Vacation Rentals & Apartments in Kissimmee

Vacation Rentals & Apartments in Kissimmee

Start comparing over 327 rentals in Kissimmee and book at the best price!

Find Vacation Rentals and Apartments in Kissimmee

Best Vacation Rentals and Apartments in Kissimmee

Guests agree: these stays are highly rated for location, cleanliness, and more.
Vacation Rental for 8 Guests in Kissimmee, Osceola County
Vacation Rental for 8 Guests in Kissimmee, Osceola County, Picture 1
Vacation Rental for 8 Guests in Kissimmee, Osceola County, Picture 2
Vacation Rental for 8 Guests in Kissimmee, Osceola County, Picture 3
Vacation Rental for 8 Guests in Kissimmee, Osceola County, Picture 4
more...
Kissimmee, Osceola County
Vacation Rental • 109 m² • 4 Bedrooms
Welcome to our stunning 4-bedroom home in Bella Vida resort, an unbeatable location near Disney parks. Surrounded by restaurants and just a 2-minute drive from Super Walmart, convenience is at your fingertips. Immerse yourself in comfort and elegance with beautiful decor. This spacious haven accommodates 8 guests and features an incredible outdoor space with a private pool. Your dream vacation awaits, immersed in the magic of Orlando! The Space: Welcome to our inviting 4-bedroom single-level home, meticulously designed to offer your family the utmost comfort. The open-concept living room se...
from CA$199 / night
Vacation Rental for 9 Guests in Kissimmee, Osceola County
Vacation Rental for 9 Guests in Kissimmee, Osceola County, Picture 1
Vacation Rental for 9 Guests in Kissimmee, Osceola County, Picture 2
Vacation Rental for 9 Guests in Kissimmee, Osceola County, Picture 3
Vacation Rental for 9 Guests in Kissimmee, Osceola County, Picture 4
more...
Kissimmee, Osceola County
Vacation 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 CA$125 / night
Vacation Rental for 8 Guests in Kissimmee, Osceola County
Vacation Rental for 8 Guests in Kissimmee, Osceola County, Picture 1
Vacation Rental for 8 Guests in Kissimmee, Osceola County, Picture 2
Vacation Rental for 8 Guests in Kissimmee, Osceola County, Picture 3
Vacation Rental for 8 Guests in Kissimmee, Osceola County, Picture 4
more...
Kissimmee, Osceola County
Vacation 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 CA$148 / night

Prices and availability

Current Vacation rental prices Kissimmee

CA$462for 29 Nov - 6 Dec
CA$620 annual average
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Average price per week

Current vacation rental availability Kissimmee

26%for 29 Nov - 6 Dec
59% annual average
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Percentage of available rentals

Find your Perfect Vacation Rentals & Apartments in Kissimmee

Discover Kissimmee's Premier Vacation Accommodations

Located just minutes from the world's most famous theme parks, vacation rentals & apartments in Kissimmee offer an ideal blend of excitement and relaxation for travelers seeking the perfect Florida getaway. These thoughtfully designed properties feature spacious layouts with contemporary amenities, providing families and groups with the comfort and convenience of a home away from home. From luxurious villas with private pools overlooking tranquil lakes to cozy apartments in gated resort communities, vacation homes in Kissimmee cater to every style and budget preference.

What sets Kissimmee's vacation accommodations apart is their unique combination of resort-style amenities and residential comfort. Most properties are situated within secure, gated communities that offer a peaceful retreat after action-packed days exploring nearby attractions.

Vacation rentals & apartments in Kissimmee typically feature modern architectural styles with open floor plans, vaulted ceilings, and large windows that showcase Florida's natural beauty. These properties are designed with families in mind, offering multiple bedrooms, spacious living areas, and outdoor spaces perfect for gathering and making memories.

Guests can expect an impressive array of amenities that enhance their stay experience. Here's what these exceptional accommodations typically offer:

  • Private swimming pools with optional heating and stunning lake or nature views
  • Fully equipped gourmet kitchens with modern appliances and dining areas
  • Air conditioning and high-speed internet throughout the property
  • In-unit washers and dryers for convenience
  • Private parking spaces and secure entry systems
  • Flat-screen TVs with cable and streaming services in multiple rooms
  • Whirlpools and spa features for ultimate relaxation
  • Game rooms with pool tables, arcade games, and entertainment systems
  • Outdoor patios and decks with premium furniture
  • Community amenities including fitness centers, tennis courts, and clubhouses

Who Should Choose Vacation Rentals & Apartments in Kissimmee

Perfect for Every Type of Traveler

Theme park enthusiasts will find vacation accommodation in Kissimmee unbeatable for its proximity to Walt Disney World (7-15 minutes), Universal Studios (20-29 minutes), and SeaWorld, making it possible to enjoy multiple park visits while returning to a private retreat each evening.

Families with children especially appreciate the spacious layouts, themed bedrooms, and private pools where kids can splash and play safely. Nature lovers can explore Kissimmee's beautiful lakefronts, conservation areas, and walking trails, while adventure seekers can experience unique attractions like Gatorland or Medieval Times Dinner & Tournament. The region's year-round warm climate makes it ideal for visiting any time, with average temperatures ranging from 61-89°F (16-32°C). Winter months (December-February) offer the most comfortable weather with highs around 75°F (24°C) and minimal rainfall, while spring and fall provide excellent conditions with moderate crowds. Summer brings hot, humid weather perfect for pool and water activities. Current accommodation availability ranges from 15-82 properties per week, with rates varying from CAD $298-$909 per night depending on the season, with winter holidays commanding premium pricing and fall offering the best value.

