Discover the magic of Osceola County, a captivating locale in Florida. Known for its exceptional cottages, the region offers 36,532 options to make your stay unforgettable.

Osceola County offers cottages that cater to a variety of tastes and budgets. With prices ranging from $39 to $20,000, you can customize your experience to match your lifestyle. Look forward to amenities such as Air conditioner, ensuring a memorable stay.

Top Features: Air conditioner, Kitchen / Kitchenette, Internet / Wifi, Pool and Parking

Local Highlights:

Ready to explore the wonders of Osceola County? Book your cottages today and dive into the unique experiences that Florida has to offer.

Top Cottages in Osceola County

Exterior
4.5
Excellent(105 Reviews)
Cottage
 in Kissimmee
Private Cottage 10 Minutes To Disney And 15 To Universal! In- house laundry!!
2 guests · 1 bedroom · 1 bath
Pool · Pets allowed · Kitchen / Kitchenette

When traveling to Osceola County, if you are looking for (business stays, family stays, couples stay, getaway vacation, etc.) this is the perfect place at $83 per night.

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Exterior
4.5
Excellent(68 Reviews)
Cottage
 in Kissimmee
Sweet 2 Bed Vacation Cottage in Sherwood Forest Resort 3 Miles to Disney World
4 guests · 2 bedrooms · 1 bath
Garden · Pool · Pets allowed

This Cottage for $85 in Osceola County, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

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Property grounds
5.0
Outstanding(48 Reviews)
Cottage
 in Lake Wales
Cottage w/ Private Pool - Walk to Lake Wales!
4 guests · 2 bedrooms · 2 baths
Garden · Pool · Kitchen / Kitchenette

Soak up the beauty of Osceola County in our Cottage, Cottage w/ Private Pool - Walk to Lake Wales!. With a range of amenities such as Air conditioner, Internet / Wifi and Laundry, you'll feel right at home.

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Pool
5.0
Outstanding(4 Reviews)
Cottage
 in Kissimmee
Private Pool Home W/themed Rooms+ Free Water Park!
Pool · Kitchen / Kitchenette · Air conditioner

Are you ready to indulge in a relaxing getaway? Our Cottage in Osceola County has everything you need for a rejuvenating stay. Treat yourself to Private Pool Home W/themed Rooms+ Free Water Park!'s exceptional amenities, such as Air conditioner, Dishwasher and Internet / Wifi.

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Pool
4.9
Outstanding(42 Reviews)
Cottage
 in Kissimmee
Gorgeous Cottage w/Private Pool + Balcony, Near Disney!
6 guests · 2 bedrooms · 2 baths
Pool · Kitchen / Kitchenette · Air conditioner

Looking for a memorable stay in Osceola County? Our Cottage might just be what you're looking for. Enjoy amenities including Air conditioner, Dishwasher and Internet / Wifi, and more during your stay.

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Property view
5.0
Outstanding(33 Reviews)
Cottage
 in Lake Wales
Cottage w/ Private Pool - Walk to Lake Wales!
4 guests · 2 bedrooms · 2 baths
Garden · Pool · Kitchen / Kitchenette

Looking for a business stay, family stay, couples stay, getaway vacation, or traveling to Osceola County, at $150 per night for your next great vacation.

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Exterior
5.0
Outstanding(26 Reviews)
Cottage
 in Kissimmee
Margaritaville 2BD Cottage near Hotel & Disney
6 guests · 3 bedrooms · 3 baths
Pool · Pets allowed · Kitchen / Kitchenette

When traveling to Osceola County, if you are looking for (business stays, family stays, couples stay, getaway vacation, etc.) this is the perfect place at $237 per night.

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Fridge, microwave, stovetop, coffee/tea maker
4.9
Outstanding(26 Reviews)
Cottage
 in Babson Park
Lakeview Cottage Escape. Close to BOK Tower Gardens, Legoland and Disney
4 guests · 2 bedrooms · 1 bath
Kitchen / Kitchenette · Air conditioner · Internet / Wifi

Experience the best of Osceola County with this Cottage available for $109. This property is equipped with amenities including Air conditioner, Internet / Wifi and Balcony / Patio, and more.

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Exterior
4.8
Outstanding(23 Reviews)
Cottage
 in Kissimmee
Contemporary Home w/ Hot Tub: 4 Mi to Disney Magic
9 guests · 4 bedrooms · 3 baths
Garden · Kitchen / Kitchenette · Air conditioner

This attractive Cottage in Osceola County, $121 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

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Exterior
5.0
Outstanding(17 Reviews)
Cottage
 in Kissimmee
1BD Margaritaville - Island-Inspired Cottage minutes from Disneyworld
4 guests · 2 bedrooms · 1 bath
Pool · Pets allowed · Kitchen / Kitchenette

Looking to create some memories in Osceola County? Look no further than our Cottage, 1BD Margaritaville - Island-Inspired Cottage minutes from Disneyworld. Enjoy top-rated amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
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Exterior
4.8
Outstanding(18 Reviews)
Cottage
 in Kissimmee
Kiwi Cottage near Disney - 4 Bd/4 Bath w/ Private Pool & Hot Tub
11 guests · 4 bedrooms · 4 baths
Pool · Kitchen / Kitchenette · Air conditioner

Enjoy the best of Osceola County in our Cottage, Kiwi Cottage near Disney - 4 Bd/4 Bath w/ Private Pool & Hot Tub. A stunning property with amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
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Pool
4.5
Excellent(21 Reviews)
Cottage
 in Kissimmee
Cozy Margaritaville Cottage w/Private Pool, Near Disney& Universal!
6 guests · 2 bedrooms · 2 baths
Pool · Kitchen / Kitchenette · Air conditioner

