Vacation rentals in Middlesex County

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Top-rated vacation rentals in Middlesex County

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Guest favorite
A wooden dining area features a long table and benches, set against a backdrop of the ocean and lush greenery. An umbrella provides shade over the table, while deck chairs invite relaxation. The inviting view of the turquoise water is visible through spacious openings.
Place to stay in Ocho Rios
4.88 out of 5 average rating, 58 reviews

Central beachfront 3 bdrm villa with chef

Villa Neptune is a newly renovated 3 bedroom 3 bathroom beachfront villa. Our guests will be able to experience a rustic and cozy setting as we have brought the outdoors in! The majority of our finishes were made from a majestic guango tree and were all custom made and hand crafted. We have a showcase of artwork from a local artist displayed throughout the villa that are also available for sale. Enjoy the outdoors even more as you lounge on our 15x45 foot deck with a drink in hand! We await!

Guest favorite
Villa in Discovery Bay
4.89 out of 5 average rating, 19 reviews

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!

Guest favorite
A modern living room features a comfortable gray sofa adorned with red and white decorative pillows. A large flat-screen TV is mounted on the wall, displaying cityscape imagery. A stylish lamp provides ambient lighting, complemented by a round mirror above. A coffee table with games sits in the foreground.
Home in Tower Isle
4.92 out of 5 average rating, 24 reviews

Coastal Escape in Riviera, Tower Isle|Beach Nearby

Welcome to Paradise on Riviera Blvd in Tower Isle –Your Ideal Getaway in just 10 minutes outside of the bustling tourist destination of Ocho Rios. Welcome to Riviera where your dream vacation becomes reality! Our luxurious 3-bedroom, 3.5-bathroom retreat offers the perfect blend of comfort and style, ensuring a memorable stay in one of Jamaica's most enchanting locations. Why You'll Love Our Home ✔︎Made for COMFORT w modern furnishings/finishes ✔︎ Close to many beaches & rafting ✔︎ LOCATION!

Guest favorite
A verandah offers a serene space with two comfortable chairs and a small table. A stack of books rests on the table beside a cup, with views of the ocean and palm trees in the background, enhancing a peaceful atmosphere.
Condo in Tower Isle
4.85 out of 5 average rating, 202 reviews

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

Guest favorite
A semi-open living area is presented with white walls and modern furnishings. A wooden coffee table sits in front of a comfortable sofa. Large windows overlook the sea, revealing two loungers on the balcony, creating a serene atmosphere with natural light.
Condo in Ocho Rios
4.83 out of 5 average rating, 284 reviews

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)

Top guest favorite
A shaded gazebo offers comfortable seating surrounded by lush greenery. Palm trees and vibrant foliage frame a view of the expansive lawn leading to the beach. The sea glimmers in the distance under a clear blue sky, creating a serene outdoor retreat.
Bungalow in Laughlands District
4.89 out of 5 average rating, 199 reviews

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.

Guest favorite
An inviting pool area is featured at dusk, surrounded by lush tropical landscaping. The gentle curve of the pool is highlighted by soft lighting, while soft hues of the evening sky reflect on the calm ocean waters in the background.
Home in Ocho Rios
4.81 out of 5 average rating, 21 reviews

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! ✨

Top guest favorite
A modern living area showcases a light-colored sofa paired with dark accent chairs. A round coffee table sits on a patterned rug, and tall windows are adorned with sheer curtains, allowing natural light to fill the space. Decorative plants and artwork enhance the inviting ambiance.
Home in Ocho Rios
4.97 out of 5 average rating, 60 reviews

Zuma Villa|3BR|Rooftop|Gated|Pool|10 min Beach

Welcome to Zuma Villa, your tropical oasis nestled in the heart of Jamaica. Surrounded by lush greenery and just moments from pristine beaches, Zuma Villa offers the perfect blend of comfort, style, and island charm. Whether you're here to relax, explore, or indulge in local culture, our villa is designed for an unforgettable stay. From the rooftop sea views to the infinity pool, you'll feel right at home while experiencing the best of Jamaica. Come as guests, leave as family!

Superhost
Home in Priory
5 out of 5 average rating, 7 reviews

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.

Top guest favorite
A two-story villa showcases a modern Caribbean design, framed by lush greenery and tropical plants. The porch features comfortable seating under shaded beams, and a stone pathway leads to a manicured garden. Large windows invite natural light, enhancing the open and airy feel of the property.
Villa in Ocho Rios
4.93 out of 5 average rating, 115 reviews

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.

Superhost
Cottage in Saint Ann's Bay
4.82 out of 5 average rating, 68 reviews

Ecoscape -Private River Eco Cottage Near Ocho Rios

Escape to Ecoscape – Where Nature Restores You You won’t want to leave this one-of-a-kind eco-retreat, tucked away in the lush mountains just 30 minutes from Ocho Rios. At Ecoscape, immerse yourself in nature as it was meant to be - fresh mountain air, flowing spring water, clay beneath your feet, and the soothing sounds of the river all around you. Wake up to the calls of yellow-billed parrots and experience Jamaica in its purest form.

Guest favorite
An open-plan living area is displayed, featuring a modern kitchen with dark cabinetry and stainless steel appliances. A comfortable sofa with colorful cushions complements a wooden coffee table. Natural light enters through large windows, enhancing the contemporary decor.
Home in Ocho Rios
4.94 out of 5 average rating, 111 reviews

Sun Shine Luxury Villas 2bedroom Pool&Gym OchoRios

Your family will be close to everything when you stay at our centrally-located Villa. Beaches ,restaurants , ATMs, Supermarkets . Attractions and Excursions . Your amenities are POOL & Gym. 🧑🏽‍🍳- Chef services are also available. 🚐- Airport Pick services Please send me a message for the additional services rates. Your vacation will be filled with fun activities everyday.🫶🏽🇯🇲

Popular amenities for Middlesex County vacation rentals