754+ Private Villas and Holiday Rentals in Castleton |
Castleton Holiday Rentals
Apartment
- Kingston
- ·
- Saint Andrew
- 1.70 mi to center
10.0Exceptional
(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
- Kingston
- ·
- Saint Andrew
- 3.28 mi to center
10.0Exceptional
(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
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
- Balcony/Terrace
- Kitchen
- Parking
- Air Conditioner
US $118/Night
7 Nights - US $826
Apartment
10.0Exceptional
(3 Reviews)
1 Bedroom
1 Bath
2 Guests
- Balcony/Terrace
- Kitchen
- Parking
- Air Conditioner
US $262/Night
7 Nights - US $1,832
Bed & Breakfast
- Montego Bay
- ·
- Robins Bay
- 1.48 mi to center
10.0Exceptional
(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
- Kingston
- ·
- Constant Spring
- 1.01 mi to center
10.0Exceptional
(3 Reviews)
3 Bedrooms
3 Baths
7 Guests
- Balcony/Terrace
- Kitchen
- Parking
- Air Conditioner
US $223/Night
7 Nights - US $1,564
House
10.0Exceptional
(3 Reviews)
2 Bedrooms
2 Baths
4 Guests
1700 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $135/Night
7 Nights - US $945
Apartment
- Kingston
- ·
- Camperdown
- 0.27 mi to center
10.0Exceptional
(3 Reviews)
1 Bedroom
1 Bath
3 Guests
- Pool
- Kitchen
- Parking
- Air Conditioner
US $112/Night
7 Nights - US $785
House
- Kingston
- ·
- Saint Andrew
- 1.07 mi to center
10.0Exceptional
(2 Reviews)
4 Bedrooms
2 Baths
6 Guests
- Balcony/Terrace
- Kitchen
- Parking
- Air Conditioner
US $270/Night
7 Nights - US $1,887
Luxury Holiday Rentals in Castleton
Over 745+ Luxury Holiday Rentals in or Near Castleton
Apartment
2 Bedrooms
2 Baths
4 Guests
- Pool
- Balcony/Terrace
- Kitchen
- Parking
Unlock the Best Price
Apartment
- Kingston
- ·
- Camperdown
- 0.33 mi to center
2 Bedrooms
1 Bath
2 Guests
- Kitchen
- Parking
- Air Conditioner
Internet
US $8,786/Night
7 Nights - US $61,500
Apartment
- Kingston
- ·
- Saint Andrew
- 2.75 mi to center
1 Bedroom
1 Bath
2 Guests
- Balcony/Terrace
- Kitchen
- Parking
- Air Conditioner
US $8,786/Night
7 Nights - US $61,500
Villa
- Montego Bay
- ·
- Robins Bay
- 1.13 mi to center
10.0Exceptional
(1 Review)
14 Bedrooms
10 Baths
30 Guests
- Oceanfront
Hot Tub- Ocean View
- Balcony/Terrace
US $5,339/Night
7 Nights - US $37,373
Apartment
- Kingston
- ·
- Pembroke Hall
- 0.39 mi to center
2 Bedrooms
1 Bath
4 Guests
Fireplace/Heating- Air Conditioner
- Internet
Child Friendly
US $4,051/Night
7 Nights - US $28,359
Apartment
- Kingston
- ·
- Saint Andrew
- 4.25 mi to center
2 Bedrooms
1 Bath
4 Guests
- Kitchen
- Parking
- Air Conditioner
- Internet
US $1,550/Night
7 Nights - US $10,850
Villa
10.0Exceptional
(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
- Kingston
- ·
- Stony Hill
- 0.74 mi to center
9.0Exceptional
(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
- Saint Mary
- ·
- Highgate
- 5.37 mi to center
5 Bedrooms
3 Baths
10 Guests
3127 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $914/Night
7 Nights - US $6,397
Top-Rated Holiday Rentals with a Pool in Castleton
Over 230+ The Best Private Villas and Holiday Rentals in Castleton with a Pool
Apartment
- Kingston
- ·
- Saint Andrew
- 1.40 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
2 Baths
4 Guests
64.58 ft²
- Pool
- Balcony/Terrace
- View
- Parking
US $140/Night
7 Nights - US $982
Apartment
10.0Exceptional
(2 Reviews)
1 Bedroom
3 Baths
5 Guests
- Pool
- Parking
- Air Conditioner
- Internet
US $136/Night
7 Nights - US $952
Apartment
- Kingston
- ·
- Saint Andrew
- 4.10 mi to center
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
2 Guests
- Hot Tub
- Pool
- Ocean View
- Balcony/Terrace
US $84/Night
7 Nights - US $590
Apartment
- Kingston
- ·
- Saint Andrew
- 4.04 mi to center
10.0Exceptional
(2 Reviews)
3 Bedrooms
3 Baths
6 Guests
4004.17 ft²
- Oceanfront
- Hot Tub
- Pool
- Ocean View
US $79/Night
7 Nights - US $554
Apartment
- Kingston
- ·
- Saint Andrew
- 1.73 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
4 Baths
6 Guests
- Pool
- Kitchen
- Parking
- Air Conditioner
