Personalized Paradise: Uncover the Caribbean Island That Matches Your Budget

By Noël Russell, Founding Team Member at Whimstay


Whimstay is emerging as a fresh and exciting leader in the vacation rental market, focused on offering the best deals on last-minute bookings. The company achieves this by partnering with professional property managers to offer exclusive discounts on properties that might otherwise remain unrented. Featuring a diverse portfolio of vacation rental homes, condos, cabins, villas, and resorts across the U.S., Canada, Mexico, and the Caribbean, Whimstay is the go-to choice for savvy travelers.


The Adventure Seeker: Exploration Awaits in Grenada

Average Savings on Whimstay: 20%

Arial view of GrenadaGrenada, known as the ‘Spice Isle,’ is an exhilarating destination for the Adventure Seeker. Dive into the world’s first underwater sculpture park at Molinere Bay, offering a unique blend of art and marine life. Trek through the verdant Grand Etang National Park to discover hidden waterfalls and exotic wildlife. Challenge yourself with a hike to the summit of Mount St. Catherine for breathtaking views. After a day of exploration, enjoy local flavors at BB’s Crabback, where the sea-to-table cuisine will revitalize you.

The Leisure Lover: St. Maarten’s Tropical Oasis  

Average Savings on Whimstay: 20%

St. Maarten, with its dual Dutch and French influences, is a leisure lover’s dream.

St.-Maarten welcome sign at the beach

Spend a day lounging on the soft sands of Maho Beach, famous for its close-up airplane sightings. Sail around the island on a catamaran, stopping at idyllic spots like Pinel Island for a tranquil snorkeling experience. Enjoy the European flair of Grand Case, where beachfront restaurants like Le Shambala offer sumptuous French-Caribbean dishes. The island’s blend of cultures creates a laid-back yet sophisticated ambiance, perfect for leisurely exploration.

The Culture Enthusiast: Historical Vibrance in Puerto Rico – Average Savings on Whimstay: 24%

Puerto RicoPuerto Rico’s rich history and vibrant culture make it an ideal spot for the Culture Enthusiast. Wander through the colorful streets of Old San Juan, where history lives in every cobblestone. Experience the lively salsa music and sample traditional dishes like mofongo at local restaurants. Learn about the island’s heritage at the El Yunque National Forest, the only tropical rainforest in the U.S. National Forest System. Discover the unique blend of Spanish, African, and Taino influences that shape the island’s cultural tapestry, making every visit a journey through time and tradition.

The Partygoer: Vibrant Nights in Aruba  

Average Savings on Whimstay: 20%

Aruba beachAruba is a paradise for Partygoers, pulsating with beach bars and nightclubs. Enjoy the lively scene in Oranjestad, chill on the beautiful Palm Beach, and take in a stunning sunset on a cocktail cruise. Aruba’s vibrant atmosphere peaks during carnival season with colorful parades and Calypso music, ensuring endless entertainment. Not to be missed is the Electric Festival, bringing electronic dance music to the Caribbean sands.

The Nature Buff: Eco-Adventures in St. John

Average Savings on Whimstay: 19%

St. JohnSt. John, with its sprawling national park, is an oasis for Nature Buffs. Explore scenic hiking trails, snorkel in Trunk Bay’s clear waters, and delve into the Virgin Islands National Park’s diverse ecosystems. Visit Coral Reef Underwater Park for vibrant marine encounters, enhancing the ecological experience. The island’s untouched beauty also makes it a prime spot for stargazing, adding a celestial touch to nature exploration.

The Romantic: Love in St. Lucia

Average Savings on Whimstay: 17%

St. LucaSt. Lucia is a haven for Romantic Couples with its stunning Pitons and luxurious resorts. Relish intimate beach dinners, couples’ massages overlooking breathtaking vistas, and romantic sunset sailing trips. Visit the tranquil Diamond Falls Botanical Gardens for leisurely strolls among colorful flora. The island’s natural hot springs offer a perfect setting for a romantic, rejuvenating soak together.

The Family Vacationer: Fun in the Bahamas

Average Savings on Whimstay: 22%

Arial view in the BahamasThe Bahamas is a paradise for Family Vacationers, featuring dolphin encounters and pirate-themed adventures. Its crystal-clear waters and family-oriented resorts promise fun-filled holidays. Explore the Exuma Cays, where interacting with swimming pigs makes for unforgettable moments. The Pirates Museum in Nassau offers an educational yet fun excursion for the whole family.

The Gastronomy Aficionado: Culinary Delights in Barbados

Average Savings on Whimstay: 22%

Barbados beach with beach chairs and yellow umbrellas Barbados is a culinary dream for Gastronomy Aficionados. Savor the island’s famous rum, enjoy the vibrant Oistins Fish Fry, and dine at innovative fusion restaurants. Embark on local rum distillery tours to understand the crafting process and taste various rums. Culinary festivals like the Food and Rum Festival highlight Barbados’s rich gastronomic culture, offering tastings and cooking demonstrations.

Featuring a diverse portfolio of vacation rental homes, condos, cabins, villas, and resorts across the U.S., Canada, Mexico, and the Caribbean, Whimstay is the go-to choice for savvy travelers. Learn more at or by downloading the Whimstay app.


GDPR Cookie Consent with Real Cookie Banner