Kissimmee Vacation Rentals

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Check prices for these dates

In two weeks
May 29 - May 31
In two months
Jul 10 - Jul 12
In three months
Aug 7 - Aug 9
In four months
Sep 4 - Sep 6

Our top choices for Kissimmee vacation rentals

7 outdoor pools, pool umbrellas, sun loungers

Vacation Village Orlando, Celebration

Vacation Village Orlando, Celebration
3.0 star property
Kissimmee
8.6 out of 10, Excellent, (4,115 reviews)
"Fanily friendly, great value, great location!"
United States
Marivette
The price is P4,980
P7,189 total
includes taxes & fees
May 17 - May 18
Vacation Village Orlando, Celebration
Outdoor pool

Affordable Stays Kissimmee

Affordable Stays Kissimmee
2.5 star property
Kissimmee
The price is P3,851
P13,507 total
includes taxes & fees
May 14 - May 15
Affordable Stays Kissimmee
2 bedrooms

Super Boho - At Lake Toho Fishing Vintage Vibes

Super Boho - At Lake Toho Fishing Vintage Vibes
2.0 star property
Historic Downtown Kissimmee
Super Boho - At Lake Toho Fishing Vintage Vibes
Lobby sitting area

The Berkley, Orlando

The Berkley, Orlando
4.0 star property
Kissimmee
9.6 out of 10, Exceptional, (2,217 reviews)
"Great stay!"
United States
Daniel
The price is P6,755
P8,287 total
includes taxes & fees
May 28 - May 29
The Berkley, Orlando
Lounge

Adeline Apartments 15m to Parks, Pet Friendly, Free Parking by Heavenly Homes

Adeline Apartments 15m to Parks, Pet Friendly, Free Parking by Heavenly Homes
4.0 star property
Kissimmee
10.0 out of 10, Exceptional, (2 reviews)
"Would stay again and so should you! "
United States
katie
The price is P5,639
P14,597 total
includes taxes & fees
May 14 - May 15
Adeline Apartments 15m to Parks, Pet Friendly, Free Parking by Heavenly Homes
Front of property

Upstay Modern 3BR Townhome With Pool Near Disney

Upstay Modern 3BR Townhome With Pool Near Disney
3.0 star property
Kissimmee
The price is P6,541
P17,763 total
includes taxes & fees
May 20 - May 21
Upstay Modern 3BR Townhome With Pool Near Disney
Outdoor pool

Harmony Ensuite Room Shared Home No Car

Harmony Ensuite Room Shared Home No Car
2.5 star property
Kissimmee
The price is P2,690
P12,189 total
includes taxes & fees
May 14 - May 15
Harmony Ensuite Room Shared Home No Car
Private kitchen

FL- 1844 GOBI DR

FL- 1844 GOBI DR
3.0 star property
Kissimmee
10.0 out of 10, Exceptional, (1 review)
The price is P6,297
P21,819 total
includes taxes & fees
May 19 - May 20
FL- 1844 GOBI DR
Outdoor pool, pool umbrellas, sun loungers

Barefoot Suites

Barefoot Suites
3.0 star property
Kissimmee
9.0 out of 10, Wonderful, (1,876 reviews)
"Great for families"
United States
Frank
The price is P4,931
P6,805 total
includes taxes & fees
May 31 - Jun 1
Barefoot Suites
Outdoor pool

Aster Cove

Aster Cove
4.0 star property
Crescent Lakes
The price is P11,884
P36,366 total
includes taxes & fees
May 14 - May 15
Aster Cove
Outdoor pool

Maple Leaf Inn & Suites

Maple Leaf Inn & Suites
2.5 star property
Kissimmee
6.8 out of 10, (71 reviews)
"The room was clean and the staff was okay "
United States
Shaneka
The price is P3,688
P4,186 total
includes taxes & fees
May 17 - May 18
Maple Leaf Inn & Suites
3 bedrooms

Super YES - Many Amenities Relax GYM Courts

Super YES - Many Amenities Relax GYM Courts
2.0 star property
Kissimmee
The price is P4,395
P19,725 total
includes taxes & fees
Jun 2 - Jun 3
Super YES - Many Amenities Relax GYM Courts
Exterior

Barefoot'n Resort Kissimmee Orlando

Barefoot'n Resort Kissimmee Orlando
2.5 star property
Kissimmee
9.0 out of 10, Wonderful, (294 reviews)
"Very nice clean place to stay"
United States
THOMAS
The price is P7,420
P9,185 total
includes taxes & fees
May 17 - May 18
Barefoot'n Resort Kissimmee Orlando
Interior

