Holiday rentals with a pool in Saint Mary

Experience Luxury/PS5/Wifi/65'TV/Cozy Bed/5min twn

Discover your dream escape in a luxurious smart home nestled in a gated community with 24 hrs security. Mins from Ocho Rios. *AC *Pool *Self check-in *Digital lock *Black-out Curtain *hot water *Fully equipped kitchen *Pots, pan, utensils *Drinking/Wine glass *Coffee/Tea station *Blender,Toaster, Microwave *Stainless Steel Appliances *Furnished backyard Gazebo *Outside Dining *Bedding *Safe *Feminine hygiene product *Toiletries *First Aid Kit *Washer & Dryer *High Chair *Baby Bath *Crib *Grill

Family · Location · River

4BR Oceanfront Villa Pool Chef Option Nr Ocho Rios

Wake up to sweeping Caribbean sea views at this private 4-bedroom oceanfront villa, just 15 mins from Ocho Rios. * Perfect for families and groups, it features en-suite bedrooms, a private pool, and inviting outdoor spaces for dining and relaxing. * Enjoy the ideal mix of seclusion and convenience — peaceful and tucked away, yet close to beaches, restaurants, and attractions. * We can arrange a private chef, housekeeping, airport transfers, and grocery pre-stocking so you can arrive and unwind.

Family · Location · Hospitality

Olive Branch Villa Oracabessa *Luxury*

Just minutes from the beach and nestled in the exotic hills of Oracabessa, Olive Branch Villa sits on beautifully landscaped grounds with a panoramic view of the Caribbean Sea. This 10,900 square foot villa boasts 4 well appointed bedrooms each with a sea view. The villa features a swimming pool with a large deck overlooking the Oracabessa Bay with a fine dining experience and first class service to leave you with a smile. If it is your first visit we are confident that it won't be your last.

Family · Location · Nearby

Catch My Drift Villa: Chef services available

Catch My Drift is a gated eco-inspired villa built and uniquely designed to incorporate locally sourced materials. Our units layer modern design with thoughtful touches and sustainability throughout. We offer the privacy and seclusion needed for complete relaxation. Enjoy our splendid view, swimming pool, outdoor kitchen with grill in our spacious backyard. We are only a 20 minute ride from Ocho Rios, home of popular attractions such as Dunns River Falls or a quick trip to the beach.

Value · Family · Pool

Beauty & Serenity at Kyah Place

At Kyah Place you can put a little distance between yourselves and the rest of the world. The lifestyle here is pure Jamaican in rhythm and tempo, "easy." We offer you a window to local culture and a different way of living. Markets, cook shops, and taxis are just steps away. Here you'll have an authentic Jamaican experience in a contemporary but homey setting, with Ocho Rios and world famous Dunn's River Falls only about an hour away. We look forward to hosting you. One Love

Location · Family · Pool

Grande Haven Villa

Grande Haven Villa - Ultimate Relaxation * Located 5 minutes from Ian Fleming International Airport * This Mediterranean style villa is nestled behind a palm tree lined driveway in the hills of Gibraltar, overlooking the infamous James Bond Beach. The villa has 4 bedrooms each with private bathrooms, outdoor pool, wraparound veranda, 3 private balconies and shady palm trees for napping or reading a good book. Grande Haven Villa has everything needed for ultimate relaxation.

Value · Location · Laundry

Lux Apartment*5 mins Beach*15 Min Ocho Rios*Secure

This luxurious ground floor apartment at the Crystal Resort with infinity pool has breath taking views, only 5 mins from the beach and 15 mins to bustling Ocho Rios offers the perfect place to stay for the most discerning holiday makers Ian Fleming airport is 5 minutes drive away, with daily flights to the USA Local shops 3 minutes drive away Walk directly from your apartment to the gorgeous pool, gazebo and outdoor shower, shared only with the hosts who rarely use it

Value · Family · Beach

Nanichi Comfort in Luxury, Serene & Convenient!

What makes Nanichi House special is the attention to detail. From the carefully prepared space to the welcoming atmosphere, every element is curated to help you and your family feel settled the moment you arrive. Whether you’re visiting for a quiet getaway, work, or a longer stay, the home adapts beautifully to your needs. Nanichi House is more than just a place to stay it’s a space designed for comfort, calm, and effortless relaxation.

Value · Location · Bathroom

A View To A Kill - Your Private Tree House Villa

Kick back and relax in this beautifully renovated stylish home. Set at the top of a hill, this idyllic home offers an expansive view of the ocean, and Jamaica’s Blue Mountains. Newly renovated, A View To a Kill has 3 bedrooms, all with full en suite bathrooms. A gorgeous modern kitchen, large pool and entertaining deck, and a full outdoor bathroom. Stay with us, relax, and get away from busy life. Great for families and friends!

Family · Value · Sleep quality

clean, comfy & quiet w/views * No Fees *

Relax in this oceanfront 1BR/1BA condo in peaceful Tower Isle, just 10 mins from Ocho Rios. Enjoy stunning sea views from your private balcony, direct beach access, a pool, A/C, Wi-Fi, and a fully equipped kitchen. Located in a gated complex. Perfect for couples, families, or remote work in paradise. Close to Dunn’s River Falls, restaurants, and local shops. Book your island escape today!

Location · Family · Bathroom

Tranquil Times villa

Tranquil Times Villa is located just minutes outside of downtown Ocho Rios. We are located in a private, gated community with 24-hour live security. We are conveniently located within minutes of all major attractions and hotels. Airport Transportation will be arranged. We are fully staffed and cannot wait to help make your vacation one you won't ever forget!!!

Value · Location · Air conditioning

3BR Beachfront Condo · Pool · Chef · Ocho Rios

Welcome to JamaicaTime “Driftwood” — a spacious renovated 3BR/3BA beachfront condo at Sea Palms, a gated complex 10 mins from Ocho Rios. Enjoy Caribbean Sea views, coastal décor, private beach cove, large pool, fully fitted kitchen, ACs, Smart TVs, WiFi & Netflix. Verandah with bar and dining. Sleeps 8 + infant, with chef, housekeeping and drivers available.

Value · Family · TV