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 $197/Night
7 Nights - US $1,376
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
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 $258/Night
7 Nights - US $1,808
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
Apartment
- Kingston
- ·
- Camperdown
- 0.27 mi to center
10.0Exceptional
(3 Reviews)
1 Bedroom
1 Bath
3 Guests
- Pool
- Kitchen
- Parking
- Air Conditioner
US $153/Night
7 Nights - US $1,073
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 $271/Night
7 Nights - US $1,896
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 $190/Night
7 Nights - US $1,330
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 $128/Night
7 Nights - US $893
Luxury Holiday Rentals in Castleton
Over 744+ 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
- ·
- Saint Andrew
- 2.75 mi to center
1 Bedroom
1 Bath
2 Guests
- Balcony/Terrace
- Kitchen
- Parking
- Air Conditioner
Unlock the Best Price
Apartment
- Kingston
- ·
- Camperdown
- 0.33 mi to center
2 Bedrooms
1 Bath
2 Guests
- Kitchen
- Parking
- Air Conditioner
- Internet
US $9,904/Night
7 Nights - US $69,326
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 $8,054/Night
7 Nights - US $56,378
Apartment
- Kingston
- ·
- Saint Andrew
- 4.25 mi to center
2 Bedrooms
1 Bath
4 Guests
- Kitchen
- Parking
- Air Conditioner
- Internet
US $7,999/Night
7 Nights - US $55,993
Cabin
2 Bedrooms
2 Baths
8 Guests
- Balcony/Terrace
Pet Friendly- Kitchen
- Parking
US $4,135/Night
7 Nights - US $28,945
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
Villa
10.0Exceptional
(1 Review)
5 Bedrooms
6 Baths
10 Guests
Private Pool- Hot Tub
- Fireplace/Heating
- Pool
US $1,850/Night
7 Nights - US $12,947
New
House
- Kingston
- ·
- Jack's Hill
- 0.28 mi to center
5 Bedrooms
6 Baths
10 Guests
- Hot Tub
- Air Conditioner
- Internet
- Child Friendly
US $1,368/Night
7 Nights - US $9,576
Top-Rated Holiday Rentals with a Pool in Castleton
Over 234+ The Best Private Villas and Holiday Rentals in Castleton with a Pool
House
- Kingston
- ·
- Jack's Hill
- 0.68 mi to center
10.0Exceptional
(2 Reviews)
9 Bedrooms
9 Baths
25 Guests
1533.86 ft²
- Oceanfront
- Hot Tub
Spa- Pool
US $208/Night
7 Nights - US $1,458
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 $117/Night
7 Nights - US $819
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 $285/Night
7 Nights - US $1,995
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 $264/Night
7 Nights - US $1,849
Apartment
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
4 Guests
1350 ft²
- Pool
- Balcony/Terrace
- Kitchen
- Parking
US $215/Night
7 Nights - US $1,502
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 $210/Night
7 Nights - US $1,470
Pet-Friendly Holiday Rentals in Castleton
Over 67+ Pet-Friendly Holiday Rentals in or Near Castleton
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 $328/Night
7 Nights - US $2,296
Apartment
9.4Exceptional
(5 Reviews)
2 Bedrooms
3 Baths
4 Guests
- Pool
- Balcony/Terrace
- View
- Pet Friendly
US $78/Night
7 Nights - US $546
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
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 $1,302/Night
7 Nights - US $9,114
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
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
Villa
- Montego Bay
- ·
- Robins Bay
- 1.15 mi to center
4 Bedrooms
3 Baths
6 Guests
- Oceanfront
- Hot Tub
- Ocean View
- Balcony/Terrace
US $491/Night
7 Nights - US $3,437
Villa
- Montego Bay
- ·
- Robins Bay
- 1.16 mi to center
1 Bedroom
1 Bath
2 Guests
- Oceanfront
- Hot Tub
- Ocean View
- Balcony/Terrace
US $330/Night
7 Nights - US $2,310
Cottage
- Montego Bay
- ·
- Robins Bay
- 1.16 mi to center
1 Bedroom
1 Bath
2 Guests
- Oceanfront
- Hot Tub
- Ocean View
- Balcony/Terrace
US $286/Night
7 Nights - US $2,002
Large Holiday Rentals and Private Villas in Castleton
Over 54+ 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 $600/Night
7 Nights - US $4,200
New
Apartment
- Kingston
- ·
- Constant Spring
- 0.55 mi to center
10.0Exceptional
(1 Review)
67 Bedrooms
10 Baths
38 Guests
11840.3 ft²
- Fireplace/Heating
- View
- Parking
- Air Conditioner
US $67/Night
7 Nights - US $470
Villa
1 Bedroom
1 Bath
2 Guests
- Hot Tub
- Balcony/Terrace
- Kitchen
- Parking
US $120/Night
7 Nights - US $840
Villa
- Montego Bay
- ·
- Port Maria
- 0.72 mi to center
9.6Exceptional
(4 Reviews)
4 Bedrooms
5 Baths
8 Guests
4000 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Pool
US $589/Night
7 Nights - US $4,123
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
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 $296/Night
7 Nights - US $2,072
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 $335/Night
7 Nights - US $2,342
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 $764/Night
7 Nights - US $5,348
Ski Chalet
- Kingston
- ·
- Silver Hill Gap
- 1.63 mi to center
2.0Average
(1 Review)
7 Bedrooms
7 Baths
40 Guests
261358 ft²
- Hot Tub
- Balcony/Terrace
- Breakfast
- Kitchen
US $960/Night
7 Nights - US $6,720
Wheelchair Accessible Holiday Homes in Castleton
