Marthas Vineyard Cottages - Vacation Rentals in Osceola County

New cottage retreat in St. Cloud with WiFi, AC. From US $122
         

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

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

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10.0 (3 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pool
5 miles from Disney & Universal! From US $164
         

10.0 (13 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pool
"Peachy Keen" 3BD Pool & Spa Cottage Near Disney From US $473
         

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

10.0 (2 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
5 Bed Cottage Close to Disney From US $347
         

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 From US $312
         

Amazing villa close to Disney with 5* Reviews From US $336
         

10.0 (280 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Osceola County

Over 7308+ Pet-Friendly Vacation Rentals in or Near Osceola County
Elegant, Spacious Townhome within 4 Miles to Walt Disney World From US $230
         

Tuscana Resort Orlando by Aston From US $99
         

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

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

Large Vacation Homes & Villas in Osceola County

Over 28319+ Large Vacation Homes & Villas in or Near Osceola County
Champions Gate Oasis, 4BR Vacation Haven From US $421
         

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

Wheelchair Accessible Vacation Homes in Osceola County

Over 4208+ Wheelchair Accessible Vacation Homes in or Near Osceola County
Vacation Meadows - Storey Lake By Shine Villas 710 2 Bedroom Apts From US $576
         

Style, Luxury & Stunning Views, Star Wars From US $253
         

10.0 (100 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
5 STAR TOP FLOOR CONDO WITH AMAZING GOLF VIEWS! From US $155
         

10.0 (89 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Attractive 3 bed townhome close to Disney parks From US $255
         

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

Over 9835+ Osceola County Vacation Rentals and Airbnb Places to Stay Under $200
Cozzy Townhouse! 925PTC-SVH From US $100
         

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

RLR2Disney #2! (3 Turns To Disney) From US $173
         

9.8 (88 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool

Instantly Bookable Vacation Homes in Osceola County

Over 30984+ Instantly Bookable Vacation Homes in or Near Osceola County
WINNER:TOP VACATION RENTAL , CERTIFICATE OF EXCELLENCE From US $202
         

About Osceola County Vacation Rentals

With more than 671 Osceola County vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Marthasvineyardcottages 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 Marthasvineyardcottages 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 1265.85 ft² on average, with prices averaging US $530 a night.

Marthasvineyardcottages 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 451
Vacation Homes 205
Resorts 7
Holiday Apartments 4
Villas 4

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

Pro Tip: Marthasvineyardcottages makes it easy to compare the best listings on Marthasvineyardcottages homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Marthasvineyardcottages 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 671 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.