Southfield Vacation Rentals

Save an average of 15% on thousands of properties with Expedia Rewards

Most properties are fully refundable. Because flexibility matters.

Search over 2.9 million properties and 550 airlines worldwide.

Find properties with these dates

Vacation Rentals in Southfield

Pool
A labour of love in the south of the island
The price is ¥44,144
¥61,409 total
includes taxes & fees
May 21 - May 22
A labour of love in the south of the island
Outdoor pool
Mountain Top Villa
3.5 star property
8.6 out of 10, Excellent, (19)
"We enjoyed our stay at the villa, we stayed there for our honey moon, they even helped us take some really nice pics after our wedding"
The price is ¥9,646
¥15,155 total
includes taxes & fees
May 16 - May 17
Mountain Top Villa
Living area | Smart TV, books, stereo
Tranquil Beachfront Oasis ~ Pool ~ Boat Tour
9.8 out of 10, Exceptional, (7)
"A bit of off the beaten path paradise was just what we needed and just what we got! Everyone was kind, responsive, and helpful. Very refreshing! Thanks everyone!"
Tranquil Beachfront Oasis ~ Pool ~ Boat Tour
Save an average of 15% on thousands of hotels when you're signed in
Beach nearby, sun loungers, beach towels
NEW LISTING!! Seaside Villa -1 minute walk to beach - DISCOUNT AVAILABLE!!
10.0 out of 10, Exceptional, (3)
"Wonderful villa with a great host and onsite staff. Walk to a quiet, beautiful beach. Plenty of room. All rooms have en-suite bathrooms! Big plus for a big crew! We had the chefs prepare two meals and both were extraordinary! Full kitchen to prepare other meals. Five star visit!"
NEW LISTING!! Seaside Villa -1 minute walk to beach - DISCOUNT AVAILABLE!!
Exterior
Oceanfront Luxury Villa: Private Beach & Staff
9.8 out of 10, Exceptional, (31)
"The house was a great place to wake up every morning. The views, the private beach and the pool were all great. We spent our nights on the beach side veranda looking directly at a perfect sunset. The house was clean, area is safe and would stay again. The owner was responsive and easy to coordinate with. Shane the property manager is a good guy, easy to work with, great cook and very help full. Thanks for the make the stay with my dad and friend memorable trip."
Oceanfront Luxury Villa: Private Beach & Staff
Indoor pool
Luxurious Beach Front Villa with Pool - Out of the Blue Villa
10.0 out of 10, Exceptional, (73)
"I loved everything about this home. The other reviews speak about all of the positives, so I’m not going to rehash those. Just know that the beach is great. The pool is great. The rooms are great. The staff is wonderful. The food was phenomenal. It was one of the most relaxing stays that I have ever had. If you want some negatives, I’ll give you two - there were a lot of bugs (welcome to a tropical island) and the road to get there was pretty trash (welcome to Jamaica). These were really minor...
Luxurious Beach Front Villa with Pool - Out of the Blue Villa
On the beach, beach towels
Zero minutes to the most prestigous cove in the area
9.4 out of 10, Exceptional, (34)
"We stayed at Villa Optima for 22 nights. The host Paolo was wonderful. He responded essentially immediately, and provided extra items for the house whenever we asked. He helped us buy fresh fish and rum and other things we needed. The private pool was very pleasant, and has some nice shaded areas so you can hang out there for a long time. The beach was just 50 yards away. It is a sandy beach and you can easily swim in the ocean. Usually there was no-one else on the beach, it was never crowded....
The price is ¥46,869
¥68,429 total
includes taxes & fees
May 23 - May 24
Zero minutes to the most prestigous cove in the area
Outdoor pool
Sweet Escape ~the villa "Your Island Utopia" The Sweetest Escape
9.8 out of 10, Exceptional, (28)
"We really enjoyed our week at Sweet Escape. The house was clean and spacious, beds were comfortable, and we loved the outdoor areas (pool, pergola, beach bed, and beach). Mark was absolutely fantastic! He made us delicious dinners and hearty breakfasts to start our day. We took care of the shopping, but he guided us at the grocery store and made recommendations. There were plenty of fun activities to do within a reasonable driving distance of the house (Black River Safari (5 min), Appleton Rum...
Sweet Escape ~the villa "Your Island Utopia" The Sweetest Escape
Terrace/patio
Villa Serene Jewel of Black River 4 bedroom 5bathrooms
9.6 out of 10, Exceptional, (11)
"The pictures do not give this Villa justice, it is beautiful! We had an amazing time there! We were looking for rest and relaxation and that is exactly what we got!! Shamoir the cook was incredible! Sheryl was quick to respond to any questions we had! We will definitely go back!"
Villa Serene Jewel of Black River 4 bedroom 5bathrooms
Beach
"Main House at Shakespeare Cottage"
9.4 out of 10, Exceptional, (3)
"A large group of us Peace Corps workers stayed there for a weekend and LOVED it. It is perfect for a large group. The communication was great and the staff is very nice. The local contact, Vaughn, could not have been more helpful and friendly. We will definitely be going back! "
The price is ¥28,121
¥32,027 total
includes taxes & fees
May 26 - May 27
"Main House at Shakespeare Cottage"
Lake
Deano's Cottages
4.5 star property
7.0 out of 10, Good, (4)
"Very nice and comfortable "
The price is ¥9,372
¥11,089 total
includes taxes & fees
May 22 - May 23
Deano's Cottages
A rooftop pool
Bramble Beach Villa -Main House
10.0 out of 10, Exceptional, (1)
"This place has everything you need! The staff, 2 pools, 2 minute walk to the beach, game room, trampoline, pickleball court, basketball court, games, the mountain views, ocean view, and all the wonderful people you meet along the way. We will definitely be back. Thank you everyone for making our trip so incredibly special."
Bramble Beach Villa -Main House
Beach nearby, beach towels
VillaMerissa Nestled between two unspoiled beaches Pool/JackSprat/WiFi/Gym/Staff
10.0 out of 10, Exceptional, (4)
"Relaxing due to the villa was away from the tourists. Great scenery going through the mountains and down to valley and seaside It was awesome"
VillaMerissa Nestled between two unspoiled beaches Pool/JackSprat/WiFi/Gym/Staff
Land view from property
Turtles Nest Villa
4.0 star property
9.6 out of 10, Exceptional, (7)
"Our stay in Treasure Beach was beyond amazing. The staff at Turtle's Nest from Owner to Zeb the care taker and Peta and Vincent the chefs that make delicious food and Peta's mom who did all our laundry and made sure we always had clean sheets and towls are all amazing. My wife and I have been to treasure beach 6 times now and we were very pleased with the entire staff including Sugar and Spice the villa dogs that made leaving our fur babies for 2 weeks soo much easier! We would highly recommend...
Turtles Nest Villa
Property grounds
Unforgettable Villa: Jamaica's Rare Private Escape
Unforgettable Villa: Jamaica's Rare Private Escape
Property grounds
Coral Bay Chateau - Luxury Villa in Treasure Beach
10.0 out of 10, Exceptional, (1)
"My husband’s 60 birthday bash with my family and friends! The Chateau is very spacious and comfortable. We were 14 adults and every couple had their own room and bathroom. The house has a wonderful outdoor space with a beautiful view and pool and many shaded areas! The staff is wonderful! The chefs made us some amazing breakfasts and dinners Jamaican style! Amazing! The beach was beautiful. We swam every day. It is a 10 minute walk. We chose the house because of the view and it didn’t...
Coral Bay Chateau - Luxury Villa in Treasure Beach
Private kitchen
Mckay's Private Appartment
9.0 out of 10, Wonderful, (2)
"Property was amazing to stay, very private and inviting."
The price is ¥7,030
¥11,248 total
includes taxes & fees
May 16 - May 17
Mckay's Private Appartment
Cabin, 1 Bedroom, Smoking, Private Pool | Exterior
Cashaw Cabin - Private Cosy A-frame
2.0 star property
The price is ¥17,908
¥20,932 total
includes taxes & fees
May 30 - May 31
Cashaw Cabin - Private Cosy A-frame
Rooftop terrace
Bramble Beach Villa
3.0 star property
10.0 out of 10, Exceptional, (1)
Bramble Beach Villa
Property grounds
Luxurious, modern, spacious two-bedroom, two-bathroom is the perfect getaway.
10.0 out of 10, Exceptional, (1)
"House was clean , the convince of home away fr how."
Luxurious, modern, spacious two-bedroom, two-bathroom is the perfect getaway.
Don't see what you're looking for?
See all available properties in Southfield
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other types of properties in Southfield you may be interested in

