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Holiday rentals in Kissimmee, FL

Search among 4081 available holiday rentals in Kissimmee from 50+ providers

If you're heading to Kissimmee and searching for somewhere to stay, on iBooked.ca you'll have a wide list of 6034 holiday rentals options to choose from. If you plan to stay close to Kissimmee Civic Center while you are in Kissimmee, you should book one of the 14 holiday villas here. Now that you know where to go, all that's left is for you to enter your dates and pick the best holiday home in Kissimmee.Hide
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18May2022Wednesday
19May2022Thursday
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6 adults
View on map11.0 km from City Centre700 m from Fun Spot USA
Offering location in Celebration district close to Dive Shop Kissimmee, this accommodation features 139 rooms and cots, a mini club and a play area.
7.0
Very good17 reviews
From   C$ 194 /nightSelect
Not available
10 adults
4 bedrooms
5 beds
View on map8.7 km from City Centre1.8 km from Gatorland
Set in Downtown Kissimmee district in Kissimmee, the property provides resort accommodation with the swimming pool.
7.0
Very good220 reviews
From   C$ 159 /nightSelect
Not available
8 adults
4 bedrooms
4 beds
5.7 km from City Centre900 m from Medieval Times
Located just off Shingle Creek Regional Park and less than 50 minutes' drive from SeaWorld Shop, this 100-room hotel with a contemporary interior features a volleyball court, a basketball court and a library.
9.2
Perfect526 reviews
From   C$ 334 /nightSelect
Not available
9 adults
4 bedrooms
5 beds
9.7 km from City Centre1.1 km from Gatorland
Situated 9 km from Kissimmee Sports Arena & Rodeo in Kissimmee, this property features a patio, a golf course and a garden.
From   C$ 144 /nightSelect
Not available
8 adults
3 bedrooms
4 beds
8.9 km from City Centre400 m from Fantasy Surf
Located in Kissimmee in Downtown Kissimmee district, this property features a patio, a swimming pool and a garden.
7.8
Very good10 reviews
From   C$ 91 /nightSelect
Not available
8 adults
4 bedrooms
4 beds
6.4 km from City Centre500 m from Capone's Dinner and Show
Situated in proximity to Medieval Times, the venue has a large pool and a play area, a game room and a playground for families with children.
7.6
Very good13 reviews
From   C$ 151 /nightSelect
Not available
8 adults
3 bedrooms
4 beds
9.4 km from City Centre
This villa, situated in the downtown area, includes an outdoor pool along with a private pool, a basketball court and a tennis court.
6.8
Nice28 reviews
From   C$ 167 /nightSelect
Not available
23.5 km from City Centre
Located 2.1 km from ChampionsGate Golf Club, the villa features an outdoor pool area and a cable flat-screen.
From   C$ 581 /nightSelect
Not available
14 adults
1 bedroom
3 beds
25.8 km from City Centre
Situated 22 km from Discovery Cove in Kissimmee, this self-catering villa features a garden and a heated pool.
7.4
Very good2 reviews
From   C$ 341 /nightSelect
Not available
6 adults
3 bedrooms
3 beds
7.4 km from City Centre1.1 km from Siesta Lago Mobile Home Vlg
Set 8 km from the city centre, this self-catering property features a Jacuzzi and a sauna.
From   C$ 142 /nightSelect
Not available
8 adults
2 bedrooms
3 beds
11.0 km from City Centre700 m from Fun Spot USA
Set 25 km from Orlando International Airport, this property features an outdoor pool, a patio and a library.
From   C$ 255 /nightSelect
Not available
12 adults
5 bedrooms
5 beds
22.7 km from City Centre
Situated 5 km from Orlando Tree Trek Adventure Park Zip Line, this property features a flat screen TV and a cable flat-screen.
Select
Not available
8 adults
5 bedrooms
5 beds
23.3 km from City Centre
Positioned in West Kissimmee district, the villa includes a kitchen, as well as an outdoor swimming pool.
From   C$ 390 /nightSelect
Not available
10 adults
5 bedrooms
5 beds
25.6 km from City Centre
Located in West Kissimmee district, this villa features a terrace along with a fully equipped kitchen.
From   C$ 103 /nightSelect
Not available
14 adults
6 bedrooms
7 beds
5.6 km from City Centre1.1 km from Medieval Times
Located 13 km from SeaWorld Orlando in Kissimmee, this upscale villa features a heated swimming pool.
10.0
Perfect1 review
From   C$ 330 /nightSelect
Not available
10 adults
4 bedrooms
4 beds
23.7 km from City Centre
Situated in West Kissimmee district, 35 km from Orlando International Airport, the venue boasts an aqua park, a sun terrace and a garden.
From   C$ 190 /nightSelect
Not available
The largest option:
5 adults
2 bedrooms
3 beds
5.9 km from City Centre400 m from Ice Factory,The
While staying in this 2-bedroom apartment with a nice balcony, guests can visit Osceola Center For the Arts.
9.0
Perfect
From   C$ 119 /nightSelect
Not available
Apartment
6 adults
2 bedrooms
2 beds
4.3 km from City Centre1.6 km from Give Kids The World Village
The accommodation consists of a kitchen, 2 bedrooms and is situated near Congo River Golf.
8.0
Great2 reviews
From   C$ 108 /nightSelect
Not available
9 adults
2 bedrooms
3 beds
18.6 km from City Centre800 m from Orlando Discount Guide
Situated 6 km from Disney's Boardwalk, this venue features an outdoor pool.
From   C$ 287 /nightSelect
Not available
8 adults
3 bedrooms
4 beds
23.9 km from City Centre
Located in the centre of Kissimmee, this hotel offers an outdoor pool and a 24-hour bar.
8.0
Great238 reviews
From   C$ 167 /nightSelect
Not available

