Cabin
10.0(159 Reviews)
1 Bedroom
6 Guests
Parking
Balcony/Terrace
Kitchen
Air Conditioner
US $501/Night
7 Nights - US $3,509
Hernando County Winter Rentals & Holiday Homes
Discover winter rentals Hernando County - We found 537 exact matches
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Compare Winter Rental in Hernando County
10.0
Villa
10.0(11 Reviews)
3 Bedrooms
8 Guests
- Parking
- Balcony/Terrace
View- Air Conditioner
US $377/Night
7 Nights - US $2,640
Cottage
10.0(5 Reviews)
1 Bedroom
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $216/Night
7 Nights - US $1,512
House
10.0(101 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- View
- Kitchen
US $336/Night
7 Nights - US $2,349
House
10.0(4 Reviews)
3 Bedrooms
8 Guests
- Parking
Pool- Balcony/Terrace
- View
US $334/Night
7 Nights - US $2,336
House
10.0(94 Reviews)
2 Bedrooms
6 Guests
- Parking
Ocean View- Balcony/Terrace
- View
US $317/Night
7 Nights - US $2,221
House
10.0(3 Reviews)
3 Bedrooms
8 Guests
- Parking
- Pool
- Balcony/Terrace
- View
US $252/Night
7 Nights - US $1,764
House
10.0(91 Reviews)
2 Bedrooms
5 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $307/Night
7 Nights - US $2,151
House
10.0(3 Reviews)
3 Bedrooms
8 Guests
Hot Tub- Parking
- Balcony/Terrace
Internet
US $222/Night
7 Nights - US $1,554
House
10.0(79 Reviews)
2 Bedrooms
4 Guests
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
US $213/Night
7 Nights - US $1,491
House
10.0(3 Reviews)
2 Bedrooms
8 Guests
- Parking
- Pool
- Balcony/Terrace
- View
US $275/Night
7 Nights - US $1,925
House
10.0(78 Reviews)
2 Bedrooms
8 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $375/Night
7 Nights - US $2,625
New
House
10.0(2 Reviews)
3 Bedrooms
6 Guests
- Parking
- Pool
- View
- Air Conditioner
US $425/Night
7 Nights - US $2,977
House
10.0(56 Reviews)
2 Bedrooms
6 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $252/Night
7 Nights - US $1,766
House
10.0(45 Reviews)
2 Bedrooms
6 Guests
Private Pool- Parking
- Pool
- Ocean View
US $337/Night
7 Nights - US $2,359
Cottage
10.0(37 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- View
- Kitchen
US $316/Night
7 Nights - US $2,213
House
10.0(37 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $292/Night
7 Nights - US $2,044
House
10.0(28 Reviews)
2 Bedrooms
6 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $207/Night
7 Nights - US $1,449
House
10.0(25 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- View
- Kitchen
US $266/Night
7 Nights - US $1,860
New
House
10.0(24 Reviews)
2 Bedrooms
6 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $317/Night
7 Nights - US $2,218
House
10.0(21 Reviews)
2 Bedrooms
6 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $478/Night
7 Nights - US $3,348
House
10.0(18 Reviews)
2 Bedrooms
5 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $334/Night
7 Nights - US $2,341
House
10.0(17 Reviews)
2 Bedrooms
7 Guests
- Parking
- Balcony/Terrace
- View
- Kitchen
US $227/Night
7 Nights - US $1,586
House
10.0(15 Reviews)
1 Bedroom
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $211/Night
7 Nights - US $1,480
About Hernando County Winter Rental on Casai.nz
Craving a winter escape in the enchanting locales of the Mediterranean or the Caribbean? Explore 537 accommodations for your upcoming winter getaway, whether you're dreaming of azure waters and sun-kissed beaches or charming coastal towns.
At Casai, we present a diverse array of listings for holiday homes and villas nestled in the picturesque landscapes of the Mediterranean and the Caribbean. From luxurious villas overlooking crystal-clear waters to charming holiday homes nestled amidst palm-fringed shores, our curated selection caters to every preference and ensures an unforgettable retreat.
Indulge in the epitome of luxury with our Mediterranean and Caribbean villas, boasting opulent amenities such as private pools, spacious outdoor terraces, serene gardens, and breathtaking ocean views. Whether you're seeking a romantic escape, a family adventure, or a group getaway, our listings offer the perfect blend of comfort and sophistication.
Escape the winter chill and bask in the warmth of the Mediterranean or Caribbean sun. Explore our collection of holiday homes and villas, meticulously curated to provide the ultimate sanctuary for your winter retreat. With Casai, your dream vacation awaits.
Winter Rental: Explore Top Destinations
Frequently Asked Questions About Hernando County Winter Rentals
What are the top rated Winter Rentals in Hernando County?
There are a lot of options in Hernando County. If you plan on staying in the Hernando County area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Hernando County:
- Little House on the River - on main river not canal,includes kayaks,paddle-board
- DIRECT WEEKI WACHEE RIVERFRONT! KEY WEST PARADISE!
- "Like a Tree House" Overlooking the Water
- NATURE LOVERS' RETREAT! RELAX - EXPLORE AT YOUR RIVERSIDE DOOR.
- 🛥️🛥️Boat House in Weeki Wachee-10 minute easy paddle to main river
- Paradise found! Private heated pool+ spa, 3700 sq ft. Near Cobat Citrus farms.
- Amazing Home in Paradise!
- Eagle Nest/Your Private Waterfront Escape on Florida's Nature Coast.
- Pine island - Weeki Wachee Ocean View Home- Walk to Beach on secluded island
- Come Enjoy Sea-renity @ Hernando Beach!
How much does it cost to rent a place to stay near Hernando County in the wintertime?
The average cost for winter rentals in Hernando County is $342 per night. Casai has a wide list of great winter places to stay near Hernando County that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Are there any winter cottages/chalets in Hernando County that allow pets?
Yes, here are the top cottage/chalet rentals in Hernando County that allow you to bring your pet or dog:
- River Run Retreat | Weeki Wachee River Cabin
- Chateau Mariposa
- Spring Hill Home - 3 Mi to Weeki Wachee Springs!
- Beautiful Home Located DIRECTLY ON RIVER!
See all pet-friendly vacation rentals in Hernando County on Casai.nz
Do you have any winter rentals in Hernando County that are suitable for families?
Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Hernando County to find what works for you.
Are there winter accommodations in Hernando County that have indoor swimming pools?
As of 2026, the data from Casai.nz shows that there are over 537 private swimming pools or indoor pools accommodations near Hernando County along with other great amenities.
Do any winter holiday rentals in Hernando County have hot tubs?
About 537 holiday rentals in Hernando County boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:
Are there luxury winter rentals in Hernando County?
Yes, there are many luxury places to stay in Hernando County for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Hernando County with all the best amenities for your next trip.
