Villas and Holiday Homes in Montego Bay

8776 Villas and Holiday Homes in Montego Bay

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • hometogo
  • sykescottages
  • expedia
  • belvilla
  • villanovo
  • interhome
Montego Bay
Search for your holiday home
Price per night
Accommodation type
Rating

Best villa offers in Montego Bay

Villas and holiday homes with private pool in Montego Bay

Pool-side living on the Caribbean coast: our villas with private pool in Montego Bay. Find your holiday home with pool in Jamaica.

Luxury 8br Villa W/ Chef & Full Staff - Montego Bay
No reviews

Luxury 8br Villa W/ Chef & Full Staff

house
Located in Montego Bay, St. James Parish, Jamaica, this expansive 8-bedroom villa offers a family-friendly atmosphere and convenient access to major city attractions.
This luxurious holiday home boasts a swimming pool and garden, providing a peaceful retreat with parking for guests and a capacity of 16, perfect for large groups seeking a welcoming base for their Jamaican adventure.
Sunset On The Hill - Montego Bay
9.6 40 reviews

Sunset On The Hill

house
Located in a secure, gated community in the hilly terrains of Montego Bay, Jamaica, this newly renovated townhouse is a mere 8-kilometre drive from Sangster's International Airport and a 5-minute drive to the famous Hip Strip and Doctor's Cave beach.
This welcoming villa rental, offering accommodation for up to 4 guests across 2 bedrooms and 2 bathrooms, features a fridge and microwave oven in the kitchen, air conditioning, a swimming pool, garden, parking, and WiFi, providing a comfortable holiday home experience.
Yanceylargo Estate - Newly Renovated 7br Beautiful Two-story W Gorgeous Mountain View Villa - Montego Bay
8.0 1 review

Yanceylargo Estate - Newly Renovated 7br Beautiful Two-story W Gorgeous Mountain View Villa

house, Montego Bay
Offering stunning mountain views, this two-storey villa in Montego Bay is conveniently located 4 kilometres from Sangster International Airport, with Luminous Lagoon 33.8 kilometres away.
This spacious holiday home boasts 7 bedrooms and 6 bathrooms, accommodating up to 49 guests, and features a fully equipped kitchen, air conditioning, a swimming pool accessible by a short drive, and on-site property caretaker for added security and assistance.
Glory @ Montego Bay, St James - Montego Bay
9.8 260 reviews

Glory @ Montego Bay, St James

cottage, Montego Bay
Offering unique aerial and ocean views overlooking Sangster International Airport and the Caribbean Sea, this cottage is located in Mango Walk, Montego Bay, a mere 5 minutes from the airport and Doctors Cave Beach.
This welcoming 2-bedroom, 2-bathroom villa rental, accommodating up to 4 guests, boasts a private garden, a swimming pool, and a Bose music system, with optional chef and transportation services available.

Villas and holiday homes by the sea in Montego Bay: sea view and coastal stays

The best holiday homes by the sea in Montego Bay sit near Doctor's Cave Beach, from coastal hillside retreats to true beachfront villas.

Cozy & Private, Steps Away From Beach & Hip Strip! Car Not Needed! - Montego Bay
9.8 56 reviews

Cozy & Private, Steps Away From Beach & Hip Strip! Car Not Needed!

cottage, Montego Bay
Sweet Serenity Cottage is located in the Hip Strip district of Montego Bay, just 300 meters from Doctor's Cave Beach and within easy walking distance of numerous restaurants and shops. This special cottage offers a secluded garden retreat, air-conditioned bedrooms, a fully equipped kitchen with a fridge and microwave, and parking, making it an excellent choice for a holiday home in Jamaica.
Hospitality Expert Cb All: Pool, Beach & Chef - Montego Bay
No reviews

Hospitality Expert Cb All: Pool, Beach & Chef

house, Montego Bay
Located in the Rose Hall district of Montego Bay, this luxury villa offers exclusive access to five 2-bedroom townhouses, situated just 300 meters from the world-famous Scotchies restaurant and within a 2-5 minute drive of other popular dining options.
This family-friendly holiday home provides accommodation for up to 30 guests, featuring stunning Caribbean Sea views, complimentary membership to the Tropical Bliss Beach Club, an infinity-edge swimming pool, and modern amenities including 150 Mbps Starlink WiFi and air conditioning in all rooms.
Tropical Oasis /Beach Access/opt Chef Service - Montego Bay
10 13 reviews

