Big Pine Resort Cottages - Vacation Rentals in Osceola County

New cottage retreat in St. Cloud with WiFi, AC. in St. Cloud From US $171
         

10.0 (32 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • TV
Lovely Margaritaville Cottage, near Attractions in Orlando From US $120
         

8.0 (1 Review)
House
  • Air Conditioner
  • Balcony/Terrace
  • Breakfast
Lakeview Home w/Private Pool & Free Water Park! in Kissimmee From US $640
         

|
10.0 (3 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pool
5 miles from Disney & Universal! in Kissimmee From US $157
         

10.0 (13 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pool
"Peachy Keen" 3BD Pool & Spa Cottage Near Disney in Kissimmee From US $465
         

10.0 (9 Reviews)
Cottage
  • Air Conditioner
  • Pet Friendly
  • Pool
Margaritaville Heated Pool &Spa, 3 mile to Disney in Kissimmee From US $794
         

10.0 (2 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
5 Bed Cottage Close to Disney in Four Corners From US $358
         

10.0 (2 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • TV

Luxury Places to Stay in Osceola County

Over 10000+ Luxury Places to Stay in or Near Osceola County

Top-Rated Vacation Rentals with a Pool in Osceola County

Over 10000+ Top-Rated Vacation Rentals with a Pool in or Near Osceola County
Water View - Pool & Spa - 3.5 miles to Disney - BBQ in Kissimmee From US $313
         

Amazing villa close to Disney with 5* Reviews in kissimmee From US $365
         

10.0 (283 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Osceola County

Over 7376+ Pet-Friendly Vacation Rentals in or Near Osceola County
Elegant, Spacious Townhome within 4 Miles to Walt Disney World in Kissimmee From US $237
         

Tuscana Resort Orlando by Aston in Kissimmee From US $99
         

|
7.7 (804 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Willow Bend in Kissimmee From US $623
         

|
10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Osceola County

Over 28475+ Large Vacation Homes & Villas in or Near Osceola County
Champions Gate Oasis, 4BR Vacation Haven in Davenport From US $421
         

|
10.0 (3 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool

Wheelchair Accessible Vacation Homes in Osceola County

Over 4363+ Wheelchair Accessible Vacation Homes in or Near Osceola County
Fireworks @ Night -storey Lake By Shine Villas 709 2 Bedroom Apts in Kissimmee From US $507
         

Style, Luxury & Stunning Views, Star Wars in Reunion From US $256
         

10.0 (100 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
5 STAR TOP FLOOR CONDO WITH AMAZING GOLF VIEWS! in Kissimmee From US $156
         

10.0 (91 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Renovated Townhome at Reunion, 6 Miles to Disney! in Kissimmee From US $229
         

Osceola County Vacation Rentals and Airbnb Places to Stay Under $200

Over 9967+ Osceola County Vacation Rentals and Airbnb Places to Stay Under $200
Cozzy Townhouse! 925PTC-SVH in Kissimmee From US $100
         

|
New
House
  • Air Conditioner
  • Parking
  • Balcony/Terrace
Elegant Villa W/private Pool/spa & Game Room! in Kissimmee From US $190
         

Instantly Bookable Vacation Homes in Osceola County

Over 31198+ Instantly Bookable Vacation Homes in or Near Osceola County
WINNER:TOP VACATION RENTAL , CERTIFICATE OF EXCELLENCE in Kissimmee From US $201
         

About Osceola County Vacation Rentals

With more than 681 Osceola County vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Bigpineresortcottages and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Osceola County.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Bigpineresortcottages Osceola County, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Osceola County. Places to stay near Osceola County are 1257.25 ft² on average, with prices averaging US $514 a night.

Bigpineresortcottages makes it easy and safe to find and compare vacation rentals in Osceola County with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Osceola County

Type Count
Cottages 459
Vacation Homes 207
Resorts 7
Holiday Apartments 4
Villas 4

Use these Quick Filters to Find a Vacation Rental in Osceola County

Pro Tip: Bigpineresortcottages makes it easy to compare the best listings on Bigpineresortcottages homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Bigpineresortcottages homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Osceola County.

Weather in Osceola County

View the weather forecast for Osceola County before booking your Osceola County Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Osceola County Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Osceola County?
How many vacation rentals are available in Osceola County?

Currently, the total number of properties listed in 2026 is over 681 in the Osceola County area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Osceola County.