Caribbean Wedding Destinations & All-Inclusive Wedding Packages | Pleasant Holidays

With an unparalleled setting on Anse Marcel Bay, this luxurious adults-only all-suite resort features a hip, vibrant atmosphere, stunning views and the largest infinity pool in the Western Caribbean. Hotel description, photos and more

This luxurious haven of mindfulness, inspiration, and nourishment is ideally situated on breathtaking Dawn Beach and features spacious rooms with resort views. Hotel description, photos and more

The historic Buccaneer, family-owned and operated since it opened in 1947, is St. Croix's premier resort. Its 131 rooms are set on 340 tropical beachfront acres near Christiansted, offering golf, tennis, spa, watersports and dining options. Hotel description, photos and more

Perched high above the Caribbean, The Westin Beach Resort & Spa at Frenchman's Reef features rooms and suites with private balconies and commanding views. It is conveniently located near the capital of the U.S. Virgin Islands, Charlotte Amalie. Hotel description, photos and more

Morningstar Buoy Haus Beach Resort at Frenchman's Reef, Autograph Collection is the epitome of an island escape. It features 94 rooms, including 2 premium suites, teeming with amenities and an exclusive-use tide pool. Hotel description, photos and more

This beautiful retreat is nestled amid lush tropical gardens and gently swaying palm trees. Hotel description, photos and more

This newly redesigned beachfront resort ushers in an era of refined style and impeccable service. Hotel description, photos and more

Whisk away to a tropical beachfront paradise in charming St. Thomas. Hotel description, photos and more

Located on a quiet stretch of beach in St. Croix, this resort combines privacy and relaxation with modern style and amenities. Hotel description, photos and more

Steeped in tradition and Bermuda history, Cambridge Beaches has been a destination for oceanfront escapes since 1923. With authentic cottage accommodations and a wealth of amenities, there’s truly no better way to experience the luxuries of Bermuda. Hotel description, photos and more

This beautiful resort overlooking the sparkling waters of the Atlantic Ocean, features beautifully appointed guest rooms. Hotel description, photos and more

This exclusive oceanfront resort delivers a grand level of relaxation and luxury with guest rooms overlooking the ocean, pool or gardens, suites with full kitchens, and an exclusive penthouse with space for 22 guests. Hotel description, photos and more

This resort on Seven Mile Beach is thoughtfully designed to be an effortless escape for couples, families and groups. Hotel description, photos and more

This well-appointed resort fronts Seven Mile Beach and affords breathtaking views.
Festive Season Celebrations: Delight in tradition and indulge in the magic of Christmas at the Westin Wonderland. Hotel description, photos and more

Located on world-famous Seven Mile Beach, this oceanfront hotel invites you to revel in relaxation. After a recent $15-million renovation, the 299-guestroom resort allows guests to unwind in style. Hotel description, photos and more

The Holiday Inn Resort Grand Cayman is where tranquility, fun and beauty are yours to enjoy. Surrounded by palm trees, the hotel is set in one of the most stunning destinations in the world. Hotel description, photos and more

*** LUXURY INCLUDED^® FOR COUPLES ***
This romantic beachfront resort on the sands of Dickenson Bay offers luxurious accommodations. Hotel description, photos and more

A luxurious escape awaits at this resort on a private beach offering exceptional vacation experience for the entire faily. Hotel description, photos and more

Set along a pristine beach, this intimate all-inclusive Caribbean hideaway will delight guests with its refined, unpretentious and relaxing atmosphere. Hotel description, photos and more

This gorgeous beachfront resort in Antigua features stunning bay views and a wide variety of outdoor activities. Hotel description, photos and more

Perfectly located on a breathtaking horseshoe bay on the southwestern shore of Antigua, Carlisle Bay is a modern Caribbean classic instilled with genuine West Indian conviviality. Hotel description, photos and more

Spanning 16 acres of lush tropical gardens, this eco-chic luxury hotel provides all the comforts of a 5-star resort without compromising the natural habitat that thrives around it. Hotel description, photos and more

This resort on Soldier's Bay features luxurious guest rooms, suites, and villas with unprecedented access to three secluded beaches and a variety of dining options and bars. Hotel description, photos and more

This hotel comprises authentic Antiguan Cottages nestled into the bluff overlooking the turquoise waters of the Caribbean. Hotel description, photos and more

Dig your toes in the sand and feel the warm Caribbean sunshine caress against your skin at the adults-only Royalton CHIC Antigua resort. Hotel description, photos and more