Middlesex Vacation Rentals from NT$2,869: Search Short-Term Rentals

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Our top choices for Middlesex vacation rentals

1. Sky Beach Rooms

Montego Bay

Clayton

NT$3,412 total

includes taxes & fees

Aug 31 - Sep 1

2. Grassroots Negril

West End

NT$2,869 total

includes taxes & fees

Sep 7 - Sep 8

House, 3 Bedrooms, Smoking, Patio | Exterior

3. Sunny-shore Hideaway

Lucea

NT$9,362 total

includes taxes & fees

Sep 5 - Sep 6

4. Turquoise Sea Villa

Montego Bay

NT$6,015 total

includes taxes & fees

Aug 31 - Sep 1

5. RUNTINGS HIDEAWAY STAY NOMPREL ROAD NEGRIL

Negril

NT$3,713 total

includes taxes & fees

Aug 31 - Sep 1

6. Claudeville Condo

Montego Bay

Devine

NT$3,509 total

includes taxes & fees

Aug 31 - Sep 1

7. Beach House Condos Negril

Negril

Elizabeth

NT$4,774 total

includes taxes & fees

Aug 31 - Sep 1

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Top Middlesex Hotel Reviews

Samsara Cliff Resort

10/10 Excellent

"The Samsara Cliff resort was a great place for a quite get away. The staff was so friendly and the manager was extremely accommodating. If you enjoy snorkeling and are not afraid of a little swell, the view under the water was excellent. The view at sunset was great too! We originally booked the garden cottages and we were not pleased with the condition of them and we were very quickly offered an ocean front room at no extra fee."

Toby's Resort

10/10 Excellent

"⭐⭐⭐⭐⭐ **Come With the Right Expectations and You’ll Really Enjoy Toby’s** We genuinely enjoyed Toby’s Resort and would absolutely recommend it. The key is knowing what to expect: this is a comfortable, casual, laid-back Jamaican resort—not a polished luxury property. We loved that you really don’t need to leave the resort. The food was delicious and reasonably priced, the drinks were well mixed, and the bartender was amazing. Drivers are available on-site, and there’s even a floral shop. The pool area is a whole vibe! The pool is open all night, so you can relax, have drinks, socialize, or create your own little party atmosphere instead of heading to the nearby bars and clubs. Our bed was unusually comfortable—we got some of the best sleep we’ve ever had while traveling! Toby’s is also minutes from the airport, yet we heard virtually no airplane noise, and the Hip Strip and Doctor’s Cave are nearby. For realistic expectations: we had ants in our room, the property’s presentation was a little more modest than I expected from the pictures online, and service moves at a noticeably relaxed pace. It was never frustratingly slow, but should be noted if speed is a deal breaker for you. What Toby’s may lack in polish, it makes up for in character, convenience, value, great food and drinks, and a relaxed Jamaican feel. If that’s what you’re looking for, I absolutely recommend it. **We would happily stay again!**"

S Hotel Montego Bay - Luxury Boutique All Inclusive Hotel

10/10 Excellent

"We absolutely loved our stay here for our anniversary! ❤️ It was our first time at S Hotel Montego Bay, and we definitely had an amazing time! The location is super convenient and so close to the airport. We also took advantage of their taxi service, which made getting around so easy and convenient. All of the restaurants and bars are definitely worth checking out! We really enjoyed the amazing food, beautiful views, and overall experience. 🌴✨ If you’re considering staying here, I definitely recommend taking advantage of the all-inclusive option—you won’t regret it! 😊 Thank you, S Hotel Montego Bay, for making our anniversary so special! ❤️"

Azul Beach Resort Negril, Gourmet All Inclusive by Karisma

10/10 Excellent

"It was a piece of paradise. The sea was divine. The rooms right In front of the beach all small villas surrounded by pools. I loved the buffet. The food was fresh and there were different kinds of cooked meals. The people were kind and friendly. Not crowded which made it peaceful. They had beautiful shows and songs in the evening. Very happy. Will come back for sure. And the sea!!!! I don’t hours and hours floating and swimming. Enough towels, plenty of beach chairs. Coffee and drinks available all the time. Loved it! Loved it! Loved it!"

Find out more about Middlesex

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Frequently asked questions

Can I find vacation rentals in Middlesex?

Yes, we have vacation rentals near popular local attractions in Middlesex, or you can choose a more remote option if you want a relaxing place to stay.

What can I see and do in Middlesex?

Explore the area and family-friendly sights such as Hope Botanical Garden and Zoo, or get out into nature at a spot like Seven Mile Beach. Half Moon Beach and Bloody Bay Beach are a couple of places you'll find in the larger area.

What are vacation rentals like in Middlesex?

Vacation rentals are private accommodations you can book for a few days or a quick weekend in Middlesex. Vacation rentals offer extras such as kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, a vacation rental can offer a sense of security away from public hotel elevators and bustling concierge desks while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great option for family trips or small group gatherings.

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Check prices for these dates

Our top choices for Middlesex vacation rentals

1. Sky Beach Rooms

2. Grassroots Negril

3. Sunny-shore Hideaway

4. Turquoise Sea Villa

5. RUNTINGS HIDEAWAY STAY NOMPREL ROAD NEGRIL

6. Claudeville Condo

7. Beach House Condos Negril

Find vacation rentals that suit your style

Top Middlesex Hotel Reviews

Samsara Cliff Resort

Deja Resort All Inclusive

Toby's Resort

Sunset at the Palms Resort - Adults Only - All Inclusive

Princess Senses The Mangrove Resort - Adults Only

S Hotel Montego Bay - Luxury Boutique All Inclusive Hotel

Couples Swept Away All Inclusive

Azul Beach Resort Negril, Gourmet All Inclusive by Karisma

Travellers Beach Resort

Find out more about Middlesex

Frequently asked questions

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