A river with a bamboo raft carrying two people, surrounded by dense green foliage.

Vacation Homes in Trelawny

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Trelawny vacation homes

A modern living room with a white sofa, yellow cushions, a wooden coffee table with decorative items, and a view of the ocean through large glass doors.

1. Luxe Grand Villa: New, Ultra Modern Luxury 6 Bedroom private beach villa.

Luxe Grand Villa: New, Ultra Modern Luxury 6 Bedroom private beach villa.
St. Ann
9.6 out of 10, Exceptional, (50 reviews)
"Accommodation were spot on, the staff made the stay exceptional."
United States
Jenifer R.
Luxe Grand Villa: New, Ultra Modern Luxury 6 Bedroom private beach villa.
A resort with a large swimming pool, multiple overwater bungalows, and a clear blue sky.

2. Richmond Villa Rental Management

Richmond Villa Rental Management
3.5 star property
Ocho Rios
6.0 out of 10, (2 reviews)
"Property met out expectations. Close to the pool. Kid friendly. Great place to have a relaxintion vacation. "
United States
Lucien
Richmond Villa Rental Management
A swimming pool with lounge chairs and a covered patio area.

3. Tropical Escape, Spacious 2 Bedroom Vacation Oasis with WiFi, AC

Tropical Escape, Spacious 2 Bedroom Vacation Oasis with WiFi, AC
Florence Hall
Tropical Escape, Spacious 2 Bedroom Vacation Oasis with WiFi, AC
A large house with a swimming pool, multiple rooms, and a covered outdoor area.

4. 5 bed villa, gated community, private pool, fully staffed, private chauffeur

5 bed villa, gated community, private pool, fully staffed, private chauffeur
Montego Bay
10.0 out of 10, Exceptional, (98 reviews)
"This is the place to stay and enjoy all Jamaica has to offer. Nikita was incredible, Javon chef skills are second to none. Ceejay our driver was safe with his driving. Our stay was 1st class."
United States
Peter M.
5 bed villa, gated community, private pool, fully staffed, private chauffeur
A man standing in a shallow water area with a rocky wall and greenery in the background.

5. Jhadano Villa 3BR Pool Shuttle 3 Mins to Beach

Jhadano Villa 3BR Pool Shuttle 3 Mins to Beach
4.0 star property
Falmouth Historic Town Centre
10.0 out of 10, Exceptional, (21 reviews)
"This is my first time staying here, and it is a must-do! It has a great location, 24/7 security, and amazing amenities! The peace of the surrounding areas was also a great benefit to staying here! "
United States
Marcia
Jhadano Villa 3BR Pool Shuttle 3 Mins to Beach
A swimming pool with lounge chairs and a signboard.

6. This is a three bedrooms three bathrooms house that is fully furnihsed

This is a three bedrooms three bathrooms house that is fully furnihsed
Florence Hall
9.0 out of 10, Wonderful, (13 reviews)
"Quick check in and great communications and house was very clean will definitely be staying again."
United States
Ava
The price is AED 454
AED 686 total
includes taxes & fees
26 Oct - 27 Oct
This is a three bedrooms three bathrooms house that is fully furnihsed
A covered outdoor area with a wooden deck, a green railing with pineapple decorations, and palm trees in the background.

7. Sunshine Lodge- Your Home Away From Home

Sunshine Lodge- Your Home Away From Home
4.0 star property
Montego Bay
7.6 out of 10, Good, (5 reviews)
"Very cool place to stay. Very few minor issues, communication was great. Any real issue we had was not reflective on the property, if you ever drove in Jamaica roads are a little bit rough and the one going up to the property is a little rough but not impossible by any means. The view is amazing the place is clean and the AC in the bedroom works amazing. We had an issue with the gas for the stove, but that might have been more of a user issue than anything else. Everything else worked out fine."
United States
DUSTIN
The price is AED 247
AED 309 total
includes taxes & fees
4 Nov - 5 Nov
Sunshine Lodge- Your Home Away From Home
A beach with clear turquoise water and white sand.

8. ONE RHYTHM VILLA - Steps to the BEACH - CHEF Included - Caribbean Sea Views

ONE RHYTHM VILLA - Steps to the BEACH - CHEF Included - Caribbean Sea Views
duncans bay
9.8 out of 10, Exceptional, (214 reviews)
"This is our 4th visit to Villa by the Sea! We relaxed, read, soaked up the sun and ate amazing meals prepared by Ms Annette. She took wonderful care of us which is such a treat. We look forward to our next visit!"
United States
N N.
ONE RHYTHM VILLA - Steps to the BEACH - CHEF Included - Caribbean Sea Views
A luxurious room with a large window overlooking a pool and the ocean. There is a white sofa with colorful cushions and a wooden coffee table in the center.

9. Silent Waters Villa - 9BR/7BTH estate - ocean and river views - fully staffed

Silent Waters Villa - 9BR/7BTH estate - ocean and river views - fully staffed
Montego Bay
10.0 out of 10, Exceptional, (18 reviews)
"We had a wonderful stay at silent waters, the staff was great, and the amenities were as described. The view and overall property was as pictured and even more breathtaking in person. Would definitely stay again"
United States
Amie P.
Silent Waters Villa - 9BR/7BTH estate - ocean and river views - fully staffed
A modern living room with a grey sectional sofa, yellow and patterned cushions, a yellow tray table, and a staircase leading to an upper level.

