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

Situated in the heart of the lively Condado district, this hotel is close to the area's best restaurants, attractions and nightlife. Hotel description, photos and more

*** ULTIMATE ALL-INCLUSIVE FOR FAMILIES & EVERYONE *** This resort on Negril's Seven Mile Beach offers a fun-filled experience for the entire family. Hotel description, photos and more

*** ULTIMATE ALL-INCLUSIVE FOR FAMILIES & EVERYONE *** Set where the mountains meet the sea, this newly renovated resort is the ultimate family vacation spot. 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

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

Resting on a beautiful peninsula amid 17 acres of tropical landscaping, sets the scene for an idyllic vacation experience. The resort is near historic Old San Juan and the vibrant Condado district. 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

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

The fun is always included at this all-inclusive, adults-only resort beloved by active guests. Set on 19 acres, on world-famous Seven Mile Beach, it is spread out yet intimate for seclusion. 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

Perfectly located between downtown San Juan and the award-winning Isla Verde Beach this hotel offers authentic Puerto Rican hospitality and spacious guest rooms with upscale amenities. Hotel description, photos and more

A multi-million dollar renovation has dramatically changed this hotel's guest rooms and raised the bar for luxury hospitality in Barbados. 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

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

This beautiful resort overlooking the sparkling waters of the Atlantic Ocean, features beautifully appointed guest rooms. 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 deluxe hotel is set on the lush tropical peninsula of Needham's Point and surrounded by two powdery soft white-sand beaches and pristine blue waters. Hotel description, photos and more

This oceanfront haven offers plush accommodations, a waterpark, superb dining, kid/teen clubs, and expansive event facilities. 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

This Spanish-colonial-style hotel affords easy access to historic landmarks such as El Morro and San Cristobal Fortress. Hotel description, photos and more

A sheltered swimming beach and first-class service make this the perfect Montego Bay escape. Hotel description, photos and more

Tranquil rainforest surroundings, rustic ambiance and health and wellness programs create the perfect backdrop for an unforgettable vacation experience at Jungle Bay 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

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 gracious and thoughtfully planned beachfront hotel features retro urban design and cosmopolitan flair. Hotel description, photos and more