Storey Lake Resort Condo w Patio5 Miles to Disney

Storey Lake Resort Condo w Patio5 Miles to Disney
3.0 star property
Kissimmee
The price is P5,624
P15,334 total
includes taxes & fees
May 14 - May 15
Storey Lake Resort Condo w Patio5 Miles to Disney
Interior

Enjoy Disney 3brs at Villas of Somerset

Enjoy Disney 3brs at Villas of Somerset
3.5 star property
Kissimmee
8.0 out of 10, Very Good, (1 review)
"Nice home but bathroom are too old "
United States
Urvin
Enjoy Disney 3brs at Villas of Somerset
Exterior

Margaritaville Cottages Orlando by Rentyl with H2O Waterpark

Margaritaville Cottages Orlando by Rentyl with H2O Waterpark
4.0 star property
Kissimmee
8.8 out of 10, Excellent, (1,962 reviews)
"Great place for families "
United States
Luis
The price is P10,697
P21,513 total
includes taxes & fees
Jun 9 - Jun 10
Margaritaville Cottages Orlando by Rentyl with H2O Waterpark
Private kitchen

LOVELY LUXURY APARTMENT CLOSE DISNEY

LOVELY LUXURY APARTMENT CLOSE DISNEY
3.5 star property
Kissimmee
8.4 out of 10, Very Good, (8 reviews)
"Nice appartment, everything you needed and clean and modern"
United Kingdom
Martyn
The price is P6,685
P18,619 total
includes taxes & fees
May 14 - May 15
LOVELY LUXURY APARTMENT CLOSE DISNEY
Interior

< 2 Mi to WDW Attractions: Luxe Family Getaway!

< 2 Mi to WDW Attractions: Luxe Family Getaway!
4.0 star property
Kissimmee
10.0 out of 10, Exceptional, (1 review)
"We really enjoyed our Disney trip! Very convenient location!"
United States
Zaily
The price is P5,685
P21,716 total
includes taxes & fees
Jun 4 - Jun 5
< 2 Mi to WDW Attractions: Luxe Family Getaway!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Kissimmee Hotel Reviews

Vacation Village Orlando, Celebration

Vacation Village Orlando, Celebration

10/10 Excellent
"was really great! we weren’t bothered once, we couldn’t hear the family next door to us, which is a huge plus, and the pool was amazing! a lil confusing to get around hut once you get the hang of it, it was a treat to stay! def will book again in the future!"
Carlin 2-night trip
Posted 1 hour ago
Vacation Village Orlando, Celebration

Find out more about Kissimmee

Search for holiday rentals in Kissimmee on Expedia! You can easily find your home rentals, villas, holiday apartments in Kissimmee using one of the methods below:

  • View our selection of featured holiday rentals in Kissimmee
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  • Enter your travel dates to view the best deals on holiday rentals in Kissimmee while they last

Look no further and take a look at our great range of rental properties in Kissimmee!

Frequently asked questions

Can I find vacation rentals in Kissimmee?

Yes, we have vacation rentals in Kissimmee close to Disney's Animal Kingdom® Theme Park, or you can select a secluded option if you'd like a relaxing place to stay. Tourists who visit Kissimmee like the fun-filled theme parks and entertainment choices. The array of shops and lively festivals are some other things you might want to check out while you're here.

What's the top vacation rental that Kissimmee has to offer?

The Berkley, Orlando: This Kissimmee vacation home rental offers a furnished patio, a terrace, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a full-sized fridge, a microwave, and a coffee maker. You can relax into your vacation with an arcade game room and a hot tub. Other favorite homes for rent in Kissimmee are Encore Resort and Casa con Piscina Privada en Orlando.

How many vacation rentals are there in Kissimmee?

Choose from 1594 Expedia vacation rentals in Kissimmee for a memorable vacation.

What can I see and do in Kissimmee?

Disney's Animal Kingdom® Theme Park and Walt Disney World® Resort are a couple of family-friendly sights, whereas cultural attractions include Medieval Times and Osceola County Welcome Center and History Museum. Other popular places to visit in the area include Old Town and Disney Springs™.

What are vacation rentals like in Kissimmee?

Vacation rentals are privately owned properties you can book for several days or more in Kissimmee. Vacation rentals offer amenities like laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of privacy away from public hotel elevators and busy concierge desks while still allowing you to travel. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive choice for a family trip.