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Vacation rental houses in Kissimmee

Vacation rental houses in Kissimmee

Book unique vacation rental houses, apartments, and more on Airbnb

Top-rated houses in Kissimmee

Guests agree: these stays are highly rated for location, cleanliness, and more.

Beautiful pool villa, gated community, near Disney
SUPERHOSTEntire house · 8 guests · 6 beds · 3 baths
Beautiful pool villa, gated community, near Disney

This villa with private pool is located on the gated community of Cumbrian Lakes, located 15 minutes from the Disney entrance and conveniently located for the other attractions. This peaceful community has a children's playground and a jogging/nature trail round one of the lakes. This home has a maximum sleeping capacity of 8.

What guests are saying:

“The place is absolutely beautiful and well worth the stay. I found there to be plenty of dishes, pots and pans etc. to handle our large family without issues. The pool is so wonderful and warm, the pond in the back is full of wildlife and so peaceful. Santiago was great with communication and quick to reply to needs. Really recommend this place.”

Private Bathroom & Close Airport,Park & Everything
SUPERHOSTPrivate room · 2 guests · 1 bed · 1 private bath
Private Bathroom & Close Airport,Park & Everything

From vacations, or business. You found the place perfect to rest in our quiet house. The bedroom with private bathroom in a residential area and CLOSE TO EVERYTHING & Faster Roads. 1 min Turnpike to Miami-Daytona Beach,528, 417, Osceola 3 Min to Miami Bus Station,Sun Rail Station,Walmart Supermarket (24 Hours), Mall and Gatorland Park 5 Min. 16 Min to Airport 22 Min.Universal,Sea-word,Aquatica, Orange County Convention Center OCC 25 Min, 20 Min. to Disney Team Park . Better location

What guests are saying:

“The place was quiet and clean. There was toiletries provided which was a plus because I didn't pack any. The place was also close to many shops and the turnpike. I would definitely recommend.”

Home near Disney 4br with pool
SUPERHOSTEntire house · 10 guests · 7 beds · 3 baths
Home near Disney 4br with pool

Ground floor house with forest reserve area in the back (more privacy). Laminate flooring in all rooms. Central air conditioning (hot / cold), equipped kitchen, private pool with security fence, safe, alarm system. Free access to the Condominium Club. Game room.

What guests are saying:

“This is a great location and house!!! We decided to come to Orlando, but not do Disney. This house was a perfect distance between Cape Canaveral and LEGOLAND. Both were easy drives. Also the house is super close to many Publix stores, Walmart and restaurants. Having a pool with the house was awesome. I recommend paying to have it heated if you go in February. That is the one thing I would do differently next time.”

Vacation rentals for every style

Get the amount of space that is right for you

  • Homes
  • Hotels
  • Unique stays

Popular house amenities in Kissimmee

  • Pool
  • Hot tub
  • Wifi
  • Air conditioning
  • Kitchen

Townhouses in Kissimmee

Terra Verde by the Lake w/a private pool.Sleeps 12
Entire townhouse
Terra Verde by the Lake w/a private pool.Sleeps 12
Price:GYD36,152 / night
Stylish Beach House with Private Pool
PLUSEntire townhouse
Stylish Beach House with Private Pool
Price:GYD13,618 / night
Luxury Townhouse/Private Pool/12 Min from Disney!
Entire townhouse
Luxury Townhouse/Private Pool/12 Min from Disney!
Price:GYD22,996 / night
Spotless,  Immaculate,  Villa ! Close to Disney!
SUPERHOSTEntire townhouse
Spotless, Immaculate, Villa ! Close to Disney!
Price:GYD14,652 / night
Mo's 4 Bed/3.5 Bath (ENTIRE HOUSE)
SUPERHOSTEntire townhouse
Mo's 4 Bed/3.5 Bath (ENTIRE HOUSE)
Price:GYD16,746 / night
Perfect Duplex w/Kitchen Nothing share. Up to 4
SUPERHOSTEntire townhouse
Perfect Duplex w/Kitchen Nothing share. Up to 4
Price:GYD13,457 / night
Thematic House 04.  Disney only 08 miles away!!!!!
SUPERHOSTEntire townhouse
Thematic House 04. Disney only 08 miles away!!!!!
Price:GYD18,510 / night
Thematic House 02. Disney only 8 miles away!!!!!!!
SUPERHOSTEntire townhouse
Thematic House 02. Disney only 8 miles away!!!!!!!
Price:GYD18,092 / night
Spacious home with private pool in gated resort
SUPERHOSTEntire townhouse
Spacious home with private pool in gated resort
Price:GYD28,407 / night
Renovated Very Clean, Great Location Lucaya Villa
SUPERHOSTEntire townhouse
Renovated Very Clean, Great Location Lucaya Villa
Price:GYD17,732 / night
*GREAT RESORT SUITE* NEAR ALL ORLANDO ATTRACTIONS
SUPERHOSTPrivate room
*GREAT RESORT SUITE* NEAR ALL ORLANDO ATTRACTIONS
Price:GYD9,419 / night
Fantasy World 2br, Wet N Wild #2, 10min to Disney!
Entire townhouse
Fantasy World 2br, Wet N Wild #2, 10min to Disney!
Price:GYD16,894 / night
Show all

