Although the city of Orlando takes the crown for the most famous city in Osceola County, Florida, best known for its theme park attractions, the neighboring city of Kissimmee is just as impressive.

The name Kissimmee means ‘Long Water,’ because it lies on the shore of Lake Tohopekaliga and is surrounded by creeks and lakes. With a smaller population than Orlando, it’s a great option for Disneyland visitors who prefer a quieter city environment.

But Kissimmee has attractions of its own. Being surrounded by water it is a hotspot for fishing, has 22 golf courses, and you can even take an airboat tour through the Everglades to spot some gators. You can also swim with docile manatees which are native to this area.

Though it is a smaller city than Orlando, it has more than 22,000 vacation rentals to choose from.

Many of these self-catering vacation rentals in Kissimmee have private swimming pools and are ideal for family visits. There are also a bunch of resorts that offer private homes and condos with access to swimming pools, gardens, and even golf courses.

With so many options to choose from, finding the right home is no easy task. That’s why we’ve prepared this guide on the best vacation rentals in Kissimmee to help you narrow down your search.

Quick Answer: These are the Top 5 Vacation Rentals in Kissimmee

Overall Best Value Vacation Rentals in Kissimmee
Modern 4 Bed House with Games Room
Overall Best Value Vacation Rentals in Kissimmee

Modern 4 Bed House with Games Room

  • > $$
  • > 10 Guests
  • > Brand new build with trendy interiors and a covered pool and Jacuzzi
  • > Down the road from top eateries and bars
Best Budget Vacation Rentals in Kissimmee
Charming 1 Bed Home with Porch
Best Budget Vacation Rentals in Kissimmee

Charming 1 Bed Home with Porch

  • > $
  • > 3 Guests
  • > A tiny home with access to a resort pool and Jacuzzi
  • > 5 miles from Disney World
Best Vacation Rentals for Couples in Kissimmee
Up Scale 1 Bed Condo with Resort Amenities
Best Vacation Rentals for Couples in Kissimmee

Up-Scale 1 Bed Condo with Resort Amenities

  • > $$
  • > 4 Guests
  • > Includes a pool, virtual golf simulator, and theatre
  • > In a bustling area just west of Kissimmee Central
Best Vacation Rentals for Families in Kissimmee
4 Bed House with Pool and Jacuzzi
Best Vacation Rentals for Families in Kissimmee

4 Bed House with Pool and Jacuzzi

  • > $$
  • > 8 Guests
  • > Island-style interiors with a huge covered pool deck
  • > In a residential neighborhood
Over-the-Top Luxury Vacation Rentals in Kissimmee
Exquisite 8 Bed Home with Themed Rooms
Over-the-Top Luxury Vacation Rentals in Kissimmee

Exquisite 8 Bed Home with Themed Rooms

  • > $$$
  • > 24 Guests
  • > Star Wars, Harry Potter, and Frozen-themed children’s rooms
  • > Just outside the heart of Kissimmee, close to everything

Types of Accommodation in Kissimmee

Lake Front Kissimmee

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Family Townhouses

One of the most common types of accommodation in Kissimmee are townhouses. Because of the warm temperatures and year-round humidity, many of these uniform-looking homes have private swimming pools and Jacuzzis.

In this area of Florida, you’ll notice that all swimming pools are covered by clear netting, designed to keep the bugs (and sometimes some much bigger animals) at bay while you enjoy the outdoor sunshine.

Depending on your budget, you could find both affordable and luxurious townhouse options in Kissimmee. Ranging in size from two to ten bedrooms, townhouses are ideal for families as well as large gatherings with young kids. Townhouses that are enclosed in compounds and complexes are also a super safe option for young families.

Apartments and Condos

As with any big city, some of Kissimmee’s top rentals can be found in apartment blocks. Whether you opt for a small studio, a family condo, or a luxurious penthouse, there’s a Florida Airbnb for every budget in this city.

Condos are a great option for couples, digital nomads, and anyone who wants to base themselves in the center of the city.

In fact, you could even find a condo located in a private estate, complex, or resort. For these condos, you might pay a premium price for added security as well as shared amenities including access to swimming pools, landscaped gardens, clubhouses, and gyms.

Historic Military Road Kissimmee

Resort Villas

In my opinion, self-catering resort villas are the best vacation rentals in Kissimmee for family visits. Typically located near the city’s theme and water parks, these resorts usually include many amazing facilities that make the slightly higher price all the more worthwhile. I’m talking waterpark-like pools, tiki bars, and on-site restaurants, gyms, and gardens.

With amenities to suit every type of guest, these are especially convenient for those with kids, who will be kept happily entertained for days on end!

Sunset Pier Kissimmee

Top 20 Vacation Rentals in Kissimmee

Kissimmee is one of the top locations to stay in when visiting Orlando Florida for its theme parks. Choose from small townhouses, budget condos or go wild and invite your extended family to stay at a massive ten-bedroom villa.