10. Ubuntu De La Villa

Ubuntu De La Villa
Ocho Rios
10.0 out of 10, Exceptional, (14 reviews)
"Property was exactly as advertised. Communication was superb as host answered questions within minutes. Location felt safe and having that pool was definitely an addition.Will definitely stay again Very family friendly"
United States
Callett
Ubuntu De La Villa
A table with a vase of flowers, surrounded by chairs, overlooking a scenic view of the ocean and lush greenery.

11. Firefly cottage with Ocean view

Firefly cottage with Ocean view
Cave District
10.0 out of 10, Exceptional, (27 reviews)
"I would recommend this cabin resort to anyone. Geneva was wonderful host, along with her beautiful family"
United States
Rick B.
The price is AED 215
AED 289 total
includes taxes & fees
7 Nov - 8 Nov
Firefly cottage with Ocean view
A large house with a swimming pool surrounded by palm trees.

12. Newly Renovated!! COCO PALMS - Exclusive villa with private pool/beach access.

Newly Renovated!! COCO PALMS - Exclusive villa with private pool/beach access.
Mammee Bay Estates
9.8 out of 10, Exceptional, (17 reviews)
"Beautiful home with a great host!"
United States
Ryan W.
Newly Renovated!! COCO PALMS - Exclusive villa with private pool/beach access.
A modern kitchen with white cabinetry, a central island with seating, and a view of the ocean through a large window.

13. Experience pure luxury at our Private Penthouse Suite in Montego Bay!

Experience pure luxury at our Private Penthouse Suite in Montego Bay!
Providence Heights
8.0 out of 10, Very good, (3 reviews)
"The host was good and was available whenever we needed throughout our entire stay. The property is exactly as the images and is just amazing, very beautifully designed and clean - we hardly left as it’s just lovely. The sea view is just perfect. I will say that the food on property and taxis in the area is very overpriced which was a shame. Overall it’s a great place if you want a peaceful break near to the sea."
United Kingdom
Amanda H.
Experience pure luxury at our Private Penthouse Suite in Montego Bay!
An outdoor patio with a wooden table and chairs, a covered seating area, and a hanging light fixture.

14. Luxurious Home

Luxurious Home
Draxhall
10.0 out of 10, Exceptional, (5 reviews)
"I found the home to be clean, in a secure location and close to shops and restaurants. The host, Martin, was quick to respond and very helpful."
United States
MICHELE
Luxurious Home
A residential area with multiple houses, paved driveways, and well-maintained gardens.

15. Ocho Rios Villa Azul at Coolshade XIII

Ocho Rios Villa Azul at Coolshade XIII
3.5 star property
St. Ann's Bay
10.0 out of 10, Exceptional, (2 reviews)
"If you 're tired of the same ole same ole all inclusive hotels that keep you in a little touristy bubble this is the way to go . Our experience here was the best we have has travelling to Jamaica. This is a house is located in a gated community within a community with real Jamaican neighbors.It was extremely quiet and private and besides a few people jogging in the mornings we hardly saw anyone. The neighbors we met at the pool were very friendly and warm. Beautiful community! The house itself...
United States
Patrice
Ocho Rios Villa Azul at Coolshade XIII
A neatly arranged bedroom with a bed, two bedside tables, a nightstand, and a wardrobe.

16. Gated Community Paradise- Trelawny

Gated Community Paradise- Trelawny
Florence Hall
9.0 out of 10, Wonderful, (2 reviews)
"Hosts were very kind and property was nice and clean"
Canada
Naya
Gated Community Paradise- Trelawny
A swimming pool with clear water, surrounded by modern buildings and palm trees.

17. Solara Blu Villa House A in Montego Bay

Solara Blu Villa House A in Montego Bay
Montego Bay
4.0 out of 10, (1 review)
Solara Blu Villa House A in Montego Bay
A covered outdoor area with a tiled floor, potted plants, and a white railing.

18. Perfect group stay in the heart of Montego Bay. 10 mins from beach

Perfect group stay in the heart of Montego Bay. 10 mins from beach
Montego Bay
Perfect group stay in the heart of Montego Bay. 10 mins from beach
A spacious living room with a large flat-screen TV, a sofa, two round coffee tables, and a kitchen in the background.

19. Edmund Ridge Estate Home Rental

Edmund Ridge Estate Home Rental
Rose Hall
8.0 out of 10, Very good, (4 reviews)
"We wanted to stay somewhere nice and quiet. It was exactly what we needed. "
Canada
Concetta B.
The price is AED 382
AED 981 total
includes taxes & fees
2 Nov - 3 Nov
Edmund Ridge Estate Home Rental
A beachside dining area with outdoor seating, a view of a cruise ship, and a pool area with people swimming and sunbathing.

20. Ocho Rios Villa at Coolshade III

Ocho Rios Villa at Coolshade III
2.5 star property
St. Ann's Bay
9.2 out of 10, Wonderful, (9 reviews)
"Very quiet and nice place"
United States
Courtney
Ocho Rios Villa at Coolshade III
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 Riu Palace Aquarelle - All Inclusive

Hotel Riu Palace Aquarelle - All Inclusive

10/10 Excellent
"Everything was perfect"
Rawsan 5-night trip
Posted less than an hour ago
Hotel Riu Palace Aquarelle - All Inclusive

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