Holiday rentals and lettings in Kissimmee

Holiday rentals and lettings in Kissimmee

Start comparing over 774 rentals in Kissimmee and book at the best price!

Find Holiday Rentals & Lettings in Kissimmee

Highlights in Kissimmee

  • Disney World
  • Family friendly
  • Everglades tours
  • Romantic holidays

Best Holiday Rentals & Lettings in Kissimmee

Guests agree: these stays are highly rated for location, cleanliness, and more.
Holiday Rental for 8 People in Kissimmee, Osceola County
Holiday Rental for 8 People in Kissimmee, Osceola County, Photo 1
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Kissimmee, Osceola County
Holiday Rental • 152 m² • 4 Bedrooms
Experience the ultimate in comfort for your incredible Disney vacation at our newly remodeled 4-bedroom townhome in Bella Vida resort. Situated just moments from Disney parks and surrounded by eateries, with a Super Walmart a mere 2-minute drive away, convenience is a given. Unwind in the cozy embrace of this villa, designed to accommodate 8 guests in pure comfort. Step into a spacious haven that opens to a fantastic outdoor area with your own private pool. Your dream Orlando vacation is about to unfold in the most magical way possible! The Space: Discover the epitome of comfort in our newl...
from £103 / night
Holiday Rental for 9 People in Kissimmee, Osceola County
Holiday Rental for 9 People in Kissimmee, Osceola County, Photo 1
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Kissimmee, Osceola County
Holiday Rental • 9 Guests • 3 Bedrooms
Guests at Fiesta Key live in holiday villa furnished with luxurious taste and elegancy, in the heart of an area that is famous for its first class theme parks, entertainment, and leisure activities. Fiesta Key gated community is on Poinciana Blvd. and US-192; and Osceola Pkwy, SR 535, Central Florida Greenway and I-4 are around it. Guests can enjoy the amenities of this community that include a heated swimming pool at the pavilion, open areas for picnics, and playgrounds for the little ones. Comfortably accommodates up to 9 guests. This villa houses 3 bedrooms: one master bedroom features a...
from £79 / night
Holiday Rental for 8 People in Kissimmee, Osceola County
Holiday Rental for 8 People in Kissimmee, Osceola County, Photo 1
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Kissimmee, Osceola County
Holiday Rental • 8 Guests • 4 Bedrooms
Experience what a vacation home in Orlando is all about! Bella Vida Resort offers great amenities and facilities including: a spacious lounge, movie theatre, cyber cafe, fitness center, basketball court, sand volleyball court, resort pool and spa, and tot lot. It is a great opportunity to spend an affordable time with family and kids when the attraction parks are not in the program for the day! Bella Vida Resort has immediate access to US 192, nearby there are convenience and grocery stores, thematic restaurants such as Medieval Times, Capone, and many other places and nature trails to expl...
from £85 / night

Other holiday ideas and property types in Kissimmee that might be interesting

Prices and availability

Current Holiday letting prices Kissimmee

£239for 23 Aug - 30 Aug
£255 annual average
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Average price per week

Current holiday letting availability Kissimmee

41%for 23 Aug - 30 Aug
61% annual average
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Percentage of available lettings

Holiday rentals and lettings in Kissimmee

Lettings in the entertainment hub of the world

Home to Disney World, Kissimmee is one of the most popular holiday destinations in the world. But many people are pleasantly surprised by how much more there is to do here aside from the world-famous theme parks. There are thousands of holiday rentals to choose from in Kissimmee, all offering easy access to the theme parks. If you are looking for a holiday rental close to Kissimmee’s other attractions, search in the Old Town area of the city, which is crammed full of things to do for the whole family.

Luxurious lettings at a great price

There are few places in the world that offer villas of this quality. Opulent villas boasting private pools and spas, games and cinema rooms, and space for up to 20 people! And as an added bonus, the lettings are surprisingly well priced. Many holiday rentals offer spectacular golf course and lake views, guaranteeing a vacation that you will always hold close to your heart.

Holidays in Kissimmee

The area and getting around

Explore Santiago’s diverse barrios

Kissimmee is a short drive from Orlando, a major airport hub connected to every major country in the world. Effectively a suburb of Orlando, Kissimmee offers great value accommodation whilst putting you right on the doorstep of the world-famous Disney World theme parks. The city borders a huge lake to the south called Lake Tohopekaliga, a wonderful place for recreational activities.

Kissimmee – the apotheosis of the holiday experience

Verdant tropical landscapes create the ideal backdrop for outdoor adventures in and around Kissimmee. Whether you are zipping around the treetops, gliding through the Everglades, or soaring above it all in a hot air balloon, there are thrills-a-penny in this holiday paradise. Natural landscapes transform into quaint downtown areas where you can embark on boutique shopping and local dining, and explore lakeside parks. At Kissimmee you will achieve a state of pure holiday nirvana in a city where thrill meets chill!

Travellers and activities

Kissimmee for romantic holidays

Couples come to Kissimmee from all over the world to experience horseback riding at Hidden Palms Ranch, clear kayak tours in the scenic canals linking Lake Virginia and Lake Osceola, hot air balloon rides over central Florida’s diverse landscape, walks hand in the beautiful Leu Gardens, performances at the Dr. Phillips Center for the Performing Arts.. and so on, and so on. There are literally a hundred holidays to be had in Kissimmee for couples, so if you haven’t come yet, make this your first time!

