Southfield Holiday Rentals
- Saint Elizabeth
- ·
- Treasure Beach
- 2.38 mi to center
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
- Saint Elizabeth
- ·
- Treasure Beach
- 1.37 mi to center
- Private Beach
- Oceanfront
- Spa
- Fireplace/Heating
- Saint Elizabeth
- ·
- Treasure Beach
- 1.12 mi to center
- Pool
- Balcony/Terrace
- Pet Friendly
- Parking
- Saint Elizabeth
- ·
- Treasure Beach
- 1.16 mi to center
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
- Saint Elizabeth
- ·
- Treasure Beach
- 1.11 mi to center
- Private Beach
- Oceanfront
- Pool
- Ocean View
- Saint Elizabeth
- ·
- Treasure Beach
- 1.11 mi to center
- Private Pool
- Hot Tub
- Pool
- Ocean View
- Saint Elizabeth
- ·
- Treasure Beach
- 0.72 mi to center
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
- Saint Elizabeth
- ·
- Treasure Beach
- 1.05 mi to center
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
- Saint Elizabeth
- ·
- Treasure Beach
- 0.67 mi to center
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
Luxury Holiday Rentals in Southfield
- Saint Elizabeth
- ·
- Treasure Beach
- 1.28 mi to center
- Private Pool
- Oceanfront
- Pool
- Ocean View
- Saint Elizabeth
- ·
- Treasure Beach
- 0.76 mi to center
- Private Pool
- Oceanfront
- Pool
- Ocean View
- Saint Elizabeth
- ·
- Treasure Beach
- 0.58 mi to center
- Private Pool
- Hot Tub
- Pool
- Ocean View
- Saint Elizabeth
- ·
- Treasure Beach
- 1.87 mi to center
- Pool
- Ocean View
- Balcony/Terrace
- View
- Saint Elizabeth
- ·
- Treasure Beach
- 1.15 mi to center
- Pool
- Ocean View
- Balcony/Terrace
- View
- Saint Elizabeth
- ·
- Treasure Beach
- 1.09 mi to center
- Private Pool
- Oceanfront
- Pool
- Ocean View
- Saint Elizabeth
- ·
- Treasure Beach
- 2.76 mi to center
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
- Saint Elizabeth
- ·
- Treasure Beach
- 0.91 mi to center
- Pool
- Ocean View
- Balcony/Terrace
- View
- Saint Elizabeth
- ·
- Treasure Beach
- 1.15 mi to center
- Pool
- Ocean View
- Balcony/Terrace
- View
Top-Rated Holiday Rentals with a Pool in Southfield
- Saint Elizabeth
- ·
- Treasure Beach
- 2.21 mi to center
- Private Pool
- Oceanfront
- Pool
- Ocean View
- Saint Elizabeth
- ·
- Treasure Beach
- 0.08 mi to center
- Hot Tub
- Pool
- Ocean View
- Balcony/Terrace
- Saint Elizabeth
- ·
- Treasure Beach
- 1.00 mi to center
- Private Pool
- Oceanfront
- Pool
- Ocean View
- Saint Elizabeth
- ·
- Treasure Beach
- 1.38 mi to center
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
- Saint Elizabeth
- ·
- Treasure Beach
- 1.01 mi to center
- Private Pool
- Oceanfront
- Hot Tub
- Pool
- Saint Elizabeth
- ·
- Treasure Beach
- 1.18 mi to center
- Private Pool
- Oceanfront
- Hot Tub
- Pool
- Saint Elizabeth
- ·
- Treasure Beach
- 2.76 mi to center
- Private Pool
- Oceanfront
- Pool
- Ocean View
- Saint Elizabeth
- ·
- Treasure Beach
- 0.53 mi to center
- Private Pool
- Oceanfront
- Pool
- Ocean View
- Saint Elizabeth
- ·
- Treasure Beach
- 2.40 mi to center
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
Pet-Friendly Holiday Rentals in Southfield
- Ocean View
- Balcony/Terrace
- View
- Pet Friendly
- Saint Elizabeth
- ·
- Santa Cruz
- 0.92 mi to center
- Balcony/Terrace
- View
- Breakfast
- Pet Friendly
- Saint Elizabeth
- ·
- Treasure Beach
- 2.75 mi to center
- Private Pool
- Oceanfront
- Pool
- Ocean View
- Saint Elizabeth
- ·
- Southfield
- 1.92 mi to center
- Pet Friendly