Tropical Oasis /Beach Access/opt Chef Service

house
Enjoying an exclusive oceanfront position within a 24-hour secure gated community in Montego Bay, this luxury villa offers direct access to a private beach and stunning views of cruise ships from a dedicated gazebo, just a 15-minute drive from the airport.
This welcoming holiday home, accommodating up to six guests across three bedrooms and three bathrooms, boasts a separate, accessible queen-sized in-law suite, a fully equipped kitchen, air conditioning, a swimming pool, garden, fitness centre, and on-site personalised services including a chef and transportation, with Marina Palms restaurant a mere 2-minute walk away.
Exclusive 4br Designer Waterfront Villa Chef Pool Beach Access Pickleball Gym - Montego Bay
10 27 reviews

Exclusive 4br Designer Waterfront Villa Chef Pool Beach Access Pickleball Gym

house, Montego Bay
This exclusive waterfront villa rental is perfectly situated on a private peninsula within a secure, family-oriented gated community in Montego Bay, offering a mere 20-minute drive to the airport and close proximity to the historic Rose Hall Great House.
Spanning 465 square meters, this luxurious holiday home accommodates up to 8 guests across four en-suite air-conditioned bedrooms, boasting a private infinity pool overlooking the ocean, a full-time professional chef, and a tennis court for an exceptional stay.

Frequently Asked Questions about Montego Bay

  • What are the must-see attractions that I should visit in Montego Bay, Jamaica?

    For a good overview of Montego Bay, Jamaica, the Rose Hall Great House is a significant historical site. Doctor's Cave Beach is a very popular spot for swimming and relaxing. For a taste of local life and crafts, the Craft Market in Montego Bay offers a variety of souvenirs.
  • Which district of Montego Bay, Jamaica is best known for its villas?

    The hills surrounding Montego Bay, Jamaica, particularly areas like Spring Hill and Ironshore, are well-known for their villas. These locations often provide elevated views and a sense of seclusion.
  • What are the advantages of staying in a villa in Montego Bay, Jamaica?

    Staying in a villa in Montego Bay, Jamaica, offers more space and privacy than a hotel. Many villas come with private pools and kitchens, which can be convenient for families or groups. It also provides a more local living experience.
  • How much does it cost to rent a villa in Montego Bay, Jamaica on average?

    The average cost to rent a villa in Montego Bay, Jamaica, can vary significantly. Prices typically range from about $300 to $1,500 USD per night, depending on the size, amenities, and location of the villa.
  • Are there villas near the city center in Montego Bay, Jamaica?

    Yes, there are villas located near the city center of Montego Bay, Jamaica. These properties offer closer proximity to local shops, restaurants, and some of the city's attractions, while still providing a private living space.
  • How far in advance should I book a villa in Montego Bay, Jamaica?

    It's advisable to book a villa in Montego Bay, Jamaica, at least three to six months in advance, especially if you are planning to travel during peak season or holidays. Popular villas can be reserved quickly.
  • Are there wineries or food tours near villas in Montego Bay, Jamaica?

    Wineries are not a common feature in Montego Bay, Jamaica. However, food tours are available that explore local Jamaican cuisine, and many can be arranged to pick up from or be near villa locations.
  • Is a car necessary to stay in a villa in Montego Bay, Jamaica?

    While not strictly necessary, having a car can be very convenient when staying in a villa in Montego Bay, Jamaica, especially if your villa is located in the hills or further from the main town. Taxis and private drivers are also readily available options.

Villas in Popular Destinations

Luxury villas and holiday homes in Montego Bay

Our curated luxury villas in Montego Bay offer the perfect blend of privacy and sophistication. Find your luxury holiday home.

Luxury 10 Bedroom Villa-millbrooks - Montego Bay
No reviews

Luxury 10 Bedroom Villa-millbrooks

house, Montego Bay
Located in Montego Bay, this villa is a mere 10-minute walk from Half Moon Point Beach and 6 kilometres from Sangster International Airport.
This 10-bedroom holiday home offers a luxurious infinity pool and a fully equipped kitchen, with a terrace providing garden views, accommodating up to 51 guests.
Hospitality Expert Sf Private Pool Beach Chef - Montego Bay
9.7 545 reviews

Hospitality Expert Sf Private Pool Beach Chef

house, Montego Bay
Boasting an exclusive location in Montego Bay, this villa is situated 2 kilometres from Half Moon Point Beach and 7 kilometres from Sangster International Airport, with the Luminous Lagoon 24 kilometres away.
This welcoming holiday home offers 100 square meters of living space with 2 bedrooms and 2 bathrooms, featuring a private swimming pool, on-site chef service, and stunning sea, pool, and garden views.
Luxury Manor 2 Bedroom /1 Bathroom House W/electric Fireplace, - Montego Bay
10 1 review

