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Villas in Trelawny

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Trelawny villas

Exterior

1. Coolshade Villas - Richmond Estate

Coolshade Villas - Richmond Estate
2.0 star property
St. Ann's Bay
7.0 out of 10, Good, (4 reviews)
"Convenient location to restaurants, beach and major tourists attractions. Quiet and secure community."
United States
Robert
The price is SAR 394
SAR 1,110 total
includes taxes & fees
1 Nov - 2 Nov
Coolshade Villas - Richmond Estate
A pool area with lounge chairs and umbrellas, overlooking a clear blue sky and ocean view.

2. 5‑Bedroom Luxury Villa – Ocean View, Infinity Pool, Private Gym, Chef & Butler

5‑Bedroom Luxury Villa – Ocean View, Infinity Pool, Private Gym, Chef & Butler
Montego Bay
10.0 out of 10, Exceptional, (81 reviews)
"Host and staff extremely friendly and accommodating. Beautiful property. I will definitely visit again. "
United States
Robbin C.
5‑Bedroom Luxury Villa – Ocean View, Infinity Pool, Private Gym, Chef & Butler
A swimming pool with blue lounge chairs and palm trees.

3. Ocho Rios Villas at Coolshade II

Ocho Rios Villas at Coolshade II
3.0 star property
St. Ann's Bay
9.4 out of 10, Exceptional, (18 reviews)
"We had a fantastic stay at Cool Shade. We were two minutes away from the pool and enjoyed the backyard oasis. We definitely will be coming back!!! "
Canada
Shyshy
Ocho Rios Villas at Coolshade II
Property entrance

4. Drax Hall Country Club 2 Bed Villa

Drax Hall Country Club 2 Bed Villa
3.0 star property
Ocho Rios
2.0 out of 10, (2 reviews)
"The property manager was horrible, she was very aggressive when communicating. She tried to take my deposit for a broken lock that I have never touched. Very poor communication, I felt like I was in prison, because I wasn’t allowed to take visitors on her property. The housekeepers were more friendly and nice. I was warned by others never to rent that property again. It was just a horrible stay, the beds were very hard and worn out. It’s like you sleeping on a piece of board. The community it’s...
United States
Noddia
Drax Hall Country Club 2 Bed Villa
A two-story building with a balcony, a circular structure with steps, and a well-maintained lawn.

5. Island Breeze Villa 1 night free after 7 nights within 2026-2028.

Island Breeze Villa 1 night free after 7 nights within 2026-2028.
Ironshore
9.8 out of 10, Exceptional, (111 reviews)
"The property was great, of course, but the big shout out goes to the STAFF! Ann Marie and Glenn were very welcoming, accommodating, and attentive to my group's every need! We would definitely book this property again, if available!"
United States
Tracy B.
Island Breeze Villa 1 night free after 7 nights within 2026-2028.
A bedroom with a wooden bed, two bedside tables, a nightstand, a red and white striped curtain, and a red wall.

6. Casa Princess Ocho Rios Vacation Villa

Casa Princess Ocho Rios Vacation Villa
3.5 star property
Ocho Rios
9.6 out of 10, Exceptional, (70 reviews)
"Beautiful, safe community and spacious property. Softer pillows would make it excellent"
United States
TRUDY ANN
Casa Princess Ocho Rios Vacation Villa
A rectangular swimming pool with a wooden gazebo in the center, surrounded by lounge chairs, and a beach view in the background.

7. Sun Kissed Villa - 6 Bedroom, sleeps 14, on the beach.

Sun Kissed Villa - 6 Bedroom, sleeps 14, on the beach.
Discovery Bay
9.4 out of 10, Exceptional, (89 reviews)
"My family thoroughly enjoyed our stay! We frequently visit Jamaica and this villa is top notch! From the staff to the views, it was awesome! Highly recommend!"
United States
April C.
Sun Kissed Villa - 6 Bedroom, sleeps 14, on the beach.
A pool area with clear blue water, lounge chairs, and a view of the sea.

8. Beachfront Villa, Staff, Boat, Pool, Tennis, Gated

Beachfront Villa, Staff, Boat, Pool, Tennis, Gated
Montego Bay
10.0 out of 10, Exceptional, (225 reviews)
"Absolutely amazing staff! The house is very clean and set up to be very comfortable for five couples or for large families. "
United States
Lisa M.
Beachfront Villa, Staff, Boat, Pool, Tennis, Gated
A pool area with a view of the sea, lounge chairs, and a pergola.

