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

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

*** LUXURY INCLUDED® FOR COUPLES *** Enjoy all-suite accommodations and Butler Elite service. Every suite features Tranquility Soaking Tub™ for two. Hotel description, photos and more

*** LUXURY INCLUDED^® FOR COUPLES ***
This resort on the south coast of Barbados offers beautiful accommodations and impeccable service. Hotel description, photos and more

Featuring an idyllic oceanfront setting, this upscale adults-only all-inclusive resort is the perfect getaway for couples and groups. Hotel description, photos and more

Waves Hotel & Spa by Elegant Hotels is an all-inclusive boutique hotel located on a stretch of pristine beach, and focuses on wellness and relaxation. 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 lovingly restored resort, recognized as the Caribbean's oldest continuously operating hotel, is perched on a cliff above Crane beach. 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

Recently redesigned and reimagined, this luxury adults-only resort attracts guests who are wanting to be pampered with a home-away-from-home feel. 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

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

This upscale hotel is situated on a white-sand beach and features upscale guest rooms and suites overlooking palm-fringed Isla Verde Beach and the sparkling Atlantic. 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

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

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

*** LUXURY INCLUDED^® FOR COUPLES ***
Set between hillside gardens and the glistening Caribbean. Enjoy sumptuous accommodations and championship golf. 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

*** LUXURY INCLUDED^® FOR COUPLES ***
Hugging the most picturesque span of Negril's stunning seven-mile beach, this resort provides ultimate luxury. Hotel description, photos and more

This secluded hotel is set amidst a 500-acre nature preserve along two pristine beaches. 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

*** LUXURY INCLUDED^® FOR COUPLES ***
Nestled on the northern shores of Jamaica this resort is renowned for its exclusive refinements. 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

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

*** LUXURY INCLUDED^® FOR COUPLES ***
This beachfront resort on Jamaica's largest private beach offers beautiful accommodations activities. 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