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Island Style Vacations

“No one Deservers A Vacation… More than You!”

Our Story

Island Style Vacations was founded on a simple but powerful belief: that travel should feel personal, purposeful, and filled with joy. At the heart of this mission is Kim Rollins-John, a Barbados native whose warm island spirit and sharp attention to detail have made her a trusted name in Caribbean and group travel planning.

Kim’s journey from accountant to travel advisor was born from a desire to help people press pause on their busy lives — to not just go somewhere, but to truly experience it. With over 15 years of industry experience, she brings a unique blend of hospitality, precision, and passion to every itinerary she designs.

From destination weddings and family adventures to romantic getaways and girls’ trips, Kim’s approach is rooted in personalization. She doesn’t just book vacations — she crafts experiences, drawing from her deep knowledge of destinations like Barbados, Jamaica, St. Lucia, and Mexico. As a Sandals and Beaches Resort specialist, she visits properties annually to offer firsthand insights on everything from the best room types to hidden gem excursions.

What sets Island Style Vacations apart is the level of care Kim puts into every step of the planning process. She offers free consultations with clients before booking their trips to better understand their vision. Her clients become like family — and their travel stories are a testament to the connection she builds through her work.

As the company has grown, so has its reach — but the heart remains the same: a commitment to thoughtful, joyful travel that brings people closer to each other and the world.

This is our story — and we’d be honored to help shape yours. Let’s start planning your next incredible getaway.

Guidance from a travel agent

Guidance

Expert insight & travel knowledge

Valuable deals and savings

Value

Irresistible rates, offers & benefits

Book with peace of mind

Peace of Mind

Reassurance to book with confidence

Diligent and attentive service

Service

Beside you every step of the way

A fun family vacation

Group Travel Is our Specialty!

We specialize in destination weddings, honeymoons, group travel, and dive group adventures, helping our clients explore the world with confidence and ease. From intimate ceremonies on tropical beaches to large-scale group itineraries packed with activities and excursions, we tailor every detail to your vision and needs.

Our group travel services are ideal for families, friends, corporate retreats, religious groups, school trips, and more. We handle everything — flights, accommodations, ground transportation, excursions, and even personalized group perks — so all you have to do is show up and enjoy. For dive groups, we work closely with certified dive resorts and liveaboard operators to coordinate unforgettable underwater experiences in some of the world’s most sought-after dive destinations.
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Dive Groups

Explore the world beneath the surface with custom group dive trips. We handle flights, resorts, and liveaboards so you can focus on the adventure.
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Destination Weddings

Say “I do” in paradise with our expertly coordinated wedding travel services. From venue selection to guest accommodations, we handle it all so you can enjoy your big day stress-free.
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Business Trips and conferences

Plan purposeful, rewarding travel for your team with ease. From executive retreats to client incentive trips, we manage the logistics so your focus stays on what matters.
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What Our Clients Are Saying
Real stories from real travelers!

🗺️
Chasten Xavia
★★★★★
“Ms. Kim did an excellent job with our group Kenya trip. She had all the details together and made sure we all had a great time and were safe. Accommodations were great, and I really enjoyed working with her. 10/10 would recommend.”
Kenya Group Trip
🌅
Debra Villar
★★★★★
“What an awesome experience my family and I had traveling to Portugal! Kim was the best travel agent—she arranged everything and hand-selected tours that wowed us at every moment. Thank you for choreographing a vacation we’ll always remember!”
Portugal Family Vacation
🦒
Kimani Burney
★★★★★
“Kim curated the most amazing trip to Nairobi, Kenya—packed days of safari, incredible lodging, and unique experiences like feeding giraffes and relaxing at the beach. This was the trip of a lifetime!”
Nairobi Safari Adventure
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Frequently Asked Questions

General Group Travel

For individual travel, such as honeymoons, there is typically no additional cost when you book your package through Island Style Vacations—we’re compensated by our travel partners. However, for group travel, including destination weddings, family reunions, and business incentive trips, we do charge a planning and coordination fee. Group travel requires extensive behind-the-scenes work: securing room blocks, managing contracts, customizing itineraries, setting up payment plans, coordinating with multiple vendors, and ensuring that all travelers’ needs are met smoothly and professionally. This fee reflects the high level of service, organization, and expertise required to manage complex group logistics—ultimately saving you time, stress, and costly mistakes. Our goal is to make your group experience seamless, memorable, and absolutely worth every moment.
A group typically starts at 10 rooms, 20 travelers, depending on the destination and travel supplier. Island Style Vacations can assist with group rates, room blocks, and added perks once the group meets the minimum threshold.
Yes! We offer flexible payment options including individual payment plans, so each traveler can pay at their own pace while keeping the group reservation intact.
Group bookings often include discounted rates, room upgrades, private events, and special amenities. You also gain the advantage of coordinated travel logistics handled by our expert team.

Destination Weddings

We recommend booking 12–18 months in advance, especially for popular Caribbean locations or peak seasons. This gives you the best availability and time to coordinate travel for guests.
Absolutely. We’ll guide you through each destination’s legal requirements, including documentation, timelines, and translation needs. Some couples opt for a symbolic ceremony abroad after a legal one at home.
Most packages include a ceremony setup, officiant, bouquet/boutonniere, cake, and a small reception. We work with resorts that also offer upgraded packages with décor, photography, and private events.

Family Travel

We recommend destinations like Jamaica, the Dominican Republic, and Riviera Maya for their mix of family-friendly resorts, activities for all ages, and easy access from U.S. cities.
Yes! Many family resorts offer adults-only areas, kids’ clubs, and teen lounges, so everyone enjoys age-appropriate activities while still coming together for family time.
We personalize each family member’s experience—coordinating accessible rooms, dietary preferences, flight schedules, and activities—to ensure a smooth and enjoyable trip for everyone.

Business & Incentive Travel

We manage everything from destination selection and resort negotiations to group coordination, custom excursions, and branded experiences that align with your business goals.
Yes! We partner with resorts that have top-notch conference facilities and event planners, and we can coordinate off-site excursions, themed dinners, and team-building activities.
We recommend consulting with a tax advisor, and we’re happy to provide detailed documentation to support your records.

Planning & Booking Process

Yes, and we highly recommend it. Travel insurance can protect against unexpected cancellations, medical emergencies, and travel delays, giving everyone peace of mind.
Definitely! We can arrange private transfers for individuals or groups, as well as curated excursions that match your interests—whether it's adventure, culture, or relaxation.
We offer personalized service, industry connections, and expert support before, during, and after your trip. From negotiating perks to solving unexpected issues, we’re your advocate every step of the way—something a booking engine just can’t do.
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