Looking for a memorable stay in Osceola County? Our Cottage might just be what you're looking for. Enjoy amenities including Air conditioner, Dishwasher and Internet / Wifi, and more during your stay.

$$$$
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Vacation rentals with air conditioning in Osceola County

Property view
5.0
Outstanding(1 Review)
Cottage
 in Kissimmee
Kissimmee Cottage w/ Resort-Style Amenities!
4 guests · 1 bedroom · 1 bath
Pool · Pets allowed · Kitchen / Kitchenette

Experience the best of Osceola County with this Cottage available for $95. This property is equipped with amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
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Pool
4.3
Excellent(19 Reviews)
Cottage
 in Kissimmee
Beach-Chic, Margaritaville Cottage w/ Private Pool!
12 guests · 5 bedrooms · 5 baths
Pool · Kitchen / Kitchenette · Air conditioner

This Cottage for $225 in Osceola County, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
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1 bedroom, iron/ironing board, travel crib, free WiFi
4.9
Outstanding(12 Reviews)
Cottage
 in Kissimmee
Jedi cottage 4 miles from Disney! Mins from universal!
4 guests · 1 bedroom · 1 bath
Pool · Kitchen / Kitchenette · Air conditioner

Looking for the perfect place to call home during your trip to Osceola County? This Cottage offers a comfort and style with top-notch amenities, including Air conditioner, Internet / Wifi and Laundry, and more.

$$$$
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Property grounds
5.0
Outstanding(10 Reviews)
Cottage
 in Kissimmee
4 miles from Disney 4 Star Resort! Location Location ! The Hidden Gem Tiny Home
6 guests · 2 bedrooms · 1 bath
Pool · Pets allowed · Kitchen / Kitchenette

Looking for a Cottage in Osceola County, this Cottage for $105 per night for your business stay, family stay, couples stay, getaway vacation, on your next trip.

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Smart TV, books, stereo
4.6
Outstanding(11 Reviews)
Cottage
 in Kissimmee
Enchanted Cottage with Pool and Mini-Golf Near Disney
3 guests · 1 bedroom · 1 bath
Garden · Pool · Pets allowed

Looking to create some memories in Osceola County? Look no further than our Cottage, Enchanted Cottage with Pool and Mini-Golf Near Disney. Enjoy top-rated amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
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Property view
4.6
Outstanding(11 Reviews)
Cottage
 in Kissimmee
Orlando Vacation Cottage near Disney
6 guests · 2 bedrooms · 1 bath
Pool · Kitchen / Kitchenette · Air conditioner

Cottage in Osceola County, for $90 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)

$$$$
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Exterior
4.8
Outstanding(8 Reviews)
Cottage
 in Lake Wales
Country Cottage at Starr Lake - Sleeps 4
4 guests · 1 bath
Garden · Pool · Kitchen / Kitchenette

Experience the best of Osceola County with this Cottage available for $102. This property is equipped with amenities including Air conditioner, Internet / Wifi and Kitchen / Kitchenette, and more.

$$$$
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Exterior
4.5
Excellent(8 Reviews)
Cottage
 in Kissimmee
Gorgeous Margaritaville Cottage w/Private Patio!
7 guests · 3 bedrooms · 3 baths
Kitchen / Kitchenette · Air conditioner · Internet / Wifi

Experience vacation in Osceola County with our Cottage, Gorgeous Margaritaville Cottage w/Private Patio!. Enjoy amenities such as Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
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2 bedrooms, WiFi
5.0
Outstanding(6 Reviews)
Cottage
 in Lake Hamilton
Luxury Cottage Near Legoland & Chain of Lakes
4 guests · 2 bedrooms · 1 bath
Air conditioner · Internet / Wifi · Parking

This Cottage for $119 in Osceola County, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
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Exterior
4.0
Good(9 Reviews)
Cottage
 in Kissimmee
Cozy Tiny Home Near Disney World & Orlando Parks!
6 guests · 1 bedroom · 1 bath
Pool · Kitchen / Kitchenette · Air conditioner

Looking for the perfect place to call home during your trip to Osceola County? This Cottage offers a comfort and style with top-notch amenities, including Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
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TV
4.3
Excellent(6 Reviews)
Cottage
 in Kissimmee
Disney, Universal and Legoland Getaway
6 guests · 2 bedrooms · 1 bath
Pool · Kitchen / Kitchenette · Air conditioner

Soak up the beauty of Osceola County in our Cottage, Disney, Universal and Legoland Getaway. With a range of amenities such as Air conditioner, Internet / Wifi and Laundry, you'll feel right at home.

$$$$
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Exterior
4.6
Outstanding(5 Reviews)
Cottage
 in Kissimmee
The Compass Cottage: A Cheerful 1 Bed / 1 Bath
3 guests · 1 bedroom · 1 bath
Garden · Pool · Kitchen / Kitchenette

Experience the best of Osceola County with this Cottage available for $75. This property is equipped with amenities including Air conditioner, Internet / Wifi and Laundry, and more.

$$$$
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Pool
4.6
Outstanding(5 Reviews)
Cottage
 in Kissimmee
Sunny Margaritaville Cottage - Private Pool, Full Kitchen & Living Area
6 guests · 2 bedrooms · 2 baths
Garden · Pool · Kitchen / Kitchenette

When traveling to Osceola County, if you are looking for (business stays, family stays, couples stay, getaway vacation, etc.) this is the perfect place at $195 per night.

$$$$
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