Kissimmee vacation rentals

Find and compare great deals on vacation rentals in Kissimmee from hundreds of travel sites

Kissimmee, FL, United States
Nov 25 — Nov 262
Kissimmee, FL, United States
Thu 11/25
Fri 11/26
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Popular Vacation Rentals in Kissimmee

Bella Vida Resort
Bella Vida Resort
Kissimmee, FL, United States
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2.9 mi from city centre, Kissimmee, FL 

This vacation rental is located in Kissimmee, only a few minutes from the Medieval Times Dinner and Tournament. It offers free Wi-Fi, an outdoor pool and laundry facilities.

Homes4uu - Disney Area Vacation Homes
Homes4uu - Disney Area Vacation Homes
7.5 Good
Kissimmee, FL, United States
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0.2 mi from city centre, Kissimmee, FL 
GoodBased on 6 reviews
7.5

Strategically located in the heart of the city, this 3-star vacation rental makes for an ideal base in Orlando. It also offers a playground, free Wi-Fi and an outdoor pool.

Runaway Beach - 2 Bd Villa (Rw12103)
Runaway Beach - 2 Bd Villa (Rw12103)
8.0 Excellent
Kissimmee, FL, United States
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4.8 mi from city centre, Kissimmee, FL 
ExcellentBased on 1 review
8.0

Located in Orlando, Runaway Beach Club Two Bedrooms Villa 12103 is a short drive from Walt Disney World Resort and SeaWorld Orlando. It also provides free Wi-Fi and a swimming pool.

Reunion Resort and Spa Home 2 U- Mary Poppins
Reunion Resort and Spa Home 2 U- Mary Poppins
Kissimmee, FL, United States
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10.6 mi from city centre, Kissimmee, FL 

Located in Orlando, Reunion Resort and Spa Home 2 U- Mary Poppins is an easy drive from Walt Disney World Resort and Disney's Animal Kingdom. It also provides a swimming pool.

Bella Vida Resort by Fidelity Vacation Homes
Bella Vida Resort by Fidelity Vacation Homes
Kissimmee, FL, United States
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3.1 mi from city centre, Kissimmee, FL 

Located in Kissimmee, this vacation rental is within walking distance of the Medieval Times Dinner and Tournament. It also offers an outdoor pool and free Wi-Fi.

Luxury 4-Bedroom Townhome Near Disney / Orlando
Luxury 4-Bedroom Townhome Near Disney / Orlando
9.4 Excellent
Kissimmee, FL, United States
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1.8 mi from city centre, Kissimmee, FL 
ExcellentBased on 15 reviews
9.4

Charming 4-bedroom Vacation Home near Disney/Orlando is located in Orlando and offers free Wi-Fi and outdoor tennis courts. It also provides a sun deck, a safe and an outdoor pool.

Favorite Vacation Homes
Favorite Vacation Homes
Kissimmee, FL, United States
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10.6 mi from city centre, Kissimmee, FL 

Conveniently positioned, Favorite Vacation Homes allows for easy access to Orlando's popular hot spots. It provides complimentary Wi-Fi, a kids pool and an outdoor pool.

Orlando House Disney Area
Orlando House Disney Area
9.0 Excellent
Kissimmee, FL, United States
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4.1 mi from city centre, Kissimmee, FL 
ExcellentBased on 71 reviews
9.0

Orlando House Disney Area provides a comfortable setting while in Orlando. It also features an outdoor pool, a sauna and free Wi-Fi.

541 Las Fuentes Drive
541 Las Fuentes Drive
Kissimmee, FL, United States
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3.0 mi from city centre, Kissimmee, FL 

This vacation rental is located in Kissimmee, and offers a swimming pool and free Wi-Fi.

Charming 3 Bed Vacation Villa near Disney (64) by Dreams VR
Charming 3 Bed Vacation Villa near Disney (64) by Dreams VR
7.3 Good
Kissimmee, FL, United States
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4.6 mi from city centre, Kissimmee, FL 
GoodBased on 3 reviews
7.3

Boasting a swimming pool, Charming 3 Bed Vacation Villa near Disney 64 by Dreams VR is situated in Orlando and offers comfortable accommodation. Guests can also make use of free Wi-Fi.

