Condo Rentals in Osceola County
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A lighthouse at sunset with a calm lake reflecting the structure and palm trees in the foreground.

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Top cities in Osceola County

A large, historic building with a tower, reflecting on a calm lake with lily pads, surrounded by trees and a sunset sky.

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Our top choices for Osceola County condo rentals

A swimming pool with two slides, surrounded by modern buildings and palm trees.

A sign for Orbit One Vacation Villas with a clear view of the surrounding landscaping and palm trees.

A reception desk with a blue accent wall, a framed sign, and a modern design.

A hotel room with a bed, a ceiling fan, a window with curtains, a chair, and a wall-mounted lamp.

1. Orbit One Vacation Villas by Coolvacay

Orbit One Vacation Villas by Coolvacay

3.0 star property

Kissimmee

9.4 out of 10, Exceptional, (1,705 reviews)

9.4/10

Exceptional

(1,705 reviews)

"It was a lovely home away from home, everything we needed was there and around"

Virginia

Orbit One Vacation Villas by Coolvacay

An outdoor patio area with wicker furniture, a fire pit, and a view of a pool and greenery.

A hotel pool area with lounge chairs and umbrellas, surrounded by palm trees and a clear sky.

A modern hotel room with a flat-screen TV, a sofa, a chair, and a large window with a view.

A reception area with a 'Welcome Home' sign, a ceiling fan, and a reception desk with a plant.

2. Parkway International Resort by Coolvacay

Parkway International Resort by Coolvacay

3.0 star property

Kissimmee

9.4 out of 10, Exceptional, (2,634 reviews)

9.4/10

Exceptional

(2,634 reviews)

"Very clean and friendly staff."

ADRIAN

Parkway International Resort by Coolvacay

A living room with a sofa, two armchairs, a coffee table, a TV stand, a ceiling fan, and a large window with a view of greenery.

A dining area with a wooden table set for four, a vase with flowers, and a ceiling fan.

A hotel corridor with a concrete walkway, palm trees, and well-maintained lawns.

A swimming pool with a lifeguard chair, lounge chairs, and a fence.

3. Alhambra Villas by Coolvacay

Alhambra Villas by Coolvacay

3.0 star property

Solivita

9.2 out of 10, Wonderful, (1,032 reviews)

9.2/10

Wonderful

(1,032 reviews)

"Friendly staff,"

Rdhamraj

Alhambra Villas by Coolvacay

A view of a park with a lake, benches, and trees.

A thatched-roof gazebo with a wooden fence, surrounded by white lounge chairs on a sandy area.

A tennis court with a surrounding fence, a palm tree, and a body of water in the background.

A kitchen with white cabinets, a refrigerator, a dishwasher, a microwave, and a dining table with chairs.

4. Lifetime of Vacations Resort

Lifetime of Vacations Resort

3.0 star property

Kissimmee

9.4 out of 10, Exceptional, (186 reviews)

9.4/10

Exceptional

(186 reviews)

"We absolutely love coming to lifetime and grand lake resort. This is our favorite place to stay!!"

Alena

$99 nightly

The price is $111

$111 total

Nov 29 - Nov 30

Total with taxes and fees

Lifetime of Vacations Resort

A modern kitchen with dark wood cabinets, a black microwave, and a built-in oven.

A building with a sign reading "High Point World Resort Welcome Center."

A living room with a sofa, a coffee table, and a TV.

A hotel room with two beds, a ceiling fan, a nightstand with a lamp, and a bathroom with a shower and toilet.

5. High Point World Resort

High Point World Resort

3.5 star property

Kissimmee

8.8 out of 10, Excellent, (178 reviews)

8.8/10

Excellent

(178 reviews)

"everything was perfect and the bed was sooo soft"

Evelyn

High Point World Resort

A large building with a central fountain, surrounded by palm trees and a well-maintained lawn.

A modern living room with a large flat-screen TV mounted on a wooden wall, a grey sofa, a black coffee table, and a world map mural on the wall.

A compact kitchen with a central island, bar stools, a microwave, a refrigerator, and a trash bin.

A swimming pool with a covered area and a building with arched windows and a tower.

6. 3BR/2B condo with views of Disney FIREWORKS!!!!

3BR/2B condo with views of Disney FIREWORKS!!!!

Kissimmee

9.8 out of 10, Exceptional, (56 reviews)

9.8/10

Exceptional

(56 reviews)

"This was a great place for a family of five. We had a great time with plenty of space."

Karen S.

3BR/2B condo with views of Disney FIREWORKS!!!!

An aerial view of a resort with a central swimming pool, sun loungers, palm trees, and a basketball court.

A beach with people swimming and walking along the shore.

A spacious living area with a round table, sofas, and potted plants.

A residential building with a well-maintained lawn, palm trees, and a clear sky.

7. 5 Star Resort minutes from Disney 3 bedrooms & 2 baths, Wi-Fi, Pool, Tennis

5 Star Resort minutes from Disney 3 bedrooms & 2 baths, Wi-Fi, Pool, Tennis

Kissimmee

9.4 out of 10, Exceptional, (103 reviews)

9.4/10

Exceptional

(103 reviews)

"Loved everything about this condo. Very clean, quiet, and 1st floor, can't get much better. We'll definitely stay again"

Philip J.

5 Star Resort minutes from Disney 3 bedrooms & 2 baths, Wi-Fi, Pool, Tennis

An aerial view of a resort with a central swimming pool, tennis courts, and a landscaped area with palm trees.

A two-story building with a central entrance, surrounded by palm trees and a landscaped garden with red and yellow flowers.

