Discover Your Perfect Jamaica Vacation Homes

Jamaica Luxury Rentals

Why Choose Rent By Owner for your Jamaica Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Jamaica

When should you plan your Vacation Rentals stay?

Choosing the right time to vacation in Jamaica, Vermont, ensures you can enjoy the region’s natural beauty and tranquil surroundings at their best; consider visiting during the shoulder seasons for fewer crowds and more favorable weather that complements your stay here.

Peak Season Highlights

winter
Winter (December to February)

During the winter months, you can enjoy the region's scenic beauty and winter sports activities, making it a popular time to visit.

Average Temperature Daytime: 25°F to 35°F - Nighttime: 10°F to 20°F
summer
Summer (June to August)

The summer season offers warm weather ideal for outdoor exploration and relaxing stays, attracting visitors seeking pleasant temperatures.

Average Temperature Daytime: 70°F to 80°F - Nighttime: 50°F to 60°F

Off-Season Highlights

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Spring (March to May)

In spring, the area experiences milder weather and fewer crowds, providing a peaceful setting for your getaway.

Average Temperature Daytime: 45°F to 60°F - Nighttime: 30°F to 40°F
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Fall (September to November)

Autumn showcases vibrant foliage colors with cooler temperatures, creating a picturesque backdrop for your stay.

Average Temperature Daytime: 55°F to 65°F - Nighttime: 40°F to 50°F

Weekly Weather Forecast for Jamaica

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.

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 scenic outdoor spaces with a private yard or garden to relax and unwind.
  • Take advantage of outdoor grilling areas for family cookouts amid the natural surroundings.
  • Make the most of nearby hiking trails by exploring the region’s picturesque landscape.
  • Relax on spacious decks or patios, ideal for soaking in the fresh mountain air.
  • Benefit from access to outdoor fire pits for cozy gatherings during cooler evenings.
  • Discover opportunities for outdoor sports or activities such as tennis or volleyball if available.
  • Experience the beauty of the area through nearby lakes or rivers perfect for kayaking or fishing.
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Family Activities

  • Jamaica State Park: You can enjoy a family picnic and explore scenic trails surrounded by the natural beauty of Vermont's lush landscape.
  • Vermont Institute of Natural Science (VINS) Bird Sanctuary: Discover local wildlife and participate in engaging educational exhibits perfect for children and adults alike.
  • Sugarbush Farm: Experience authentic maple sugaring with family-friendly tours that showcase traditional Vermont methods in a charming farm setting.
  • Kid-Friendly Skiing at Smugglers' Notch Resort: Embrace winter adventures with beginner slopes and ski lessons ideal for families staying in cozy Vermont vacation rentals here.
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Adult Activities

  • Hiking the Long Trail: Explore the scenic trails of the Long Trail, offering breathtaking views and a rejuvenating outdoor experience in this region.
  • Visiting local art galleries: Discover the vibrant art scene by browsing through galleries that showcase talented local artists inspired by the area's natural beauty.
  • Enjoying craft breweries: Sample diverse local brews at the region's renowned craft breweries, perfect for relaxing after a day outdoors.
  • Fishing on nearby lakes and rivers: Cast your line in tranquil lakes and rivers, providing a peaceful escape and great opportunities for leisurely fishing here.

Jamaica Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Seasons: Take advantage of the region’s distinct seasons by planning outdoor activities during the summer or enjoying scenic winter views from your rental.
  • Choose a Prime Location: Select vacation rentals situated close to key attractions and outdoor recreation spots to maximize your exploration and convenience.
  • Experience Authentic Dining: Savor locally owned restaurants and cafes nearby to immerse yourself in the area's culinary traditions.
  • Participate in Regional Events: Check the local calendar for seasonal festivals and events that provide unique cultural insights during your stay.

Transportation Options

  • Jamaica, Vermont Transit Services: Public bus routes connect this scenic destination to neighboring towns, making it easy for you to explore the region without a car.
  • Rental Cars in Jamaica, Vermont: Car rentals are readily available here, offering you the flexibility to discover the area's outdoor attractions at your own pace.
  • Local Taxis and Rideshare Options: Taxis and rideshare services provide convenient transportation within the region, ideal for short trips or last-minute travel needs.
  • Nearby Airport Transfers: The closest airports offer shuttle services and private transfers that simplify your journey to this peaceful destination.

Local Customs Options

  • Respect for Local Craftsmanship: You’ll find that appreciating handcrafted goods and local artistry is a valued custom here, reflecting the region’s rich cultural heritage.
  • Engaging with Community Events: Participating in seasonal festivals and community gatherings offers an authentic way to connect with the area's traditions.
  • Mindful Environmental Practices: The region encourages eco-friendly habits, such as conserving natural resources while enjoying the outdoor activities available here.
  • Politeness and Hospitality: Displaying courteous behavior and openness will help you experience the warm, welcoming spirit of this destination's residents.

Frequently Asked Questions About Jamaica?

2. Which vacation homes in Jamaica are best for families?

If you are looking for a family-friendly vacation home in Jamaica, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Jamaica:

3. How many Rentbyowner vacation rentals are available in Jamaica?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 122 in the Jamaica 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 Jamaica. 

4. What is the cancellation policy for vacation rentals in Vermont?

Cancellation policies vary by listing, so it’s important to review the specific terms on the property’s page before booking. Some rentals offer flexible options, while others may have stricter rules. If you need further clarification, contacting the host directly can provide additional details.

5. Are there any age restrictions or requirements when booking a vacation rental here?

Many listings require guests to meet certain age criteria, often 21 years or older, to ensure responsible occupancy. It's best to check the individual property details or contact the host if you have questions about age restrictions for your stay.

6. How do I find a pet-friendly vacation rental in the area?

To find pet-friendly accommodations, use the search filters available on the booking site and select the option indicating that you will be bringing pets. Always review the host’s pet policy in the listing to confirm any restrictions or additional fees.

7. What amenities are typically included in Vermont vacation rentals, and how can I verify them?

Most listings specify included amenities such as Wi-Fi, kitchen facilities, heating, and parking. To confirm what’s available at a particular property, carefully review the listing details or reach out directly to the owner for clarification.

8. What should I know about the check-in and check-out procedures for these rentals?

Check-in and check-out times are generally outlined in each listing. Many hosts offer flexible arrangements, but it’s recommended to communicate directly with the owner to coordinate arrival and departure times, ensuring a smooth stay.