- Parking
- Child Friendly
- Laundry
- Saint Elizabeth
- ·
- Burnt Savanna
- 0.16 mi to center
- Balcony/Terrace
- Pet Friendly
- Kitchen
- Parking
- Saint Elizabeth
- ·
- Treasure Beach
- 2.72 mi to center
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
- Saint Elizabeth
- ·
- Treasure Beach
- 1.14 mi to center
- Private Pool
- Hot Tub
- Pool
- Ocean View
- Saint Elizabeth
- ·
- Santa Cruz
- 0.87 mi to center
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Saint Elizabeth
- ·
- Treasure Beach
- 2.76 mi to center
- Private Pool
- Oceanfront
- Pool
- Ocean View
Large Holiday Rentals and Private Villas in Southfield
- Saint Elizabeth
- ·
- Treasure Beach
- 0.75 mi to center
- Private Pool
- Oceanfront
- Pool
- Ocean View
- Saint Elizabeth
- ·
- Treasure Beach
- 2.10 mi to center
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
- Saint Elizabeth
- ·
- Treasure Beach
- 1.34 mi to center
- Oceanfront
- Spa
- Fireplace/Heating
- Pool
- Saint Elizabeth
- ·
- Treasure Beach
- 2.10 mi to center
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
- Saint Elizabeth
- ·
- Treasure Beach
- 1.08 mi to center
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
- Saint Elizabeth
- ·
- Treasure Beach
- 0.75 mi to center
- Hot Tub
- Pool
- Ocean View
- Balcony/Terrace
- Saint Elizabeth
- ·
- Treasure Beach
- 1.77 mi to center
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
- Saint Elizabeth
- ·
- Treasure Beach
- 2.31 mi to center
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
- Saint Elizabeth
- ·
- Treasure Beach
- 1.00 mi to center
- Private Pool
- Oceanfront
- Pool
- Ocean View
Wheelchair Accessible Holiday Homes in Southfield
- Saint Elizabeth
- ·
- Treasure Beach
- 0.61 mi to center
- Private Pool
- Oceanfront
- Pool
- Ocean View
- Saint Elizabeth
- ·
- Santa Cruz
- 0.43 mi to center
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
- Saint Elizabeth
- ·
- Treasure Beach
- 1.16 mi to center
- Spa
- Pool
- Balcony/Terrace
- Kitchen
- Saint Elizabeth
- ·
- Treasure Beach
- 0.61 mi to center
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
- Saint Elizabeth
- ·
- Southfield
- 2.38 mi to center
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
Southfield Private Villas and Holiday Homes Under $200
- Saint Elizabeth
- ·
- Treasure Beach
- 0.24 mi to center
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
- Saint Elizabeth
- ·
- Treasure Beach
- 0.29 mi to center
- View
- Parking
- Internet
- Child Friendly
- Saint Elizabeth
- ·
- Treasure Beach
- 0.47 mi to center
- Spa
- Pool
- Ocean View
- Balcony/Terrace
- Saint Elizabeth
- ·
- Treasure Beach
- 0.09 mi to center
- Ocean View
- Balcony/Terrace
- View
- Kitchen
- Manchester
- ·
- Mandeville
- 3.44 mi to center
- Balcony/Terrace
- View
- Parking
- Internet
- Saint Elizabeth
- ·
- Treasure Beach
- 0.29 mi to center
- Pool
- Ocean View
- Balcony/Terrace
- View
- Saint Elizabeth
- ·
- Treasure Beach
- 0.41 mi to center
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
- Pool
- Ocean View
- Balcony/Terrace
- View
Instantly Bookable Holiday Homes in Southfield
- Saint Elizabeth
- ·
- Treasure Beach
- 0.45 mi to center
- Private Pool
- Oceanfront
- Pool
- Ocean View
- Saint Elizabeth
- ·
- Treasure Beach
- 1.07 mi to center
- Pool
- Ocean View
- Balcony/Terrace
- View
- Saint Elizabeth
- ·
- Treasure Beach
- 0.79 mi to center
- Pool
- Ocean View
- Balcony/Terrace
