Diamond Vacation Packages 2026 from $416

Diamond flight + hotel vacation packages

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

Magdalena Grand Beach & Golf Resort

$416

per person

Sep 19 - Sep 21

found 2 days 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.

Villa Being - Tobago Luxury B&B

$725

per person

Oct 23 - Oct 26

found 1 day ago

Roundtrip non-stop flight included

New York (JFK) 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.

Plantation Beach Villas

$910

per person

Oct 23 - Oct 26

found 1 day ago

Roundtrip non-stop flight included

New York (JFK) to Tobago (TAB)

This villa features a bar/lounge, a poolside bar, and an outdoor pool. Families will appreciate the onsite laundry facilities and babysitting. Guests will appreciate free perks like free self parking and WiFi in public areas.

Robbie's Place Tobago

$795

per person

Nov 5 - Nov 9

found 1 day ago

Roundtrip flight included

New York (NYC) to Tobago (TAB)

An outdoor pool, free self parking, and laundry facilities are featured at this apartment. WiFi in public areas is free. A terrace, a picnic area, and barbecue grills are also on offer.

Crown Point Beach Hotel

$882

per person

Oct 18 - Oct 22

found 1 day ago

Roundtrip non-stop flight included

New York (NYC) to Tobago (TAB)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Guests will appreciate free perks like free self parking and WiFi in public areas. A garden, a grocery/convenience store, and a library are also on offer.

Top Diamond hotels deals

Tropikist Beach Hotel & Resort

77 Old Store Bay Rd Crown Point Tobago

$135 nightly

$148 total

Sep 15 - Sep 16

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.

Coco Reef Resort and Spa

Coconut Bay Crown Point Tobago

$309 nightly

$340 total

Aug 18 - Aug 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.

Comfort Inn & Suites Tobago

30 Orange Hill Road Scarborough Tobago

Free Cancellation

$209 nightly

$228 total

Aug 30 - Aug 31

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.

Starfish Tobago Resort

Courland Bay Plymouth Tobago

Free Cancellation

Reserve now, pay when you stay

$166 nightly

$183 total

Sep 14 - Sep 15

Total with taxes and fees

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.

Magdalena Grand Beach & Golf Resort

Tobago Plantations Estate Lowlands Tobago

$258 nightly

$312 total

Sep 13 - Sep 14

Total with taxes and fees

Blue Waters Inn

Batteaux Bay Speyside Tobago

$119 nightly

$131 total

Aug 18 - Aug 19

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.

Don't see what you're looking for?

See all available properties in Diamond

View all properties

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 $416, 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.