Condo vacation rentals in Osceola County

Find and book unique condos on Airbnb

Top-rated condo rentals in Osceola County

Guests agree: these condos are highly rated for location, cleanliness, and more.

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Guest favorite

Condo in Kissimmee

4.94 out of 5 average rating, 186 reviews

Lakeview Escape close to Disney&retail therapy

Our condominium is located at resort-style community ( with FREE parking, No resort FEES) with a beautiful clubhouse featuring a game room, gathering rooms, fitness center and outside, a tranquil free-form heated pool with plenty of deck chairs for all the vacationers. This resort also features a second pool, golf cage, tennis, basketball and volleyball courts, a playground, carwash area, picnic pavilions and grills, and scenic walking trails around landscaped wooded areas, fountains and ponds.

Oct 3 – 10

G$23,735 GYD per night

Guest favorite

Condo in Kissimmee

4.97 out of 5 average rating, 160 reviews

New Lovely 3-bedroom Condo 5 minutes from Disney’s

This is a totally remodel Beautiful Condo! Nice small community with heated pool, fitness center, barbecue area, tennis courts in a quiet private park like setting! Enjoy breakfast on a comfortable screened balcony overlooking a serene conservation area. This 3/2 First floor condo is in a perfect location, just 5 miles from Disney World with lots of shopping & restaurants close by...for golfers, the property is surrounded by lots of beautiful courses, don't delay schedule your Vacations today!

Oct 7 – 14

G$31,064 GYD per night

Guest favorite

Condo in Kissimmee

4.96 out of 5 average rating, 154 reviews

Welcome to our Son Shine condo ....

Thank you for taking the time to look at our home. As you enter, our hope is that whether you are looking to escape the hustle and bustle of busy life or be close to area attractions (Disney (10 mins) Universal Studios, Walmart, Grocery Stores & various restaurants that you will be able to relax and enjoy the surroundings. Swim at the Tropical Landscape Pool, Kiddie Activity Pool or relax in the Whirlpool Spa & Fitness Center steps away from the condo. Our hope is you can relax and enjoy.

Oct 31 – Nov 7

G$28,868 GYD per night

Guest favorite

Condo in Kissimmee

4.98 out of 5 average rating, 163 reviews

Remodeled, Stylish and Affordable Close to Disney

Ready to have "The Royal Experience" of your life? Then this is the place for you and your family! Our place is only miles from Disney parks, Old Town and Medieval Times. Quiet and safe area but close to everything and fully remodeled. Very spacious with a large living room, TVs in all bedrooms, fully equipped kitchen, nice deck for the evenings relaxation, assigned parking and much more. We have made sure we got all you need for a perfect vacation and You will be glad you chose us.

Dec 2 – 9

G$31,064 GYD per night

Guest favorite

Condo in Kissimmee

4.94 out of 5 average rating, 158 reviews

Affordable condo 3 miles from Disney and Golf!

Amazing Location 10 minutes from Disney and Golf with dining within walking distance. Clean, extra-large Condo in a gated community, Free WIFI and parking. Two Bedroom, fully furnished with a stocked kitchen everything you need to have for the perfect Orlando vacation. King master bed, 2 twin beds and Sofa Sleeper in the Living room. Private screened in balcony facing conservation area to enjoy quite time before you hit the theme parks. Community pool/hot tub. Smoke and Pet Free

Jan 9 – 16

G$25,528 GYD per night

Guest favorite

Condo in Kissimmee

4.84 out of 5 average rating, 105 reviews

Orlando Oasis-Refreshed luxe clean Villa by Disney

Runaway Beach Club Resort just 2.5 miles from Disney! This one bedroom villa boasts everything you will need to make it your home away from home. You can choose to take part in all Orlando has to offer or just relax and enjoy all the amenities the neighborhood encompasses. The pool area has splashpad for kids, adult pool and hot tub. We are a gated family friendly community with walmart and Target nearby along with many, many other shops and restaurants including a Tanger outlets.

Aug 27 – Sep 3

G$23,028 GYD per night

Guest favorite

Condo in Kissimmee

4.9 out of 5 average rating, 179 reviews

Perfect Condo | Pool & Tiki Bar | 15 min. Disney

Perfect Space! Perfect Vibe! Perfect location! Perfect Price! Very close to DISNEY and H2O WATER PARK. Conveniently located in the gated Windsor Palms resorts with lots of restaurants and activities nearby. Tastefully furnished, top floor, two-bedrooms / two-bathrooms condominium (Quiet 3rd-floor unit). Included high-speed internet allows you to work while you are away. If you have a bigger party, check my other condo in the building by looking at Airbnb.com rooms/52778689

May 12 – 19

G$22,089 GYD per night

Guest favorite

Condo in Kissimmee

4.96 out of 5 average rating, 136 reviews

55B-DISNEY-STAR ISLAND, 1 BR DELUX-TENNIS/POOL/SPA

Parking & resort fees included. An Orlando Adventure with All the Extras. Star Island, a 5 star resort located Just 10 minutes from Walt Disney World®, offers so many fun on-site amenities and activities, it actually rivals the magic of Orlando itself. Enjoy the resort at a fraction of the cost of the parks. 2 pools, SPA's, Fitness center, Golf-Driving range, Tennis Courts, Basketball Courts, Pickle Ball courts, Volleyball courts, Water sports, Pool Bar, Ping Pong, Game Room.

May 1 – 8

G$21,806 GYD per night

Guest favorite

Condo in Kissimmee

4.99 out of 5 average rating, 152 reviews

Bright, Airy Home near Disney and Attractions

This top floor condo with tall ceilings is lofty, elegant, and fresh and it is located in one of the nicest communities in the area. Reunion is an oversized, private golfing resort that is exceptionally pristine, safe and quiet. It is situated only minutes from the Disney front gates and offers a welcoming retreat after a long day at the parks. Reunion is home to six beautiful pools that are accessible to all guests and the scenic views of three award winning golf courses.

Aug 12 – 19

G$30,096 GYD per night

Guest favorite

Condo in Kissimmee

4.94 out of 5 average rating, 109 reviews

Cheery 2BR Condo w/zero entry pool near Disney

Ideal location 15 minutes from Disney yet removed from the melee! **New Dishwasher** Second floor condo with fully equipped kitchen in gated community. Free WIFI and parking. Everything you need to have a magical Orlando holiday! King master bedroom, 2 twin beds in second bedroom, a queen sofa bed in living room. Private screened balcony facing lake to enjoy a tranquil moment. Community zero-entry pool, fitness center, game room, sports courts. Smoke and pet free.

Oct 14 – 21

G$19,769 GYD per night

Guest favorite

Condo in Kissimmee

4.94 out of 5 average rating, 159 reviews

Like Home Family Getaway

Awesome place for families. Just a few Miles from all Disney parks with no more than a 15-20 minute drive depending on the park. Also close by is a Super Target, Publix, and Walmart for shopping. Not to mention the countless restaurants all within a few minutes drive. Also some gift shops and miniature golf very close by. Come get away, but have the luxury of feeling like you’re at home.

Dec 5 – 12

G$19,048 GYD per night

Guest favorite

Condo in Kissimmee

4.89 out of 5 average rating, 136 reviews

2BD/2BA condo close to Disney at Storey Lake #96

An amazing lake-view vacation condo for you to relax and spend time with your family and friends. With the prime location in Kissimmee near Disney World, major parks and restaurants, shops and so much more, this 2BD/2BA condo unit is designed for your best family vacation.

Nov 12 – 19

G$26,948 GYD per night