9. Sandpebbles - Private Beachfront Villa with Pool, Cook, Butler and Housekeeper

Sandpebbles - Private Beachfront Villa with Pool, Cook, Butler and Housekeeper
Rio Bueno, St. Ann
9.8 out of 10, Exceptional, (134 reviews)
"Great staff, comfortable home, great food"
United States
Greg H.
Sandpebbles - Private Beachfront Villa with Pool, Cook, Butler and Housekeeper
A coastal property with multiple houses, a swimming pool, and a view of the ocean.

10. Half Hill 1BR

Half Hill 1BR
3.5 star property
Montego Bay
10.0 out of 10, Exceptional, (1 review)
"The property was convenient to the airport about 10 minutes without traffic. Villas was clean and exactly as shown. On-site staff was attentive and very responsive, so was the entire hospitality expert team. Would stay again."
United States
Nye
The price is SAR 492
SAR 757 total
includes taxes & fees
1 Nov - 2 Nov
Half Hill 1BR
A poolside area with chairs and a view of the ocean at sunset.

11. Archer's Rock-Luxurious Ocean front cottage at Chukka Cove w/Private Plunge Pool

Archer's Rock-Luxurious Ocean front cottage at Chukka Cove w/Private Plunge Pool
Laughlands
9.8 out of 10, Exceptional, (71 reviews)
"We had an excellent stay at Archer's Rock. The property is absolutely beautiful, with incredible ocean views that make it hard to leave.The beds were extremely comfortable and made for a great night's sleep every night. Breakfast by Ms. Carleen was fantastic and really added to the experience. It was also very easy to order groceries, which made the stay even more convenient.We especially loved the cliff swimming are, which was such a unique and memorable experience. The only small downside was...
United States
Isha D.
Archer's Rock-Luxurious Ocean front cottage at Chukka Cove w/Private Plunge Pool
A modern outdoor bar area with a pool, lounge chairs, and a view of the ocean.

12. OCEANVIEW LUX 5BR VILLA 180 VIEWS POOL, BEACH/GOLF HALF MOON RESORT MEMBERSHIP

OCEANVIEW LUX 5BR VILLA 180 VIEWS POOL, BEACH/GOLF HALF MOON RESORT MEMBERSHIP
Montego Bay
10.0 out of 10, Exceptional, (38 reviews)
"The staff was wonderful !!!!The food was better than most restaurants!!We didn’t want for anything. All was perfect!We will definitely return !"
United States
Robert A.
OCEANVIEW LUX 5BR VILLA 180 VIEWS POOL, BEACH/GOLF HALF MOON RESORT MEMBERSHIP
A large, multi-story building with a swimming pool, surrounded by lush greenery.

13. Most Affordable Private Villa with pool In Runaway Bay

Most Affordable Private Villa with pool In Runaway Bay
Cardiff Hall
9.6 out of 10, Exceptional, (21 reviews)
"The privacy, pool and location."
United States
Donic R.
Most Affordable Private Villa with pool In Runaway Bay
A clear blue infinity pool with a hot tub, surrounded by palm trees and a white gazebo.

14. Allamanda Villa- Tryall Resort Membership- van/driver- nanny

Allamanda Villa- Tryall Resort Membership- van/driver- nanny
Montego Bay,
10.0 out of 10, Exceptional, (55 reviews)
"Immaculate, spacious, and comfortable home with the most wonderful staff. Our three generation family enjoyed every minute at Allamanda Villa!!!! And the membership to Tryall Club allowed daily beach, pickleball, and fitness room access. An amazing place can’t wait to return!"
United States
Laura S.
Allamanda Villa- Tryall Resort Membership- van/driver- nanny
A two-story house with a tiled roof, a front door, and a small garden with various plants and a palm tree.

15. Villa at The Palms

Villa at The Palms
3.5 star property
St. Ann's Bay
6.0 out of 10, (3 reviews)
"The villa was very family oriented . The pool area very clean and enjoyable. Surrounding very quiet and clean, location very nice."
United States
Michelle
The price is SAR 583
SAR 1,197 total
includes taxes & fees
12 Nov - 13 Nov
Villa at The Palms
Beach

16. Luxury 4-Bedroom villa

Luxury 4-Bedroom villa
5.0 star property
St. Ann's Bay
9.0 out of 10, Wonderful, (2 reviews)
Luxury 4-Bedroom villa
Terrace/patio

17. Breathtaking View Villa

Breathtaking View Villa
3.0 star property
Falmouth
9.0 out of 10, Wonderful, (7 reviews)
"Quiet property, outside of the city, is a wonderful place to get away and enjoy some peace and beautiful scenery. Friendly staff, very accommodating and helpful. They were happy to give us recommendations and directions to other places to visit. "
United States
Deena
Breathtaking View Villa
A residential area with multiple houses, a swimming pool, and a tennis court.

