Kissimmee Holiday Rentals

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Holiday Rentals in Kissimmee

Seralago Hotel & Suites Main Gate East

3.0 star property
5.2 out of 10, (5565)
"I had to wait 20 minutes for the front counter lady to come in from smoking. The security guard was sitting in the lobby playing on his phone and he just kept saying she will be back soon.. Then she told me I had booked a double bed room and I said no I booked a family suite.. So I had to show her my email and she said well I don't know why they put you in another room, let me make sure I have a clean one.. After standing in the lobby for a total of 40 minutes (including her smoke break time), I...
The price is AU$100
includes taxes & fees
26 Nov - 27 Nov
Seralago Hotel & Suites Main Gate East

Ramada by Wyndham Hotel & Water Park

3.0 star property
6.8 out of 10, (1298)
"The perfect size waterpark for families with kids. Good value. "
The price is AU$182
includes taxes & fees
1 Dec - 2 Dec
Ramada by Wyndham Hotel & Water Park

Margaritaville Resort Orlando Cottages by Rentyl

4.0 star property
8.8 out of 10, Excellent, (1084)
"Very pretty, and spacious- but a bit far from the resort "
Margaritaville Resort Orlando Cottages by Rentyl

Vacation Village at Parkway

3.0 star property
8.4 out of 10, Very good, (1394)
"Near parks"
Vacation Village at Parkway

Regal Oaks Resort Vacation Townhomes by IDILIQ

4.0 star property
8.4 out of 10, Very good, (2800)
"Overall we really enjoyed our stay at Regal Oaks. We had a two bedroom, 2.5 bath townhouse with private hot tub and it was perfect for our group of 4. My only critics is the hot tub cover desperately needs to be replaced (stained and cracked which would leave little pieces floating in the hot tub). And pretty much all the toilet paper roll holders were broken and the toilet paper kept falling off of them. But everything else was clean and the beds were very comfortable. Location was pretty much...
The price is AU$460
includes taxes & fees
24 Nov - 25 Nov
Regal Oaks Resort Vacation Townhomes by IDILIQ

The Berkley, Orlando

4.0 star property
9.4 out of 10, Exceptional, (1599)
"Clean, relaxing, spacious, lots of amenities."
The Berkley, Orlando

Club Wyndham Cypress Palms

3.5 star property
8.8 out of 10, Excellent, (1603)
"Great location, great resort, full kitchen - washer dryer, fridge, coffee make and very comfortable bed. Will definitely be back "
Club Wyndham Cypress Palms

Modern Luxury Villa with Everything

9.8 out of 10, Exceptional, (346)
"House was not as clean as I like. Kitchen cabinets need to be fixed. More towels would be nice. Otherwise stay was good and lots of fun was had."
Modern Luxury Villa with Everything

Reunion Resort & Golf Club

5.0 star property
8.6 out of 10, Excellent, (1182)
"Nice!!"
The price is AU$377
includes taxes & fees
24 Nov - 25 Nov
Reunion Resort & Golf Club

Encantada Resort Vacation Townhomes by IDILIQ

3.0 star property
8.6 out of 10, Excellent, (1311)
"This rental is ideal if you’re planning a trip to Disney, with its convenient location near Disney Springs, theme parks, and plenty of shopping. However, there were several drawbacks. The community gate was broken upon arrival, remaining open all weekend, which made the security guard feel redundant. I specifically chose this rental for the hot tub, but it was disappointing to find that only half the jets were working. While the outdoor area is screened in, there were spider webs and flies,...
The price is AU$437
includes taxes & fees
26 Nov - 27 Nov
Encantada Resort Vacation Townhomes by IDILIQ

Lakeview Luxury Villa with Everything

9.8 out of 10, Exceptional, (292)
"Great property for a big family! Property was clean and communication was top-notch. The boys loved having the movie theatre and the kiddos loved the arcade room. We also appreciated that there was ample parking given that our family had a total of four vehicles. Would recommend!"
Lakeview Luxury Villa with Everything

Magic Village Yards, Trademark Collection by Wyndham

4.0 star property
9.2 out of 10, Wonderful, (1103)
"Best option "
Magic Village Yards, Trademark Collection by Wyndham

Lifetime of Vacations Resort

3.0 star property
9.2 out of 10, Wonderful, (110)
"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

Home w/ Pool, Hot Tub & Game Room, 6 Mi to Disney!

