Discover a selection of 1,000 vacation rentals in Kissimmee, FL, US that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including private pool and pool. Prices start at C$ 95 per night, and house rentals and villa rentals are popular options for a stay in Kissimmee. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Kissimmee

What are the top vacation rentals in or near Kissimmee?

Whatever your getaway needs, you'll find a rental in or around Kissimmee that's a match made in heaven. Here are some of our favorites:

  • Take advantage of handy amenities like high-speed internet services and a nearby zoo at "Theme Rooms, Splashpad, Movie Theater". Located around 19 kilometers from Kissimmee, this property has 7 bedrooms and is a hit with guests.
  • Alternatively, make yourself comfy at "Luxurious Family - 4bedroom - Privacy Fenced Pool Hot Tub". Located around 19 kilometers from the heart of Kissimmee, it has 4 bedrooms and comes with a nearby hospital and a fenced yard.

For even more great options, use the search bar at the top of the page to find the perfect Kissimmee vacation rental for you.

What are the best tiny house vacation rentals in or near Kissimmee?

You need only step inside one of our tiny house vacation rentals in Kissimmee to recognize that awesome things really do come in tiny packages. Smartly designed to maximize space, these pint-sized pads promise a big vacation experience:

  • Take a few days off to get back to basics at "Brand New Tiny House Near Orlando Attractions And Central Florida Beaches". Located in Clermont, a garden and a swimming pool are just a couple of the amenities you can expect here.
  • Alternatively, book a weekend away at "The Cottage - Quaint Tiny Home Filled With Charm". Located in Princeton - Silver Star, this itty-bitty abode comes with a kitchen and a barbecue grill.

What are the top-rated vacation rentals for weekend getaways in or near Kissimmee?

Clock out on Friday afternoon and then pack your overnight bag. If you're ready for some fun and relaxation, these retreats in and near Kissimmee are the perfect weekend getaway:

  • "Welcome To The Windsor Fantasy" is a favorite option around 19 kilometers west of central Kissimmee. You'll never have to wander far to find something fun to do around this property. Pull out your map and head for Princeton Park and Split Oak Forest Mitigation Park. Activities like fishing and kayaking will perfectly round off your weekend trip.
  • Alternatively, enjoy some downtime at "Minutes To Disney5 - Starman". About 19 kilometers west of Kissimmee, activities around here include golf and tennis. Prefer to go sightseeing? Pencil in a visit to Split Oak Forest Mitigation Park and Orange County National Golf Club.

Can I find studio apartments for rent in and around Kissimmee?

Typically small, easy on the pocketbook and well located, it's not difficult to fall for the charms of a studio apartment. Get comfy in one of these options and experience the energy of Kissimmee up close:

  • Make "Sensational Water View 1 Mile To Disney Newly Renovated Superb Location" your home for a couple of days or more. This great vacation rental features amenities including a microwave oven and a balcony.
  • Another awesome choice is "Upgraded Huge Lakefront 1br/2ba Blue Heron Beach Resort Condominium". Make use of nearby birdwatching activities, a kitchen and other conveniences during your getaway.

There are many sights around Kissimmee you shouldn't miss. Nourish the culture vulture in you by visiting Wizardz Magic Theater and Orlando Repertory Theater.

Can I find short term rentals in or near Kissimmee?

Every once in a while, you've just got to take a break from it all, even if it's only for two or three days. Enjoy a nice mix of sightseeing and relaxation at one of these short-term rentals in or around Kissimmee:

  • If you're eager to be near the action, "Welcome To The Windsor Magic" is calling your name. It's within easy reach of the center of Kissimmee and a handy base to explore sights like Amway Center and Camping World Stadium.
  • "Clean Themed Rooms, Private Lakeview Yard" is another appealing option. Remember to add Mall at Millenia and Orlando Science Center to your to-do list when it's time to sightsee.

What are the best romantic weekend getaways in or near Kissimmee?

