Diamond Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Diamond Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Tropikist Beach Hotel & Resort
$1,783
per person
Oct 29 - Nov 5
found 1 day ago
Roundtrip flight included
New York (JFK) to Tobago (TAB)
Book a stay at this beach resort in Crown Point. Enjoy free breakfast, free parking, and 2 outdoor pools. Our guests praise the breakfast and the pool in our reviews. Popular attractions Pigeon Point Beach and Fort Millford are located nearby.
Every member of staff were very kind and helpful.
The property gives you both a pool and beach option.
The rooms could be updated however they were very clean and otherwise comfortable.
Reviewed on Aug 4, 2026
Coco Reef Resort and Spa
$2,262
per person
Oct 29 - Nov 5
found 1 day ago
Roundtrip flight included
New York (JFK) to Tobago (TAB)
Book a stay at this beach hotel in Crown Point. Enjoy free parking, 2 restaurants, and a private beach. Our guests praise the helpful staff in our reviews. Popular attractions Pigeon Point Beach and Swallows Beach are located nearby.
Food and location
Reviewed on Aug 6, 2026
Starfish Tobago Resort
$1,897
per person
Oct 29 - Nov 5
found 1 day ago
Roundtrip flight included
New York (JFK) to Tobago (TAB)
Book a stay at this beach hotel in Plymouth. Enjoy free breakfast, free WiFi, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions Pigeon Point Beach and Turtle Beach are located nearby.
Mount Irvine Bay Resort
$1,869
per person
Oct 29 - Nov 5
found 1 day ago
Roundtrip flight included
New York (JFK) to Tobago (TAB)
Book a stay at this beach resort in Black Rock. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Pigeon Point Beach and Mount Irvine Bay are located nearby.
The resort is outdated and in need for major upgrades and maintenance. The walkways to the rooms were poorly lit with portions being without lights and many parts were flooded due to leaks in the roof leading the tiles to be extremely slippery and hazardous.
The room was outdated and not cleaned properly as the sheets and towels had hair on them. When the room was cleaned on the first night it appears that the housekeeper left the door open leading to many rain flies being dead on the bed and in the room, we did not discover this until we returned late at night and there is no phone in the room to contact the receptionist. The beds were also very uncomfortable and small for 2 persons.
Breakfast tasted good and the staff were pleasant and accommodating. We did not enjoy eating with cats running around us, this was also extremely upsetting as there appeared to be many cats on the compound including outside our room on one occasion.
When we arrived on Saturday we noticed the pool closed we enquired when it would reopen and were informed that it would reopen soon. Up to when we checked out on Monday the pool had not reopened.
We needed to add another night to our stay however opted to check out and go to another hotel, I could not wait to leave. The only positive experience of our stay was interacting with the staff who were extremely professional, accommodating and welcoming. The resort is beautiful and can be a vibrant hotel on the island once given the necessary TLC.
Reviewed on Jul 13, 2026
Magdalena Grand Beach & Golf Resort
$2,276
per person
Oct 29 - Nov 5
found 1 day ago
Roundtrip flight included
New York (JFK) to Tobago (TAB)
Book a stay at this beach resort in Lowlands. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Pigeon Point Beach and Gulf City Mall are located nearby.
Overall, we had a good experience at the Magdalena Grand. The hotel was clean, comfortable, and the staff were friendly and helpful throughout our stay. The service we received from the team was appreciated, especially when dealing with an unexpected issue.
On our first night, there was a plumbing problem and we were unable to use the water for showering. The issue was resolved later that night, and the staff made an effort to provide alternative arrangements so we could manage while it was being fixed. Their willingness to assist helped make the situation less frustrating.
The breakfast was decent and similar to what you would expect at many hotels. The selection was somewhat limited and it was not particularly spectacular, but it was also not disappointing.
Overall, the Magdalena Grand provided a pleasant stay. While there were a few areas that could be improved, the cleanliness, friendly staff, and good customer service contributed to an enjoyable experience
Reviewed on Aug 5, 2026
Blue Haven Hotel
$1,968
per person
Oct 29 - Nov 5
found 1 day ago
Roundtrip flight included
New York (JFK) to Tobago (TAB)
Book a stay at this beach hotel in Scarborough. Enjoy 2 restaurants, a beach locale, and breakfast (surcharge). Popular attractions Fort King George and Tobago Museum are located nearby.
Diamond Vacation Packages
Trying to figure out a way to package your Diamond flight and hotel, while saving some money? The AARP Travel Center Powered by Expedia® Diamond vacation packages can help. We're here to book everything you'll need to make your Diamond trip one to remember. Our Travel Center is a one-stop shop where you can put together the best Diamond vacation package for you. AARP Travel Center has a fabulous selection of flights and lodgings, and local activities to choose from.
