Kissimmee Holiday Rentals

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Kissimmee

Seralago Hotel & Suites Main Gate East

3.0 star property
5.2 out of 10, (5588)
"Women at the front are not approachable, more on the rude side. They completely ignore you until you say excuse me. Besides that everything and everyone else was very helpful and pleasant. "
The price is S$86
includes taxes & fees
9 Dec - 10 Dec
Seralago Hotel & Suites Main Gate East

Ramada by Wyndham Hotel & Water Park

3.0 star property
6.8 out of 10, (1301)
"Pleasant check in and overall stay"
The price is S$153
includes taxes & fees
5 Dec - 6 Dec
Ramada by Wyndham Hotel & Water Park

Margaritaville Resort Orlando Cottages by Rentyl

4.0 star property
8.8 out of 10, Excellent, (1094)
"Great location "
Margaritaville Resort Orlando Cottages by Rentyl

Vacation Village at Parkway

3.0 star property
8.4 out of 10, Very good, (1398)
"Good place for large family!"
Vacation Village at Parkway

Regal Oaks Resort Vacation Townhomes by IDILIQ

4.0 star property
8.4 out of 10, Very good, (2807)
"Great place!"
The price is S$407
includes taxes & fees
12 Dec - 13 Dec
Regal Oaks Resort Vacation Townhomes by IDILIQ

The Berkley, Orlando

4.0 star property
9.4 out of 10, Exceptional, (1608)
"I enjoyed my stay at The Berkeley Orlando property.....the unit's interior was really nice, quiet and spacious. The front desk agent that checked me in was polite and very professional. I will definitely stay there again. "
The Berkley, Orlando

Club Wyndham Cypress Palms

3.5 star property
9.0 out of 10, Wonderful, (1605)
"Lovely customer service, when we ran into an issue and needed maintenance… the front desk and maintenance was on it to fix the issue. My 2nd stay here and would definitely consider staying again. "
Club Wyndham Cypress Palms

Reunion Resort & Golf Club

5.0 star property
8.6 out of 10, Excellent, (1188)
"This is the best bang for your buck in the area. The two bedroom suite at the Grande has a ton of space and is close to one of the nicest pools in the resort. "
Reunion Resort & Golf Club

Encantada Resort Vacation Townhomes by IDILIQ

3.0 star property
8.6 out of 10, Excellent, (1313)
"We loved the location and the community amenities. House was nice, clean and exactly what we needed. "
The price is S$437
includes taxes & fees
5 Dec - 6 Dec
Encantada Resort Vacation Townhomes by IDILIQ

Magic Village Yards, Trademark Collection by Wyndham

4.0 star property
9.2 out of 10, Wonderful, (1104)
"Best option "
Magic Village Yards, Trademark Collection by Wyndham

Lifetime of Vacations Resort

3.0 star property
9.2 out of 10, Wonderful, (111)
"I loved the charming feel of the property. The rooms were very spacious and clean. The property was very well maintained and the staff was terrific "
Lifetime of Vacations Resort

Vacation Villas 2, a Ramada by Wyndham

3.5 star property
8.6 out of 10, Excellent, (1239)
"Loved the room. The price and how quiet and comfortable everything was. "
Vacation Villas 2, a Ramada by Wyndham

Grand Lake Resort

3.0 star property
9.0 out of 10, Wonderful, (100)
"My family and I loved our experience! We enjoyed the warm pool, and the spacious room! "
Grand Lake Resort

Caribe Cove Resort

3.5 star property
8.8 out of 10, Excellent, (2240)
"It was spacious and felt like you were at home"
Caribe Cove Resort

Formosa Valley Resort by UNE Homes

4.0 star property
9.4 out of 10, Exceptional, (128)
"The place is beautiful, clean and Romy for a big family"
Formosa Valley Resort by UNE Homes

Barefoot Suites

3.0 star property
9.0 out of 10, Wonderful, (1644)
"Second time here and this time was not as good as the first one, but still, pretty decent. My 2 complains were about the coffee machine (they ran out of filter and I had to buy my own - not a problem, if they did not advertise as “complete kitchen”) and tv WiFi not working. We had a fire alarm and the staff handled it well! I’d totally book this hotel again my next time in Orlando area. "
The price is S$143
includes taxes & fees
8 Dec - 9 Dec
Barefoot Suites
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.
Don't see what you're looking for?
See all available properties in Kissimmee
Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in Kissimmee you may be interested in

Hilton Vacation Club Mystic Dunes Orlando

9.0 out of 10, Wonderful, (3401)
"The Tv remote was not user-friendly as there are no numbers on it that granted my wife and I direct access to our perferred channels and the tv guide channel was not easily found. We anticipate returning but we would appreciate if our noted concern could be address. "
The price is S$188
includes taxes & fees
9 Dec - 10 Dec
Hilton Vacation Club Mystic Dunes Orlando

Seralago Hotel & Suites Main Gate East

3.0 star property
5.2 out of 10, (5588)
"Women at the front are not approachable, more on the rude side. They completely ignore you until you say excuse me. Besides that everything and everyone else was very helpful and pleasant. "
The price is S$86
includes taxes & fees
9 Dec - 10 Dec
Seralago Hotel & Suites Main Gate East

Margaritaville Resort Orlando

4.0 star property
9.0 out of 10, Wonderful, (3184)
"We have stayed here twice now. Resort is amazingly clean, and staff is friendly. Its one of our favorite resorts. "
The price is S$247
includes taxes & fees
17 Dec - 18 Dec
Margaritaville Resort Orlando
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

Can I find holiday rentals in Kissimmee?

Yes, there are holiday rentals in Kissimmee close to Disney's Animal Kingdom® Theme Park, or you can select a more secluded option if you're looking for a relaxing 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 are some of the best holiday rentals that Kissimmee has to offer?

The Berkley, Orlando: This highly rated holiday home rental in Kissimmee offers a furnished patio, a terrace and a BBQ 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 holiday with an arcade/games room and 1 hot tub.

How many holiday rentals are there in Kissimmee?

Choose from 17564 Expedia holiday rentals in Kissimmee for a memorable holiday.

What can I see and do in Kissimmee?

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

What are holiday rentals like in Kissimmee?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Kissimmee. Holiday rentals feature amenities like laundry facilities and kitchens so you'll have everything you want. If you're concerned about a sanitised environment, a holiday rental can offer a sense of seclusion away from public hotel lifts and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great choice for a small group gathering.