US $331/Night
7 Nights - US $2,317
Apartment
- Montego Bay
- ·
- Robins Bay
- 1.74 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
4 Guests
- Pool
- Balcony/Terrace
- Kitchen
- Parking
US $207/Night
7 Nights - US $1,446
Apartment
- Kingston
- ·
- Saint Andrew
- 2.17 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
2 Guests
- Pool
- Balcony/Terrace
- Kitchen
- Parking
US $204/Night
7 Nights - US $1,429
Condo
- Kingston
- ·
- Saint Andrew
- 4.10 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
4 Guests
- Pool
- Balcony/Terrace
- Kitchen
- Parking
US $186/Night
7 Nights - US $1,302
Apartment
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
4 Guests
1350 ft²
- Pool
- Balcony/Terrace
- Kitchen
- Parking
US $170/Night
7 Nights - US $1,190
Pet-Friendly Holiday Rentals in Castleton
Over 69+ Pet-Friendly Holiday Rentals in or Near Castleton
Apartment
- Montego Bay
- ·
- Robins Bay
- 0.67 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
2 Guests
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $138/Night
7 Nights - US $966
Apartment
- Kingston
- ·
- Camperdown
- 0.34 mi to center
9.1Exceptional
(27 Reviews)
1 Bedroom
1 Bath
2 Guests
Pet Friendly- Parking
- Air Conditioner
- Internet
US $54/Night
7 Nights - US $378
Cottage
- Kingston
- ·
- Jack's Hill
- 0.51 mi to center
1 Bedroom
1 Bath
- Pet Friendly
- Kitchen
- Parking
- Internet
US $120/Night
7 Nights - US $840
House
9.6Exceptional
(13 Reviews)
2 Bedrooms
1 Bath
4 Guests
1615 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Pet Friendly
US $77/Night
7 Nights - US $537
House
- Montego Bay
- ·
- Port Maria
- 0.76 mi to center
8.0Excellent
(2 Reviews)
2 Bedrooms
3 Baths
4 Guests
796.53 ft²
Private Beach- Ocean View
- Balcony/Terrace
- View
US $77/Night
7 Nights - US $536
Villa
- Montego Bay
- ·
- Robins Bay
- 1.07 mi to center
9.0Exceptional
(13 Reviews)
2 Bedrooms
1 Bath
6 Guests
900 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $578/Night
7 Nights - US $4,046
Cabin
- Montego Bay
- ·
- Robins Bay
- 1.32 mi to center
9.0Exceptional
(13 Reviews)
2 Bedrooms
1 Bath
4 Guests
450 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $58/Night
7 Nights - US $406
Apartment
- Kingston
- ·
- Patrick City
- 0.19 mi to center
6.0Good
(2 Reviews)
2 Bedrooms
1 Bath
4 Guests
600 ft²
- Balcony/Terrace
- Pet Friendly
- Kitchen
- Parking
US $150/Night
7 Nights - US $1,050
Cabin
2 Bedrooms
2 Baths
8 Guests
- Balcony/Terrace
- Pet Friendly
- Kitchen
- Parking
US $820/Night
7 Nights - US $5,740
Large Holiday Rentals and Private Villas in Castleton
Over 58+ Large Holiday Rentals and Private Villas in or Near Castleton
Bed & Breakfast
- Kingston
- ·
- Jack's Hill
- 0.53 mi to center
10.0Exceptional
(1 Review)
5 Bedrooms
3 Baths
13 Guests
1 ft²
- Balcony/Terrace
Breakfast- Kitchen
- Parking
US $479/Night
7 Nights - US $3,350
Apartment
- Kingston
- ·
- Camperdown
- 0.36 mi to center
9.6Exceptional
(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
- Saint Mary
- ·
- Highgate
- 6.77 mi to center
6.0Good
(2 Reviews)
1 Bedroom
1 Bath
2 Guests
- Pool
- Balcony/Terrace
- Kitchen
- Parking
US $89/Night
7 Nights - US $625
Villa
- Montego Bay
- ·
- Port Maria
- 0.72 mi to center
9.4Exceptional
(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
- Saint Mary
- ·
- Castleton
- 0.18 mi to center
9.2Exceptional
(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
- Kingston
- ·
- Jack's Hill
- 1.11 mi to center
9.4Exceptional
(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
- Montego Bay
- ·
- Port Maria
- 0.70 mi to center
8.0Excellent
(1 Review)
5 Bedrooms
5 Baths
10 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Kitchen
US $165/Night
7 Nights - US $1,155
House
- Kingston
- ·
- Saint Andrew
- 0.93 mi to center
6.0Good
(2 Reviews)
4 Bedrooms
3 Baths
10 Guests
- Balcony/Terrace
- Kitchen
- Parking
- Internet
US $233/Night
7 Nights - US $1,632
Villa
- Kingston
- ·
- Molynes Gardens
- 0.25 mi to center
6.0Good
(1 Review)
9 Bedrooms
9 Baths
18 Guests
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
