
Middlesex Holidays from NZ$1,321
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The Latest Middlesex Holiday Deals
Price found within the past 48 hours. Click for updated prices.

237 Bratton Ave
Ironshore
Price was NZ$1,695, price is now NZ$1,321 per person
NZ$1,321
per person
17 May - 23 May
found 5 hours ago
Return direct flight included
Los Angeles (LAX) to Montego Bay (MBJ)
7.8/10 Good! (39 reviews)
This was a great stay for my friends and I. It is a quaint black owned family business. The staff were very friendly and helpful and tried to cater to all of our needs. The breakfast we ordered and ate was absolutely scrumptious. The Wi-Fi was not the greatest at times but, we understood that due to the storm some parts of the island has no Wi-Fi or electricity. That being said, having a lack of Wi-Fi gave us an opportunity to have actual conversations with other guest and a chance to rejuvenate and actually digitally detox. It was tranquil and relaxing. I would definitely be back again.
Reviewed on 20 Mar 2026

Hotel Riu Palace Jamaica - Adults Only - All Inclusive
Save 100% on your flight
Price was NZ$4,984, price is now NZ$3,117 per person
NZ$3,117
per person
17 May - 23 May
found 5 hours ago
Return direct flight included
Los Angeles (LAX) to Montego Bay (MBJ)
8.8/10 Excellent! (1,641 reviews)
The staff was incredible! Housekeeping, room service, bar tenders, etc! Excellent hospitality.
Reviewed on 2 Apr 2026

Deja Resort All Inclusive
Hip Strip
Price was NZ$2,226, price is now NZ$1,637 per person
NZ$1,637
per person
17 May - 23 May
found 5 hours ago
Return direct flight included
Los Angeles (LAX) to Montego Bay (MBJ)
8/10 Very Good! (1,621 reviews)
3.5 ⭐ – Good stay overall
Clean rooms, friendly staff, and very good food.
Be aware the hotel is not directly on the beach — you need to cross the strip (staff assist), and beach chairs cost extra. Minibar could be better stocked with local beer options.
Overall, we enjoyed our stay, just important to know what to expect.
Reviewed on 4 Apr 2026

Round Hill Hotel And Villas
Save 100% on your flight
Price was NZ$7,152, price is now NZ$5,411 per person
NZ$5,411
per person
17 May - 23 May
found 5 hours ago
Return direct flight included
Los Angeles (LAX) to Montego Bay (MBJ)
9.6/10 Exceptional! (288 reviews)
Classy, timeless, elegant, spotless, farm-to-table…our second trip here did not disappoint. Great couples getaway in a beautiful villa with warm, friendly staff. Also no trouble accommodating our gluten free friends.
Reviewed on 10 Feb 2026

S Hotel Montego Bay - Luxury Boutique All Inclusive Hotel
Hip Strip
Save 100% on your flight
Price was NZ$5,624, price is now NZ$4,407 per person
NZ$4,407
per person
17 May - 23 May
found 5 hours ago
Return direct flight included
Los Angeles (LAX) to Montego Bay (MBJ)
9.4/10 Exceptional! (2,141 reviews)
We had an ocean view room which was truly amazing. The hotel is luxurious, with great attention to detail. The staff were friendly and made you feels very special, nothing was too much trouble and they catered to your every need, even had drinks service on the beach! There was always a selection of food and drinks and again if you wanted you could have pool service. We had an amazing stay and would highly recommend this hotel for couples or friends or even solo travellers.
Reviewed on 4 Apr 2026
Middlesex Holiday
Our pick of the best Middlesex Hotel Deals

Princess Grand Jamaica Resort - All Inclusive
Industry Cove Green Island Hanover
The price is NZ$871 per night from 4 May to 5 May
NZ$871
4 May - 5 May
includes taxes & fees
8.8/10 Excellent! (810 reviews)
Fantastic stay. Friendly staff. Only issue was a la carte wait times. Just would have preferred an estimate of time.
Reviewed on 5 Apr 2026

Deja Resort All Inclusive
92 Gloucester Avenue Montego Bay Saint James
The price is NZ$395 per night from 6 May to 7 May
NZ$395
6 May - 7 May
includes taxes & fees
8/10 Very Good! (1,667 reviews)
3.5 ⭐ – Good stay overall Clean rooms, friendly staff, and very good food. Be aware the hotel is not directly on the beach — you need to cross the strip (staff assist), and beach chairs cost extra. Minibar could be better stocked with local beer options. Overall, we enjoyed our stay, just important ...
Reviewed on 4 Apr 2026

Princess Senses The Mangrove Resort - Adults Only
Industry Cove Green Island Hanover
The price is NZ$1,309 per night from 20 Apr to 21 Apr
NZ$1,309
20 Apr - 21 Apr
includes taxes & fees
9.2/10 Wonderful! (579 reviews)
Enjoyed the property especially since it was Adults only!
Reviewed on 4 Apr 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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