Diamond Vacation Packages 2026 from $169

Diamond flight + hotel vacation packages

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

Top Ranking Guesthouse

$169

per person

Nov 6 - Nov 9

found 1 day ago

Roundtrip flight included

Port of Spain (POS) to Tobago (TAB)

This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and laundry facilities are also on offer.

Villa Being - Tobago Luxury B&B

Save 100% on your flight

$255

per person

Nov 6 - Nov 9

found 1 day ago

Roundtrip flight included

Port of Spain (POS) to Tobago (TAB)

This villa doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden, dry cleaning, and luggage storage are also on offer.

Native Abode

Save 100% on your flight

$219

per person

Nov 28 - Dec 1

found 1 day ago

Roundtrip flight included

Port of Spain (POS) to Tobago (TAB)

This guesthouse doesn't skimp on freebies - guests receive free buffet breakfast, free self parking, and a free ferry terminal shuttle. Traveling on business? Take advantage of the business center and free WiFi in public areas. A terrace, a garden, and express check-in are also on offer.

Magdalena Grand Beach & Golf Resort

Save 100% on your flight

$510

per person

Nov 25 - Nov 28

found 1 day ago

Roundtrip flight included

Port of Spain (POS) to Tobago (TAB)

This resort features a golf course, a full-service spa, and a nightclub. There's fun for all ages with a free kid's club and a playground, and families will appreciate the onsite laundry facilities. Enjoy a meal in one of the 6 restaurants and perks like free buffet breakfast and free self parking.

Starfish Tobago Resort

$1,138

per person

Oct 18 - Oct 24

just found

Roundtrip non-stop flight included

New York (JFK) to Tobago (TAB)

This hotel features 2 bars/lounges, a poolside bar, and a restaurant. Enjoy the outdoor pool and free perks like buffet breakfast and WiFi in public areas. A coffee shop, a terrace, and a garden are also on offer.

Top Diamond hotels deals

Tropikist Beach Hotel & Resort

77 Old Store Bay Rd Crown Point Tobago

$147 nightly

$160 total

Sep 18 - Sep 19

Total with taxes and fees

2 outdoor pools, 2 restaurants, and a bar/lounge are among this resort's featured amenities. Relax with a drink at the poolside bar and enjoy free perks like buffet breakfast and valet parking. Free self parking, free WiFi in public areas, and a terrace are also offered.

Pool

Breakfast included

Coco Reef Resort and Spa

Coconut Bay Crown Point Tobago

$273 nightly

$300 total

Sep 18 - Sep 19

Total with taxes and fees

A private beach, 2 restaurants, and 2 outdoor tennis courts are all featured at this traditional hotel. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Families will appreciate the free kid's club, onsite laundry facilities, and in-room childcare.

On private beach

Pool

Starfish Tobago Resort

Courland Bay Plymouth Tobago

Free Cancellation

Reserve now, pay when you stay

$185 nightly

$201 total

Sep 21 - Sep 22

Total with taxes and fees

Pool

Breakfast included

Comfort Inn & Suites Tobago

30 Orange Hill Road Scarborough Tobago

Free Cancellation

$198 nightly

$215 total

Sep 23 - Sep 24

Total with taxes and fees

A full-service spa, an outdoor pool, and a restaurant are all featured at this smoke-free hotel. Business travelers can take advantage of the free WiFi in public areas. Enjoy the gym and free perks like local cuisine breakfast and free self parking.

Pool

Breakfast included

Blue Waters Inn

Batteaux Bay Speyside Tobago

$109 nightly

$122 total

Sep 22 - Sep 23

Total with taxes and fees

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the outdoor tennis court and perks like free self parking and free WiFi. There's a beach bar on site, and a terrace and laundry facilities are also provided.

Pool

Parking included

Magdalena Grand Beach & Golf Resort

Tobago Plantations Estate Lowlands Tobago

$277 nightly

$302 total

Sep 18 - Sep 19

Total with taxes and fees

Pool

Breakfast included

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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

How much are vacation packages to Diamond?

With vacation packages available for just $169, it's not necessary to wipe out your bank balance for your getaway to Diamond. Travelocity can help. Bundle up experiences, flights and hotels into a convenient package and land fantastic discounts. The more you book, the more you save.

How long should my Diamond vacation be?

An average of 3 nights is how long most visitors spend exploring Diamond. Wondering whether that'll be sufficient time to tick everything off your sightseeing list? Stay another night or two so you don't miss a thing.

Where can I get the best vacation package deals for Diamond?

Your dream escape is waiting for you at Travelocity. With access to 400 air carriers and 1,000,000 hotels all over the world, finding the perfect Diamond package deal couldn't be easier.

Why should I book my Diamond vacation package via Travelocity?

We take the hassle out of travel planning. Whether you're seeking an amazing new place to roam around or want to ensure you get the best price on offer, we've got you covered. Our 24/7 customer care, top-quality service and Price Match Guarantee mean you can book with confidence with Travelocity.

Will I save money on my Diamond car rental if I combine it with hotels and flights?

Certainly. And our Diamond vacation packages will help you do it. With just a few clicks you can save cash as well as time by combining your bookings. Pick up the keys to your rental car then chart your own course. Looking for things to do? Add a few tours to your package and save on those too.

What is the best time of year to go to Diamond?

If funds are a bit tight, is a great month to go to Diamond, whereas is the dearest time of year. June, July and August is high season. If you'd prefer to avoid the crowds, January, May and December tend to be quieter.

Which airport is best for Diamond?

Piarco Intl. Airport (POS) is one place you can kick off your Diamond adventure. About 55 mi southwest of Diamond, it welcomes visitors from all over every day. Another popular option is A.N.R. Robinson Intl. Airport (TAB), 6 mi away from central Diamond.

Where should I stay when visiting Diamond?

The Faiths Villa Of Tobago is the number one choice of many travelers. Book as soon as possible before it's too late.