Best Vacation Homes in Trelawny
Villa
10.0(93 Reviews)
3 Bedrooms
3 Baths
6 Guests
2800 ft²
Private Pool
Pool
Ocean View
Balcony/Terrace
US $690/Night
7 Nights - US $4,830
House
10.0(7 Reviews)
5 Bedrooms
4 Baths
10 Guests
15230.93 ft²
Oceanfront- Pool
- Ocean View
- Balcony/Terrace
US $123/Night
7 Nights - US $861
Resort
10.0(2 Reviews)
1 Bath
Hot Tub
Spa- Pool
- Balcony/Terrace
US $3,779/Night
7 Nights - US $26,453
Villa
10.0(56 Reviews)
4 Bedrooms
4 Baths
10 Guests
5500 ft²
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
US $1,283/Night
7 Nights - US $8,981
House
10.0(4 Reviews)
2 Bedrooms
2 Baths
5 Guests
1097.92 ft²
- Pool
- Balcony/Terrace
Parking
Air Conditioner
US $130/Night
7 Nights - US $910
Villa
10.0(38 Reviews)
6 Bedrooms
6 Baths
14 Guests
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
US $1,500/Night
7 Nights - US $10,500
Villa
10.0(31 Reviews)
8 Bedrooms
9 Baths
17 Guests
- Pool
- Balcony/Terrace
Kitchen- Air Conditioner
US $2,665/Night
7 Nights - US $18,653
House
10.0(14 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Pool
- Kitchen
- Parking
- Air Conditioner
US $88/Night
7 Nights - US $619
Trelawny Luxury Rentals
Resort
7.6(271 Reviews)
18 Baths
39 Guests
857.52 ft²
Private Beach- Oceanfront
- Spa
- Pool
US $2,670/Night
7 Nights - US $18,690
Villa
10.0(1 Review)
1 Bedroom
1 Bath
- Private Pool
- Oceanfront
- Hot Tub
- Spa
US $2,250/Night
7 Nights - US $15,750
Villa
10.0(6 Reviews)
7 Bedrooms
7 Baths
14 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $1,843/Night
7 Nights - US $12,898
House
4 Bedrooms
4 Baths
6 Guests
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
US $1,773/Night
7 Nights - US $12,411
Villa
5 Bedrooms
5 Baths
12 Guests
- Private Pool
- Oceanfront
- Hot Tub
Fireplace/Heating
US $1,573/Night
7 Nights - US $11,011
US $1,452/Night
7 Nights - US $10,164
Villa
9.4(87 Reviews)
6 Bedrooms
3 Baths
14 Guests
4000 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Pool
US $1,333/Night
7 Nights - US $9,331
Villa
9.8(133 Reviews)
5 Bedrooms
5 Baths
10 Guests
5000 ft²
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
US $1,333/Night
7 Nights - US $9,331
Trelawny Pet Friendly Vacation Rentals
Villa
10.0(5 Reviews)
3 Bedrooms
3 Baths
10 Guests
1450 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
View
US $207/Night
7 Nights - US $1,447
House
9.6(12 Reviews)
2 Bedrooms
2 Baths
4 Guests
1302.43 ft²
- Pool
- View
Breakfast
Pet Friendly
US $86/Night
7 Nights - US $603
House
9.8(19 Reviews)
1 Bedroom
1 Bath
6 Guests
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $219/Night
7 Nights - US $1,531
Villa
10.0(1 Review)
3 Bedrooms
3 Baths
7 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Pet Friendly
US $215/Night
7 Nights - US $1,505
Apartment
8.8(5 Reviews)
1 Bedroom
1 Bath
2 Guests
484.38 ft²
- View
- Pet Friendly
- Parking
Internet
US $55/Night
7 Nights - US $385
Villa
10.0(1 Review)
3 Bedrooms
3 Baths
10 Guests
1450 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $214/Night
7 Nights - US $1,496
Villa
10.0(1 Review)
2 Bedrooms
2 Baths
8 Guests
1300 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $147/Night
7 Nights - US $1,031
House
10.0(1 Review)
2 Bedrooms
2 Baths
6 Guests
- Balcony/Terrace
- Pet Friendly
- Kitchen
- Parking
US $84/Night
7 Nights - US $587
Trelawny Large Vacation Homes
House
10.0(8 Reviews)
7 Bedrooms
7 Baths
16 Guests
6000 ft²
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
US $845/Night
7 Nights - US $5,915
Villa
9.7(7 Reviews)
3 Bedrooms
3 Baths
6 Guests
69750.14 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $121/Night
7 Nights - US $849
US $285/Night
7 Nights - US $1,993
Villa
10.0(3 Reviews)
6 Bedrooms
6 Baths
12 Guests
6000 ft²
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
US $911/Night
7 Nights - US $6,377
Villa
9.3(4 Reviews)
3 Bedrooms
2 Baths
6 Guests
1270.14 ft²
- Oceanfront
- Pool
- Ocean View
- View
US $195/Night
7 Nights - US $1,363
House
10.0(1 Review)
5 Bedrooms
5 Baths
12 Guests
6000 ft²
- Hot Tub
- Pool
- Ocean View
- Balcony/Terrace
US $1,216/Night
7 Nights - US $8,512
Villa
10.0(1 Review)
8 Bedrooms
8 Baths
18 Guests
6000 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $824/Night
7 Nights - US $5,768
Villa
10.0(1 Review)
4 Bedrooms
5 Baths
8 Guests
- Private Pool
- Hot Tub
- Pool
- Breakfast
US $800/Night
7 Nights - US $5,600
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
Florence Hall Village
Luminous Lagoon
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.
Trelawny Vacation Rental Frequently Asked Questions
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 322 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
House
10.0(11 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $117/Night
7 Nights - US $818
House
10.0(6 Reviews)
3 Bedrooms
2 Baths
6 Guests
1269 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $155/Night
7 Nights - US $1,085
House
10.0(4 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Pool
- Balcony/Terrace
- Kitchen
- Parking
US $174/Night
7 Nights - US $1,215
House
10.0(2 Reviews)
4 Bedrooms
5 Baths
8 Guests
6000 ft²
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
US $612/Night
7 Nights - US $4,284
House
10.0(2 Reviews)
3 Bedrooms
2 Baths
6 Guests
1377.78 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $260/Night
7 Nights - US $1,820
House
10.0(1 Review)
3 Bedrooms
3 Baths
8 Guests
- Pool
- Balcony/Terrace
- Kitchen
- Parking
US $205/Night
7 Nights - US $1,436
House
10.0(1 Review)
3 Bedrooms
2 Baths
8 Guests
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $161/Night
7 Nights - US $1,129
House
10.0(1 Review)
3 Bedrooms
3 Baths
6 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Pool
US $140/Night
7 Nights - US $980