An outdoor bar area with wicker furniture and umbrellas, a pool in the background, and palm trees.

A sign for Windsor Palms, a gated resort community.

8. GREAT PRICE! TOP RESORT! On Disney's Doorstep!

GREAT PRICE! TOP RESORT! On Disney's Doorstep!

Kissimmee

9.8 out of 10, Exceptional, (297 reviews)

9.8/10

Exceptional

(297 reviews)

"Wonderful property with great amenities. Anna was a great host. Very responsive. Sad to see our vacation end."

Lisa N.

GREAT PRICE! TOP RESORT! On Disney's Doorstep!

A resort with multiple swimming pools, a large lake, and a well-maintained landscape.

A modern kitchen with white cabinets, a dining area with a wooden table and chairs, a gray sofa, and a ceiling fan.

A modern living room with a sofa, armchairs, a coffee table, and a dining area with a table and chairs. There is a balcony with a view of the outdoors.

A modern kitchen with white cabinetry, a central island with stools, a dining table with chairs, and a coffee machine.

9. Disney-themed bedrooms + sleeps 9 + water view + resort/lazy river

Disney-themed bedrooms + sleeps 9 + water view + resort/lazy river

Kissimmee

10.0 out of 10, Exceptional, (5 reviews)

10/10

Exceptional

(5 reviews)

"We loved our stay. The unit was spacious and comfortable. The balcony felt private and had a nice lake view. We were impressed with how well stocked the unit was, we had everything we needed. The decor had so many fun touches without being cheesy or over the top. The host was great at answering all our questions. We would absolutely book this unit again. "

Emily S.

Disney-themed bedrooms + sleeps 9 + water view + resort/lazy river

A swimming pool with lounge chairs, surrounded by palm trees and a building with a thatched roof.

A living room with a blue sofa, a dining area with a table and chairs, a kitchen with wooden cabinets and a refrigerator, and a ceiling fan.

A reception area with a wooden desk, a reception counter, a seating area with a wicker chair, and a ceiling fan.

A kitchen with wooden cabinets, stainless steel appliances, a dishwasher, and a microwave.

10. Magic Tree Resort by Coolvacay

Magic Tree Resort by Coolvacay

3.0 star property

Kissimmee

9.8 out of 10, Exceptional, (8 reviews)

9.8/10

Exceptional

(8 reviews)

"Great hotel friendly staff definitely would recommend"

Tristen

Magic Tree Resort by Coolvacay

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

View all properties

Top reviews in Osceola County

A beach with a wooden deck and lush greenery in the foreground.

A living room with a sofa, a table, and chairs, a window with a view of the ocean, and a painting on the wall.

A living room with a view of the beach, a sofa, a chair, a small table, and a glass coffee table.

A person working on a laptop at a table with a view of the beach and ocean.

Tuckaway Shores Resort

Indialantic By The Sea

10/10 Excellent

Very relaxing, get the beach view, you will love the sunrises...

mark

Reviewed January 24, 2015Reviewed January 24, 2015

Tuckaway Shores Resort

Lifetime of Vacations Resort

Kissimmee

10/10 Excellent

The kitchen was fully equipped and there were plenty of beds, all of which were comfortable. The grounds are gorgeous! An excellent play are for kids is provided and the pool is huge, and clean. The staff are all friendly and personable. When I return in May, this is where I will stay again. Highly recommend!

Robin

Reviewed March 30, 2026Reviewed March 30, 2026

Lifetime of Vacations Resort

A rooftop pool area with lounge chairs and umbrellas, overlooking a beach and ocean.

A wooden boardwalk leading to a sandy beach with a clear view of the ocean.

A hotel room with a balcony, a television, a sofa, a chair, and a table.

An aerial view of a hotel with multiple buildings, a pool area, and a beach.

Oceanique Resort

Indian Harbour Beach

10/10 Excellent

Cleaners good condición

Miguel

Reviewed September 29, 2022Reviewed September 29, 2022

Oceanique Resort

A resort with a swimming pool, a dock, and a view of the surrounding neighborhood.

A resort with a large swimming pool, lounge chairs, and a view of a large body of water.

An aerial view of a beach with lounge chairs, palm trees, and thatched umbrellas.

A resort with a swimming pool, surrounded by lush greenery and a large body of water.

Bahama Bay 515 Rum run unit 515

Bahama Bay

10/10 Excellent

The apartment is very nice, closed to Disney World resort, while in a quiet community.

Joyce

Reviewed May 19, 2026Reviewed May 19, 2026

Bahama Bay 515 Rum run unit 515

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Search and Rent Osceola County Condos

Bundle & Save

OneKeyCash

Upfront pricing

Top cities in Osceola County

Kissimmee

Find vacation rentals that suit your style

Check prices for these dates

Our top choices for Osceola County condo rentals

1. Orbit One Vacation Villas by Coolvacay

2. Parkway International Resort by Coolvacay

3. Alhambra Villas by Coolvacay

4. Lifetime of Vacations Resort

5. High Point World Resort

6. 3BR/2B condo with views of Disney FIREWORKS!!!!

7. 5 Star Resort minutes from Disney 3 bedrooms & 2 baths, Wi-Fi, Pool, Tennis

8. GREAT PRICE! TOP RESORT! On Disney's Doorstep!

9. Disney-themed bedrooms + sleeps 9 + water view + resort/lazy river

10. Magic Tree Resort by Coolvacay

Top reviews in Osceola County

Tuckaway Shores Resort

10/10 Excellent

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