lake with an island in the middle full of beautiful birds on Lake Berkley resort in Kissimmee. Being one of only seven villas ...

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Featured review

"Great location"

Stayed here in April for 2 weeks as a family of 6 adults. Villa is in a great location with easy access to the parks. It is on the main lake with beautiful views. Lots of wildlife. Saw a family of otters ...

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$258
avg per night
Kissimmee Apartment
Sleeps 4, 1 bedroom, 1 bathroom

Distance to park: 7 miles to Disney World

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

1/1 Condo. Queen sofabed in living room. Queen bed in master with desk and chair. Full kitchen. Just 7 miles from Disney, centrally located. Gated community , Complex has 2 pools, gym, tennis courts. Laundry room with full size washer/dryer in unit. Free wifi and streaming. Second floor unit.No elevators. No ...

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$81
avg per night
Kissimmee Villa
Sleeps 12, 6 bedrooms, 5 bathrooms

Distance to park: 7 miles to Disney's Animal Kingdom Theme Park

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Experience Luxury and Comfort at Our 6-Bedroom, 3,200 sq. ft. Villa – Perfect for Families and Groups!Escape to our stunning luxury villa, featuring 6 spacious bedrooms (9 beds) and 3,200 sq. ft. of beautifully appointed living space. With 2 luxurious en-suites, 3 king-sized beds, 2 cozy living ...

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$173
avg per night
Kissimmee Villa
Sleeps 12, 6 bedrooms, 4.5 bathrooms
9 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

The Villa is fully air conditioned, pool has solar heating, all rooms have cable tv, Free WIFI, local calls are free, Safe and baby equipment also available for use at no extra cost.The villa has a 30ft South West facing solar heated Pool/Spa with a large patio area with table chairs and sun loungers,Also ...

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Featured review

"Extremely Satisfied"

My family and I enjoyed our stay at Brendas home. It was clean and very comfortable. It felt just like “home”. Though it was too cold that week in Florida, we weren’t able to enjoy the pool and jacuzzi ...

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$207
avg per night
Kissimmee House
Sleeps 16, 8 bedrooms, 6 bathrooms
9 reviews

Key Amenities

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

About this property

5 star Property!Welcome to Sunset Magic Villa!Delightful Windsor at Westside Resort home villa8 bedrooms (2 Downstairs/6 Upstairs) and 6 full bathrooms. Space for up to 16 guests, (stretch out and relax with all the comforts of home) WEST facing private pool ensuring stunning sunset ...

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$352
avg per night
Kissimmee House
Sleeps 14, 6 bedrooms, 3 bathrooms
1 review

Distance to park: 5 miles to Disney World

Key Amenities

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

About this property

Experience a relaxing & unforgettable vacation in this stunning Tiffany Blue-colored villa, nestled in a peaceful & safe residential neighborhood. Enjoy easy access to theme parks, golf, restaurants, and supermarkets, all just a short drive away. Don't miss out - contact me with any questions!...

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Featured review

"Amazing family-friendly home w/ a stunning pool"

Excellent location very close to Disney World. Beautiful and clean home. Host is very welcoming and helpful. The pool is stunning. The pictures do not do it justice. Wish we would have stayed longer!

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$180
avg per night
Kissimmee House
Sleeps 14, 6 bedrooms, 4.5 bathrooms
3 reviews

Key Amenities

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

About this property

Welcome to your dream vacation home located in Windsor at Westside! This 6 bedroom, 4.5 bathroom sleeps 12 perfectly and is pure luxury. This home has 3 king bedrooms, 2 rooms with a twin and double and then one room with twin bunkbeds. The bedrooms are really fun for the kids with a Harry Potter theme ...

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Featured review

"Disney vacay"

Mickeys mansion was wonderful. Very clean. Everything you may need in kitchen. We paid extra for heated pool and the adult kids and grandchildren loved it. We would definetly go back and rent this again.

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$295
avg per night
Kissimmee Villa
Sleeps 14, 7 bedrooms, 4.5 bathrooms
3 reviews

Distance to park: 4 miles to Animal Kingdom

Key Amenities

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

About this property

Conveniently located on the Exclusive Emerald Island Resort. With 7 Bedrooms and 4.5 bathrooms, Berni’s Home from Home can easily accommodate two families travelling together or will give one family plenty of space.Enjoy relaxing by your very own private extended south facing pool or spend some ...

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Featured review

"Very well maintained home"

This home was lovely and very well kept. Would rent again if the occasion arose that we needed a home this big again.

