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Caribbean Flight + Hotel packages

Caribbean Hotels

See all 7,820 Hotels in Caribbean
Hotel El Convento

Hotel El Convento

100 Cristo St, San Juan
5.0 out of 5.0
4.6 out of 5 (171 reviews)

Formerly a convent dating from 1651, this boutique hotel is in the center of Old San Juan across from the San Juan Cathedral and two blocks from La Fortaleza, ...

$224

$224
Hotel Plaza De Armas Old San Juan

Hotel Plaza De Armas Old San Juan

Viejo San Juan, San Jose St, 202, San Juan
2.5 out of 5.0
3.4 out of 5 (41 reviews)

Located in Old San Juan, this hotel is within a 10-minute walk of Museo del Nino's, Plaza de Armas, and Museum of the Americas. Museo de Casa Blanca is 0.3 mi ...

$140

$140
British Colonial Hilton - Nassau

British Colonial Hilton - Nassau

Number One Bay St, Nassau
4.5 out of 5.0
4.1 out of 5 (106 reviews)

Serving as the island's social and business hub, the 288-room beachfront hotel is across from the Straw Market and 5 blocks from Parliament Square. A seaside ...

$249

$249
Sheraton Old San Juan Hotel

Sheraton Old San Juan Hotel

100 Brumbaugh Street, San Juan
4.5 out of 5.0
3.9 out of 5 (461 reviews)

Located along the water in Old San Juan, this contemporary Puerto Rico resort is across from cruise-ship piers and 3 blocks from the massive Fort San ...

$178

$178
The Reef at Atlantis, Autograph Collection

The Reef at Atlantis, Autograph Collection

Paradise Beach Drive, Paradise Island
5.0 out of 5.0
4.3 out of 5 (78 reviews)

The Reef at Atlantis, Autograph Collection, located directly on a white-sand beach, is close to numerous attractions including Atlantis Aquarium, Cabbage Beach, ...

Boutique Hotel Palacio

Boutique Hotel Palacio

Calle Duarte 106, Santo Domingo
4.0 out of 5.0
4.3 out of 5 (38 reviews)

Located in Colonial Zone, this hotel is within a 10-minute walk of Regional Museum of Archaeology, Parque Colon, and Cathedral of Santo Domingo. Alcazar de Colon ...

$77

$77
Comfort Suites Paradise Island

Comfort Suites Paradise Island

Paradise Island Drive, Paradise Island
4.5 out of 5.0
3.8 out of 5 (574 reviews)

This casual, all-junior suite property provides guests access to Atlantis and full use of their resort facilities just one block away, and two golf courses are ...

$324

$324
The Royal at Atlantis, Autograph Collection

The Royal at Atlantis, Autograph Collection

Paradise Beach Drive, Paradise Island
4.5 out of 5.0
4.1 out of 5 (319 reviews)

These spire-topped towers contain 1,201 rooms and embody the Lost Continent theme offered by the water-park and marine-life Atlantis resort on Paradise Island, ...

The Coral at Atlantis, Autograph Collection

The Coral at Atlantis, Autograph Collection

One Casino Drive, Paradise Island
4.0 out of 5.0
3.9 out of 5 (192 reviews)

Atlantis resort on Paradise Island, which connects by bridge to Nassau, features 5 hotels located on a 4-mile beach, surrounded by marine-life attractions and ...

Renaissance Aruba Resort & Casino

Renaissance Aruba Resort & Casino

L G Smith Boulevard 82, Oranjestad
4.5 out of 5.0
4.2 out of 5 (351 reviews)

Renaissance Aruba Resort & Casino is split between 2 properties. The Marina Hotel is exclusive to adults, while the Ocean Suites are a resort-style located right ...

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Experience Your Best Caribbean Vacation

No matter the tropical fix you seek, a Caribbean vacation will undoubtedly deliver. Surrounded by the Caribbean Sea, the glorious West Indies brings year-round sunshine, 28 unique island countries, and adventures for every age and desire.

Laze in pink or white sugar sands and dive world-famous treasures. Hike to towering waterfalls and secluded caves, or nap in a hammock. Shop in local markets, experience culinary gems, sail and golf.

From Jamaica, Puerto Rico and the Dominican Republic to Aruba, St. Lucia and Bermuda, Orbitz can help you narrow it down. Our Caribbean travel guide gives you the scoop on the best time to go, top 10 attractions and insider gems.

Best time to take a vacation to Caribbean

The Caribbean features a tropical climate with sunshine year-round, making a Caribbean vacation worthwhile no matter what time of the year. The region experiences dry and wet seasons, plus much warmer months, so the best time to visit boils down to whether you prefer perfect weather or lower hotel rates.

January to May tend to be drier months, and are more popular with travelers -- especially in January. From early spring through summer, more rain and hotter temperatures (plus cool trade winds) make this an ideal time to find great deals on a Caribbean vacation. Hurricane season officially spans from June through November, and early December is the best time to go for low hotel rates and few crowds.

Insider tips for Caribbean travel

Try The Fish Fry restaurant in Nassau

Try The Fish Fry restaurant in Nassau near Arawak Cay for authentic Bahamian conch salad, fried fish and cold Kalik beer.

Do the Dolphin Cay Deep Water Swim at Atlantis

Do the Dolphin Cay Deep Water Swim at Atlantis and snorkel alongside a dolphin using your own water scooter.

Buy some bling in St. Martin

Buy some bling in St. Martin, where you’ll find some of the best deals on silver and gold in all of the duty-free Caribbean.

Eat at Scotchie’s in Montego Bay and Ocho Rios

Eat at Scotchie’s in Montego Bay and Ocho Rios for fantastic Jamaican jerk food, plus traditional fried dough and breadfruit.

Rent a scooter in Bermuda

Rent a scooter in Bermuda for great exploration, with stops in Dockyard, Hamilton City, St. George and the famous Swizzel Inn.

* Prices reflect the lowest "base rate" found over the next 30 days. Rates are subject to change and may not include taxes and fees, hotel service charges, extra person charges, or incidentals, such as room service. All rates are displayed in USD unless otherwise noted. Converted rates are provided for your convenience. They are based on today's exchange rate, but the hotel will charge you in the local currency.