Luxury Island Travel Planner (Hybrid - Remote/On-site)

Little Gem Resorts

Cochituate (MA)

Hybrid

USD 50,000 - 70,000

Full time

14 days+

A complete application in a minute

Tailored resume and cover letter, ready to send.

Get past ATS filters

Job summary

Winnetu Oceanside Resort, The Nantucket Hotel, and Lovango Resort & Beach Club in a boutique hospitality group are seeking a full-time Reservations Specialist for a hybrid role based in Wayland, MA. You will be the friendly voice guiding guests through island getaways.

The position emphasizes travel planning, luxurious accommodations, and collaboration with a close-knit team to deliver unforgettable experiences, with training and a flexible schedule.

Qualifications

  • Loves talking on the phone and connecting with guests.
  • Strong focus on guest experience with multi-tasking ability.
  • Willingness to contribute to a collaborative environment.
  • Experience with Martha's Vineyard, Nantucket or USVI is a plus but not required.

Responsibilities

  • Engage guests in informative phone conversations about accommodations and island experiences.
  • Provide expert travel planning and transportation options for island getaways.
  • Collaborate with the team to continuously improve guest satisfaction and luxury service.

Skills

Phone etiquette/communication
Cheery personality
Computer proficiency
Professional and reliable
Team player
Self-starter
Idea generator

Job description

Winnetu Oceanside Resort, The Nantucket Hotel, and Lovango Resort & Beach Club in a boutique hospitality group are seeking a full-time Reservations Specialist for a hybrid role based in Wayland, MA. You will be the friendly voice guiding guests through island getaways.

The position emphasizes travel planning, luxurious accommodations, and collaboration with a close-knit team to deliver unforgettable experiences, with training and a flexible schedule.

Get your free, confidential resume review.

or drag and drop your file here.

Similar jobs

Similar jobs worth comparing

Hybrid Reservations Specialist – Luxury Island Getaways
Hybrid Reservations Specialist – Luxury Island Getaways

Stanmar Inc. • Wayland (MA)

Hybrid
USD 42,000 - 54,000
Reservations Specialist (2026)
Reservations Specialist (2026)

Stanmar Inc. • Wayland (MA)

On-site
USD 42,000 - 54,000
Remote All-Inclusive Resort Planner - Entry Level
Remote All-Inclusive Resort Planner - Entry Level

Wanderwell Collective • Texas

Remote
USD 42,000 - 65,000
Fully remote work flexibility
Ongoing training and professional dev.
Access to industry tools, resources, &
+4
Rooms Division Lead - Nantucket Luxury Resort
Rooms Division Lead - Nantucket Luxury Resort

Nantucket Island Management Llc. • Wauwinet (MA)

On-site
USD 85,000 - 120,000
Health, vision and dental
Paid vacation
401(K) plan
+1
Luxury Front Office Manager – Nantucket Resort Leader
Luxury Front Office Manager – Nantucket Resort Leader

White Elephant Resorts • Mikas Pond (MA)

On-site
USD 85,000 - 115,000
Health, Vision & Dental
Paid Vacation
401(K) Plan
+1
Remote Luxury Travel Planner | Bespoke Itineraries
Remote Luxury Travel Planner | Bespoke Itineraries

TWN • San Diego (CA)

Remote
USD 70,000 - 110,000
Remote Travel Planner: Hotels, Cruises & Resorts
Remote Travel Planner: Hotels, Cruises & Resorts

Wanderwell Collective • Vermont

Remote
USD 17,000 - 28,000
Flexible schedule
Training provided
Travel perks
+1
Rooms Division Manager - Wauwinet
Rooms Division Manager - Wauwinet

White Elephant Resorts • Nantucket (MA)

On-site
USD 110,000 - 170,000
Competitive salary and bonus plan
Health, vision and dental
Paid vacation
+3
Lux Reservations Specialist – Seasonal Luxury Hospitality
Lux Reservations Specialist – Seasonal Luxury Hospitality

Gurney's Montauk • Montauk (NY)

On-site
USD 22,503 - 32,049
Health insurance
Dental insurance
Vision insurance
+2
Island Resort Operations Leader — Luxury UHNW Experience
Island Resort Operations Leader — Luxury UHNW Experience

Little Palm Island, a Noble House Resort • Florida

On-site
USD 110,000 - 190,000
Six-figure compensation
Health benefits
Travel benefits
+2