Sun-Drenched Caribbean with Pleasant Holidays

Looking for more than just a hotel room? Enjoy modern and spacious alternative options ranging from resort condominiums, villas, suites and more.

From the Gulf Stream waters of the north to the wondrous shores, vibrant wildlife and lush rainforests of the southern Caribbean, these picturesque islands adorn the sea like a necklace of gems awaiting discovery. Your greatest challenge is deciding which beautiful pearl to choose. 


A vacation rental at a villa, cottage or residence gives you the freedom and flexibility to discover your island paradise while enjoying the comforts of home. From secluded luxury hideaways to hassle-free family fun, there’s a vacation here for every visitor - and just like the islands of the Caribbean, no two are the same.


Our Recommended Getaways

be sure to ask your advisor for other personalized options for travel in the Caribbean.

Sugar Beach, A Viceroy ResortMay 03, 2021 - May 08, 2021 (5 nights)

Soufriere, Saint Lucia | Luxury Villa Room
USD $2,258 Per Person Incl taxes
Includes savings up to 30% off daily rate and complimentary full American breakfast for 2 adults per bedroom. Must be booked by 10/31/20.

Nestled in 192 acres of magnificent rainforest by the sea, this 96-room hotel is located between the Piton Mountains in one of the most awe-inspiring locations in the world. Each of the first class private villa luxury accommodations gives guests the feeling of complete serenity and breathtaking views. All rooms feature a private plunge pool for refreshment any time, day or night. The resort offers water sports as well as a fabulous spa, two fine restaurants and bars. Pricing available for longer stays or other travel dates.

CuisinArt Golf Resort & SpaMay 03, 2021 - May 08, 2021 (5 nights)

Anguilla | Beachfront Junior Suite
USD $2,820 Per Person Incl taxes
Includes daily breakfast.

The award-winning CuisinArt Golf Resort & Spa is regarded as one of the top luxury hotels in Anguilla and the Caribbean. The resort offers a unique blend of relaxed elegance and five-star service, with instantly recognizable Mediterranean architecture, diverse culinary programs, top tier golf and spa programming. Its collection of 91 suites and 7 villas offer spacious accommodations overlooking lush grounds and the white sand beaches and turquoise waters of Rendezvous Bay, one of the best beaches in the world. Pricing available for longer stays or other travel dates.

West Bay ClubMay 03, 2021 - May 08, 2021 (5 nights)

Providenciales, Turks and Caicos | One Bedroom Oceanfront Suite
USD $1,882 Per Person Incl taxes
Includes daily breakfast.

West Bay Club is one of Turks & Caicos' finest luxury boutique ocean front resorts. It features extravagantly appointed ocean front suites and a boutique range of amenities - all placed directly on the white sands of Turks and Caicos' most famous attraction, Grace Bay Beach. Pricing available for longer stays or other travel dates.

Round Hill Hotel and VillasMay 03, 2021 - May 08, 2021 (5 nights)

Montego Bay, Jamaica | Deluxe Villa Suite
USD $1,811 Per Person Incl taxes
Includes non-motorized water sports

Open and inviting, richly appointed and steeped in tradition, Round Hill Hotel and Villas takes you far beyond the ordinary vacation getaway, from the 36 oceanfront guest rooms to one of the 26 luxury villas, you can book as your private home with dedicated staff, or a spacious villa suite. This elegant resort offers discreet impeccable service, attention to detail, and warm Jamaican hospitality. Experience our world class-spa, with Elemis treatments and enjoy sumptuous meal prepared by our award winning chef. Pricing available for longer stays or other travel dates.

Casa de Campo Resort & VillasMay 03, 2021 - May 08, 2021 (5 nights)

La Romana, Dominican Republic | Elite Suite
USD $3,847 Per Person Incl taxes
Includes non-motorized water sports

Casa de Campo, a 7,000-acre luxury resort in La Romana, offers a distinctive experience for discerning travelers. Accommodation options include elegantly appointed rooms, suites and exquisite villa homes with expansive living areas, private pools and a dedicated villa staff. The resort features a variety of dining options including The Beach Club by Le Cirque and La Cana by Il Circo; unparalleled sports experiences such as 63-holes of Pete Dye-designed golf, a shooting center, polo and tennis; fishing/sailing from a world-class marina and Casa de Campo Yacht Club; exclusive beaches at the resort and at Catalina Island; a full-service spa; Altos de Chavon artists' village, with a wide array of museums, art galleries, boutique shopping; a Wedding chapel; and a 5,000-seat outdoor amphitheater. Casa de Campo is a member of Great Golf Resorts of the World and Leading Hotels of the World. Pricing available for longer stays or other travel dates.

Whether you are interested in a luxury getaway or a budget vacation, looking for romance or adventure, or wanting to travel far or stay close to home. Five-star resort and all-inclusive getaways, adult-only-escapes or family-friendly vacations. Pleasant Holidays has everything you need at the value you want to the places you want to explore!  

Terms & Conditions

1Rate is per person, land only, based on double occupancy for check-in on 05/03/2021, in room categories shown. Unless otherwise indicated: rates quoted are accurate at time of publication, & are per person, based on double occupancy. Airfare, taxes, surcharges, gratuities, transfers & excursions are additional. Advertised rates do not include any applicable daily resort or facility fees payable directly to the hotel at check-out; such fee amounts will be advised at the time of booking. Rates, terms, conditions, availability, itinerary, government taxes, surcharges, deposit, payment, cancellation terms/conditions & policies subject to change without notice at any time. Cruise rates capacity controlled. Other restrictions may apply, including, but not limited to baggage limitations & fees, standby policies & fees, non-refundable tickets & change fees with pre-flight notification deadlines, & blackout dates. Fees & policies vary among airlines. Contact airline directly for any details or questions. Not responsible for errors or omissions. Pleasant Holidays acts only as an agent for cruise & tour providers listed. CST# 1007939-10. Copyright©2020 Pleasant Holidays, LLC. All Rights Reserved.


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