Over 52+ 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 $203/Night
7 Nights - US $1,421
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
- 3.92 mi to center
8.0Excellent
(5 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Fireplace/Heating
- Pool
- Kitchen
- Parking
US $170/Night
7 Nights - US $1,192
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
- 1.99 mi to center
8.0Excellent
(4 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Hot Tub
- Pool
- Balcony/Terrace
- Kitchen
US $150/Night
7 Nights - US $1,048
Apartment
- Kingston
- ·
- Saint Andrew
- 1.49 mi to center
1 Bedroom
1 Bath
2 Guests
9688 ft²
- Balcony/Terrace
- Kitchen
- Parking
- Air Conditioner
US $749/Night
7 Nights - US $5,242
Apartment
- Kingston
- ·
- Saint Andrew
- 1.49 mi to center
1 Bedroom
2 Baths
4 Guests
19375 ft²
- Balcony/Terrace
- Kitchen
- Parking
- Air Conditioner
US $582/Night
7 Nights - US $4,077
![Choose To Be Happy @ Twenty 2A #201 & #203 [2-Bedroom w/Pool]](https://imgservice.casai.com/640x287/choose-to-be-happy-twe-jm-kingston-ha-3214211193-0.jpg)
Apartment
2 Bedrooms
2 Baths
4 Guests
- Pool
- Balcony/Terrace
- Kitchen
- Parking
US $555/Night
7 Nights - US $3,888
Castleton Private Villas and Holiday Homes Under $200
Over 559+ Castleton Private Villas and Holiday Homes Under $200
Apartment
- Kingston
- ·
- Constant Spring
- 1.00 mi to center
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
2 Guests
- Balcony/Terrace
- Kitchen
- Parking
- Air Conditioner
US $76/Night
7 Nights - US $530
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
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
4 Guests
- Balcony/Terrace
- Kitchen
- Parking
- Air Conditioner
US $197/Night
7 Nights - US $1,378
New
Apartment
- Kingston
- ·
- Saint Andrew
- 1.85 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
4 Guests
15069.47 ft²
- Pool
- Parking
- Air Conditioner
- Internet
US $122/Night
7 Nights - US $851
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 $190/Night
7 Nights - US $1,332
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 $175/Night
7 Nights - US $1,224
Apartment
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
5 Guests
1100 ft²
- Balcony/Terrace
- Kitchen
- Parking
- Air Conditioner
US $164/Night
7 Nights - US $1,145
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 $156/Night
7 Nights - US $1,090
Instantly Bookable Holiday Homes in Castleton
Over 292+ Instantly Bookable Holiday Homes in or Near Castleton
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 $223/Night
7 Nights - US $1,559
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
House
- Montego Bay
- ·
- Port Maria
- 0.62 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
2 Baths
6 Guests
- Balcony/Terrace
- Kitchen
- Parking
- Air Conditioner
US $144/Night
7 Nights - US $1,006
Apartment
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
2 Guests
450 ft²
- Balcony/Terrace
- Kitchen
- Parking
- Air Conditioner
US $128/Night
7 Nights - US $894
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 $105/Night
7 Nights - US $736
Apartment
- Kingston
- ·
- Saint Andrew
- 3.95 mi to center
9.8Exceptional
(16 Reviews)
1 Bedroom
1 Bath
2 Guests
- Pool
- Ocean View
- Balcony/Terrace
- View
US $120/Night
7 Nights - US $843
Apartment
- Kingston
- ·
- Constant Spring
- 0.79 mi to center
9.8Exceptional
(9 Reviews)
1 Bedroom
1 Bath
2 Guests
- Balcony/Terrace
- Kitchen
- Parking
- Air Conditioner
US $64/Night
7 Nights - US $450
Apartment
- Kingston
- ·
- Saint Andrew
- 2.27 mi to center
9.8Exceptional
(6 Reviews)
1 Bedroom
1 Bath
2 Guests
- Balcony/Terrace
- Kitchen
- Parking
- Air Conditioner
US $91/Night
7 Nights - US $637
Apartment
- Kingston
- ·
- Saint Andrew
- 2.92 mi to center
9.6Exceptional
(5 Reviews)
1 Bedroom
1 Bath
2 Guests
- Kitchen
- Parking
- Air Conditioner
- Internet
US $106/Night
7 Nights - US $739
Book a Last Minute Place to Stay in Castleton
About Casai's Private Villas and Holiday Rentals in Castleton
Discover more than 753 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 947.32 ft², with nightly prices averaging US $309.
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.
Show more
Show less
Top Accommodation Types in Castleton
| Type | Count |
|---|---|
| Holiday Apartments | 453 |
| Vacation Homes | 189 |
| Villas | 32 |
| 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
- Elegant, Quiet & Cozy Kingston Home
- Luxury one bed room apartment with AC, roof top pool, WIFI located in Kingston.
- Remodeled Vacation home on private property
- Joy Luxury Estate Villa
- ★ Cozy Kingston Getaway ★ Relaxing, Quaint & Centrally Located ★
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
- Tapicoa Village Retreat
- Far-I Guesthouse Modern studio apartment in rural Jamaica
- Sky's Villa Resort
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:
- Escape to breathtaking natural beauty yet 5 minutes from major shopping centers
- Angella Mansions
- Cambridge Heights Guest House
How many Casai.com holiday rentals are available in Castleton?
As of 2026, Casai boasts over 753 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
Map
