
Caribbean Islands Holidays from NZ$4,852
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The Latest Caribbean Islands Holiday Deals
Price found within the past 48 hours. Click for updated prices.



La Playa Orient Bay
per person
21 Jun - 27 Jun
found 11 hours ago
Return flight included
Auckland (AKL) to Philipsburg (SXM)
9.4/10 Exceptional! (482 reviews)
The hotel was the same as the pictures on their website. The room we had on the third floor was excellent with a nice size refrigerator and freezer which we used only to store some wine, water and I made some ice just because there was an ice tray. The hotel had a very convenient large ice machine. The staff were very friendly and helpful for the most part ,we had some miscommunication issues with the staff replenishing the coffee in the room but they made up for it by giving us some extra. It was no big deal. Only other issue was that when we went to lunch the first few days at the very convenient beach side restaurant the staff kept asking us if we had reservations even though the restaurant was never fully occupied. We then said we would like a reservation every day for lunch and the issue ended. The restaurant had many tables available every day so I’m not sure why they made such a requirement. The breakfast was a nice meal with a great view. Very relaxing way to start the day. There are many restaurants (8 or 9) for dinner a short walk from the hotel as well as a two small grocery stores which also sell wine and spirits, a good pizzeria ,ice cream shop, bakery and deli. Everything you would need plus a beautiful beach.
Reviewed on 29 Apr. 2025

Esmeralda Resort
per person
21 Jun - 27 Jun
found 11 hours ago
Return flight included
Auckland (AKL) to Philipsburg (SXM)
8.6/10 Excellent! (446 reviews)
Location is amazing! Staff is too! Swimming pool right outside the patio door, mini kitchen worked great. L’Astrolabe breakfast was perfect and dinners were too! Fridays and Mondays are a do not miss. A few quick minutes to the beach where your chair awaits, with staff to help you there! The beach restaurant’s food is also amazing! If you do not rent a car, it is easy to get a taxi. I used the same person the whole time. He was great. This property is lovely and I would definitely come back! There’s bird watching, the surf is perfect, food, entertainment for my style, bar, and no clocks. It is lovely.
Reviewed on 26 Apr. 2025

Holland House Beach Hotel
per person
21 Jun - 27 Jun
found 11 hours ago
Return flight included
Auckland (AKL) to Philipsburg (SXM)
9/10 Wonderful! (1,002 reviews)
Beautiful and clean! Staff always about to assist in anything needed. Reuben, Kelly and Kenisha at the beach bar were so great
Reviewed on 30 Apr. 2025
Our guide on where to stay in Caribbean Islands
Find the best Caribbean Islands areas and neighborhoods for the activities you enjoy most. Learn more about Caribbean Islands

Isla Verde
5/5(1 area review)
Visitors to Isla Verde rave about its stunning beaches, fantastic nightlife and first-class casinos. You might also want to make some time to see Carolina Beach or Isla Verde Beach while you're exploring the neighbourhood.
Caribbean Islands Holiday
Our pick of the best Caribbean Islands Hotel Deals

Serenade Punta Cana Beach & Spa Resort - All Inclusive
Carretera Cabeza de Toro, Punta Cana, La Altagracia
The price is NZ$450 per night from 20 May to 21 May
NZ$450
includes taxes & fees
20 May - 21 May
8/10 Very Good! (5,821 reviews)
"Very nice."
Reviewed on 30 Apr. 2025

Grand Hyatt Baha Mar
One Baha Mar Boulevard, Nassau, New Providence
Fully refundableReserve now, pay when you stay
The price is NZ$867 per night from 18 May to 19 May
NZ$867
includes taxes & fees
18 May - 19 May
8.4/10 Very Good! (4,102 reviews)
"The overall experience was lovely and I would head back to Baha Mar in a heartbeat! My family and I thoroughly enjoyed, as there was so much to do. BUT I felt like there were areas that weren’t properly cleaned and that was an issue for me. I wish I took photos, only just realising I could have uploaded ..."
Reviewed on 30 Apr. 2025

The Condado Plaza Hotel
999 Ashford Avenue, San Juan
Fully refundableReserve now, pay when you stay
The price is NZ$467 per night from 21 May to 22 May
NZ$467
includes taxes & fees
21 May - 22 May
7.6/10 Good! (1,113 reviews)
"I don’t know why it doesn’t have great reviews because honestly this place was so nice and clean and great pools and location and beach. Perfect for everything! Will go again for sure!!"
Reviewed on 29 Apr. 2025
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.
Frequently asked questions
Discover the most popular places to visit in Caribbean Islands

El Yunque National Forest
4/5(1 review)
This tropical rainforest offers many great hiking options, including stunning mountain views and beautiful waterfalls.

Luquillo Beach
Sample local street food or doze under a palm tree on this picturesque stretch of coast.

Sapphire Beach
Enjoy sunbathing, swimming and fun-filled watersports at this peaceful arched bay.
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