Holiday rentals in Middlesex County

4.86 out of 5 average rating, 191 reviews

Home in Portmore

🏝🏝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

4.97 out of 5 average rating, 70 reviews

Newly Furnished/24hr Sec./AC/Fast Wi-Fi/ NHV4 -1BR

Come relax a while at this centrally-located place in New Harbour Village. Located on a quiet street this home is clean, comfortable and cozy with a stylish design. Enjoy waking up in a comfy queen-size bed, having a warm rain shower bath, eating your choice of foods and selecting your choices for entertainment. You will be two minutes away from the Old Harbour Town Centre where you can enjoy local foods, shopping and round town travels. What are you waiting for? Come! You will love it here.

4.89 out of 5 average rating, 220 reviews

Apartment in Ocho Rios

One of Ocho Rios Best Getaway Airbnb!

Welcome to Marazul, a picturesque vacation condo at upscale Columbus Heights in the hills of Ocho Rios. The perfect gateway with postcard-like panoramic ocean views and all the amenities to make your stay feel right at home. Surrounded by beautifully manicured rainforest gardens and direct access to 1 of 5 community pools. For your convenience, we are centrally located near restaurants, beaches, and the most popular attractions in the area only minutes away. Do you see yourself here?

Superhost

Guest suite in Boscobel

4.75 out of 5 average rating, 161 reviews

Beach bungalow beside Ochi Rios /Ian Flem Airport

Relax in a very comfortable self contained villa 10 minutes from the town of Ochi Rios and 3 minutes from Ian Fleming Airport on your very own Private beach. Walking distance from super markets, markets, Beaches Boscobel resort and golf club hotel, drinking saloons with friendly local people. Private enclosed parking with monitored security. The beach sits on a ocean wildlife protected sanctuary so pardon us if its not more refined, it is still great for swimming and relaxation.

5 out of 5 average rating, 26 reviews

Flat in Mandeville

Luxury suite with gym/ pool

Nestled in the cool hills of Mandeville this newly constructed apartment offers everything you have been looking for in your stay. It has an amazing view of this beautifully landscaped property with amenities that include swimming pool, gym, jog trail, assigned parking, club house and 24 hours security. The enviable location of this property allows for easy access to Mandeville town center, banks, hospital and shopping centers which are all within five minutes walking distance.

4.97 out of 5 average rating, 35 reviews

Home in Galina

Oasis Getaway in Saint Mary

Escape to OD’s Oasis, a charming one-bedroom retreat in Galina, St. Mary! Just 10 minutes from Ian Fleming Airport and minutes from the iconic Galina Lighthouse, this cozy getaway is perfect for two. Tucked in the community of Lighthouse, it features an open-concept kitchen and living area for ultimate comfort. The road has a few bumps, but the peace, charm, and convenience make it worth it. With Ocho Rios and Port Maria nearby, your dream island escape starts here!

4.95 out of 5 average rating, 21 reviews

Flat in Linstead

SG Apartment Complex (Apt #1)

Kick back and relax in this calm, stylish space. We are only 30 minutes away from Ocho Rios and 45 minutes outside of Kingston via toll. Not to mention, we are 5 minutes or walking distance from the famous Grant's Jerk Center, 5 mins from Fj's Smokehouse, and 25 mins away from Bush Trails Excursions Tours. The apartment is ultra-modern with all the amenities for the comfort of you and yours. Come, stay with us, we are here to serve you!

4.89 out of 5 average rating, 37 reviews

Flat in May Pen

Home

Kick back and relax in this calm, stylish space. Home is centrally located in a gated secure premises in May Pen, Clarendon. It is 2 mins from the nearest hospital. Doctors offices, restaurants, shopping, spas, salons, etc. Attractions in Clarendon includes, the Milk River Mineral bath, Farquahar beach, salt River mineral spring and other hidden gems. Home is also 2 mins away from the high way 2000.

Superhost

Flat in Bog Walk

5 out of 5 average rating, 4 reviews

Church Road Haven

Relax in this modern 1-bedroom, 1-bathroom apartment, just 3 minutes from Linstead and Bog Walk. Offering privacy, comfort, and all amenities, it’s perfect for solo travelers or couples. Enjoy a stylish, cozy retreat in a central yet peaceful location. Whether for business or leisure, this space provides the ideal blend of convenience and relaxation. Book now and make it your home away from home!