Reception
Sea Coast Inn & Suites
3.0 star property
7.2 out of 10, Good, (11)
"The host was amazing and chef made some great breakfast also very positive employee and great morning view "
The price is ¥15,502
¥19,155 total
includes taxes & fees
May 16 - May 17
Sea Coast Inn & Suites
Pool
A labour of love in the south of the island
The price is ¥44,144
¥61,409 total
includes taxes & fees
May 21 - May 22
A labour of love in the south of the island
Beach bar
Jakes
3.5 star property
9.2 out of 10, Wonderful, (259)
"Jake’s is perhaps the most charming hotel on the island. I am a repeat visitor because the quality of service and sheer beauty of the property are unmatched - you will never experience anything quite like Jake’s anywhere in the world. "
The price is ¥23,544
¥28,409 total
includes taxes & fees
May 26 - May 27
Jakes
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

Can I find a vacation rental in Southfield?

Yes, we offer vacation rentals close to popular attractions in Southfield, or you can select a secluded option if you'd like a relaxing place to stay.

What's the top vacation rental that Southfield has to offer?

"Main House at Shakespeare Cottage": This vacation home rental near Southfield is located on a river and has a balcony, a garden, and free WiFi to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family. Make the most of the spa tub in this rental home to help you unwind.

What can I see and do in Southfield?

While you're exploring the area, Jamaica Beaches and Calabash Bay are a couple of picturesque spots to get outside and enjoy nature. In the larger area, you’ll find Lovers Leap and Billy Bay Beach.

What are vacation rentals like in Southfield?

Vacation rentals are privately owned properties you can book for a few days or a quick weekend in Southfield. Vacation rentals offer amenities such as laundry facilities and kitchens so you'll feel right at home. If you're concerned about a clean environment, vacation rentals can provide a sense of privacy away from public hotel elevators and busy lobbies while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive choice for families.