Luxury Manor 2 Bedroom /1 Bathroom House W/electric Fireplace,

house, Montego Bay
Conveniently located just 0.6 miles from Sangster International Airport, this Montego Bay villa offers excellent access to the Luminous Lagoon, situated 18 miles away.
This welcoming holiday home provides 93 square meters of living space with 2 bedrooms and 1 bathroom, accommodating up to 7 guests, and features a patio with garden views and a balcony offering mountain vistas, alongside on-site parking and free WiFi.
Chateau Gloria Luxury Villa - Montego Bay
No reviews

Chateau Gloria Luxury Villa

house, Montego Bay
Chateau Gloria Luxury Villa is located in Montego Bay, just 4 kilometres from Sangster International Airport.
This expansive 7-bedroom villa rental offers exclusive use of a private swimming pool, a beautiful garden with barbecue facilities, and a terrace with stunning sea views, accommodating up to 18 guests with free WiFi and parking.

Villas and family holiday home rentals in Montego Bay

Our hand-picked holiday homes for families in Montego Bay offer the privacy and space to make lasting memories together. Find your family-friendly villa.

Canary Retreat - Montego Bay
No reviews

Canary Retreat

house, Montego Bay
Offering a private retreat, this welcoming villa on Mountain View Drive in Montego Bay is just 300 meters from Doctor's Cave Beach and a short drive from Montego Bay Airport.
This spacious holiday home comfortably accommodates up to 11 guests, featuring three bedrooms, two bathrooms, a fully equipped kitchen with a fridge and microwave oven, air conditioning, a terrace, a balcony, and garden, plus internet access and parking.
165 M² House ∙ 3 Bedrooms ∙ 6 Guests - Montego Bay
No reviews

165 M² House ∙ 3 Bedrooms ∙ 6 Guests

house, Montego Bay
Located in Montego Bay, this exclusive house offers an authentic local living experience and is just 300 meters from the nearest beach, making it a superb holiday home for exploring the region.
This 165 square meter villa rental accommodates up to six guests across three bedrooms, each with an en-suite bathroom, and features a fully equipped self-catering kitchen, air conditioning, and garden access, providing a welcoming base for your Jamaican adventure.
3br Townhome W/ Beach Access, Pool & Gym - Montego Bay
9.9 93 reviews

3br Townhome W/ Beach Access, Pool & Gym

house
Located within the exclusive Freeport gated community in Montego Bay, this luxurious villa offers a prime position with a 3-minute walk to a communal swimming pool and a 6-minute walk to a rustic beach.
This family-friendly holiday home, accommodating up to 6 guests, boasts air conditioning, a well-equipped kitchen, and a private patio, all supported by a supplemental generator for uninterrupted comfort, with optional airport transfers and private chef services available.
Apartment 4 @ Top Bay Apartments - Montego Bay
6.0 2 reviews

Apartment 4 @ Top Bay Apartments

house, Montego Bay
Conveniently located on Upton Hill in Montego Bay's city centre, this villa rental is just 3 kilometres from Sangster International Airport and 8 minutes' drive to Doctor's Cave Beach.
This family-friendly holiday home offers 2 bedrooms, 2 bathrooms, and accommodates up to 5 guests, featuring a private swimming pool, air conditioning, and a garden, with game walks and birdwatching opportunities nearby.

Rental villas and holiday homes with jacuzzi in Montego Bay

Our villas with hot tub in Montego Bay are the perfect choice for a romantic stay: a private jacuzzi for two in an exceptional setting. Find your holiday home with hot tub.

Ironshore Luxury 7 Bdrm Villa With Pool - Montego Bay
8.0 1 review

Ironshore Luxury 7 Bdrm Villa With Pool

house
The Sun Seeker Villa Ja. 7 Bedroom Villa With Butler & Chef, And Housekeeping. - Montego Bay
10 35 reviews

The Sun Seeker Villa Ja. 7 Bedroom Villa With Butler & Chef, And Housekeeping.

house, Montego Bay
All-inclusive 5br Luxury Villa - Montego Bay
No reviews

All-inclusive 5br Luxury Villa

house
Crystal Jamaica Villa Tours - Montego Bay
No reviews

Crystal Jamaica Villa Tours

house, Montego Bay
copyright © 2026 villapicker.com