Best Vacation Homes in Castleton
Apartment
10.0(7 Reviews)
2 Bedrooms
2 Baths
4 Guests
1020 ft²
Balcony/Terrace
Kitchen
Parking
Air Conditioner
US $158/Night
7 Nights - US $1,108
Apartment
10.0(12 Reviews)
1 Bedroom
1 Bath
1 Guest
796.53 ft²
- Balcony/Terrace
View- Parking
- Air Conditioner
US $100/Night
7 Nights - US $700
Apartment
10.0(2 Reviews)
1 Bedroom
1 Bath
- Balcony/Terrace
- Kitchen
- Parking
- Air Conditioner
US $118/Night
7 Nights - US $826
House
10.0(3 Reviews)
3 Bedrooms
3 Baths
7 Guests
- Balcony/Terrace
- Kitchen
- Parking
- Air Conditioner
US $223/Night
7 Nights - US $1,564
Bed & Breakfast
10.0(5 Reviews)
1 Bedroom
1 Bath
2 Guests
355.21 ft²
Oceanfront
Pool
Ocean View- Balcony/Terrace
US $109/Night
7 Nights - US $765
House
10.0(3 Reviews)
2 Bedrooms
2 Baths
4 Guests
1700 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $135/Night
7 Nights - US $945
Apartment
10.0(3 Reviews)
1 Bedroom
1 Bath
3 Guests
- Pool
- Kitchen
- Parking
- Air Conditioner
US $112/Night
7 Nights - US $785
House
10.0(2 Reviews)
4 Bedrooms
2 Baths
6 Guests
- Balcony/Terrace
- Kitchen
- Parking
- Air Conditioner
US $270/Night
7 Nights - US $1,887
Castleton Luxury Rentals
Apartment
2 Bedrooms
2 Baths
4 Guests
- Pool
- Balcony/Terrace
- Kitchen
- Parking
Unlock the Best Price
Apartment
2 Bedrooms
1 Bath
2 Guests
- Kitchen
- Parking
- Air Conditioner
Internet
US $8,786/Night
7 Nights - US $61,500
Apartment
1 Bedroom
1 Bath
2 Guests
- Balcony/Terrace
- Kitchen
- Parking
- Air Conditioner
US $8,786/Night
7 Nights - US $61,500
Apartment
2 Bedrooms
1 Bath
4 Guests
Fireplace/Heating- Air Conditioner
- Internet
Child Friendly
US $4,051/Night
7 Nights - US $28,359
Apartment
2 Bedrooms
1 Bath
4 Guests
- Kitchen
- Parking
- Air Conditioner
- Internet
US $1,550/Night
7 Nights - US $10,850
Villa
10.0(1 Review)
5 Bedrooms
6 Baths
10 Guests
Private Pool
Hot Tub- Fireplace/Heating
- Pool
US $1,476/Night
7 Nights - US $10,333
Villa
9.0(2 Reviews)
5 Bedrooms
5 Baths
10 Guests
5700 ft²
- Private Pool
- Hot Tub
- Pool
- Ocean View
US $1,140/Night
7 Nights - US $7,980
Villa
5 Bedrooms
3 Baths
10 Guests
3127 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $914/Night
7 Nights - US $6,397
Castleton Pet Friendly Vacation Rentals
Apartment
10.0(1 Review)
1 Bedroom
1 Bath
2 Guests
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $138/Night
7 Nights - US $966
Apartment
10.0(1 Review)
3 Bedrooms
3 Baths
6 Guests
4004.17 ft²
- Oceanfront
- Hot Tub
- Pool
- Ocean View
US $79/Night
7 Nights - US $554
US $120/Night
7 Nights - US $840
House
9.6(13 Reviews)
2 Bedrooms
1 Bath
4 Guests
1615 ft²
- Private Pool
- Pool
- Balcony/Terrace
Pet Friendly
US $77/Night
7 Nights - US $537
Apartment
9.1(27 Reviews)
1 Bedroom
1 Bath
2 Guests
- Pet Friendly
- Parking
- Air Conditioner
- Internet
US $54/Night
7 Nights - US $378
Cabin
9.0(13 Reviews)
2 Bedrooms
1 Bath
4 Guests
450 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $30/Night
7 Nights - US $210
Apartment
6.0(2 Reviews)
2 Bedrooms
1 Bath
4 Guests
600 ft²
- Balcony/Terrace
- Pet Friendly
- Kitchen
- Parking
US $106/Night
7 Nights - US $742
Cabin
2 Bedrooms
2 Baths
8 Guests
- Balcony/Terrace
- Pet Friendly
- Kitchen
- Parking
US $820/Night
7 Nights - US $5,740
Castleton Large Vacation Homes
Bed & Breakfast
10.0(1 Review)
5 Bedrooms
3 Baths
13 Guests
1 ft²
- Balcony/Terrace
Breakfast- Kitchen
- Parking
US $479/Night
7 Nights - US $3,350
Apartment
9.6(13 Reviews)
6 Bedrooms
6 Baths
18 Guests
555.42 ft²
- Oceanfront
- Ocean View
- View
- Parking
US $228/Night
7 Nights - US $1,594
Villa
6.0(2 Reviews)
1 Bedroom
1 Bath
2 Guests
- Pool
- Balcony/Terrace
- Kitchen
- Parking
US $89/Night
7 Nights - US $625
Villa
9.4(3 Reviews)
4 Bedrooms
5 Baths
8 Guests
4000 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Pool
US $466/Night
7 Nights - US $3,264
House
9.2(7 Reviews)
13 Bedrooms
7 Baths
16 Guests
152.23 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $120/Night
7 Nights - US $840
House
9.4(3 Reviews)
3 Bedrooms
2 Baths
10 Guests
3500 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
US $261/Night
7 Nights - US $1,826
Villa
8.0(1 Review)
5 Bedrooms
5 Baths
10 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Kitchen
US $165/Night
7 Nights - US $1,155
House
6.0(2 Reviews)
4 Bedrooms
3 Baths
10 Guests
- Balcony/Terrace
- Kitchen
- Parking
- Internet
US $233/Night
7 Nights - US $1,632
Why Choose Rent By Owner for your Castleton 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 Castleton
When should you plan your Vacation Rentals stay?