If you’re not sure which accommodation is right for you, read one to see our top 20 vacation rentals in Kissimmee.

Best Overall Vacation Rental in Kissimmee | 4 BR Home W/ Games

Modern 4 Bed House with Games Room

If you’re looking for an all-rounder holiday home in Kissimmee, we have you covered. This spacious family home sleeps ten guests and is located right in the heart of the city.

The home has been designed using modern interiors and lots of windows to invite an abundance of natural light into the space. With finishing touches of modern poster art and indoor plants, you’ll feel right at home in this family-friendly spot.

As well as this, there are some unique features that are ideal for keeping children busy, such as the private covered swimming pool and Jacuzzi, as well as the well-equipped games room in the garage.

Best Budget Vacation Rental in Kissimmee | 1 Bed Home W/ Porch

Charming 1 Bed Home with Porch

Sometimes, all you need is an affordable place to rest your head after a busy day in Kissimmee. Although this property is small, it will certainly exceed expectations – it’s clean, modern, and has everything you need from a self-catering vacation rental in Kissimmee. Clever storage solutions make the space seem much larger than it is.

This vacation rental in Kissimmee is located on a 4* resort just 5 minutes away from Disneyland. It has one large bedroom with a queen-sized bed, and a pull-out couch in the living area, making enough space for up to four guests.

The entire apartment has been decorated using pops of yellow, from the carpeting to the chairs to the pillows. There is even a spacious enclosed outdoor seating area decorated with pot plants, which makes for the perfect spot to escape the bugs and enjoy some sun. 

Most Beautiful Vacation Rental in Kissimmee | 4 Bed Villa with Pool

Exquisite 4 Bed Villa with Outdoor Pool

Settle into this luxurious Mediterranean-inspired villa in Kissimmee. Not only is this one of the most beautiful vacation rentals in the area, but it’s also one of the most luxurious (not to mention, it certainly has some of the best views). 

Located on a golf course estate, take in lush views of golf greens and forests from the pool and balconies. In fact, this gorgeous home has balconies jutting off just about every room.

Perfect for a long or short visit, the home is fully equipped with a gourmet level kitchen, washer/dryer facilities, and a spacious yard. What other luxuries can you expect? There’s also a Jacuzzi and pool with an outdoor summer kitchen, a billiard room, and a private theatre.

Most Luxurious Vacation Rental in Kissimmee | 8 Bed Home

Exquisite 8 Bed Home with Themed Rooms

Without sounding too excited, we might have just landed on the most outlandishly-themed luxury vacation rental in Kissimmee. This massive eight-bedroom home can sleep up to 24 guests and is the ideal spot for a huge family gathering. 

Perfect for kids, each of the twin bedrooms is decorated following a different theme. Choose from Frozen, Marvel, or Star Wars-themed kids’ rooms, or relax and enjoy the neutral colors in the more sophisticated bedrooms. 

Aside from a spacious outdoor yard area with a covered pool and Jacuzzi, this home also has a Harry Potter-themed games room, which doubles as a dorm for extra guests.

Best Vacation Rental in Kissimmee for Families | 4 Bed Home W/ Pool

4 Bed House with Pool and Jacuzzi

Generally speaking, Kissimmee is most often visited by families exploring the water and theme parks in the area. There are three things that make this Airbnb in Orlando‘s neighboring city perfect for families. Firstly, it includes a large outdoor area, with a covered swimming pool, Jacuzzi, and dining table – perfect for a family meal by the pool.

Second, this spot is centrally located in a residential neighborhood just outside the city center, close to all the main attractions in the area.

Finally, one of the biggest pulls to this home is its affordability. You can expect to drop some dollars at the theme parks, so it’s a great option to save a bit on accommodation where you can.

Best Vacation Rental in Kissimmee for Digital Nomads | 1 Bed Condo

Cozy 1 Bed Condo with Pool Access

No matter where you are visiting from, a weekend away in the magical land of Disney is always a great idea. Strangely enough, we recommend this modern condo as one of the top spots for both a quick trip and long stay visitors. 

It’s only a few miles from Disney and sits in a real estate complex equipped with swimming pools, Jacuzzis, tennis courts, and a clubhouse. The simple condo is fitted with a full kitchen with everything you might need from a self-catering vacation rental in Kissimmee. 

Long stay visitors will be able to make use of the private washer/dryer facilities too. Another plus? You’ll be allowed to bring your pet along for a small additional charge. Because of its facilities and affordability, we think it would make the perfect vacation rental for digital nomads visiting Kissimmee.

