Diamond Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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.

Top Diamond Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Tropikist Beach Hotel & Resort

Tropikist Beach Hotel & Resort

3 out of 5
Price was CA $427, price is now CA $319 per person
CA $319
per person
Jan 8 - Jan 11
found 9 hours ago
Roundtrip flight included
Port of Spain (POS) to Tobago (TAB)
8/10 Very good! (1,014 reviews)

Starfish Tobago Resort

Starfish Tobago Resort

3 out of 5
Price was CA $703, price is now CA $435 per person
CA $435
per person
Jan 8 - Jan 11
found 9 hours ago
Roundtrip flight included
Port of Spain (POS) to Tobago (TAB)
6.8/10 (713 reviews)

Villa Being - Tobago Luxury B&B

Villa Being - Tobago Luxury B&B

4 out of 5
Price was CA $2,280, price is now CA $1,589 per person
CA $1,589
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tobago (TAB)
9.4/10 Exceptional! (48 reviews)
Overall a great stay.

Reviewed on Oct 3, 2026

Half Moon Blue

Half Moon Blue

3 out of 5
Price was CA $572, price is now CA $414 per person
CA $414
per person
Jan 8 - Jan 11
found 9 hours ago
Roundtrip flight included
Port of Spain (POS) to Tobago (TAB)
7.8/10 Good! (176 reviews)

Kariwak Village Holistic Haven

Kariwak Village Holistic Haven

3 out of 5
Price was CA $541, price is now CA $416 per person
CA $416
per person
Jan 8 - Jan 11
found 9 hours ago
Roundtrip flight included
Port of Spain (POS) to Tobago (TAB)
8.6/10 Excellent! (77 reviews)

Ready to book your vacation to Diamond?

 

Choose your dates

Diamond Hotel Deals

Tropikist Beach Hotel & Resort

Tropikist Beach Hotel & Resort

3 out of 5
77 Old Store Bay Rd Crown Point Tobago
Get rates
Tropikist Beach Hotel & Resort
Coco Reef Resort and Spa

Coco Reef Resort and Spa

4 out of 5
Coconut Bay Crown Point Tobago
The price is CA $412 per night from Nov 27 to Nov 28
CA $412
CA $455 total
Nov 27 - Nov 28
includes taxes & fees
7/10 Good! (556 reviews)
"beach was excellent"

Reviewed on Oct 17, 2026

Coco Reef Resort and Spa
Starfish Tobago Resort

Starfish Tobago Resort

3 out of 5
Courland Bay Plymouth Tobago
Fully refundableReserve now, pay when you stay
The price is CA $225 per night from Nov 27 to Nov 28
CA $225
CA $280 total
Nov 27 - Nov 28
includes taxes & fees
Starfish Tobago Resort
See all 544 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

What to do in Diamond

Clear Kayaking in Tobago

Clear Kayaking in Tobago

CA $35
per adult
Clear Kayaking in Tobago
empty boats anchored near the beach in Trinidad and Tobago

Glass-Bottom Boat & snorkeling with Tobago Highlights Tour

CA $165
per adult
74% of travellers recommend
Glass-Bottom Boat & snorkeling with Tobago Highlights Tour
Argyle Waterfall

Half Day Group Tour to Tobago Atlantic Coast

CA $113
per adult
Half Day Group Tour to Tobago Atlantic Coast
See all activities in Diamond

Frequently asked questions

How much does a Diamond vacation package cost?
You'll find cheap prices from CA $319 on Expedia for your Diamond escape. However, a range of factors like the length of stay, the season and your choice of hotel will influence how much your vacation to Diamond costs.
What are the cheapest months to go to Diamond?
If you're hoping to snag a cheap Diamond vacation package, consider visiting in April, May and September. You're likely to find lower rates on airfares and hotels during these months — perfect for a budget-friendly break.
How many days is enough for Diamond?
Diamond vacations come in all shapes and sizes, but to get a true feel for this destination, we think 4 days is a good ballpark. In this timeframe, you can visit top attractions like Fort King George and Botanical Gardens along with hidden gems. Don't miss out on neighbourhoods such as Lower Scarborough and Orange Hill either. If you're clever with your time, you can even allow for a day trip or two from Diamond too.
How to find the best Diamond package deals?
Finding a cheap Diamond package deal is a breeze with Expedia. Once you've entered your travel dates and destination under our "Packages" tab, set your maximum budget, add some filters and see what's available. You can tweak your search by "Amenities," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to discover the most affordable Diamond package deals. Want a simple trick to score the biggest savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are typically lower.
Is it cheaper to book a Diamond vacation as a package?
An Expedia vacation package could score you significant savings when compared to arranging flights and hotels individually. Better still, you can tailor your Diamond escape to fit your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a vacation package to Diamond?
If you're considering a spur-of-the-moment Diamond adventure, browse our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can find sensational deals on your flights and hotels by booking ahead.
How to plan a trip to Diamond?

  1. Choose when to go: Check your schedule and get your bags packed. Your favourite time of year and the available activities will also help you decide when to visit Diamond.
  2. Plan your budget wisely: Besides the price of your accommodations, you should consider other expenses. These include flights, transportation and food. Also, put aside a little extra for unexpected expenses that could crop up during your trip to Diamond.
  3. Decide your trip length: Think about how much time you'd like to spend exploring Diamond. Plan your itinerary so you can get to all the attractions and activities you're interested in without rushing.
  4. Bundle your hotel and flights: Epic destination, check. Length of stay, check. Now all that's left is to find a Diamond vacation package that brings all your bookings together.

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.