Pet-friendly houses

Just steps away from Disney. You will love it !
SUPERHOSTEntire house
Just steps away from Disney. You will love it !
Price:GYD33,282 / night
5*Clean Rated-Movie/Game Room, 3348 SF, 12p Dining
SUPERHOSTEntire house
5*Clean Rated-Movie/Game Room, 3348 SF, 12p Dining
Price:GYD50,536 / night
Spacious Lakefront House w/ Pool, Hot Tub, Boating
Entire house
Spacious Lakefront House w/ Pool, Hot Tub, Boating
Price:GYD49,638 / night
Downtown Orlando COTTAGE all to yourself
SUPERHOSTEntire house
Downtown Orlando COTTAGE all to yourself
Price:GYD11,033 / night
Amazing Vacation Home /Pool/Near Disney 16 Mins
SUPERHOSTEntire house
Amazing Vacation Home /Pool/Near Disney 16 Mins
Price:GYD23,743 / night
DISNEY AREA LAKE FRONT LUXURY HOUSE RESORT
SUPERHOSTEntire house
DISNEY AREA LAKE FRONT LUXURY HOUSE RESORT
Price:GYD56,307 / night
Large Home /Private pool/Close To Disney /Amazing
SUPERHOSTEntire house
Large Home /Private pool/Close To Disney /Amazing
Price:GYD33,791 / night
Great House  w/Heated Pool;Near all Parks!
SUPERHOSTEntire house
Great House w/Heated Pool;Near all Parks!
Price:GYD21,979 / night
Pool House Close to Airport /Disney and more!
SUPERHOSTEntire house
Pool House Close to Airport /Disney and more!
Price:GYD30,352 / night
Exquisite Destination Villas
SUPERHOSTEntire house
Exquisite Destination Villas
Price:GYD25,119 / night
Disney area Pool Home
Entire house
Disney area Pool Home
Price:GYD23,174 / night
SPECIAL OFFER, Pool, 4 bed, Game Room, Allison
SUPERHOSTEntire house
SPECIAL OFFER, Pool, 4 bed, Game Room, Allison
Price:GYD20,693 / night
Show all

Houses with pools

Beautiful pool villa, gated community, near Disney
SUPERHOSTEntire house
Beautiful pool villa, gated community, near Disney
Price:GYD20,333 / night
Home near Disney 4br with pool
SUPERHOSTEntire house
Home near Disney 4br with pool
Price:GYD22,397 / night
Elegant & Contemporary 3 Bedroom Pool Home I-Drive
SUPERHOSTEntire house
Elegant & Contemporary 3 Bedroom Pool Home I-Drive
Price:GYD23,025 / night
The Nook Vacation Home
SUPERHOSTEntire house
The Nook Vacation Home
Price:GYD24,761 / night
Comfy Lilo & Stitch bedroom by Disney! With pool!
SUPERHOSTPrivate room
Comfy Lilo & Stitch bedroom by Disney! With pool!
Price:GYD4,306 / night
Private Room/bath(a)-Pool/sauna
SUPERHOSTPrivate room
Private Room/bath(a)-Pool/sauna
Price:GYD8,164 / night
Great 4Room House/Pool-Gran Casa 4 Cuartos/Piscina
SUPERHOSTEntire house
Great 4Room House/Pool-Gran Casa 4 Cuartos/Piscina
Price:GYD19,019 / night
Disney area 3 Bedroom 2 Baths Private Pool -3260
Entire house
Disney area 3 Bedroom 2 Baths Private Pool -3260
Price:GYD21,022 / night
Amazing Vacation Home /Pool/Near Disney 16 Mins
SUPERHOSTEntire house
Amazing Vacation Home /Pool/Near Disney 16 Mins
Price:GYD23,743 / night
You’ll❤️ This Spacious Pool Home~14Mins from Disney
SUPERHOSTEntire house
You’ll❤️ This Spacious Pool Home~14Mins from Disney
Price:GYD24,939 / night
3 bedroom Orlando Florida pool home
Entire house
3 bedroom Orlando Florida pool home
Price:GYD21,321 / night
The Robyn's Nest- 8 min to Airport -I can help
SUPERHOSTPrivate room
The Robyn's Nest- 8 min to Airport -I can help
Price:GYD11,513 / night
Show all

Learn more about Kissimmee

What types of vacation rentals are available in Kissimmee?

Here in Kissimmee, there are plenty of options for places to stay. Here are a few examples:
  • Houses (6,263 rentals)
  • Townhouses (4,306 rentals)
  • Villas (3,342 rentals)

Are there houses with pools?

Who doesn’t want a pool at their house? Here in Kissimmee, you’ll find 5,774 houses that have pools.

What are the top attractions in Kissimmee?

Locals agree that these attractions are worth a visit:
  • Old Town (338 rentals)
  • Shingle Creek Regional Park - Steffee Landing (62 rentals)
  • Museum of Military History (790 rentals)
  • Fun Spot America Kissimmee (337 rentals)
  • Kissimmee Lakefront Park (43 rentals)

What are some kid-friendly activities in Kissimmee?

Locals agree—these are all great places to take the kids:
  • Old Town
  • Fun Spot America Kissimmee
  • Island H2O Live!
  • The LOOP-Kissimmee
  • Kissimmee Lakefront Park

What are the top places to eat in Kissimmee?

Whether you’re looking for a tasty treat or a hearty meal, here’s where the locals say to go:
  • Medieval Times Dinner & Tournament
  • Olive Garden Italian Restaurant
  • Miller's Ale House - Kissimmee
  • Bahama Breeze
  • TGI Fridays