Apartment
10.0(29 Reviews)
1 Bedroom
2 Guests
Parking
Ocean View
Balcony/Terrace
View
CA $112/Night
7 Nights - CA $783
St. Michael, BB Winter Rentals & Holiday Homes
Discover winter rentals St. Michael - We found 87 exact matches
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Compare Winter Rental in St. Michael
10.0
CA $1,817/Night
7 Nights - CA $12,719
CA $499/Night
7 Nights - CA $3,493
Apartment
10.0(16 Reviews)
2 Bedrooms
4 Guests
Oceanfront- Parking
Pool- Ocean View
CA $954/Night
7 Nights - CA $6,677
CA $429/Night
7 Nights - CA $3,005
Apartment
10.0(11 Reviews)
2 Bedrooms
5 Guests
- Parking
- Ocean View
- View
Kitchen
CA $355/Night
7 Nights - CA $2,488
Apartment
10.0(7 Reviews)
3 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
CA $1,553/Night
7 Nights - CA $10,871
Condo
10.0(6 Reviews)
3 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
CA $1,280/Night
7 Nights - CA $8,960
Condo
10.0(5 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
CA $592/Night
7 Nights - CA $4,144
Apartment
10.0(3 Reviews)
3 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
CA $1,343/Night
7 Nights - CA $9,402
House
10.0(3 Reviews)
4 Bedrooms
11 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
CA $445/Night
7 Nights - CA $3,114
Apartment
10.0(3 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
CA $301/Night
7 Nights - CA $2,103
Condo
10.0(2 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
CA $1,007/Night
7 Nights - CA $7,046
House
10.0(2 Reviews)
2 Bedrooms
4 Guests
Hot Tub- Parking
- Kitchen
Internet
CA $311/Night
7 Nights - CA $2,180
Apartment
10.0(1 Review)
3 Bedrooms
6 Guests
Private Pool- Oceanfront
- Parking
- Pool
CA $3,162/Night
7 Nights - CA $22,135
Condo
10.0(1 Review)
3 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
CA $1,373/Night
7 Nights - CA $9,614
Villa
10.0(1 Review)
4 Bedrooms
8 Guests
- Private Pool
- Parking
- Pool
- Ocean View
CA $1,295/Night
7 Nights - CA $9,067
Condo
10.0(1 Review)
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
CA $1,133/Night
7 Nights - CA $7,930
Apartment
10.0(1 Review)
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
CA $999/Night
7 Nights - CA $6,995
Condo
10.0(1 Review)
1 Bedroom
4 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
CA $253/Night
7 Nights - CA $1,768
Condo
9.8(15 Reviews)
3 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
CA $1,381/Night
7 Nights - CA $9,663
Condo
9.8(8 Reviews)
3 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
CA $1,802/Night
7 Nights - CA $12,614
Apartment
9.8(6 Reviews)
3 Bedrooms
7 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
CA $1,082/Night
7 Nights - CA $7,578
House
9.6(15 Reviews)
3 Bedrooms
6 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
CA $273/Night
7 Nights - CA $1,909
About St. Michael Winter Rental on Casai.ca
Craving a winter escape in the enchanting locales of the Mediterranean or the Caribbean? Explore 87 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 St. Michael Winter Rentals
What are the top rated Winter Rentals in St. Michael?
There are a lot of options in St. Michael. If you plan on staying in the St. Michael area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in St. Michael:
- Contemporary Beachfront Condo - Allure 403
- Cozy Corner - Vacation Rental in Beautiful Barbados
- Spacious 3-bedroom, 3 1/2 bathroom house with WiFi and AC in lovely Bridgetown.
- Exceptional Beachfront Condo - Allure 301 (2 bed)
- Twin Palm, on the Beach, Garden Apartment
- Large 2-bed townhouse with shared pool
- Beautiful Barbados Property On the Beach. No Driving, No Packing Up.
- Modern Two Bedroom Apartment located in Historic Area of Bridgetown, Barbados
- Cozy comfortable one bedroom apartment with all the comforts of home.
- Eco-friendly Hummingbird Apartment
How much does it cost to rent a place to stay near St. Michael in the wintertime?
The average cost for winter rentals in St. Michael is $638 per night. Casai has a wide list of great winter places to stay near St. Michael that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Are there any winter cottages/chalets in St. Michael that allow pets?
Yes, here are the top cottage/chalet rentals in St. Michael that allow you to bring your pet or dog:
- Almond Palm Apartment
- Tantalus Villa
- Hilton Barbados Resort
- Stunning New Luxury Beachfront Condo - Allure 202
See all pet-friendly vacation rentals in St. Michael on Casai.ca
Do you have any winter rentals in St. Michael that are suitable for families?
Most of our rentals homes are suitable for families. Check out the complete list of places to stay in St. Michael to find what works for you.
Are there winter accommodations in St. Michael that have indoor swimming pools?
As of 2026, the data from Casai.ca shows that there are over 87 private swimming pools or indoor pools accommodations near St. Michael along with other great amenities.
Do any winter holiday rentals in St. Michael have hot tubs?
About 87 holiday rentals in St. Michael boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:
Are there luxury winter rentals in St. Michael?
Yes, there are many luxury places to stay in St. Michael for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near St. Michael with all the best amenities for your next trip.