- View
- Pool
- Ocean View
- Balcony/Terrace
- View
- Saint Elizabeth
- ·
- Treasure Beach
- 1.08 mi to center
- Pool
- Ocean View
- Balcony/Terrace
- View
- Private Pool
- Oceanfront
- Pool
- Ocean View
- Manchester
- ·
- Mandeville
- 2.85 mi to center
- Balcony/Terrace
- Kitchen
- Parking
- Internet
- Pool
- Ocean View
- Balcony/Terrace
- View
- Manchester
- ·
- Mandeville
- 3.26 mi to center
- Kitchen
- Parking
- Internet
- Child Friendly
Book a Last Minute Place to Stay in Southfield
About Casai's Private Villas and Holiday Rentals in Southfield
Discover more than 229 vacation rentals available in Southfield. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Southfield.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Southfield, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Southfield. On average, places to stay near Southfield offer 518.25 ft², with nightly prices averaging US $356.
With Casai, finding and comparing holiday rentals in Southfield is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
Top Accommodation Types in Southfield
| Type | Count |
|---|---|
| Villas | 91 |
| Vacation Homes | 83 |
| Holiday Apartments | 26 |
| Cottages | 10 |
Use these Quick Filters to Find a Holiday Rental in Southfield
★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Southfield.
Top Attractions Around Southfield, JM
Casai offers a large selection of top attractions around Southfield . Research things to do on your vacation before you visit Southfield.
Frequently Asked Questions About Southfield?
What are the top holiday rentals in Southfield?
With numerous options available in Southfield, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Southfield:
- Luxurious Beach Front Villa with Pool - Out of the Blue Villa
- THE BEACH HOUSE YOU HAVE BEEN DREAMING ABOUT!
- The Most Beautiful 4-acre Private Beachfront Villa with Pool and Chef
- Large private villa with swimming pool, gazebo and 2 decks. Great for groups.
- Lots of Outdoor Spaces at This Beautifully Appointed Seaside Villa
- Doubloon Villa - Conde Nast Traveller Top 11 Jamaican Villa 2026
- Sandy Rose Villa - Your tropical paradise getaway
- Villa de la Sable located on the edge of the sea with spectacular views
- Spectacular views of the Caribbean Sea await you in this bright, airy home.
- Turtles Nest, luxury beachfront villa with private pool and personal chef.
How many holiday rentals have private pools in Southfield?
Discover a selection of holiday rentals with private pools near Southfield with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.
- Boho Chic 5-bedroom Beachfront Villa, 2 Private Pools Plus Personal Cook & Staff
- Beyond Sunset Resort & Villas
- Driftwood Private Seafront Villa w/Pool, 3-Bedrooms & Private Cook
- LARGE Private Pool - 1 minute walk to beach AC in ALL bedrooms !
Which holiday homes in Southfield are best for families?
If you're searching for a family-friendly holiday home in Southfield, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Southfield:
- Boho Chic 5-bedroom Beachfront Villa, 2 Private Pools Plus Personal Cook & Staff
- Azteca Villas
- Beyond Sunset Resort & Villas
How many Casai.com holiday rentals are available in Southfield?
As of 2026, Casai boasts over 229 properties listed in the Southfield area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Southfield.






































