18. Jam Villa, A Private 7 or 13 Bedroom Villa Resort in a Gated Beach Community

Jam Villa, A Private 7 or 13 Bedroom Villa Resort in a Gated Beach Community
Mammee Bay Estates
9.8 out of 10, Exceptional, (58 reviews)
"My guests and loved our stay at Jam Villa. The staff was amazing!! The beds were comfy, and the food was great! Thank you so much for making sure our guests were happy and felt at home. You all are the best!"
United States
A J.
The price is SAR 5,629
SAR 6,428 total
includes taxes & fees
13 Nov - 14 Nov
Jam Villa, A Private 7 or 13 Bedroom Villa Resort in a Gated Beach Community
A spacious living area with a view of the ocean, a pool, and outdoor furniture.

19. SeaEsta - Exclusive Luxury Beachfront Villa with Chef, Housekeeper and Butler

SeaEsta - Exclusive Luxury Beachfront Villa with Chef, Housekeeper and Butler
Rio Bueno
10.0 out of 10, Exceptional, (59 reviews)
"Had the most wonderful stay at SeaEsta for my 50th birthday. Conley was the highlight, who made it extra special with decorations, his attentiveness and professionalism. But the entire staff was great too! The villa was perfect for our group of 7 women - highly recommend! "
United States
Jessica S.
SeaEsta - Exclusive Luxury Beachfront Villa with Chef, Housekeeper and Butler
A wooden table set for dining with a view of the ocean and lounge chairs under a pergola.

20. Seahorse- - A Slice Of Caribbean Paradise On A Private Beach, Gated Community

Seahorse- - A Slice Of Caribbean Paradise On A Private Beach, Gated Community
Rio Bueno
10.0 out of 10, Exceptional, (97 reviews)
"We greatly enjoyed our stay! The location was excellent and the on-site staff went above and beyond to ensure that we had a wonderful time."
United States
Kyle C.
Seahorse- - A Slice Of Caribbean Paradise On A Private Beach, Gated Community
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.
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Top Trelawny Hotel Reviews

Hotel 39 Jamaica

Hotel 39 Jamaica

10/10 Excellent
"Twitter was the BEST host! All the staff were friendly and accommodating. Mr. Jarrett (The GM) made our stay awesome!"
Patrice A 7-night trip
Posted 5 hours ago
Hotel 39 Jamaica

Frequently asked questions

How much do villas in Trelawny cost?
Rates for villas in Trelawny range between SAR 757 and SAR 6,428 per night. No matter your budget, you can find someplace that suits your needs with Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What are the best villas in Trelawny?
There are multiple villas in Trelawny with a total average guest review rating of 9.6, so you're sure to find the ideal place. Basing yourself in Falmouth? Take a look at Completely Renovated Villa On The Carribean Seaside. This popular 3.5-star villa comes with a barbecue grill and an ocean view. Breathtaking View Villa is also a hit with many travelers. A cafe and a yard are a couple of the amenities you'll find at this 3-star option in Falmouth.
How many villas are there in Trelawny?
Browse our 535 villas in Trelawny and then reserve your favorite. Whether you're organizing a vacation with all the family or kicking it with friends, your perfect stay is just clicks away.
Are there any 5-star villas in Trelawny?
While you won't find 5-star villas in Trelawny, there are still chic properties to select from. Falmouth on your list of places to visit? Red Fox By The Sea, Silver Sands is a 4-star retreat that has a swimming pool and a separate dining area. Honeycombe Villa By Jamaican Treasures is another top pick in Falmouth. Also rated 4 stars and featuring a swimming pool and a separate sitting area, it'll feel like your home away from home.
Why book your villa in Trelawny with Expedia?
We think arranging a vacation should be hassle-free, so if you're in search of villas at an affordable price, Expedia has you covered. Stick to the budget and pick an all-inclusive stay, or book a luxury villa to spoil the ones you love most. Use our convenient search filters to find a property in Trelawny that matches your needs.
How can I find cheap villas in Trelawny?
With Expedia's filter tool, sourcing cheap villas in Trelawny is easy. To discover options that give you the most bang for your buck, refine your search results by star rating, amenities and budget.