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$250
avg per night
Kissimmee Condo
Sleeps 4, 1 bedroom, 1 bathroom

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Beautiful and clean unit with two queen size beds upstairs, it is part of a recently renovated condo-hotel furnished with modern design and great taste, with fenced pool, playground, gym, and indoor and outdoor dining/resting/seating areasTouristic area, super close to the parks, located on the main 192 ...

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Kissimmee Townhome
Sleeps 8, 4 bedrooms, 3 bathrooms
9 reviews

Key Amenities

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

About this property

Private 2 story home with 4 Bedroom/3 Bathroom with private pool which has all of the spacious and convenient accommodations for your entire family vacation. Storey Lake is near to all of the major parks & attractions of Disney World, Epcot, Animal Kingdom, Disney Water Parks, Universal Studios and ...

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Featured review

"Great place"

We stayed here for a tournament at Orange County Convention and this was a perfect location and the amenities were amazing!! We loved this townhouse and would love to stay here again

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$164
avg per night
Kissimmee Villa
Sleeps 6, 3 bedrooms, 2 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

This newly remodeled pool Villa is the perfect getaway. From the new kitchen and bath to the newly resurfaced pool. Large pool deck with room to spread out. A covered area for dining and tons of pool deck for those who love the sun. The pool is south facing. Sunsets are spectacular.#3 bedrooms. ...

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Featured review

"Strafford park"

Best hol for years.we had a great time .the Fords restaurant was a brilliant place to eat and of course,we breakfasted at Dennys

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$145
avg per night
Kissimmee Townhome
Sleeps 7, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to our stunning townhouse located at 2600 Lodi Crescent in the charming city of Kissimmee, FL. This tastefully furnished property is the perfect choice for your next getaway. Whether you're visiting the magical Walt Disney World or exploring the vibrant attractions of Orlando, our townhouse ...

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$107
avg per night
Kissimmee Townhome
Sleeps 11, 4 bedrooms, 3 bathrooms
1 review

Key Amenities

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

About this property

New 4-bedroom, 3-baths townhouse with a private pool. Nestled in the peaceful Preserve Area of Storey Lake Resort, this property can accommodate up to 11 guests.It's totally equipped: - Kitchen has everything you need to cook - Towels & linen - Wifi - Basic cable and TVs - Enough free ...

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Featured review

"Excelente lugar para vacacional y pasar un tiempo en familia."

Nuestra estancia fue excelente desde la reservacion, el host muy atento, accesible y comunicador. La propiedad la encontramos en excelentes condiciones como así la vimos en las imágenes. Todo muy bonito, ...

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$171
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 6, 3 bedrooms, 2 bathrooms
7 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

This stunning 3 Bed 2 Bath villa is located on the Lake Berkley 5-star Resort. it is gated and has 24/7 security. It is close to shops, restaurants, just 1 minute from the 192 main road that runs through Kissimmee and less than 20 minutes from Disney.If you enjoy fishing, then you only need to walk ...

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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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$145
avg per night
Kissimmee Villa
Sleeps 10, 5 bedrooms, 4.5 bathrooms
2 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 12 guests.The villa benefits from 2 sitting rooms. One is classed as ...

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Featured review

"Great Location"

Wonderful villa in a quiet location. Villa was spotless on arrival. Close to all attractions and suoermarkets.

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$165
avg per night
Kissimmee House
Sleeps 10, 5 bedrooms, 4 bathrooms
4 reviews

Key Amenities

  • Air conditioning
  • Pet friendly
  • Pool
  • WiFi

About this property

This newly refurbished 5 bed, 4 bath villa can be found on the resort of Hampton Lakes, with direct access to Highway 27 and is ideally located for all the attractions!This home is a haven of modern living, offering both comfort and style for your Florida vacation.You can sleep up to 10 guests ...

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Featured review

"Emerald Island Resort"

Enjoy my 12 days stay with family kids had a blast at the theme parks. There were some minor problems but they were very responsive and was dealt with in a timely manner.

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$165
avg per night
Kissimmee House
Sleeps 10, 5 bedrooms, 4 bathrooms

Distance to park: 6 miles to Disney World

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

This beautiful 5 bedroom house is located in Crystal cove gated community. Perfect vacation home for families with small children or large groups. This vacation villa offers a sunny private pool, relaxing spa overlooking the lake. There are 2 master suites, private pool, community pool / gym. Pool ...

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$232
avg per night
New
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 10, 5 bedrooms, 3 bathrooms
14 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to this beautiful luxury villa on the gated 5 Star Resort of Lake Berkley. This villa has 5 bedrooms, 2 of which are on the ground floor and 3 are on the first floor. It can sleep up to 10 comfortably.This is a perfect location for fishing on 3 well stocked lakes. Fish all day long whilst ...