Finding the ideal time to visit here can enhance your experience, as the best seasons for enjoying the natural beauty and relaxed atmosphere in this destination typically align with its warm, inviting climate and favorable weather conditions.
Peak Season Highlights
December to April
During these months, you can enjoy a warm and dry climate ideal for outdoor activities and exploring the region's natural beauty. This is the most popular time for visitors seeking a tropical getaway in the area.
Average Temperature Daytime: 85°F - Nighttime: 75°F
July to August
This peak summer period offers lush landscapes and vibrant local events, attracting travelers eager to experience the lively atmosphere while benefiting from warm weather.
Average Temperature Daytime: 88°F - Nighttime: 77°F
Off-Season Highlights
May to June
The early summer months tend to be quieter, providing a more relaxed environment to enjoy the area's natural serenity without the crowds.
Average Temperature Daytime: 83°F - Nighttime: 73°F
September to November
As the region transitions into the rainy season, this period offers fewer visitors and lush scenery, making it a great time for those seeking tranquility and lower prices on vacation rentals.
Average Temperature Daytime: 82°F - Nighttime: 72°F
Weekly Weather Forecast for Castleton
How to Book Your Castleton 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 Castleton
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 to cool off while taking in the scenic surroundings.
- Relax on a spacious veranda or patio perfect for outdoor dining and sunset views.
- Take advantage of lush gardens or landscaped yards that offer tranquil spaces for relaxation.
- Utilize outdoor grilling facilities to prepare delicious meals amid the tropical climate.
- Benefit from a shaded area or gazebo, ideal for lounging and enjoying the breezes.
- Experience direct access to nearby hiking trails or nature walks within the area’s natural beauty.
- Make the most of outdoor recreational areas, such as courts or play zones, if available, for added entertainment.
Top Attractions Around Castleton
What attractions are nearby?
Nearby, you can explore vibrant local markets, enjoy scenic coastal walks, and experience authentic Jamaican culture just moments from your rental in this picturesque region.
Family Activities
- Blue Mountain Bicycle Tours: Embark on family-friendly cycling adventures that let you explore the scenic beauty and lush landscapes of the region at your own pace.
- Cultural Tours in the Region: Discover local history and Jamaican traditions through guided cultural tours designed to engage visitors of all ages in this inviting destination.
- Hiking Trails Nearby: Enjoy exploring well-marked trails surrounded by tropical flora, perfect for family hikes that provide breathtaking views and fresh air.
- Local Craft Markets: Visit vibrant markets where your family can experience authentic crafts and souvenirs, supporting local artisans in this lively area.
Adult Activities
- Exploring the Blue Mountain Peak Trail: Embark on a scenic hike that offers breathtaking views and a chance to experience the region’s lush natural beauty firsthand.
- Visiting the Fern Gully: Discover this stunning rainforest corridor filled with towering ferns and vibrant flora, perfect for nature enthusiasts seeking tranquility in the area.
- Enjoying local cuisine at nearby eateries: Savor authentic Jamaican flavors by dining at local restaurants that showcase the culinary richness of this destination.
- Learning about local history and culture: Visit nearby cultural sites or museums to deepen your understanding of the region’s heritage and traditions during your stay.
Other Places to Stay in Castleton
Castleton Gardens
Castleton Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Cuisine: Take advantage of the area's authentic Jamaican eateries nearby your vacation rental to enjoy local flavors and cultural dishes.
- Plan Outdoor Adventures: Make the most of the region’s natural beauty by scheduling excursions like hiking or exploring scenic spots close to your accommodation.
- Discover Nearby Attractions: Use your stay as a base to visit popular sites in the region, ensuring you experience the area's rich history and vibrant community.
