Kissimmee Vacation Rentals

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Check prices for these dates

In two weeks
Oct 31 - Nov 2
In one month
Nov 14 - Nov 16
In two months
Dec 12 - Dec 14
In three months
Jan 9 - Jan 11

Vacation Rentals in Kissimmee

Vacation Village at Parkway
Aerial view

Vacation Village at Parkway

3.0 star property
8.6 out of 10, Excellent, (2956)
"Had every thing you would need for a family trip Perfect loved it "
The price is ￥13,606
￥18,018 total
includes taxes & fees
Oct 14 - Oct 15
Vacation Village at Parkway
Margaritaville Cottages Orlando with H2O Waterpark by Rentyl
Interior

Margaritaville Cottages Orlando with H2O Waterpark by Rentyl

4.0 star property
8.8 out of 10, Excellent, (1654)
"It was a great stay !"
Margaritaville Cottages Orlando with H2O Waterpark by Rentyl
Club Wyndham Cypress Palms
Private pool

Club Wyndham Cypress Palms

3.5 star property
9.0 out of 10, Wonderful, (1822)
"Nice place to stay"
Club Wyndham Cypress Palms
The Berkley, Orlando
Lobby

The Berkley, Orlando

4.0 star property
9.6 out of 10, Exceptional, (1947)
"Great stay!"
The price is ￥19,112
￥23,217 total
includes taxes & fees
Oct 14 - Oct 15
The Berkley, Orlando
Reunion Resort & Golf Club
Water park

Reunion Resort & Golf Club

5.0 star property
8.8 out of 10, Excellent, (1410)
"amazing place for families"
Reunion Resort & Golf Club
Regal Oaks Resort Vacation Townhomes by IDILIQ
View from property

Regal Oaks Resort Vacation Townhomes by IDILIQ

4.0 star property
8.4 out of 10, Very Good, (2986)
"Loved the location of the property and that the property was gated"
Regal Oaks Resort Vacation Townhomes by IDILIQ
Encantada Resort Vacation Townhomes by IDILIQ
2 outdoor pools, pool umbrellas, sun loungers

Encantada Resort Vacation Townhomes by IDILIQ

3.0 star property
8.6 out of 10, Excellent, (1386)
"The unit was great for our large group of people. The only issue was some cheaply made furniture that seemed very wobbly. "
Encantada Resort Vacation Townhomes by IDILIQ
Magical Dreams
Outdoor pool

Magical Dreams

4.0 star property
10.0 out of 10, Exceptional, (1)
"estaba algo caliente pero nos contactamos con los encargados y nos solucionaron el problema "
The price is ￥8,107
￥19,496 total
includes taxes & fees
Oct 14 - Oct 15
Magical Dreams
Magic Village Yards, Trademark Collection by Wyndham
Outdoor pool, pool umbrellas, sun loungers

Magic Village Yards, Trademark Collection by Wyndham

4.0 star property
9.2 out of 10, Wonderful, (1146)
"Spacious accommodations near Disney, with some amenities. "
Magic Village Yards, Trademark Collection by Wyndham
Barefoot'n Resort Kissimmee Orlando
Exterior

Barefoot'n Resort Kissimmee Orlando

2.5 star property
9.0 out of 10, Wonderful, (149)
"Awesome place to stay. This is my 3rd time staying at this resort. Its my favorite place, its roomy, calm, an apt all to myself what else can i ask for."
The price is ￥11,744
￥15,216 total
includes taxes & fees
Oct 14 - Oct 15
Barefoot'n Resort Kissimmee Orlando
Club Wyndham Star Island
Exterior

Club Wyndham Star Island

3.5 star property
8.2 out of 10, Very Good, (440)
"The rooms were very clean & equipped with every little item we were going to need in the kitchen/bedrooms/bedrooms. We also had washer/dryer to leave with clean clothes from our stay. I will definitely recommend this place for a family/friend getaway. "
Club Wyndham Star Island
Grand Lake Resort
Dock

