Holiday rentals with a pool in St. James Parish

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in St. James Parish

Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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Superhost

Condo in Montego Bay

4.83 out of 5 average rating, 371 reviews

Modern apartment with a pool & amazing views!

Modern, 1BR, ground level apartment with all the modern amenities you will need for a perfect stay. Start your day having coffee on the patio gazing at the awe-inspiring coastline and turquoise lagoon. The property is part of a secure, gated development with a private community pool for guests to laze away while perfecting their tan, or hide in the shade sipping on a cold drink. You're close enough to the airport, shopping malls and nightlife - but nestled on the outskirts for quiet relaxation.

Superhost

Condo in Montego Bay

4.84 out of 5 average rating, 210 reviews

1 Bedroom Miramar Condo

1 bedroom 900 square feet spacious condo in a secure gated community across from the natural beach. Close to public transport. About 10-15 minutes drive from downtown Montego Bay and 20-25 mins drive from the airport. Great amenities including 24 hour security, pool, laundry, fully equipped kitchen. Elevate Lounge - 3 mins drive, Fairview Shopping Center (Uncorked, Mystic Thai, Tutti Frutti, HILO, Progressive Foods Fairview, Fontana Pharmacy, Palace Multiplex movie theater etc.) - 10 mins drive.

Guest favourite

Condo in St. James Parish

4.89 out of 5 average rating, 127 reviews

Luxury In Paradise: Pool, Jacuzzi, Gated, 3rd Flr

Whether you’re in Jamaica for work or vacation, this condo will check all your boxes. Located in Ironshore, one of Montego Bay’s most prominent communities, sits Dream 36. A luxury condominium complex that’s close to entertainment, beaches, restaurants, and airport (12 mins). This one bedroom condo is extremely spacious at 900 sq ft. It boasts modern furnishings with a warm feel. You can truly relax with amazing amenities such as gated 24/7 security, lounge, pool, and rooftop views. Book now 😁

Top Guest favourite

Townhouse in Montego Bay

4.98 out of 5 average rating, 170 reviews

2BR Townhouse with staff, gym, pool & beach access

Escape@20 is a lovely townhome that guarantees a truly relaxing and memorable experience. A friendly housekeeper/cook is included at NO EXTRA COST!! You just need to purchase the groceries. The townhome has an open floor plan with living and dining room opening out to a covered patio and a backyard. Guests can enjoy breathtaking views of the neighboring yacht docking area, swimming pool, gazebo/bbq grill space, gym, playground for kids, 24 hour security and complimentary beach access nearby.

Guest favourite

Condo in Reading

4.89 out of 5 average rating, 110 reviews

Luxury Garden 2 BDR, 2 BTH Condo w/ pool

Reading’s Rose is a new apartment located in the heart of Montego Bay. It is a 1 min walk from your nearest Restaurant and a 5 min drive from all major grocery stores, pharmacies, restaurants, shopping centres and medical facilities. A small and peaceful community, it is perfect for couples, families, business travelers and friend groups. This gated complex features a pool on the property and jogging trail. The nearest beach is 5 mins away and the famous Doctor’s Cave beach is 13 mins away.

Guest favourite

Condo in Montego Bay

4.95 out of 5 average rating, 133 reviews

1br Lux Oceanfront Apt Pool Beach Gym Pickleball

Discover the ultimate tropical retreat at the Soleil Residences, where luxury meets serenity. This elegant oceanfront one-bedroom condominium features a stunning balcony with 180-degree views of the Bay, inviting you to bask in the beauty of Jamaica's coastline. Highlights - Lge Waterfront Pool & Pool Deck * Private Beach Access * Gym * Tennis/Pickleball* Kids Play Area * Gated Community * Fast Fibre WiFi* Chef on request * Spa Services * Concierge Services * Full Time Driver Upon Request

Guest favourite

Cottage in Montego Bay

4.92 out of 5 average rating, 221 reviews

Glory @ Montego Bay

Welcome to “Glory”. The cottage is situated on the grounds of our home “Victory“. We invite you to experience our concept of “Jamaican Home Living”. Glory overlooks the Sangster International Airport and the Caribbean Sea and is 5 mins from world-famous Doctors Cave Beach. We are also conveniently 5 minutes drive from the airport. We own the SeaGull @ Little Bay Country Club in Negril, and are Airbnb SuperHosts; we know how to take care of our guests. Join us for a special experience.

Guest favourite

Apartment in Montego Bay

4.94 out of 5 average rating, 124 reviews

2BR Getaway w/Pool, Near Beach in Montego Bay

This gorgeous apartment has been furnished to feel like a true getaway. It’s the ideal retreat for an adventurous & up-scale stay, located in a gated community that is close to the absolute heart of Montego Bay. We believe it’s the ultimate location to experience this part of the island. At only 10 minutes walking distance from Doctor's Cave Beach and the main Hip Strip, you will be very close to all the action. Settle in by zoning out with family or friends and enjoy your getaway.

Top Guest favourite

Home in St. James Parish

5 out of 5 average rating, 104 reviews

Luxury Oceanview 4BR Villa w/ Balcony, Pool & BBQ

Indulge in luxury at our 4-bedroom Baywatch Villa. Marvel at breathtaking views day and night, creating unforgettable moments. Perfect getaway with friends or family. Our spacious home guarantees endless fun. Explore the state-of-the-art kitchen and convenient laundry room. Stay connected with seamless Wi-Fi coverage everywhere, even by the pool. With whole-house solar power for backup, rest assured the "lights" will never dim and the fans will always spin. - No AC on Backup Power

Guest favourite

Villa in Montego Bay

4.89 out of 5 average rating, 108 reviews

Hospitality Expert EL1: Private Pool, Beach, Chef

Eden Luxe 1 is set on a beautiful hillside offering panoramic views of the sparkling Caribbean Sea. This 2 BR ultra luxurious villa is part of the Nianna Eden Estate, set in the heart of Spring Farm, an upscale Montego Bay community, right above the Half Moon Golf Club. Luxe 1 sleeps up to 6 guests, a private chef is available for hire and we offer pre-stocking services. All our properties come with complimentary access to Tropical Bliss Beach Club. Add-on services offered.

Superhost

Condo in Montego Bay

4.84 out of 5 average rating, 139 reviews

Stella's Condo

You deserve the tranquility of a gorgeous Caribbean view located in an exclusive Montego Bay neighborhood. Enjoy our luxurious private pool and upscale gated community. Rest easy with a 24-hour security detail. Stella’s Condo is the perfect retreat—both intimate and spacious. Whether you’re planning that next Girls Trip, seeking a romantic getaway, or craving the rest and relaxation of creative quietude, we got you covered at Stella’s. Come… Whoosah with us!

Guest favourite

Apartment in Montego Bay

4.85 out of 5 average rating, 110 reviews

LionHideVilla GD: salt water pool&ocean view roof

The Green Door apartment is a modern space with lots of amenities: A/C, hot water, Wi-Fi, ceiling fans, flat screen smart TV/cable, plug in speaker, linens/towels, full kitchen with granite countertops. It has its own patio with seating & is fully grilled with screened windows. The property is fully gated. The lot is well fruited with mango, ackee, june plum, orange, lime, cherry, breadfruit & avocado trees.