Vacation rentals in Middlesex County

🏝🏝HIDDEN GEMS 💎 💎 🏝🏝 Vacation Home 🏡🏞

This carefully designed house is ideal for persons looking for a cool refreshing modern and comfortable vacation stay . It is perfectly located in quiet and secure gated community Phoenix park village ,in the well developed sunshine city of portmore st catharine . It is most suitable for you because of its convenient access to all it has to offer around it ,its famous helshure beach, movie theater ,shopping malls ,clubs ,restaurants etc . it is the place for families ,couples, or just friends

5-Star Oceanview 3BR Villa w/Pool, Chef & Driver

Welcome to Villa Amore, a spacious 5-star 3-bedroom villa with pool & stunning sea views! Features: ▪ Fully equipped kitchen & dining area perfect for family sharing. ▪ Spacious living room with direct access to your private pool ▪ Convenient shared guest bathroom Each bedroom offers: ▪ Private en suite bathroom for full comfort ▪ Balcony with stunning pool & sea views Relax in lush gardens with secure parking and just a short walk to Puerto Seco Beach - your perfect tropical retreat awaits!

2 bedroom Oceanfront condo with a pool

Kick back and relax in this calm, stylish 2 bedroom Condo on the ocean with an infinity pool. 5 minutes east of Ocho Rios, within walking distance to an oceanfront restaurant, local jerk centre, bar and grocery store. We can host up to four guests. As we have many couples traveling we offer a discounted base rate for two guests and then each additional guest comes with an additional fee up to a maximum of four. For two guests we will often close the second bedroom unless otherwise requested

Seafront Apartment nxt to Beach

My place is in Ocho Rios Jamaica , walking distance from Ocho Rios Town centre . Its a homely seafront, split level apartment within a traditional 1960s style past resort directly next to Mahogany beach. Breathtaking sea views, set within a beautiful garden. The people are lovely and the sea and beach/bar are so relaxing. You can book and set sail from the beach on a Cool Runnings catamaran cruise. My place is good for couples, solo adventurers, business travellers, and families (with kids)

Cheerful three bedrooms with large backyard space

Forget all your worries in this spacious green and serene space. Five (5) minutes from the beach for total relaxation. Grab your juicy Jamaican patties in Town and then don't forget your jerk chicken and jerk pork right in the back yard. Swing in comfort and enjoy cool breeze on your phones or reading a book under the overflow of Jamaican fruit trees. Cut your favourite rose in the lush garden. 15 minutes from the Ian Flemmings Int'l Airport and 35 mins from the famous Dunns River Falls.

Kling Kling Beach House

Kling Kling is a beach house with a family feel, set within a large lawn running down to an almost fully private beach, a river for freshwater swimming, a reef for snorkelling, a fantastic housekeeper cook and a one of a kind man about the place. Just mins drive to shops or tourist facilities. Nearby scuba facilities, waterfalls, water parks, markets, tennis , golf, riding, the list goes on, both mainstream and off piste local. For more pics follow our Instagram: klingklingbeachhouse.

Paradise Penthouse w/ Private Chef & Oceanfront

🌞 2026 Winter Discount. Skip the Resort 🌞 Escape to Paradise Penthouse in the heart of Ocho Rios! This 3 story oceanfront gem is nestled in the exclusive, 24 hour gated community of Crystal Cove, offering the ultimate tropical getaway. Relax in style with stunning ocean views, chef prepared breakfast and dinner , access to a driver, and endless comfort. Perfectly located on Main Street, you’re minutes away from local culture and adventure. Your dream Jamaican vacation awaits! ✨

Royale Escape

Phenomenal, luxurious, amazing!! This upscale north coast Runaway Bay chill-spot is a modern retreat, that is tastefully furnished, boasting swimming pool, gym and a clubhouse with breathtaking ocean views. Easy drive from Montego Bay Airport and close proximity to Jamaica's best attractions, featuring great foods and amazing entertainment spots. Dunns River Falls, Dolpins Cove, Mystic Mountain, Puerto Seco to name a few. Dive right in and enjoy this unparalled home away from home.

Holiday House 4Bdr Villa with Housekeeper

Welcome to Holiday House—a newly renovated 4-bedroom villa in Coolshade at Richmond Estate, Priory St Ann . Perfect for up to 8 guests, this breezy retreat offers daily housekeeping, a private cook (optional), a fully equipped kitchen, and spacious living areas. Enjoy access to a pool, gym, tennis court, supermarket, beach, and more. Whether you're here to relax, work remotely, or explore, Holiday House is your stylish and comfortable island home away from home.

Ocean front luxury Villa in Jamaica

Welcome to Tikal, an ocean front luxury villa, exquisitely remodeled in May 2021, with an airy modern Caribbean style. We are adjacent to Chukka Cove Horse & Adventure Farms, noted as Jamaica's premier tourist attraction provider. We are conveniently nestled between Montego Bay and Ocho Rios, only 50 minutes from Montego Bay International Airport. We are within 30 minutes of most major tourist attractions, and the cruise ship port in Ocho Rios.

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!!!

Papa Curvin's Cottages & Seaside Tropical Garden

Quite small but very cosy - you will love it! Our newly build Umbrella Hut on Real Jamaica´s big property is waiting for you. Have a look at the pictures, they will tell you everything :-) There are two other houses to book, just have a look on Airbnb for: Real Jamaica - Cabin right beside the sea; and: Real Jamaica - The Artist House