Grand Lake Resort

3.0 star property
9.2 out of 10, Wonderful, (141)
"Amber was great we had a ball definitely coming back resort was beautiful "
Grand Lake Resort
Barefoot Suites
Dock

Barefoot Suites

3.0 star property
9.0 out of 10, Wonderful, (1775)
"Barefoot Suites is just an overall an awesome place to stay."
Barefoot Suites
Enchanted Fantasy
Terrace/patio

Enchanted Fantasy

3.5 star property
The price is ￥8,844
￥20,332 total
includes taxes & fees
Oct 14 - Oct 15
Enchanted Fantasy
Formosa Valley Resort by UNE Homes
Private pool

Formosa Valley Resort by UNE Homes

4.0 star property
9.4 out of 10, Exceptional, (173)
"Great stay"
Formosa Valley Resort by UNE Homes
Lifetime of Vacations Resort
Lake view

Lifetime of Vacations Resort

3.0 star property
9.4 out of 10, Exceptional, (147)
"Quiet place "
Lifetime of Vacations Resort
Modern Luxury Villa with Everything
TV, foosball, stereo

Modern Luxury Villa with Everything

9.8 out of 10, Exceptional, (441)
"It was a great stay. The house was clean and close to everything."
Modern Luxury Villa with Everything
Enchanted Dreams
Full-size fridge, microwave, oven, stovetop

Enchanted Dreams

3.5 star property
8.0 out of 10, Very Good, (4)
"Clean, comfortable home. Everything was excellent from the security to amenities. I will book again, share with friends and family. "
The price is ￥10,319
￥22,007 total
includes taxes & fees
Oct 14 - Oct 15
Enchanted Dreams
Spacious Bowling Villa, Lake Views, 14 Bdr/14bath, close to Disney, Sleeps 38
Outdoor pool, a heated pool

Spacious Bowling Villa, Lake Views, 14 Bdr/14bath, close to Disney, Sleeps 38

10.0 out of 10, Exceptional, (27)
"Very spacious and fun house, very easy to get to Parks, groceries, and outletsHost was amazing and available!"
Spacious Bowling Villa, Lake Views, 14 Bdr/14bath, close to Disney, Sleeps 38
Glam Villa Near the Parks w Gamer & Princess BRs, Huge Theater, Arcade, Spa Pool
Outdoor pool, a heated pool

Glam Villa Near the Parks w Gamer & Princess BRs, Huge Theater, Arcade, Spa Pool

9.6 out of 10, Exceptional, (48)
"The home was perfect for our family trip to Disney! Its conveniently located near all of the FUN!! Great place to stay! I would definitely stay here again!"
Glam Villa Near the Parks w Gamer & Princess BRs, Huge Theater, Arcade, Spa Pool
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

Ramada by Wyndham Hotel & Water Park

Ramada by Wyndham Hotel & Water Park

10/10 Excellent
"Excellent place to stay. "
Jose 2-night trip
Posted 14 hours ago
Ramada by Wyndham Hotel & Water Park

Price trends for vacation rentals in Kissimmee

Less expensive
More expensive
This month
Next month
April
December
￥18,212
￥16,757
Month
Price
January
￥20,728
February
￥20,713
March
￥16,779
April
￥14,010
May
￥15,263
June
￥19,011
July
￥17,610
August
￥16,989
September
￥14,102
October
￥18,212
November
￥16,757
December
￥22,772
Price trend information excludes taxes and fees and is based on base rates for a nightly stay for 2 adults found in the last 7 days on our site and averaged for commonly viewed vacation rentals in Kissimmee.

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
  • Use the map to find apartments and other holiday homes in the Kissimmee neighbourhood you prefer
  • 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 lively festivals. The array of shops and renowned opera 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 Formosa Valley Resort by UNE Homes and Glam Villa Near the Parks w Gamer & Princess BRs, Huge Theater, Arcade, Spa Pool.

How many vacation rentals are there in Kissimmee?

Choose from 15140 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.