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4081 hotels found

FAQs about holiday lettings in Kissimmee

Read these 8 answers to plan your perfect trip to Kissimmee.

What are the most popular holiday rentals in Windsor Palms area?

Our visitors usually stay in high-rated holiday places in such districts as — Windsor Palms and Windsor Palms.

What are the top pet-friendly holiday rentals in Kissimmee?

Legacy Dunes Resort In Orlando Kissimmee Near Disney is an excellent choice among 37 pet-friendly holiday rentals in Kissimmee.

What budget holiday rentals in Kissimmee would you recommend?

Some of the top budget holiday rentals are:
Luxury Three Bedroom Condo Near Disney World from 136C$/night
Florida Vacation Villas from 183C$/night.
Click here to see more popular budget accommodation options.

How much does a 2-bedroom holiday house cost for a week?

A 2-bedroom holiday home costs about 511C$ per week for instance, check Laguna Bay'S Dream Condo.

How much does a 3-bedroom holiday house cost for a week?

A 3-bedroom house for rent costs approximately 80C$ per week try this popular option — Truro Vacation Condo In The Windsor Palms Resort By Ipg Florida.

What are the top-ranked holiday apartments next to a beach?

If you are searching for a beach villa, Bahama Bay Orlando By Owners is a great option to consider.

What are the most popular Kissimmee holiday rentals for a family stay?

Families heading to Kissimmee can stay close to Medieval Times Dinner & Tournament by booking Sonoma 7 Bedroom Pool Home 1852Sn.

What are the best holiday rentals with free wifi in Kissimmee?

According to guest ranking above 5.0/5, the best property providing free wi-fi is Letty'S Be Home.

Holiday rentals in Kissimmee

Handpicked holiday rentals in Kissimmee

If you want to admire nice views, book an apartment during your city escape close to Kissimmee Korners Shopping Center of Kissimmee. 5 apartments are within a short walk of Kissimmee Korners Shopping Center. Explore these superb offers and book the place you relish!

Exclusive luxury places to stay in Kissimmee

Luxury house rentals and apartments in Kissimmee are an optimal choice for those who want to feel on top of the world while on holiday. Kissimmee has a rich selection of luxury holiday rentals, including exclusive villas and apartments for rent that will you plunge in the exclusivity of this city. We will help you find the most splendid accommodation in Kissimmee.

High graded cheap holiday homes in Kissimmee

What happened to getting higher value for less money? Accommodations in Kissimmee are s