Diamond Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, 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.
Villa Being - Tobago Luxury B&B
CA $506
per person
Dec 2 - Dec 5
found 1 day ago
Roundtrip flight included
Port of Spain (POS) to Tobago (TAB)
9.4/10 Exceptional! (44 reviews)
The villa itself is beautiful, and the scenery is absolutely breathtaking. Everything around the property is gorgeous, and the views are amazing.
My only complaints are regarding cleanliness and transportation. When we first arrived, the toilet was filled with poop and clearly had not been cleaned. We also dropped something and wanted to clean up the mess, but there was no broom or dustpan available. If you’re planning to stay at this villa and spend time exploring outside of the property, I strongly recommend renting your own 4x4 vehicle. Do not depend solely on the villa’s driver to take you around. You may have to walk down and back up a very steep hill, and it can be difficult and unsafe. I actually fell while walking on it and injured my hands and knees. Despite these issues, the villa is beautiful, the scenery is stunning, and the surrounding area is absolutely gorgeous. With better cleaning and easier transportation access, the experience would be much better.
Reviewed on Sep 17, 2026
Ready to book your vacation to Diamond?
Diamond Hotel Deals
Tropikist Beach Hotel & Resort
77 Old Store Bay Rd Crown Point Tobago
CA $180
CA $222 total
Oct 20 - Oct 21
includes taxes & fees
Coco Reef Resort and Spa
Coconut Bay Crown Point Tobago
CA $381
CA $420 total
Sep 22 - Sep 23
includes taxes & fees
7/10 Good! (545 reviews)
"Lovely accommodation and tasty food."
Reviewed on Sep 13, 2026
Starfish Tobago Resort
Courland Bay Plymouth Tobago
Fully refundableReserve now, pay when you stay
CA $214
CA $261 total
Oct 21 - Oct 22
includes taxes & fees
6.8/10 (713 reviews)
"T"
Reviewed on Sep 18, 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.
What to do in Diamond
Glass-Bottom Boat & snorkeling with Tobago Highlights Tour
CA $162
per adult
74% of travellers recommend
Frequently asked questions
How much does a Diamond vacation package cost?
You'll find cheap prices from CA $321 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?
- 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.
- 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.
- 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.
- 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
- Villa Being
- Birdie's Nest condo #2 with ocean view
- Bethel Hotels
- Beach Hotel Hotels in Tobago
- Beach Hotel Hotels in Crown Point
- Providence Hotels
- Diamond Hotels
- Private villa apartment with pool and within 15 minute walk to 3 beaches.
- Bon Accord Village Hotels
- Luxury Hotels in Tobago
- Buccoo Reef Bliss
- All Inclusive Resorts and in Crown Point
- All Inclusive Resorts and in Tobago
- Hotels near Stonehaven Bay
- Cheap Hotels in Crown Point
- Hotels near Store Bay
- Patience Hill Hotels
- Hotels near Turtle Beach
- Villas in Black Rock
- Black Rock Hotels
- Hotels near Buccoo Beach
- Lowlands Hotels
- Escarlet HOTEL
- Scarborough Hotels
- Vip Holiday Resort
- Casino Hotels in Tobago
- Tobago Hotels
- Comfort Inn & Suites Tobago
- Villas in Tobago
- Canaan Hotels
- Hotels near Pigeon Point Beach
- Greenhaven Cottage B&B
- Hotels near Mount Irvine Bay
- Villas in Bacolet
- Guest Houses in Tobago
- Hotels near A.N.R. Robinson Intl.
- Ocean Winds Suite Hotel
- Beach Hotel Hotels in Bethel
- Plymouth Hotels
- Crown Point Hotels
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- Flights from Fort Lauderdale (FLL) to Tobago (TAB)
- Flights to Canaan
- Flights from Regina (YQR) to Tobago (TAB)
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- Flights from New York (JFK) to Tobago (TAB)
- Flights from Toronto (YYZ) to Tobago (TAB)
- Flights from Calgary (YYC) to Tobago (TAB)
- Flights from Ottawa (YOW) to Tobago (TAB)
- Flights from Kingston (KIN) to Tobago (TAB)
- Flights from Port of Spain (POS) to Tobago (TAB)
- Flights to Scarborough
- Flights from Fort Collins (FNL) to Tobago (TAB)
- Flights from Toronto (YTZ) to Tobago (TAB)
- Flights from Kelowna (YLW) to Tobago (TAB)
- Flights from Winnipeg (YWG) to Tobago (TAB)
- Flights to Tobago
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- Flights from Halifax (YHZ) to Tobago (TAB)
- Flights from Bridgetown (BGI) to Tobago (TAB)
- Flights from Saskatoon (YXE) to Tobago (TAB)
- Flights from Thunder Bay (YQT) to Tobago (TAB)
- Flights from Montreal (YUL) to Tobago (TAB)
- Flights from Fredericton (YFC) to Tobago (TAB)
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