Best Vacation Rental in Kissimmee with a Pool | 2 BR Condo

Contemporary 2 Bed Condo with Lake Views

One of Kissimmee’s classiest vacation rentals sits right on the banks of Storey Lake. Located in a gated resort, guests can enjoy access to the shared gym, beach bar, and sporting courts. 

With Florida’s humidity and constant sunshine, choose to spend a day at the shared swimming pools on the property or ride around on a golf cart. In fact, these waterslide pools could easily qualify as a waterpark in themselves. There is even a pool called the ‘lazy river’ which, quite literally, follows the form of a river.

The property itself can sleep up to six guests in its two bedrooms and 3.5 bathrooms, and comes with a spacious living area and open-plan kitchen and dining area. There is also a top-floor balcony where you can sit and watch the kayakers go by on the nearby canal.

Super Accessible Vacation Rental in Kissimmee | 5 Bed Home W/ Pool

Gorgeous 5 Bed House with Pool

Without a doubt, this is one of the best vacation rentals in Kissimmee for wheelchair users. You won’t have to worry about any tight spaces or unexpected steps in this classic home. 

The home has five bedrooms, each with sleeping space for two (there is also a sleeper couch for those who wish to squeeze in a few extra guests, but we don’t recommend this for wheelchair users who need space for movement).

Located in a secure residential complex, visitors can also make use of the winding lagoon pool as well as the gym, spa, and clubhouse. To make your stay just that much more convenient, there is even a convenience store and the option to rent out meeting rooms on-site – perfect for digital nomads.

And for those wheelchair users wanting a little adventure, Kissimmee is home to the world’s only wheelchair-accessible zip line at Gatorland.

Most Central Vacation Rental in Kissimmee | 4 BR Home W/ Garden

Trendy 4 Bed Home with Garden

If a central location is what you’re after, renting out a townhouse is probably your best bet. This quaint resort townhouse has four spacious bedrooms and is completely wheelchair-friendly, making it one of the best holiday rentals in Kissimmee. There is also a fully equipped kitchen with a dishwasher and a microwave, a washing machine, and 2 bathrooms with a shower.

This townhouse lies in the center of a private residential resort, which is dotted with different shared amenities including a lagoon-style swimming pool.

This unique pool includes caves and grottos as well as fun fountains for kids to splash around in. When the theme parks get too overwhelming, feel free to spend a day at the resort tiki bar while the kids enjoy the pool zone.

Best Vacation Rental for a Big Family in Kissimmee | Themed Villa

Themed 9 Bed Villa with Theatre and Slides

This home is all about fun and games. Perfect for a large family, you could easily fit sixteen guests into this nine-bedroom villa.

Aside from the pool and Jacuzzi area (which are quite common in Kissimmee) this spot has a private home theatre and a massive arcade-themed games room with a pool table, air hockey, and online gaming stations.

While the main living room and the kitchen are designed using contemporary furniture and neutral colors, the bedrooms are another story. Choose from an underwater cabin-themed bedroom, an Aladdin-inspired room, and a Harry Potter suite. Kids will fight over the Spider-Man dorm which has slides as well as ladders!

Best Vacation Rental in Kissimmee for Friends | 4 BR Home

Classy 4 Bed House with New Kitchen

This classic family home has been kitted out in a contemporary style. Picture geometric linens, modern art, glass tables, and neutral tones throughout the home.

With four private ensuite bedrooms, you’ll always have your own space to enjoy even when traveling with friends.

However, the central living area is where you’ll want to spend most of your time. The beautiful kitchen is equipped with everything you need to prepare a friendly cookout, making this one of the top luxury vacation rentals in Kissimmee for a getaway with friends.

Most Unique Vacation Rental in Kissimmee | Harry Potter Themed Home

Harry Potter Themed 5 Bed Home

Witches and Wizards unite! We’ve found the most unique home in Kissimmee for Harry Potter fans. Only a ten-minute drive from Orlando Studios’ Wizarding World of Harry Potter, a stay in this home will make sure your magical experience begins from the moment you wake up. 

You’ll find this enchanting wizarding home in a quiet neighborhood a few miles from Disney. Four of five bedrooms represent each of the Hogwarts Houses while the master suite is designed to look like the headmaster’s office. Here, we call the living room the ‘common room’ and the dining room the ‘great hall’.

While it is close to all the best things to do in Orlando, we think you might find yourself having too much fun in this home.

Best Vacation Rental in Kissimmee for Honeymooners | 1 BR Condo

Bright 1 Bed Condo with Spacious Kitchen

Beautifully remodeled using warm wooden flooring, neutral colors, and pops of quirky color and unique furniture, this apartment is oozing with romance.

With one bedroom boasting a four-poster bed and a full bathroom fitted with marble tiling, this spot is perfect for two guests. 

If you need to fit in an additional guest, the sleeper couch offers plenty of space for a good night’s rest. The kitchen in this condo is fit for royalty, with a granite countertop center island, stainless steel appliances, and modern cabinetry.