Top 5 Must-Experience Attractions in Kissimmee

Unforgettable Local Highlights

Discover Kissimmee's most captivating destinations that showcase the area's unique blend of natural beauty, entertainment, and family fun. These carefully selected attractions offer experiences you won't find anywhere else in Florida.

  1. Kissimmee Lakefront Park
  2. Gatorland Wildlife Adventure
  3. Medieval Times Dinner Experience
  4. Old Town Historic Entertainment District
  5. Shingle Creek Regional Park

Kissimmee Lakefront Park

This 38-acre waterfront paradise offers stunning views of Lake Tohopekaliga with walking trails, fishing piers, and a splash pad for families. The park features an amphitheater hosting live concerts and events, plus beautiful picnic areas perfect for sunset viewing.

Gatorland Wildlife Adventure

Known as the "Alligator Capital of the World," this 110-acre theme park and wildlife preserve houses over 2,000 alligators and crocodiles. Experience thrilling zip lines, educational shows, and up-close encounters with native Florida wildlife in a natural setting.

Medieval Times Dinner Experience

Step back in time at this immersive dinner theater featuring knights on horseback, royal pageantry, and a four-course medieval feast. The two-hour spectacle combines authentic tournament competition with exceptional entertainment in an 11th-century castle setting.

Old Town Historic Entertainment District

This pedestrian-friendly entertainment complex captures authentic Americana with vintage shops, classic amusement rides, and nostalgic dining. Weekend car shows and live music events create a vibrant atmosphere reminiscent of 1950s small-town charm.

Shingle Creek Regional Park

Explore the headwaters of the Florida Everglades through pristine nature trails, boardwalks, and observation decks. This hidden gem offers incredible birdwatching opportunities, kayak rentals, and interpretive programs showcasing Central Florida's natural ecosystem.

After a hectic day at theme parks, relax in a beautiful villa with panoramic lake views and spectacular sunset fireworks.

Exceptional Dining Experiences in Kissimmee

Top-Rated Local Restaurants

Kissimmee's diverse culinary scene reflects its multicultural community, offering exceptional dining experiences that complement any vacation. These highly-rated establishments provide memorable meals that showcase both international flavors and regional specialties.

  • Pa' Paraguaná Venezuelan Latin Restaurant (4.9 stars) - Authentic Venezuelan cuisine featuring traditional arepas, empanadas, and flavorful grilled meats in a warm, family-friendly atmosphere that brings South American hospitality to Central Florida.
  • Perico Ripiao Latin Food (4.8 stars) - A local favorite serving generous portions of Dominican and Caribbean specialties, known for their perfectly seasoned rice dishes, tender roasted chicken, and vibrant tropical atmosphere.
  • 192 Crab & Lobster Juicy Seafood and Bar (4.7 stars) - Fresh seafood destination offering Cajun-style preparations, steamed crab legs, and signature seafood boils in a casual setting perfect for families and seafood enthusiasts.

Essential Travel Tips for Your Kissimmee Stay

Local Insights and Practical Information

Savvy travelers know that insider knowledge makes the difference between a good vacation and an unforgettable experience. Pool heating services are available for an additional CAD $35-36 per day, but must be requested at least seven days in advance to avoid service fees - particularly valuable during cooler winter months when evening temperatures can dip into the 60s.

Local hosts recommend stopping at nearby Walmart (just 2 minutes from most properties) immediately upon arrival to stock up on groceries, snacks, and any forgotten essentials at unbeatable prices. Trash collection occurs twice weekly in most communities, and properties provide convenient containers for daily use.

The self-check-in process uses personalized codes sent 24 hours before arrival, eliminating the need for key exchanges. Take advantage of complimentary amenities including high-speed WiFi, Netflix access, and North American long-distance calling to stay connected with loved ones. Vacation homes to rent in Kissimmee often include exclusive community amenities like fitness centers, tennis courts, and nature trails that provide entertainment without leaving the resort. Many properties offer stunning fireworks views during holidays, particularly New Year's Eve and Independence Day, when Disney's spectacular displays can be enjoyed from private pools. For the ultimate flexibility and space, consider a luxury vacation rental in Kissimmee with multiple bedrooms, perfect for multi-generational families or groups seeking premium comfort near world-class attractions.

FAQs: Vacation Rentals and Apartments in Kissimmee

What is the average price for vacation rentals in Kissimmee?

Based on our data, Kissimmee has an average price of CA$415.49 per night, a relatively high one for a city in the USA.

During which months can you find the best price for vacation rentals in Kissimmee?

If you would like to save as much as possible during your visit to Kissimmee, travel in May (CA$386.06 per night on average), November (CA$386.33), or August (CA$387.24), to find the lowest prices for the whole year.

In which months is it more expensive to rent a vacation rental in Kissimmee?

When booking a vacation rental in Kissimmee, the highest prices are usually found in the month of March (with an average of CA$471.26 per night), followed by February (CA$454.58), and April (CA$452.86).

Are there usually many vacation rentals available in Kissimmee?

It is better to book sooner than later in Kissimmee as only 41% of the accommodations remain available throughout the year, according to our 2020 data.

Which months offer the highest availability?

The most available months are, on average, May (with an availability of 54.4%), September (53.5%), and August (52.6%), according to the trends observed in 2020.

When will it be harder to find an available vacation rental in Kissimmee?

The month with the highest average booked rental figures is February (only 9.2% of properties were available on average in 2020). Followed by March (20.75%), and January (26%).

How many vacation rentals does Holidu have in Kissimmee?

We have grouped together the offers from 13 different providers in Kissimmee, so we can provide you with around 3600 properties. You're going to have a hard time deciding which one to go with!