- Interact with the Community: Engage with locals during your visit to gain insider tips and immerse yourself in the destination's welcoming atmosphere.
Transportation Options
- Car Rentals: Exploring the area at your own pace is easy with local car rental services available here, giving you the flexibility to visit scenic spots in Saint Mary.
- Public Buses: The region's bus system offers an affordable and reliable way to travel between key destinations in the area for convenient transportation.
- Taxis and Ride-Sharing: Taxis and ride-sharing options provide quick and comfortable transfers for those who prefer a more private travel experience in this destination.
- Private Shuttle Services: Many local operators offer private shuttles that cater to travelers seeking door-to-door service within the region's most popular locations.
Local Customs Options
- Local Music and Dance: Engaging with the vibrant reggae and dancehall rhythms that are an integral part of the area's cultural expression provides a lively connection to the local scene.
- Ganja Culture: Understanding the local customs surrounding the medicinal and spiritual use of cannabis offers insight into the region's relaxed attitude towards this plant.
- Community Festivals: Participating in or observing traditional festivals and celebrations reveals the area's rich heritage and communal spirit.
- Traditional Cuisine: Sampling authentic Jamaican dishes prepared using age-old recipes allows you to experience the region’s culinary traditions firsthand.
Castleton Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Castleton?
There are a lot of options in Castleton. If you plan on staying in the Castleton area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Castleton:
- Kingston Oasis One Bedroom
- Book a PREMIER EXPERIENCE | 4 min from Bob Marley Museum
- Cottage at Forever
- Studio Chateau - Manor Park, Kingston 8
- Suite 7 At The Rochesters
- Elegant, Quiet & Cozy Kingston Home
- Hidden Gem Emerald in Buff Bay,
- Luxury one bed room apartment with AC, roof top pool, WIFI located in Kingston.
- Remodeled Vacation home on private property
- ★ Cozy Kingston Getaway ★ Relaxing, Quaint & Centrally Located ★
2. How many vacation rentals have private pools in Castleton?
There are 26 vacation rentals with private pools near Castleton. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Castleton are best for families?
If you are looking for a family-friendly vacation home in Castleton, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Castleton:
4. How many Rentbyowner vacation rentals are available in Castleton?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 745 in the Castleton 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 Castleton.
5. What is the cancellation policy for vacation rentals in this area?
Cancellation policies vary by listing, so it's important to review the specific terms outlined in the property description or contact the owner directly to understand the refund eligibility and timeframes.
6. How do I confirm the availability of a vacation rental in Saint Mary, Jamaica?
Availability can be checked instantly through the listing on this destination's website. If you have questions or need assistance, reaching out to the owner will ensure you get the most accurate and up-to-date information.
7. Are there any additional fees I should be aware of when booking here?
Additional fees such as cleaning charges, security deposits, or service fees are typically noted on the property listing. Always review the detailed pricing before confirming your reservation to avoid surprises.
8. Can I find pet-friendly vacation rentals in this region?
Pet policies differ between properties; some listings accommodate pets while others do not. You should verify with the owner directly to confirm whether bringing your pet is permitted during your stay.
9. What amenities are usually included in vacation rentals in this part of Jamaica?
Most rentals offer key amenities like Wi-Fi, kitchen facilities, and air conditioning. For specifics about what’s included and to meet your needs, reviewing individual listings or contacting the host is recommended.
Castleton Top Rated Vacation Rentals
Apartment
10.0(2 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Pool
- Balcony/Terrace
- View
- Parking
US $140/Night
7 Nights - US $982
Apartment
10.0(2 Reviews)
1 Bedroom
3 Baths
5 Guests
- Pool
- Parking
- Air Conditioner
- Internet
US $136/Night
7 Nights - US $952
Apartment
10.0(2 Reviews)
1 Bedroom
1 Bath
2 Guests
- Hot Tub
- Pool
- Ocean View
- Balcony/Terrace
US $84/Night
7 Nights - US $590
Apartment
10.0(1 Review)
3 Bedrooms
4 Baths
6 Guests
- Pool
- Kitchen
- Parking
- Air Conditioner
US $331/Night
7 Nights - US $2,317
Apartment
10.0(1 Review)
2 Bedrooms
1 Bath
4 Guests
- Pool
- Balcony/Terrace
- Kitchen
- Parking
US $207/Night
7 Nights - US $1,446
Apartment
10.0(1 Review)
1 Bedroom
1 Bath
2 Guests
- Pool
- Balcony/Terrace
- Kitchen
- Parking
US $204/Night
7 Nights - US $1,429
Condo
10.0(1 Review)
2 Bedrooms
2 Baths
4 Guests
- Pool
- Balcony/Terrace
- Kitchen
- Parking
US $186/Night
7 Nights - US $1,302
Apartment
10.0(1 Review)
2 Bedrooms
2 Baths
4 Guests
1350 ft²
- Pool
- Balcony/Terrace
- Kitchen
- Parking
US $170/Night
7 Nights - US $1,190