US $614/Night
7 Nights - US $4,297
Wheelchair Accessible Holiday Homes in Castleton
Over 55+ Wheelchair Accessible Holiday Homes in or Near Castleton
Apartment
- Kingston
- ·
- Saint Andrew
- 1.85 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
3 Baths
4 Guests
- Hot Tub
- Pool
- Balcony/Terrace
- Kitchen
US $151/Night
7 Nights - US $1,058
Apartment
10.0Exceptional
(4 Reviews)
2 Bedrooms
2 Baths
4 Guests
1194.79 ft²
- Parking
- Air Conditioner
- Internet
- Child Friendly
US $106/Night
7 Nights - US $742
Apartment
- Kingston
- ·
- Constant Spring
- 1.25 mi to center
6.0Good
(1 Review)
1 Bedroom
1 Bath
- Pool
- Balcony/Terrace
- Kitchen
- Parking
US $90/Night
7 Nights - US $630
Apartment
- Kingston
- ·
- Saint Andrew
- 2.12 mi to center
9.8Exceptional
(6 Reviews)
2 Bedrooms
2 Baths
4 Guests
1600 ft²
- Pool
- Balcony/Terrace
- Kitchen
- Parking
US $129/Night
7 Nights - US $901
Apartment
- Kingston
- ·
- Saint Andrew
- 2.18 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
4 Guests
226.04 ft²
- Balcony/Terrace
- Parking
- Air Conditioner
- Internet
US $100/Night
7 Nights - US $700
Apartment
- Kingston
- ·
- Saint Andrew
- 3.92 mi to center
8.0Excellent
(5 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Fireplace/Heating
- Pool
- Kitchen
- Parking
US $127/Night
7 Nights - US $888
Apartment
- Kingston
- ·
- Saint Andrew
- 1.99 mi to center
8.0Excellent
(4 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Hot Tub
- Pool
- Balcony/Terrace
- Kitchen
US $135/Night
7 Nights - US $942
New
Apartment
- Kingston
- ·
- Saint Andrew
- 1.49 mi to center
1 Bedroom
2 Baths
4 Guests
19375 ft²
- Balcony/Terrace
- Kitchen
- Parking
- Air Conditioner
US $568/Night
7 Nights - US $3,978
Apartment
- Kingston
- ·
- Saint Andrew
- 2.17 mi to center
3 Bedrooms
2 Baths
6 Guests
- Pool
- Balcony/Terrace
- Kitchen
- Parking
US $510/Night
7 Nights - US $3,570
Castleton Private Villas and Holiday Homes Under $200
Over 567+ Castleton Private Villas and Holiday Homes Under $200
House
- Kingston
- ·
- Ziadie Gardens
- 0.23 mi to center
10.0Exceptional
(2 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Balcony/Terrace
- Kitchen
- Parking
- Air Conditioner
US $163/Night
7 Nights - US $1,143
Apartment
10.0Exceptional
(2 Reviews)
3 Bedrooms
1 Bath
6 Guests
796.53 ft²
- Fireplace/Heating
- View
- Parking
- Internet
US $123/Night
7 Nights - US $863
Apartment
- Kingston
- ·
- Molynes Gardens
- 0.31 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
- Pool
- Balcony/Terrace
- Kitchen
- Parking
US $123/Night
7 Nights - US $861
Apartment
- Kingston
- ·
- Pembroke Hall
- 0.38 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Kitchen
- Parking
- Air Conditioner
- Internet
US $82/Night
7 Nights - US $573
Apartment
- Kingston
- ·
- Stony Hill
- 0.28 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
3 Guests
1001.04 ft²
- View
- Parking
- Air Conditioner
- Internet
US $65/Night
7 Nights - US $454
House
- Kingston
- ·
- Molynes Gardens
- 0.26 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
3 Baths
9 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $163/Night
7 Nights - US $1,138
Apartment
- Kingston
- ·
- Constant Spring
- 1.18 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $162/Night
7 Nights - US $1,132
Condo
- Kingston
- ·
- Molynes Gardens
- 0.79 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
4 Guests
- Pool
- Kitchen
- Parking
- Air Conditioner
US $159/Night
7 Nights - US $1,114
Apartment
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
4 Guests
- Balcony/Terrace
- Kitchen
- Parking
- Air Conditioner
US $151/Night
7 Nights - US $1,060
Instantly Bookable Holiday Homes in Castleton
Over 392+ Instantly Bookable Holiday Homes in or Near Castleton
Apartment
- Kingston
- ·
- Saint Andrew
- 3.89 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
2 Guests
- Kitchen
- Parking
- Internet
- Child Friendly
US $215/Night
7 Nights - US $1,503
House
- Kingston
- ·
- Constant Spring
- 0.75 mi to center
6 Bedrooms
5 Baths
16 Guests
- Air Conditioner