4.94 out of 5 average rating, 31 reviews

Colbeck Villa

Relax with the whole family at this peaceful place to stay. The Colbeck Villa located in a gated community with pool gym. The home is a beautiful 2 bedroom 1 bathroom house with all modern amenities. The home is fully Air Condition with ceiling fans. Clean and spacious bedrooms living room and kitchen. Comfortable beds, sofa and chairs. You will enjoy you stay at the Colbeck Villa.

4.94 out of 5 average rating, 47 reviews

Home in Spanish Town

Studio Serenity

Modern, peaceful studio in Angels Grove, perfect for your Jamaican getaway. Minutes from restaurants and the Knutsford Express depot. Easy toll road access to north coast attractions. Equipped with WiFi, AC, and kitchenette. Ideal for solo travelers, couples, or business trips. Your serene home base for island exploration.

Guest house in Summerfield

5 out of 5 average rating, 5 reviews

Naseberry Suite @ HershyB's

Forget your worries in this spacious and serene space. The guesthouse has a large bedroom with king size bed, a bathroom and has a open concept living and kitchen, that has a day bed that would be suitable for a third person or for a child. it's perfect for a small family of 3 to relax.

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Other great holiday rentals in Middlesex County

4.98 out of 5 average rating, 54 reviews

Home in Portmore

The Palms at Phoenix

NadineRating, 5 stars2 weeks ago

This was my second time staying at Ken’s home, and once again, it truly felt like my home away from home. Ken is the best of the best—patient, caring, and always going above and beyond to make your stay unforgettable. The house is warm, inviting, impeccably clean, and cool—everything you could ask for. I didn’t miss a thing from home because Ken’s home had it all. Thank you, Ken, for your incredible hospitality, kindness, and understanding. If you’re ever visiting Jamaica, I highly recommend booking this property—you won’t regret it. Looking forward to my next stay! Nadine Chambers

4.89 out of 5 average rating, 45 reviews

Flat in Spanish Town

Home in St. Catherine

FijauhnRating, 5 stars3 weeks ago

Is the best and will always be the best I’ll recommend anyone using this Airbnb app to stay right here

4.67 out of 5 average rating, 3 reviews

Modern Home New Harbour (Village Old Harbour)

KevinRating, 5 stars1 month ago

The host at Modern Home Old Harbour was incredibly friendly and helpful the responded to my messages promptly. The place was clean elegant and nice and I felt like I was being treated like a valued customer, and I appreciate that. I would recommend this place to anyone

5 out of 5 average rating, 12 reviews

Flat in Mandeville

Cozy Haven Apartment with Gym, Pool and WiFi

JermaineRating, 5 stars1 week ago

My stay was a home away from home 🏡. peaceful and private 😌. communication was friendly and accommodating.

Home in Crooked River

4.83 out of 5 average rating, 6 reviews

Livingwell Homes Jamaica

QuintonRating, 5 stars2 months ago

if you haven't booked yet... DO IT!! Jodyanns place is remarkable and she is the best host ever. Jodyanns place is very remote and exactly the vibes I was looking for. The place is huge and clean, it comes with dishes pots pans cutlery everything you need to disconnect and have some quality time or family time. The community vibe was some icing on the cake. The host has several resources very close to help with anything you need. I was taken to a local grocery to purchase food items that I would have never found by myself. Directions to a local waterfall and llocation of the center of the island... which you can see from their farm. We were given sugar cane and food items LIKE CACAO pineapple oranges and mango from a farm located on the same street as jodyanns place (actually a family farm). We were in direct and responsive communication with resources that made our trip even better.

5 out of 5 average rating, 17 reviews

The Cherryhill of Old Harbor

AleneRating, 5 stars5 days ago

Vance was very quick to respond whenever I message him. His place was welcoming and I looks just like the picture. I would definitely stay there again.

5 out of 5 average rating, 14 reviews

Apartment in Ocho Rios

Beachfront apartment Ocho Rios

MarciaRating, 5 stars1 week ago

I stayed at this apartment for 3 weeks and had no complaints. The host was great and her response time was on point. Attention to detail was apparent throughout the apartment (A26) I will be booking this apartment again on my next trip to Ocho Rios.