Cottage
10.0(135 Reviews)
1 Bedroom
2 Guests
Parking
Pool
Balcony/Terrace
View
R3,432/Night
7 Nights - R24,033
Smith's Winter Rentals & Holiday Homes
Discover winter rentals Smith's - We found 40 exact matches
- Up-front pricing
- No markup
- Trusted partners
Compare Winter Rental in Smith's
10.0
Apartment
9.5(15 Reviews)
2 Bedrooms
4 Guests
Oceanfront
Breakfast
EV Charge Station- Parking
R6,662/Night
7 Nights - R46,634
R23,084/Night
7 Nights - R161,588
Apartment
10.0(117 Reviews)
1 Bedroom
2 Guests
Private Pool- Parking
- Pool
Ocean View
R5,615/Night
7 Nights - R39,306
House
10.0(18 Reviews)
8 Bedrooms
16 Guests
- Private Pool
- Oceanfront
Hot Tub- Parking
R82,902/Night
7 Nights - R580,314
Resort
8.5(97 Reviews)
24 Guests
Private Beach- Oceanfront
- Hot Tub
- Breakfast
R6,262/Night
7 Nights - R43,836
Cottage
10.0(18 Reviews)
1 Bedroom
6 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
R6,593/Night
7 Nights - R46,151
Cottage
10.0(13 Reviews)
5 Bedrooms
18 Guests
- Oceanfront
- Hot Tub
- Parking
- Ocean View
R27,510/Night
7 Nights - R192,566
Villa
10.0(11 Reviews)
5 Bedrooms
9 Guests
- Parking
- Pool
- Balcony/Terrace
Kitchen
R58,176/Night
7 Nights - R407,234
House
10.0(4 Reviews)
4 Bedrooms
8 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
R68,788/Night
7 Nights - R481,516
House
10.0(4 Reviews)
3 Bedrooms
6 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
R33,250/Night
7 Nights - R232,755
House
10.0(4 Reviews)
3 Bedrooms
6 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
R5,778/Night
7 Nights - R40,439
House
10.0(1 Review)
3 Bedrooms
6 Guests
- Oceanfront
- Hot Tub
- Parking
- Ocean View
R18,405/Night
7 Nights - R128,827
House
10.0(1 Review)
3 Bedrooms
6 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
R17,983/Night
7 Nights - R125,879
House
9.8(141 Reviews)
3 Bedrooms
7 Guests
- Parking
- Balcony/Terrace
- Kitchen
Air Conditioner
R7,722/Night
7 Nights - R54,062
Villa
9.8(12 Reviews)
5 Bedrooms
10 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
R31,078/Night
7 Nights - R217,549
Apartment
9.6(27 Reviews)
1 Bedroom
3 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
R3,956/Night
7 Nights - R27,697
Apartment
9.2(15 Reviews)
2 Bedrooms
4 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
R4,606/Night
7 Nights - R32,244
Apartment
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
R13,259/Night
7 Nights - R92,819
New
Apartment
1 Bedroom
3 Guests
- Air Conditioner
Internet
Child Friendly
Laundry
R4,189/Night
7 Nights - R29,330
Apartment
10.0(89 Reviews)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
R2,165/Night
7 Nights - R15,156
Cottage
10.0(48 Reviews)
1 Bedroom
2 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
R1,615/Night
7 Nights - R11,309
House
10.0(1 Review)
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
R8,426/Night
7 Nights - R58,976
About Smith's Winter Rental on Casai.co.za
Craving a winter escape in the enchanting locales of the Mediterranean or the Caribbean? Explore 40 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.
Frequently Asked Questions About Smith's Winter Rentals
What are the top rated Winter Rentals in Smith's?
There are a lot of options in Smith's. If you plan on staying in the Smith's area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Smith's:
- Grotto Bay Beach Resort
- Beautiful Water Front Property - Snorkel, Fish, or RELAX in the BEST LOCATION!
- Stunning Waterfront Vacation Rental with Amazing View
- Chateau Getaway 2 Bermy Style SLEEPS 2 1 Bed/Bath
- Chateau Getaway Bermy Style -SLEEPS 4- 2 Bed1 Bath
- deleted from vrbo
- Private Apartment in the Heart of Tucker's Town; Walk to Beach!
- Sunset Paradise Oceanview 1Bedroom Lower Apartment Near Beaches & Railway Trail
- Coral Sea private beachfront oasis
- ROSEWOOD BERMUDA GOLF VILLA NEW YEARS WEEK AVAILABLE
How much does it cost to rent a place to stay near Smith's in the wintertime?
The average cost for winter rentals in Smith's is $999 per night. Casai has a wide list of great winter places to stay near Smith's that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Are there any winter cottages/chalets in Smith's that allow pets?
Yes, here are the top cottage/chalet rentals in Smith's that allow you to bring your pet or dog:
- Pool House Studio In A Garden Setting + EV chargers
- Frognal Apartment
- Rosewood Bermuda
- Water Front property with great views, pool, use of Kayaks, & strong Wi-Fi.
See all pet-friendly vacation rentals in Smith's on Casai.co.za
Do you have any winter rentals in Smith's that are suitable for families?
Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Smith's to find what works for you.
Are there winter accommodations in Smith's that have indoor swimming pools?
As of 2026, the data from Casai.co.za shows that there are over 40 private swimming pools or indoor pools accommodations near Smith's along with other great amenities.
Do any winter holiday rentals in Smith's have hot tubs?
About 40 holiday rentals in Smith's boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:
Are there luxury winter rentals in Smith's?
Yes, there are many luxury places to stay in Smith's for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Smith's with all the best amenities for your next trip.