Hotels in Diamond
Our listings include hotels that are close to all the Diamond points of interest, and some that are just outside the city center for a peaceful retreat.
We have competitive rates on everything from family-friendly resorts that satisfy all the vacation must-haves to inexpensive accommodations perfect for those on wanting to save a little money. You can search all the possibilities and choose the accommodation that is best for you and your family. With AARP Travel Center's Diamond hotel packages, you not only get a great rate on your flight, but also a wonderful place to stay.
Things to do in Diamond
You'll find that Diamond usually has something going on. A little curiosity and asking the right people, like your hotel's concierge, goes a long way into having a unique experience.
If you need more suggestions, then make sure to click on AARP's "Things to Do" page.
Package Your Diamond Vacation and Save
With so much going on in Diamond, you'll be wanting to plan your outings, not devoting time to searching for the hotel with the lowest rate. The AARP Travel Center Powered by Expedia® allows you to easily book all you want, and save money while doing it. You can coordinate your whole vacation, including things to do in Diamond from just one site. The hardest packing you'll have to do is for your suitcase. Bundle today and save!
Top Hotel Deals
Tropikist Beach Hotel & Resort
77 Old Store Bay Rd Crown Point Tobago
Book a stay at this beach resort in Crown Point. Enjoy free breakfast, free parking, and 2 outdoor pools. Our guests praise the breakfast and the pool in our ...
Coco Reef Resort and Spa
Coconut Bay Crown Point Tobago
Book a stay at this beach hotel in Crown Point. Enjoy free parking, 2 restaurants, and a private beach. Our guests praise the helpful staff in our reviews. Popular ...
Starfish Tobago Resort
Courland Bay Plymouth Tobago
Book a stay at this beach hotel in Plymouth. Enjoy free breakfast, free WiFi, and a beach locale. Our guests praise the helpful staff in our reviews. Popular ...
Comfort Inn & Suites Tobago
30 Orange Hill Road Scarborough Tobago
Book a stay at this spa hotel in Scarborough. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular ...
Blue Waters Inn
Batteaux Bay Speyside Tobago
Stay at this hotel in Speyside. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Speyside Bay and Little Tobago are located ...
Magdalena Grand Beach & Golf Resort
Tobago Plantations Estate Lowlands Tobago
Book a stay at this beach resort in Lowlands. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular ...
Bacolet Beach Club
73 Bacolet Street Scarborough Tobago
Book a stay at this beach hotel in Scarborough. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff in our reviews. Popular ...
Kariwak Village Holistic Haven
Store Bay Local Road Crown Point Tobago
Book a stay at this business-friendly hotel in Crown Point. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions Pigeon Point Beach and Store ...
PeSheres Inn & Spa
Lot C, John Gorman Road Crown Point Tobago
Book a stay at this luxury guesthouse in Crown Point. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...
Shepherd's Inn
Old Store Bay Road Crown Point
Book a stay at this business-friendly hotel in Crown Point. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
CROWN HOTEL TOBAGO
ROBERT STREET, BON ACCORD, TOBAGO Crown Point
Stay at this hotel in Crown Point. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Pigeon Point Beach and Swallows Beach are located ...
Merci Buccoo
9-11 Miller Street Scarborough Scarborough
Book a stay at this beach hotel in Scarborough. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Pigeon Point Beach and The Kimme Museum ...
Crown Point Beach Hotel
Old Store Bay Rd Crown Point
Stay at this hotel in Crown Point. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Pigeon Point Beach and Swallows Beach are located ...
Le Grand Courlan Spa Resort - Adults Only
Stonehaven Bay Black Rock Tobago
Book a stay at this beach resort in Black Rock. Enjoy free parking, 2 restaurants, and 4 hot tubs. Our guests praise the breakfast and the pool in our reviews. ...
Grafton Beach Resort
Stonehaven Bay Black Rock Tobago
Book a stay at this beach resort in Black Rock. Enjoy free parking, 2 outdoor pools, and 3 restaurants. Our guests praise the breakfast and the helpful staff ...
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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Tue, Nov 17 - Thu, Nov 19
JFK
John F. Kennedy Intl.
TAB
A.N.R. Robinson Intl.
$525
Roundtrip
found 5 days ago
Tue, Nov 17 - Wed, Nov 18
JFK
John F. Kennedy Intl.
TAB
A.N.R. Robinson Intl.
$548
Roundtrip
found 5 days ago
Wed, Nov 18 - Thu, Nov 19
JFK
John F. Kennedy Intl.
TAB
A.N.R. Robinson Intl.
$558
Roundtrip
found 5 days ago
Mon, Nov 16 - Thu, Nov 19
JFK
John F. Kennedy Intl.
TAB
A.N.R. Robinson Intl.
$565
Roundtrip
found 5 days ago
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