Tips for booking a vacation rental in Kissimmee

Cheapest month:September
Most expensive month:July
Average price in Kissimmee:$154/night
Absolute cheapest price found:$33/night
Cheapest day:Wednesday
Most expensive day:Sunday
$119 - $182
Average price per night. Prices are not fixed and may vary with time.
$138 - $174
Average price per night. Prices are not fixed and may vary with time.

Cheapest vacation rentals in Kissimmee

Show all 12,429 vacation rentals
Bella Vida Resort by Fidelity Vacation Homes
Bella Vida Resort by Fidelity Vacation Homes
Kissimmee, FL, United States
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3.1 mi from city centre, Kissimmee, FL 

Located in Kissimmee, this vacation rental is within walking distance of the Medieval Times Dinner and Tournament. It also offers an outdoor pool and free Wi-Fi.

$26
Avg. per night
541 Las Fuentes Drive
541 Las Fuentes Drive
Kissimmee, FL, United States
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3.0 mi from city centre, Kissimmee, FL 

This vacation rental is located in Kissimmee, and offers a swimming pool and free Wi-Fi.

$64
Avg. per night
Charming 3 Bed Vacation Villa near Disney (64) by Dreams VR
Charming 3 Bed Vacation Villa near Disney (64) by Dreams VR
7.3 Good
Kissimmee, FL, United States
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4.6 mi from city centre, Kissimmee, FL 

Boasting a swimming pool, Charming 3 Bed Vacation Villa near Disney 64 by Dreams VR is situated in Orlando and offers comfortable accommodation. Guests can also make use of free Wi-Fi.

$98
Avg. per night
Newport Condo At Legacy Dunes Resort
Newport Condo At Legacy Dunes Resort
Kissimmee, FL, United States
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14.3 mi from city centre, Kissimmee, FL 

Featuring a swimming pool, Newport Condo at Legacy Dunes Resort is located in Orlando and provides comfortable accommodation. Those staying at the property can also enjoy complimentary wireless internet.

$108
Avg. per night
Relaxing 3 Bedroom Villa Near Disney (174)
Relaxing 3 Bedroom Villa Near Disney (174)
Kissimmee, FL, United States
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4.6 mi from city centre, Kissimmee, FL 

This property is located in Kissimmee, and features an express check-in and check-out feature, a swimming pool and free Wi-Fi.

$109
Avg. per night
Deluxe Waterfront
Deluxe Waterfront
9.1 Excellent
Kissimmee, FL, United States
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1.6 mi from city centre, Kissimmee, FL 

Featuring an outdoor pool, Deluxe Waterfront is situated in Orlando and provides comfortable accommodation. It also offers a library, a terrace and a garden.

$110
Avg. per night
Crestwynd Bay Orlando
Crestwynd Bay Orlando
Kissimmee, FL, United States
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10.7 mi from city centre, Kissimmee, FL 

Crestwynd Bay Orlando is located in Orlando and is close to Walt Disney World Resort. It also offers free Wi-Fi, an outdoor pool and an airport shuttle.

$114
Avg. per night
The Villas at Seven Dwarfs Lane
The Villas at Seven Dwarfs Lane
9.4 Excellent
Kissimmee, FL, United States
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3.4 mi from city centre, Kissimmee, FL 

The Villas at Seven Dwarfs Lane is situated in Kissimmee, just 30 minutes from Orlando International Airport. It also provides free Wi-Fi, laundry facilities and an outdoor pool.

$127
Avg. per night

Where to stay in Kissimmee

Kissimmee vacation rental FAQs

  • How much does a vacation rental in Kissimmee cost?

    $155 per night is how much a vacation rental in Kissimmee costs, on average. $33 per night was the cheapest price recently found by our users, though anything for $124 per night or less is a good deal. Keep in mind that Kissimmee vacation rental prices fluctuate throughout the year: the most expensive month to book is November, and the cheapest time to book is September.

  • What’s the closest vacation rental to Orlando Airport?

    It’s only 11.1 mi from Orlando Airport to Homes4uu - Disney Area Vacation Homes (the nearest Kissimmee vacation rental to the airport).