100 deals from our U.S. site*
* Taxes and fees may be additional.
Source: Puerto Rico

Score hotel and vacation deals as part of the island-wide Summer is Easy promotion

Deals into September
Source: British Virgin Islands

Retreat to a private island resort or yacht across the channel to explore 60+ islands

Deals into December
Source: Aruba

Beachfront resorts, vacations and flight deals

Deals into December
Source: Cayman Islands

Enjoy beautiful beaches, top diving and snorkeling, Stingray City deals

Deals through December
Source: Sonesta Collection

Escape to St. Maarten for romance, family time or a luxurious getaway with a Travelzoo-exclusive deal on three all-inclusive resorts.

Through Oct. 31
Source: Casa de Campo

Conde Nast Traveler readers rated this the No. 1 resort in the Caribbean. Exclusive deal offers daily breakfast and 50% savings.

Travel through August 31
Source: CheapCaribbean.com

Spend five nights at the Presidential Suites in Punta Cana

August-September departures; additional available
Source: CheapCaribbean.com

Spend five nights at an oceanfront hotel in Jamaica

May-July departures; additional available
Source: Apple Vacations

Spend three nights at a 4-star beachfront resort in Punta Cana with this all-inclusive package

Select departures, May-June
Source: CheapCaribbean.com

Just off the coast of Puerto Rico, this island getaway is the ultimate unspoiled paradise

August-November departures; additional available
Source: Liberty Travel

Set sail from Miami on this three-night Bahamas cruise aboard Norwegian Sky

Depart: Nov. 13
Source: Liberty Travel

Depart from San Juan with this cruise that includes stops in St. Thomas, St. Croix, St. John and Castries

Depart: Dec. 12
Source: Delta Vacations

Includes roundtrip air, five nights at the Sunshine Suites Resort, all transfers and taxes

Priced for July; more dates available
Source: Liberty Travel

Steal away to the Bahamas with this four-night package that includes air, hotel transfers and a complimentary shallow water dolphin experience

Aug. 10-14
Source: Liberty Travel

This four-night St. Lucia beachfront vacation includes round-trip air, hotel transfers and a $50 resort credit

Aug. 17-21
Source: Brickell Bay Beach Club & Spa

The hotel is located in Palm Beach, which is the entertainment and shopping area for beachgoers.

Through September
Source: Grand Cayman Beach Suites

Bring the whole family along to an oceanview suite at this 4-star resort.

Aug. 15 - Oct. 31; +$88 April 25 - Aug. 14
Source: El San Juan Resort & Casino, A Hilton Hotel

Frommer's says it's got one of Puerto Rico's best hotel beaches due to its South Miami vibe.

Sundays-Thursdays, June-August; +$40 weekends
Source: Brac Reef Beach Resort

This all-inclusive vacation is for divers who want a less touristy base in the Cayman Islands.

Through Dec. 20
Source: W Retreat & Spa Vieques

Vieques Island was named among Conde Nast Traveler's Top 10 Islands in the Caribbean & Atlantic.

Aug. 2 - Oct. 31; +$11 June 1 - July 7
Cheap Roundtrip Fares to Grand Cayman from:
(Per person, including taxes and fees. Click a price to verify availability now.)
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Travelzoo Tips

Anna Heinemann — Travel, Entertainment and Local Deal Expert
Anna Heinemann
Deal Expert, Chicago
So get your travel dates set and start planning early for the best opportunities. More