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Kissimmee Vacation Rentals with Private Pool

(167 rentals)
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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$130
avg per night
Kissimmee House
Sleeps 14, 7 bedrooms, 5.5 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Located on the upscale 5 Star Solterra Resort with amazing communal facilities including large pool, water slide and lazy river. Kids will just love it.This exceptional 7-bedroom, 5.5-bathroom home is your gateway to unparalleled relaxation and excitement. This luxury home boasts a heated pool and...

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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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$220
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 townhouse 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 resort...

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$120
avg per night
Kissimmee Villa
Sleeps 8, 4 bedrooms, 4 bathrooms
31 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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$300
avg per night
Kissimmee Villa
Sleeps 8, 4 bedrooms, 2 bathrooms
10 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

This stunning 4 Bed 2 Bath Villa enjoys one of the premier positions on Lake Berkley Resort with an unspoilt beautiful view over the lake. Enjoy breakfast, lunch or dinner on the pool patio whilst watching the wildlife on the lake. If you enjoy fishing then you only need to walk a few yards to fish in...

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Featured review

"Outstanding Villa To Rent"

We just finished up our month long stay at this gorgeous villa over looking the lake. The villa is equipped with everything you use at home. The home was very clean and well presented when we checked. The...

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$125
avg per night

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Kissimmee Villa
Sleeps 8, 4 bedrooms, 3 bathrooms
16 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

"Great vacation home"

Very clean, lots of room, vacation home. Great location in the middle of everything. Room for family of 10

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$155
avg per night
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 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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$297
avg per night
Kissimmee House
Sleeps 16, 7 bedrooms, 4 bathrooms
12 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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$265
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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$367
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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$136
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 House
Sleeps 16, 9 bedrooms, 5 bathrooms
29 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Welcome to The Pixar Palace, a fully Pixar themed, lakefront resort vacation home that sleeps 25 people, and features four KING bedrooms, private pool & spa, arcade, gaming room, and themed rooms for the kids including Toy Story, Finding Nemo, Cars, Incredibles and more Pixar! Enjoy resort amenities...

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$514
avg per night
Kissimmee Villa
Sleeps 24, 9 bedrooms, 6 bathrooms
14 reviews

Distance to park: 2 miles to Sunday's Grill

Key Amenities

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

About this property

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

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Featured review

"Excellent"

Thank You Ann great service. Me and my family will be renting from you again in the future

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$319
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 14, 7 bedrooms, 7.5 bathrooms
2 reviews

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

"Fantastic Place"

This was our second visit to the Orlando area, and although this house did not have as many bedrooms as the previous home, it worked great for our needsGood location, a Walmart within two minutes, a...

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$250
avg per night
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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