Luxury Maui Rentals - Vacation Rentals in Osceola County

Diamond Lake Waterfront Cabin with Deck and Dock! From US $572
         

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10.0 (2 Reviews)
House
  • Parking
  • Accessibility
  • Security/Safety
Osceola Grand Hotel From US $105
         

8.0 (367 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Vacation at Big Lake From US $170
         

9.6 (105 Reviews)
Cottage
  • Parking
  • TV
  • View
Wilderness Retreat & Cross-Country Ski Center! From US $350
         

10.0 (5 Reviews)
House
  • Air Conditioner
  • Parking
  • Balcony/Terrace
Cozy cabin in the woods From US $150
         

10.0 (104 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • Pet Friendly
Diamond Lake Waterfront Cabin w/Deck + Dock! From US $292
         

10.0 (78 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • TV
Maple Lane Lake House From US $315
         

10.0 (61 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • Balcony/Terrace

Luxury Places to Stay in Osceola County

Over 110+ Luxury Places to Stay in or Near Osceola County
The Lodge at Meemo's Farm & Retreat From US $2,285
         

10.0 (3 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • TV
Lakeside Lodge Retreat From US $1,063
         

New
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Two Riverfront Homes | Hot Tub, Sauna, Kayaks + More From US $987
         

Lake Lure Family Retreat From US $707
         

9.6 (10 Reviews)
House
  • Air Conditioner
  • TV
  • View
Hersey River Retreat From US $621
         

New
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Riverfront Retreat | Fire, Sunroom, Kayaks, Tubes From US $582
         

Lakeside Retreat | Hot Tub, Kayak, Arcade, Pontoon From US $562
         

Top-Rated Vacation Rentals with a Pool in Osceola County

Over 3+ Top-Rated Vacation Rentals with a Pool in or Near Osceola County
Osceola Grand Hotel From US $129
         

7.5 (235 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Rose Lake Shores Cottage From US $409
         

New
Cottage
  • Air Conditioner
  • Pool
  • TV

Pet-Friendly Vacation Rentals in Osceola County

Over 40+ Pet-Friendly Vacation Rentals in or Near Osceola County
Remodeled 3BR 2BA Beachfront Cottage, Pet Friendly. All-Sports Lakefront From US $263
         

Wildlife Haven Retreat From US $233
         

10.0 (2 Reviews)
House
  • Parking
  • Pet Friendly
  • View
Gabriel`s Cabin in the Woods From US $120
         

10.0 (16 Reviews)
Cabin
  • Parking
  • Pet Friendly
  • Balcony/Terrace
Luxury Glamping Yurt with Loft, Wood-Fired Hot Tub From US $111
         

10.0 (9 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • Pet Friendly
Keefer Cabin on the Hersey Creek From US $136
         

10.0 (7 Reviews)
Cabin
  • Parking
  • Pet Friendly
  • Balcony/Terrace
Modern Riverfront Chalet w/Firepit & Hot Tub From US $327
         

10.0 (3 Reviews)
Ski Chalet
  • Air Conditioner
  • Parking
  • Pet Friendly
Riverfront | Hot Tub, Fireplace, Kayaks & Tubes From US $352
         

9.8 (17 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Osceola County

Over 29+ Large Vacation Homes & Villas in or Near Osceola County
Custom Log Cabin with Deck and 45 Acres By Pine River! From US $352
         

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10.0 (2 Reviews)
House
  • Parking
  • Accessibility
  • Security/Safety
Rustic Tustin Cabin on 7 Acres w/Fire Pit & Porch From US $471
         

9.8 (84 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • TV
Custom Log Cabin w/Deck & 45 Acres By Pine River! From US $329
         

9.4 (33 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • TV
A-Frame | Hot Tub, Fireplace, River, Kayaks &Tubes From US $513
         

9.2 (20 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • Pet Friendly
Secluded | Sauna, Fire Pit & 20 Acres of Trails From US $330
         

9.2 (7 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • Pet Friendly
Secluded Riverfront Cottage | Sauna, Fire & Kayaks From US $360
         

Waterfront Evart Getaway w/Fire Pit on 82 Acres! From US $411
         

8.2 (10 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • TV

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

Over 36+ Osceola County Vacation Rentals and Airbnb Places to Stay Under $200
Charming Stone Cottage in Marion w/Fire Pit! From US $161
         

10.0 (4 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • TV
Harvest Village From US $126
         

9.0 (1 Review)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Designated Smoking Area
A Peaceful Escape for Outdoor Enthusiasts From US $188
         

10.0 (2 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • TV
Charming Rose Lake beach house From US $197
         

9.8 (107 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Unplug and kick back! Simple, relaxing cabin on the Clam River. From US $155
         

Instantly Bookable Vacation Homes in Osceola County

Over 39+ Instantly Bookable Vacation Homes in or Near Osceola County
Secluded Tustin Cabin with Fire Pit and Hiking Trails From US $303
         

Brand New Barndominium on 40 Acres with Private Lake From US $207
         

Secluded Yurt Wood-Fired Hot Tub Outdoor Shower From US $120
         

9.4 (13 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • Pet Friendly
Hidden Gem Tiny House, Outdoor Screened-In Kitchen From US $123
         

9.4 (3 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • Pet Friendly
Secluded Luxury Glamping Compound - Wood-Fired Tub From US $357
         

About Osceola County Vacation Rentals

With more than 119 Osceola County vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Luxurymauirentals 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 Luxurymauirentals 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 911.78 ft² on average, with prices averaging $293 a night.

Luxurymauirentals 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
Vacation Homes 51
Cabin Rentals 41
Cottages 17
Others 3
B&B 2
Hotels with Suites 2
Ski Chalet Rentals 2
Holiday Apartments 1

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

Pro Tip: Luxurymauirentals makes it easy to compare the best listings on Luxurymauirentals homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Luxurymauirentals 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 119 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.