Best Vacation Homes in Trelawny
2800 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Ocean View
Villa
- Private Pool
- Pool
- Ocean View
R11,399/Night
For 7 Nights R79,795
15230.93 ft²
10 Guests
5 Bedrooms
4 Bathrooms
Free Cancellation
House
- Oceanfront
- Pool
- Ocean View
R1,750/Night
For 7 Nights R12,250
1 Bathroom
Family Friendly
Resort
- Hot Tub
- Spa
- Pool
R61,805/Night
For 7 Nights R432,635
5500 ft²
10 Guests
4 Bedrooms
4 Bathrooms
Ocean View
Villa
- Private Pool
- Pool
- Ocean View
R20,983/Night
For 7 Nights R146,883
1097.92 ft²
5 Guests
2 Bedrooms
2 Bathrooms
Free Cancellation
House
- Pool
- Balcony/Terrace
- Parking
R2,126/Night
For 7 Nights R14,883
14 Guests
6 Bedrooms
6 Bathrooms
Ocean View
Villa
- Private Pool
- Pool
- Ocean View
R24,532/Night
For 7 Nights R171,726
17 Guests
8 Bedrooms
9 Bathrooms
Family Friendly
Villa
- Pool
- Balcony/Terrace
- Kitchen
R43,868/Night
For 7 Nights R307,079
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Pool
- Kitchen
- Parking
R1,302/Night
For 7 Nights R9,110
Trelawny Luxury Rentals
857.52 ft²
39 Guests
18 Bathrooms
Ocean View
Resort
- Private Beach
- Oceanfront
- Spa
R43,667/Night
For 7 Nights R305,672
R36,798/Night
For 7 Nights R257,589
14 Guests
7 Bedrooms
7 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Pool
R30,134/Night
For 7 Nights R210,945
6 Guests
4 Bedrooms
4 Bathrooms
Family Friendly
House
- Private Pool
- Pool
- Balcony/Terrace
R28,998/Night
For 7 Nights R202,980
12 Guests
5 Bedrooms
5 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Hot Tub
R25,726/Night
For 7 Nights R180,083
R23,747/Night
For 7 Nights R166,231
4000 ft²
14 Guests
6 Bedrooms
3 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Hot Tub
R21,507/Night
For 7 Nights R150,546
5000 ft²
10 Guests
5 Bedrooms
5 Bathrooms
Ocean View
Villa
- Private Pool
- Pool
- Ocean View
R21,425/Night
For 7 Nights R149,974
Trelawny Pet Friendly Vacation Rentals
1450 ft²
10 Guests
3 Bedrooms
3 Bathrooms
Ocean View
Villa
- Oceanfront
- Ocean View
- Balcony/Terrace
R3,336/Night
For 7 Nights R23,355
1453.13 ft²
20 Guests
6 Bedrooms
6 Bathrooms
Ocean View
Villa
- Oceanfront
- Pool
- Ocean View
R2,639/Night
For 7 Nights R18,465
6 Guests
1 Bedroom
1 Bathroom
Ocean View
House
- Oceanfront
- Pool
- Ocean View
R3,577/Night
For 7 Nights R25,039
7 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
Villa
- Fireplace/Heating
- Pool
- Balcony/Terrace
R3,515/Night
For 7 Nights R24,614
1302.43 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Free Cancellation
House
- Pool
- View
- Breakfast
R1,409/Night
For 7 Nights R9,862
1450 ft²
10 Guests
3 Bedrooms
3 Bathrooms
Ocean View
Villa
- Oceanfront
- Ocean View
- Balcony/Terrace
R3,336/Night
For 7 Nights R23,355
1300 ft²
8 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Villa
- Oceanfront
- Pool
- Ocean View
R3,075/Night
For 7 Nights R21,523
6 Guests
2 Bedrooms
2 Bathrooms
Pet Friendly
House
- Pet Friendly
- Air Conditioner
- Internet
R1,372/Night
For 7 Nights R9,600
Trelawny Large Vacation Homes
6000 ft²
16 Guests
7 Bedrooms
7 Bathrooms
Ocean View
House
- Private Pool
- Pool
- Ocean View
R13,820/Night
For 7 Nights R96,739
69750.14 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Free Cancellation
Villa
- Oceanfront
- Fireplace/Heating
- Ocean View
R1,984/Night
For 7 Nights R13,885
R4,657/Night
For 7 Nights R32,595
6000 ft²
12 Guests
6 Bedrooms
6 Bathrooms
Ocean View
Villa
- Private Pool
- Pool
- Ocean View
R14,899/Night
For 7 Nights R104,295
1270.14 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Free Cancellation
Villa
- Oceanfront
- Pool
- Ocean View
R3,184/Night
For 7 Nights R22,292
6000 ft²
12 Guests
5 Bedrooms
5 Bathrooms
Ocean View
House
- Hot Tub
- Pool
- Ocean View
R17,794/Night
For 7 Nights R124,558
R13,084/Night
For 7 Nights R91,587
6000 ft²
18 Guests
8 Bedrooms
8 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Pool
R12,764/Night
For 7 Nights R89,347
Why Choose Rent By Owner for your Trelawny Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Trelawny
When should you plan your Vacation Rentals stay?