Kissimmee for Disney fans

There are four theme parks at Walt Disney World where you will forge memories of a lifetime. Magic Kingdom, home to the iconic Cinderella Castle, is a magical theme park with rollercoasters, carousels, 4D cinemas and the like. Epcot, which means Experimental Prototype Community of Tomorrow, has two main sections, Future World, which fuses learning with entertainment in spellbinding pavilions where your imagination is encouraged to run riot, and World Showcase, which provides a fascinating taste of 11 countries in miniature. Disney's Hollywood Studios is home to unforgettable rides and shows based on films such as Star Wars and Indiana Jones. Last but not least, Disney's Animal Kingdom is a fun-fuelled concoction of live animals such as tigers, elephants and rhinos and traditional rides and shows. The million-dollar question is where to start?!

Kissimmee is a place where’s childhood memories are set in stone, with the greatest collection of theme parks in the world!

Top 5 travel tips in Kissimmee

1. Take a day trip to the sea

Daytona beach on the Atlantic is the closest beach to Kissimmee, just 1.5 hours away by car. This lovely beach entices visitors to its family-friendly activities and outdoor activities such as parasailing, kayaking, and eco-boat tours.

2. Get close up to Florida’s most notorious inhabitant

Gatorland is the area’s most highly-rated gator park, with knowledgeable guides, an aviary, a small zoo where you can touch the animals, various animal shows and a natural alligator farm. Don’t miss the spectacular feeding show where crocs jump high out of the water!

3. Take a swamp boat tour of the Everglade!

Explore "real Florida" on a swamp boat: a trip on the famed Everglades swamps on a boat powered by an aircraft-type propeller is a must-do activity for visitors to Kissimmee. For the best views, book a sunset tour.

4. Shake hands with Florida’s greatest sports stars

Florida Sports Hall of Fame displays many of the notable Floridian sports celebrities with waxwork models of internationally renowned sports legends such as Jack Nicklaus, Chris Evert, and Otis Birdsong. Amazingly, it's free to get in!

5. Take a fossil hunting tour

Fossil Funatics is an outdoor adventure into ancient times. The central Florida Waterways are a mecca for fossil lovers who come for daylong tours which provide you with everything you need to embark on a fun fossil hunting expedition!

Information about holiday lettings in Kissimmee

🏡 Holiday lettings available: 660 properties.
💳 Discount available: up to -56%.
🌙 Minimum price per night: from £44.
⭐ Most popular amenities: Wi-Fi, air conditioning and swimming pool.
🐾 Pet-friendly: 121 properties.
📶 For workation: 99% of the properties.
🏊 With pool: 592 properties.

FAQs: Holiday Rentals & Lettings in Kissimmee

Which amenities can you typically find at the holiday lettings in Kissimmee?

Among the services you can find on Holidu, it appears that the holiday lettings in Kissimmee have everything that tourists want! Here, holiday lettings generally offer a variety of amenities, the most popular being: Wi-Fi (99%), air conditioning (97%), and swimming pool (89%)... What are you waiting for?

How are the holiday lettings usually rated in Kissimmee?

The holiday lettings in Kissimmee have many good reviews from guests. Many (45%) have a rating of 4.5 stars, which tells us that here it is possible to find the perfect holiday letting for your next holiday!

Are the holiday lettings in Kissimmee suitable for families with children?

Holidu's insights reveal that less than 10% of holiday lettings in Kissimmee are suitable for families with children. Here, it will probably be easier to book for groups of friends.

Are the holiday lettings in Kissimmee suitable for holiday-makers who wish to travel with their pets?

According to Holidu's information, a small percentage of holiday lettings in Kissimmee accept pets. We can therefore advise that there are more suitable destinations in the USA for owners and their pets.

Do the holiday lettings in Kissimmee often come with an internet connection?

Of course! According to Holidu's data, 99% of holiday lettings in Kissimmee offer an internet connection. So no need to panic, you will be able to browse the internet throughout your stay!

How much does it usually cost for holiday lettings in Kissimmee?

A big percentage of holiday lettings in Kissimmee (91%) cost less than £100 a night. This is the dream destination for finding an affordable holiday letting!

Do the holiday lettings in Kissimmee mostly have a swimming pool?

Yes! Judging by information from Holidu, 89% of holiday lettings in Kissimmee are equipped with a swimming pool. It is the perfect destination for spending hot summer days by the pool! In addition,46% even have a barbecue!

Are the holiday lettings in Kissimmee suitable for trips with several people or better for an escape as a couple?

Here, based on last year's information, 83% of holiday lettings welcome groups of up to eight guests, and 81% of these holiday lettings have at least four bedrooms. But 99% of holiday lettings are also suitable for up to four travellers, and 98% of the holiday lettings are made up of at least two separate bedrooms. Kissimmee is, therefore, the ideal destination for groups of friends of all sizes!

Do the holiday lettings in Kissimmee offer outdoor space to enjoy?

61% of holiday lettings have a balcony or terrace, and 0% have a view. However, it is not very common, so availability can be limited. If this is a priority for you, you should anticipate a bit more time for research. Also, don't forget to use the filters to be sure to find the holiday letting of your dreams. However, 36% of holiday lettings in Kissimmee have gardens, where you can enjoy the outdoors. If you like to have lunch or dinner outside, and especially if you like barbecues, 46% of the holiday lettings have them.

If you are thinking of travelling to Kissimmee do you know the best time to do it?

Looking at the characteristics of the holiday lettings in Kissimmee, it is easy to say that this is an ideal summer destination. This is because according to the data, 89% of the properties here have a swimming pool, 36% have a garden and 97% have air conditioning. Don't wait any longer to book your accommodation in Kissimmee to enjoy an unforgettable holiday.