9.6 out of 10, Exceptional, (20)
"We had a good time and enjoyed the house "
Home w/ Pool, Hot Tub & Game Room, 6 Mi to Disney!

Caribbean Villa

9.0 out of 10, Wonderful, (19)
"Convenient location, and a very positive experience at the property itself. Communication with the property manager was excellent. "
The price is AU$381
includes taxes & fees
4 Dec - 5 Dec
Caribbean Villa

Ultimate Lakeview Villa with Everything!

9.8 out of 10, Exceptional, (311)
"Fantastic stay in an amazing villa with our family. The kids and adults all loved it so spacious and very centrally located. The pool was great. Would recommend. "
Ultimate Lakeview Villa with Everything!

Luxury 4 bedroom 3 bath pool Home 283

9.2 out of 10, Wonderful, (20)
"Well located and in a quiet, pleasant area. Space worked well for us and kids enjoyed the pool. It’s a little tired and dated but was good value. Communication with host was quick and easy, and we did a later check-out for a small fee which was very helpful with a later flight home. Would stay again. "
Luxury 4 bedroom 3 bath pool Home 283

Drive-In Theater, Forest Bedroom, Huge Pirate Ship, Arcade, Pool Table, Grill: Movie Magic

9.4 out of 10, Exceptional, (20)
"Well thought out theme rooms that were loved by the youngest to the oldest family member. We had plenty of room for all 18 of us, everything we needed was there, the movie room and rhe pool were the two locations that we loved the most. "
Drive-In Theater, Forest Bedroom, Huge Pirate Ship, Arcade, Pool Table, Grill: Movie Magic

Family Resort Home w Private Pool, BBQ, PingPong

8.4 out of 10, Very good, (6)
"Home was amazing even better than it looks online . Due to the weather we couldn’t experience all it had to offer . Check in was easy . Homeowner communicated in a timely manner throughout the stay . There were some issues with cleanliness , broken furniture and a few more issues but they were address as promptly as possible ."
Family Resort Home w Private Pool, BBQ, PingPong

Vacation Villas 2, a Ramada by Wyndham

3.5 star property
8.6 out of 10, Excellent, (1238)
"Loved the room. The price and how quiet and comfortable everything was. "
Vacation Villas 2, a Ramada by Wyndham
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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Other types of properties in Kissimmee you may be interested in

Hilton Vacation Club Mystic Dunes Orlando

9.0 out of 10, Wonderful, (3410)
"So welcoming and polite. Property was very quiet and amenities and room were excellent. "
The price is AU$215
includes taxes & fees
26 Nov - 27 Nov
Hilton Vacation Club Mystic Dunes Orlando

Seralago Hotel & Suites Main Gate East

3.0 star property
5.2 out of 10, (5565)
"I had to wait 20 minutes for the front counter lady to come in from smoking. The security guard was sitting in the lobby playing on his phone and he just kept saying she will be back soon.. Then she told me I had booked a double bed room and I said no I booked a family suite.. So I had to show her my email and she said well I don't know why they put you in another room, let me make sure I have a clean one.. After standing in the lobby for a total of 40 minutes (including her smoke break time), I...
The price is AU$100
includes taxes & fees
26 Nov - 27 Nov
Seralago Hotel & Suites Main Gate East

Margaritaville Resort Orlando

4.0 star property
9.0 out of 10, Wonderful, (3173)
"Nothing else "
The price is AU$328
includes taxes & fees
16 Dec - 17 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

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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 entertainment choices. The array of shops and lively festivals 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. Some other homes for rent in Kissimmee include Home w/ Pool, Hot Tub & Game Room, 6 Mi to Disney! and ⭐⭐⭐⭐⭐Expansive family-friendly vacation home, themed rooms, water park, fitness.

How many holiday rentals are there in Kissimmee?

Choose from 18571 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 Capone's Dinner Show. 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.