Choosing the right time to visit this destination ensures you experience its natural beauty and vibrant culture at their finest, making your stay in Trelawny even more memorable.
Peak Season Highlights
December to April
During this period, you can enjoy the warm and inviting weather that makes the region ideal for outdoor activities and relaxation. The area is lively with visitors seeking a sunny getaway, so booking your vacation rentals early ensures you secure the best properties.
Average Temperature Daytime: 80°F to 85°F - Nighttime: 70°F to 75°F
July to August
This summer months bring a vibrant atmosphere, perfect for exploring the local culture and enjoying the beaches. Expect higher demand for vacation rentals, so planning ahead helps you find the most comfortable accommodations at competitive rates.
Average Temperature Daytime: 88°F to 91°F - Nighttime: 76°F to 79°F
Off-Season Highlights
May to June
As the region transitions into the rainy season, you might find fewer crowds and better deals on vacation rentals. This is an excellent time to experience a more relaxed atmosphere while still enjoying pleasant temperatures and fewer tourists.
Average Temperature Daytime: 84°F to 86°F - Nighttime: 74°F to 76°F
September to November
The late summer to fall months offer lower prices and a quieter environment, making it ideal for those who prefer a peaceful retreat. Be mindful of potential rain showers, but overall, the weather remains warm and inviting for your stay.
Average Temperature Daytime: 83°F to 86°F - Nighttime: 73°F to 75°F
Weekly Weather Forecast for Trelawny
How to Book Your Trelawny Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Trelawny
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy a private outdoor swimming pool, perfect for relaxing under the sun in this tropical destination.
- Take advantage of lush gardens or landscaped yards that offer a peaceful setting for outdoor gatherings.
- Utilize a spacious patio or veranda to unwind while soaking in scenic views of the area's natural beauty.
- Benefit from direct access to nearby beaches or waterfronts for outdoor water activities.
- Make use of outdoor grills or barbecue areas to host memorable cookouts in this inviting region.
- Relax on a sun deck or loungers, ideal for sunbathing amid the warm Caribbean climate.
- Explore well-maintained walking or biking paths that weave through the property's outdoor spaces and beyond.
Top Attractions Around Trelawny
What attractions are nearby?
Here, you can enjoy a variety of outdoor activities and cultural experiences just moments from your vacation rentals in Trelawny, Jamaica, making it easy to immerse yourself in the region’s natural beauty and vibrant local heritage.
Family Activities
- Rose Hall Great House Tour: Discover the rich history and stunning architecture of this historic plantation estate, offering an engaging experience for the whole family in the area.
- Chukka Caribbean Adventures: Embark on exciting outdoor excursions such as horseback riding, zip-lining, or river tubing that bring adventure and fun to your family vacation here.
- Jamaica Climb: Challenge yourselves with rock climbing activities suitable for all ages, set amidst the scenic landscapes of this destination’s lush environment.
- Mahogany Beach: Relax and enjoy a day at this popular sandy spot, perfect for swimming, picnicking, or building sandcastles with loved ones along the coast.
Adult Activities
- Visit the Glistening Waters Luminous Lagoon: Experience a mesmerizing night tour where you can witness one of the world's rare bioluminescent phenomena right here in this destination.
- Explore Martha Brae River Rafting: Enjoy a peaceful bamboo raft ride along the scenic Martha Brae River, offering a relaxing way to take in the natural beauty of the region.
- Discover the Winding Trails at Trelawny’s Nature Reserves: Embark on guided hikes through lush forests and scenic trails that showcase the area's vibrant flora and fauna.
- Indulge in Local Cuisine and Nightlife: Savor authentic Jamaican dishes at local restaurants or experience lively bars that offer an authentic taste of the area's vibrant culture.
Other Places to Stay in Trelawny
Saint Andrew Parish
Windsor
Windsor Caves
Luminous Lagoon
Florence Hall Village
Blue Waters Beach Club
Merrywood
Corral Spring
Falmouth
Duncans
Rio Bueno
Bengal
Trelawny Travel Tips
How Can You Make the Most of Your Stay?
- Explore local dining options: Tasting authentic Jamaican cuisine at nearby eateries offers a true taste of the area's vibrant culinary scene and enhances your overall experience.
- Plan outdoor activities early: Take advantage of the region’s warm climate by scheduling outdoor excursions during the cooler parts of the day to maximize enjoyment and comfort.
