House
10.0(44 Reviews)
2 Bedrooms
4 Guests
Parking
Ocean View
Balcony/Terrace
View
US $193/Night
7 Nights - US $1,352
Paynes Bay Winter Rentals & Holiday Homes
Discover winter rentals Paynes Bay - We found 37 exact matches
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Compare Winter Rental in Paynes Bay
10.0
US $153/Night
7 Nights - US $1,073
House
10.0(14 Reviews)
5 Bedrooms
10 Guests
Private Pool- Parking
Pool- Balcony/Terrace
US $877/Night
7 Nights - US $6,141
House
10.0(5 Reviews)
3 Bedrooms
6 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $721/Night
7 Nights - US $5,044
House
10.0(1 Review)
4 Bedrooms
8 Guests
- Private Pool
- Parking
- Pool
- Ocean View
US $2,648/Night
7 Nights - US $18,534
House
10.0(1 Review)
5 Bedrooms
10 Guests
- Private Pool
Hot Tub- Parking
- Pool
US $714/Night
7 Nights - US $5,000
House
10.0(1 Review)
3 Bedrooms
8 Guests
- Hot Tub
- Parking
Kitchen
Air Conditioner
US $403/Night
7 Nights - US $2,823
Apartment
9.4(80 Reviews)
2 Bedrooms
4 Guests
Oceanfront- Parking
- Ocean View
- Balcony/Terrace
US $160/Night
7 Nights - US $1,120
House
9.2(53 Reviews)
3 Bedrooms
6 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $185/Night
7 Nights - US $1,295
Apartment
9.2(24 Reviews)
2 Bedrooms
4 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $192/Night
7 Nights - US $1,344
US $3,475/Night
7 Nights - US $24,325
US $3,405/Night
7 Nights - US $23,836
Villa
6 Bedrooms
12 Guests
- Private Pool
- Hot Tub
Breakfast- Parking
US $2,807/Night
7 Nights - US $19,650
Villa
5 Bedrooms
8 Guests
- Private Pool
- Pool
- Balcony/Terrace
- View
US $1,610/Night
7 Nights - US $11,270
Apartment
1 Bedroom
2 Guests
- Air Conditioner
Internet
Laundry
Barbecue/Outdoor Cooking
US $82/Night
7 Nights - US $571
House
10.0(4 Reviews)
3 Bedrooms
6 Guests
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
US $407/Night
7 Nights - US $2,846
Villa
9.6(8 Reviews)
3 Bedrooms
7 Guests
- Pool
- Ocean View
- Balcony/Terrace
- View
US $312/Night
7 Nights - US $2,184
House
9.0(4 Reviews)
3 Bedrooms
6 Guests
Skiing- Kitchen
- Air Conditioner
- Laundry
US $78/Night
7 Nights - US $543
Villa
5.0(3 Reviews)
7 Bedrooms
12 Guests
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
US $5,500/Night
7 Nights - US $38,500
US $3,500/Night
7 Nights - US $24,500
Condo
5 Bedrooms
10 Guests
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
US $3,252/Night
7 Nights - US $22,764
Villa
6 Bedrooms
12 Guests
- Private Pool
- Hot Tub
- Pool
- Balcony/Terrace
US $3,101/Night
7 Nights - US $21,707
US $3,000/Night
7 Nights - US $21,000
Villa
6 Bedrooms
12 Guests
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
US $2,936/Night
7 Nights - US $20,553
About Paynes Bay Winter Rental on Casai.com
Craving a winter escape in the enchanting locales of the Mediterranean or the Caribbean? Explore 37 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 Paynes Bay Winter Rentals
What are the top rated Winter Rentals in Paynes Bay?
There are a lot of options in Paynes Bay. If you plan on staying in the Paynes Bay area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Paynes Bay:
- Evergreen in Sandy Lane by Personal Villas - Ideal for Families, Beautiful Pool
- Amberley Estate Luxury villa
- Vistamar Luxury villa
- Amberley Estate (4/6 Rooms)
- Impressive 4 bedroom villa with large private pool
- Buttsbury House Luxury villa
- Escape to a delightful spacious family villa in Saint James
- Buttsbury House (4/5 Rooms)
- Escape to a delightful spacious family villa in Saint James
- Life's a Beach by The Villa Life
How much does it cost to rent a place to stay near Paynes Bay in the wintertime?
The average cost for winter rentals in Paynes Bay is $1,498 per night. Casai has a wide list of great winter places to stay near Paynes Bay that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Are there any winter cottages/chalets in Paynes Bay that allow pets?
Yes, here are the top cottage/chalet rentals in Paynes Bay that allow you to bring your pet or dog:
- Stunning detached property near Sandy Lane on beautiful West Coast of Barbados
- Sandy Bliss Condominiums
- Stunning Retreat with Pool and Sunset Views - Northlight
- Stunning Retreat with Pool and Sunset Views - Northlight (3 bed)
See all pet-friendly vacation rentals in Paynes Bay on Casai.com
Do you have any winter rentals in Paynes Bay that are suitable for families?
Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Paynes Bay to find what works for you.
Are there winter accommodations in Paynes Bay that have indoor swimming pools?
As of 2026, the data from Casai.com shows that there are over 37 private swimming pools or indoor pools accommodations near Paynes Bay along with other great amenities.
Do any winter holiday rentals in Paynes Bay have hot tubs?
About 37 holiday rentals in Paynes Bay boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:
Are there luxury winter rentals in Paynes Bay?
Yes, there are many luxury places to stay in Paynes Bay for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Paynes Bay with all the best amenities for your next trip.
