Diamond Vacations from $193

Book a Hotel + Flight or Car together to unlock savings

Your Diamond Vacation

Say goodbye to planning worries and hello to a Diamond vacation package. With everything organized before you go, you can focus on discovering the best of this city, starting with Golden Grove, which is great for hiking, views and nature. Scarborough Botanical Garden, Fort King George and Botanical Gardens are just some of the many attractions you'll want to explore during your trip to Diamond. A couple of quick clicks is all it takes to put together the perfect Diamond vacation on Expedia.

The Latest Diamond vacation packages

Price found within the past 48 hours. Click for updated prices.
ESCARLET HOTEL

ESCARLET HOTEL

2.5 out of 5
Price was $234, price is now $193 per person
$193
per person
Oct 17 - Oct 19
found 1 day ago
Roundtrip flight included
Port of Spain (POS) to Tobago (TAB)
9/10 Wonderful! (13 reviews)
Escarlet was lovely, the room the stay, lovely Garden and pool. We enjoyed and will surely be going back. Thanks Escarlet.

Reviewed on Aug 20, 2025

Villa Being - Tobago Luxury B&B

Villa Being - Tobago Luxury B&B

4 out of 5
Price was $1,043, price is now $748 per person
$748
per person
Oct 17 - Oct 20
found 23 hours ago
Roundtrip flight included
New York (JFK) to Tobago (TAB)
9/10 Wonderful! (26 reviews)
This place is ABSOLUTELY serenity! I must tell you go shopping

Reviewed on Sep 15, 2025

Tropikist Beach Hotel & Resort

Tropikist Beach Hotel & Resort

3 out of 5
Save 100% on your flight
Price was $519, price is now $384 per person
$384
per person
Oct 20 - Oct 23
found 2 hours ago
Roundtrip flight included
Port of Spain (POS) to Tobago (TAB)
7.6/10 Good! (799 reviews)
The ambiance, the scenic environment, the beach jetty, pool design and the quiet privacy

Reviewed on Sep 12, 2025

Magdalena Grand Beach & Golf Resort

Magdalena Grand Beach & Golf Resort

4 out of 5
Save 100% on your flight
Price was $469, price is now $377 per person
$377
per person
Oct 17 - Oct 19
found 1 hour ago
Roundtrip flight included
Port of Spain (POS) to Tobago (TAB)
7.4/10 Good! (676 reviews)
Nice hotel, very nice staff. The pool wasn’t the cleanest. There was caution tape on some of the stairwells and walkways.

Reviewed on Sep 2, 2025

Starfish Tobago Resort

Starfish Tobago Resort

3 out of 5
Price was $917, price is now $741 per person
$741
per person
Oct 17 - Oct 20
found 23 hours ago
Roundtrip flight included
New York (JFK) to Tobago (TAB)
6.8/10 (671 reviews)
I like the over all space however have more stuff to do at night

Reviewed on Aug 22, 2025

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Discover the most popular places to visit in Diamond

Fort King George

Fort King George

4.5/5(38 reviews)

You can find out about the history of Scarborough with a trip to Fort King George. Stroll along the seaside in this relaxing area, or check out its top-notch restaurants.

Fort King George

Scarborough Botanical Garden

4/5(28 reviews)

Explore the great outdoors at Scarborough Botanical Garden, a lovely green space in Lower Scarborough. Wander the beautiful beaches and seaside in this relaxing area.

Scarborough Botanical Garden

Shaw Park Cultural Complex

You can get tickets for a performance at Shaw Park Cultural Complex on your trip to Scarborough. Wander the beaches in this relaxing area.

Shaw Park Cultural Complex

What to do in Diamond

Parlatuvier

Around the Island

$115
per adult
Around the Island
Half Day Group Tour to Tobago Atlantic Coast

Half Day Group Tour to Tobago Atlantic Coast

$100
per adult
Half Day Group Tour to Tobago Atlantic Coast
Bioluminescence Tour

Bioluminescence Tour

$150
per adult
Bioluminescence Tour
See all activities in Diamond

Diamond Hotel Deals

Benn's Apartment Rentals

Benn's Apartment Rentals

2 out of 5
Signal Hill, Scarborough
Get rates
Benn's Apartment Rentals
Cozy and Spacious Apartment in Lambeau, Tobago

Cozy and Spacious Apartment in Lambeau, Tobago

Lambeau Village
10/10 Exceptional! (4 reviews)
"We had the best time, the service was excellent. This place was the best!"

Reviewed on Aug 12, 2025

Get rates
Cozy and Spacious Apartment in Lambeau, Tobago
Cody one bedroom apartment

Cody one bedroom apartment

2 out of 5
Scarborough
$110 nightly
The price is $110 total per night from Sep 16 to Sep 17
$110 total
Sep 16 - Sep 17
Total with taxes and fees
Cody one bedroom apartment
See all 507 properties in Diamond
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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Frequently asked questions

How much does a Diamond vacation package cost?
You can snap up a vacation package to this top destination from $193 on Expedia. But how much your vacation to Diamond costs will depend on factors like your hotel choice, season and length of stay.
What are the cheapest months to go to Diamond?
If you'd like to score a cheap Diamond vacation package, consider visiting in January, May and December. You'll typically find better rates on flights and hotels during these quieter months — ideal for budget-conscious travelers.
How many days is enough for Diamond?
Generally, a handful of days is enough to tick off the top attractions during your Diamond vacation. But if you'd like to have time to rest or take day trips, consider extending your itinerary.
How to find the best Diamond package deals?
Use Expedia's handy filters to help you find some terrific Diamond package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your adventure for midweek, or browse for Diamond package deals in the off-season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to lock in your vacation package as early as possible.
Is it cheaper to book a Diamond vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging hotels and flights individually. Better still, you can tailor your Diamond trip to fit your exact style. Pick your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a vacation package to Diamond?
If you've got your Diamond vacation dates locked in, book as early as you can to grab some terrific deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spur-of-the-moment trips? Our last-minute deals are ideal for traveling on a whim.
Does Expedia offer Book Now, Pay Later Diamond vacation packages?
Set off on your ideal getaway to Diamond with Expedia's Book Now, Pay Later vacations. There's no need to save like crazy or wait for your next payday — we've partnered with online lender Affirm to offer you flexibility with your finances. Our vacation packages with payment plans allow you to split the cost across 3, 6 or 12 months. With no hidden or late payment fees, you can easily stick to your budget and snap up cheap deals while they last.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.