Best Vacation Rental in Kissimmee for Nightlife | 2 BR Condo

Stylish 2 Bed Condo with Natural Light

While the city is known for its child-friendly theme parks, Kissimmee is also dotted with trendy bars, nightclubs, and restaurants for the more mature clientele. If a night on the town is what you’re after, this trendy condo will provide you with everything you need and more. 

This holiday rental in Kissimmee comfortably sleeps five guests in two bedrooms and has an open-concept living space. Comfortable yet contemporary, this is the perfect vacation to begin and end a night out on the town.

Best Vacation Rental in Kissimmee with a View | Lakeside Cottage

Romantic Lakeside Cottage for 2

Romance and nature often go hand in hand, and when you look at this property, it’s easy to see why. This beautiful river cottage sits on the banks of a pristine lake with nothing between it and the water but lush lawns and a turquoise blue pool.

Hidden by flourishing trees and draped in string lights, the best part of this home is its views. Although the suite only has basic self-catering facilities, it won’t be difficult to find delicious eateries and dining options nearby. This small and cozy home is perfect for couples as it only sleeps who guests.

Most Romantic Vacation Rental in Kissimmee for Couples | 1 BR Condo

Up Scale 1 Bed Condo with Resort Amenities

There’s no doubt in my mind that this is one of the top luxury vacation rentals in Kissimmee. Couples staying here can live like a celebrity in this luscious condo with high ceilings, modern lighting, and contemporary furniture. 

The shared amenities are what make this spot so special. Not only can you enjoy the luxuries of swimming pools, spas, Jacuzzis, and gyms, but you’ll even have access to a golf simulator room and a movie theatre. 

The home itself has one bedroom and one bathroom, but has a pullout couch in the living area if you want to invite two more guests to stay with you.

Best Vacation Rental in Kissimmee for small families | 4 BR Family Home

4 Bed Family Home with Pool

With so many activities for kids, booming city life, and extraordinary nature, Kissimmee can be a great city for digital nomads and families to settle into. This family house has a covered pool and Jacuzzi, as well as a spacious front yard.

The home is equipped with everything necessary requirement for a long stay, including a playroom for the kids, free parking on the premises, and washer/dryer facilities. Most useful for digital nomads, this spot even has a private office space.

Best Lakeside Vacation Rental in Kissimmee | 3 BR Home W/ Pool

Lakeside 3 Bed House with Pool

Make yourself at home in this lakeside house in the center of Kissimmee. If you need an escape from the abundance of man-made theme parks, basing yourself in an area surrounded by nature is a great call. 

This family house sits between a myriad of lakes, in a local community resort. With a covered pool and outdoor dining area, feel free to invite some friends over for a family cookout and enjoy the lake views.

Inside the home, there are three bedrooms and two bathrooms, a formal living space, and a large family room with a 60″ smart Tv. There is also a coffee/tea bar and a couple of bottles of wine at no extra cost. So if the house hasn’t sold you, the promise of free wine might!

Best Vacation Rental in Kissimmee with Gardens | 4 BR Penthouse

Gorgeous 4 Bed Penthouse with Garden Views

This luxury vacation rental in Kissimmee scores for both its beautiful views and lush gardens. Kitted out with modern furniture, neutral color tones, and a gourmet chef’s kitchen, the hosts have thought of every detail to ensure you have the best stay possible.

The condo sits in a lakeside neighborhood with access to public pools and manicured gardens. Located on the fourth floor, you’ll be able to admire beautiful garden views from every window in the penthouse (not to mention from the spacious balcony).

Best Pet-Friendly Vacation Rental in Kissimmee | 2 Bed Condo in Resort

Stunning 2 Bed Condo in Resort

In my personal opinion, this might be one of the top spots in the entire city. Aside from being pet-friendly, this modern space has been completely designed using modern interiors and top-of-the-range appliances, as well as being fitted with cozy yet contemporary furniture. 

Gaze out just about every window and patio in the condo for one of the most beautiful lake views in the area. This is the perfect spot for pets because it sits on the ground floor of the building and is surrounded by lush lawns for your pooch to enjoy.

Final Thoughts

Kissimmee is no doubt an ideal place to stay for families visiting the surrounding Disney and Orlando theme parks. Scattered with resort-style accommodation and self-contained condos, Kissimmee has plenty of vacation rentals suited to all types of travellers.

Whether you’re after a peaceful retreat for you and your loved one or a luxurious villa with themed bedrooms, we have no doubt you will find the best vacation rental in Kissimmee.

If we had to choose a favourite, we would have to pick the Hogwarts-themed home. We are a sucker for unique homes and this one really caught our eye. Do you have a favourite from this list? Let us know in the comments.

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