- Leverage your vacation rentals for relaxation: Your chosen accommodation provides a perfect base to unwind after daytime adventures, making it easier to enjoy everything this destination has to offer.
- Connect with local guides: Engaging with knowledgeable guides can enrich your visit, providing personalized insights into the culture and hidden gems of the area.
Transportation Options
- Rental Car Services: Renting a car gives you the freedom to explore the region at your own pace, with numerous local providers offering convenient options for travelers staying in Trelawny.
- Public Buses and Minivans: Affordable and reliable, public buses and minivans connect popular spots around here, making them a practical choice for budget-conscious visitors.
- Taxis and Private Transfers: Taxis and private transfer services provide direct, comfortable transportation from the airport or around this area, ensuring a hassle-free journey to your vacation rentals.
- Shuttle Services: Many accommodation providers offer shuttle services to key destinations, offering an easy way to get around without the need for personal transportation.
Local Customs Options
- Local Dance Traditions: You can immerse yourself in lively dance styles like ska and reggae, which are integral to the area's cultural celebrations.
- Festivals and Celebrations: Participating in annual events such as the Maroons Festival offers a glimpse into the region’s rich history and community spirit.
- Traditional Cuisine: Sampling authentic Jamaican dishes prepared with locally sourced ingredients provides a flavorful experience of the area's culinary customs.
- Craftsmanship and Art:** Supporting local artisans by exploring handmade crafts reveals the region's vibrant artistic heritage.
Frequently Asked Questions About Trelawny?
1. What are the top vacation rentals in Trelawny?
There are a lot of options in Trelawny. If you plan on staying in the Trelawny area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Trelawny:
- Seahorse- - A Slice Of Caribbean Paradise On A Private Beach, Gated Community
- SeaEsta at Bengal ; Cool Chic and all Caribbean.
- Villa FANTASY - ON PRIVATE BEACH IN A GATED COMMUNITY
- 8Br, 7Ba, fully staffed Jamaica Villa for rent with Chef and Butler
- New Quiet Gated Ocean View Home
- 2 bedrooms 2bath home in gated area. 24 hours security.
- MODERN BEACH SIDE VILLA
- L&V Paradise Vacation Home with Pool and Gym
- Good Hope Coach House, historic cut stone house with modern amenities
- The Crystal at Stonebrook Manor, Falmouth, Trelawny, Jamaica
2. How many vacation rentals have private pools in Trelawny?
There are 18 vacation rentals with private pools near Trelawny. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Trelawny are best for families?
If you are looking for a family-friendly vacation home in Trelawny, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Trelawny:
4. How many Rentbyowner vacation rentals are available in Trelawny?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 320 in the Trelawny area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Trelawny.
5. What is the cancellation policy for vacation rentals in Trelawny, Jamaica?
The cancellation policy varies depending on the property listing. You should review the specific rental's terms and conditions before booking or contact the owner directly for detailed information.
6. Are there any additional fees I should be aware of when booking a vacation rental in this destination?
Additional fees such as cleaning fees, security deposits, or service charges are often outlined in the listing details. It is recommended to read the property description carefully or reach out to the host for clarification.
7. How do I secure my reservation at a vacation rental in the region?
Reservations are typically secured through the booking platform with a payment method specified by the owner. For further assurance, consult the listing’s payment policies or contact the host directly.
8. What amenities can I expect at a vacation rental here?
Amenities vary from one property to another but often include essentials like Wi-Fi, air conditioning, and kitchen facilities. Details about amenities are listed on each property's page, or you can inquire with the owner for more information.
9. Is there a minimum stay requirement for booking a vacation rental in this area?
Minimum stay policies depend on the individual property and can differ based on seasonal demands. Check the specific listing for minimum night requirements or contact the owner for clarification.
Trelawny Top Rated Vacation Rentals
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Pool
- Ocean View
R1,843/Night
For 7 Nights R12,904
1269 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Pool
R2,395/Night
For 7 Nights R16,764
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Pool
- Balcony/Terrace
- Kitchen
R2,667/Night
For 7 Nights R18,677
6000 ft²
8 Guests
4 Bedrooms
5 Bathrooms
Ocean View
House
- Private Pool
- Pool
- Ocean View
R9,993/Night
For 7 Nights R69,950
1377.78 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Pool
- Ocean View
R4,252/Night
For 7 Nights R29,766
1200 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
House
- Pool
- Kitchen
- Parking
R2,431/Night
For 7 Nights R17,009
8 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
House
- Pool
- Balcony/Terrace
- Kitchen
R5,054/Night
For 7 Nights R35,376
8 Guests
3 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Pool
- Ocean View
R2,639/Night
For 7 Nights R18,465