Forget about flowers and chocolates. Sometimes all you need is to take off for the weekend, just you and your honey. At Vrbo, we've got romantic getaways in and around Kissimmee that would make even old Cupid swoon. Here are some to tempt you:

  • Sneak off on Friday for a few nights of passion at "Theme Rooms, Splashpad, Movie Theater". Roughly 19 kilometers from Kissimmee, it comes with lots of nice touches, like air conditioning and a swimming pool.
  • "Luxurious Family - 4bedroom - Privacy Fenced Pool Hot Tub" is another top option that'll impress. It's approximately 19 kilometers from Kissimmee and has beauty services and winery tours.

What's the best place to stay if you're looking to rent a house for a weekend in or near Kissimmee?

Approximately 19 kilometers from Kissimmee, Windsor Hills is the perfect place to go if you don't have much time but want an adventure. Spend your days exploring this popular lakeside residential community and your evenings relaxing at one of our lovely vacation homes. Or, check out our range of rental houses in the residential residential community of Bellavida, about 6 kilometers from Kissimmee.

What are the best large group vacation rentals in or near Kissimmee?

Vacation with others and multiply the fun. Whether you're organizing an adventurous getaway with pals or a big family gathering, you'll have your pick of large group vacation rentals in and around Kissimmee:

  • There's plenty of space to enjoy yourselves at "Theme Rooms, Splashpad, Movie Theater". Around 19 kilometers west of Kissimmee, this grand retreat has 7 bedrooms sleeping up to 16 guests. Quality amenities include a swimming pool and a kitchen.
  • "Welcome To The Windsor Fantasy" is another terrific option. It's around 19 kilometers to the west of Kissimmee, has 5 bedrooms and sleeps as many as 12 guests. A kitchen and a swimming pool are just a couple of things that'll help make your group getaway even more comfortable.

Are there large vacation rentals that sleep 30 or more in or near Kissimmee?

Whether you're hosting a big event like a wedding or an unforgettable vacation with your favorite people, we'll help you find the right place for your group. Bring together the troops and explore these large vacation rentals in or around Kissimmee:

  • "Championsgate, 9 Bed Luxury Exec Villa": With 9 bedrooms accommodating up to 30 people, space isn't a problem at this sizable rental. A water park and a kitchen are a sample of its numerous amenities.
  • "24 Bedrooms In Two Homes Just One House Between. All Set Up And Ready For You": Offering space, comfort and privacy, this vacation home houses up to 76 people in its 24 bedrooms. A swimming pool and a kitchen will help keep your crew happy and comfortable.

What are the best houses for rent with a pool in or near Kissimmee?

Nothing says fun times like a pool. Grab your inflatable flamingo and check out these rental houses in or near Kissimmee that feature this added perk:

  • Treat your loved ones to an unforgettable stay at "5 Stars House With Wifi, Game Room". There's plenty to love about this getaway apart from its pool, such as a porch and nearby birdwatching activities.
  • Spend leisurely days swimming or simply unwinding beside the water at "Awesome Deals - Fantastic 5bedroom House". This property is also a firm favorite and offers childrens activities, coffee and tea making facilities and more.

Not sure how to pack for your Kissimmee escape? This impressive destination has a humid subtropical climate. In the summertime, expect average temperatures ranging from 75null to 90null. Browse our selection of Kissimmee vacation rentals by using the search bar at the top of the page. Simply adjust the filters to get more inspiration on where to stay.

Explore destinations around Kissimmee

839 vacation rentals
Cumbrian Lakes
137 vacation rentals
Venetian Bay Villages
265 vacation rentals
Eagle Pointe South
359 vacation rentals
Historic Downtown Kissimmee
232 vacation rentals
185 vacation rentals
Lakeside Estates
27 vacation rentals
Bass Lakes Estates
713 vacation rentals
Morgan Point
19 vacation rentals
Liberty Village
92 vacation rentals
Country Creek Estates
301 vacation rentals
Mill Run
22 vacation rentals
Villas at Shadow Bay
103 vacation rentals