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

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

This is a NON SMOKING condo *Community: Sweetwater Club VillasFloors: Ground Floor Condo.Pets: NOT PET FRIENDLY.Rooms: 3 Bed rooms, 2 Bath rooms. En-suite in Master bedroom.Bed Configuration: King bed (1) Queen bed (1), Full Bed (2). Sleeps 6.Flooring: Hard wood throughout with ...

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$120
avg per night
New
Kissimmee House
Sleeps 12, 4 bedrooms, 3 bathrooms
1 review

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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$138
avg per night
Kissimmee House
Sleeps 16, 8 bedrooms, 5 bathrooms
5 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 brand new luxury finished 3600 Sqft pool home at beautiful Crystal Cove Resort. It is conveniently located close to shopping and dining (less than 1 mile away). Disney is only 6 miles away. Just minutes from major attractions like Sea World, Universal Studios, Aquatica and the Convention ...

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Featured review

"Very good! Great Location!"

Really enjoyed our stay. Convenient location, spacious house, very clean. Close to Disney parks, grocery stores, restaurants, etc. We'd like to stay again for our next trip.

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$251
avg per night
Kissimmee Villa
Sleeps 18, 9 bedrooms, 6 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

(AWAITING PROFESSIONAL PHOTOS)South-west facing private pool & spa Complimentary BBQ Recently upgraded with modern furnishings throughout All nine bedrooms throughout are immaculately furnished, each with a unique design Great themed bedrooms to appeal to younger family members Situated on ...

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$553
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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$175
avg per night
Kissimmee Villa
Sleeps 11, 4 bedrooms, 3 bathrooms
1 review

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

"Paradise for family stay"

The house is absolutely great for our famaly of 10, kids didn’t want to leave! Disney parks are very close just 15-20 min drive. Hot tub with amazing Lake view was super! Will definitely come back again

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$250
avg per night
New
Kissimmee House
Sleeps 10, 4 bedrooms, 2 bathrooms

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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$150
avg per night
Kissimmee Villa
Sleeps 10, 5 bedrooms, 3 bathrooms
8 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Your villa is located on the gated 5 Star Lake Berkley Resort in Kissimmee. 5 Beds, 3 Bath home that is beautifully furnished throughout (Big TV/Games Room/Heated Pool/Free Internet). Our villa is furnished to a very high standard and being all one level is ideal for one or two families. The villa ...

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Featured review

"Lake Berkley Villa"

We have rented from this agent multiple times and are always beyond pleased. Each home we have rented were great and the location is perfect. Any communications before, during and after have always been ...

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$160
avg per night
New
Kissimmee House
Sleeps 17, 9 bedrooms, 5 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Coco’s Castle Escape is a magical 9-bedroom villa 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 ultimate ...

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$323
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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$119
avg per night
New
Kissimmee House
Sleeps 14, 5 bedrooms, 5 bathrooms
1 review

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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$202
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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$355
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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$321
avg per night
Kissimmee Townhome
Sleeps 8, 3 bedrooms, 2.5 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Pet friendly
  • 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

"Ernest & June"

Emerald Isles Resort. 2725 Sun Key Place, Kissimmee Fla. We were there for 2 months , great place very beautiful, well kept and neighbors were great. The Club house and pool are fantastic. Anyone who wants ...

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$79
avg per night
Kissimmee House
Sleeps 8, 4 bedrooms, 3 bathrooms
2 reviews

Distance to park: 12 miles to Disney World

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Beautiful lakeside home with a private south facing pool in a gated community 12 miles from Disney. Enjoy fishing in the lake behind the house. Game room with pool table, skeet ball, foosball table and a gaming system with hundreds of old favorites like Pac Man and Mario Brothers. 4 bedrooms and 3 bathrooms. ...

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Featured review

"Wonderful home!"

This is a lovely home, in a lovely neighborhood. The house had everything needed to make your stay enjoyable and have the same comforts of your own home. The pool is huge and you have a beautiful view with ...

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$180
avg per night
Kissimmee House
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 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

"Wonderful Vacation Home"

Our family of 12 spent 2 weeks at 2662 Emerald Island Blvd. Everyone had a wonderful time and hated to leave when our vacation was over. The house has very comfortable furniture and everyone said their ...

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$166
avg per night
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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

How many vacation rentals are there in/around Kissimmee?

There are 229 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 $55 per night with an average price per night of $172.

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 177 vacation rentals in Kissimmee with a pool on FloridaRentals.com. Search using our filters and book one for your next vacation!