- Internet
- Child Friendly
Laundry
US $571/Night
7 Nights - US $3,995
Apartment
- Kingston
- ·
- Constant Spring
- 0.75 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
4 Guests
- Hot Tub
- Balcony/Terrace
- Kitchen
- Parking
US $144/Night
7 Nights - US $1,005
Apartment
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
5 Guests
1100 ft²
- Balcony/Terrace
- Kitchen
- Parking
- Air Conditioner
US $141/Night
7 Nights - US $987
House
- Montego Bay
- ·
- Robins Bay
- 1.37 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
3 Guests
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
US $140/Night
7 Nights - US $980
House
- Kingston
- ·
- Saint Andrew
- 3.56 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
2 Baths
6 Guests
- Air Conditioner
- Internet
- Child Friendly
- Laundry
US $136/Night
7 Nights - US $953
House
- Montego Bay
- ·
- Port Maria
- 0.62 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
2 Baths
7 Guests
- Balcony/Terrace
- Kitchen
- Parking
- Air Conditioner
US $125/Night
7 Nights - US $875
Apartment
- Kingston
- ·
- Constant Spring
- 0.78 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
4 Guests
- Balcony/Terrace
- Kitchen
- Parking
- Air Conditioner
US $99/Night
7 Nights - US $691
Apartment
- Kingston
- ·
- Saint Andrew
- 2.91 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
2 Guests
800 ft²
- Oceanfront
- Ocean View
- View
- Kitchen
US $91/Night
7 Nights - US $634
Book a Last Minute Place to Stay in Castleton
About Casai's Private Villas and Holiday Rentals in Castleton
Discover more than 754 vacation rentals available in Castleton. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Castleton.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Castleton, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Castleton. On average, places to stay near Castleton offer 921.19 ft², with nightly prices averaging US $263.
With Casai, finding and comparing holiday rentals in Castleton is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
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Top Accommodation Types in Castleton
| Type | Count |
|---|---|
| Holiday Apartments | 446 |
| Vacation Homes | 192 |
| Villas | 34 |
| Cottages | 13 |
Use these Quick Filters to Find a Holiday Rental in Castleton
★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Castleton.
Weather in Castleton, JM
View the weather forecast for Castleton before booking your Castleton Vacation Rentals to confirm your best time to go.
December - February
High 88°F Low 73°F
March - May
High 89°F Low 75°F
June - August
High 92°F Low 75°F
September - November
High 90°F Low 75°F
Top Attractions Around Castleton, JM
Casai offers a large selection of top attractions around Castleton . Research things to do on your vacation before you visit Castleton.
Frequently Asked Questions About Castleton?
What are the top holiday rentals in Castleton?
With numerous options available in Castleton, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday 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
- Tropical Bliss cozy Kgn apt equipped with security, AC, balcony, WiFi, kitchen
- 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
How many holiday rentals have private pools in Castleton?
Discover a selection of holiday rentals with private pools near Castleton with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.
- Kozy Kingston Condo at Merrivale Apartments
- Sky's Villa Resort
- Far-I Guesthouse Modern studio apartment in rural Jamaica
- 1BR on Private Estate
Which holiday homes in Castleton are best for families?
If you're searching for a family-friendly holiday home in Castleton, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Castleton:
How many Casai.com holiday rentals are available in Castleton?
As of 2026, Casai boasts over 754 properties listed in the Castleton area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Castleton.
People Also Ask
Finding the best prices in Castleton
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