3 Private Homes | 14 Bedrooms | 8.5 Bathrooms | Sleeps 27 | 2 Heated Pools

Welcome to The Fleet, an extraordinary private Nantucket estate featuring three distinctive homes, thoughtfully brought together to create the ultimate island getaway.

Located on beautifully landscaped grounds between downtown Nantucket and Cisco, The Fleet offers a rare opportunity to enjoy an entire private compound exclusively for your group. With 14 bedrooms, 8.5 bathrooms, two heated swimming pools, multiple outdoor entertaining spaces, and accommodations for up to 27 guests, this one-of-a-kind property is designed for unforgettable gatherings.

Whether you're planning a multigenerational family vacation, milestone celebration, reunion, or group retreat, The Fleet offers the perfect balance of togetherness, luxury, and privacy.

THREE HOMES. ONE PRIVATE ESTATE.

Unlike a traditional vacation rental, The Fleet includes three separate homes, each with its own character, accommodations, and living spaces.

Your reservation includes exclusive access to all three properties:

THE STOWAWAYS | 7 BEDROOMS | 4 FULL BATHROOMS, 2 HALF BATHROOMS | SLEEPS 12

The grand main house of the estate, The Stowaways offers generous accommodations and thoughtfully designed spaces for relaxing, entertaining, and spending time together.

Inside, guests can enjoy multiple living areas, a full kitchen, an additional kitchenette, and dedicated spaces for both entertainment and relaxation.

Highlights include:
- Seven bedrooms accommodating up to 12 guests
- Five bathrooms
- Full kitchen and additional kitchenette
- Multiple living and gathering spaces
- Private office for remote work
- Home gym
- Dedicated movie theater
- Game room and sports bar barn
- Heated swimming pool

THE CREW | 6 BEDROOMS | 2 BATHROOMS | SLEEPS 13

The Crew is a welcoming garden guest house designed to bring everyone together while offering the comfort of a separate home.

With six bedrooms, a full kitchen, comfortable living spaces, and access to outdoor entertaining areas, The Crew is ideal for families and groups looking for additional room to spread out.

Highlights include:
- Six bedrooms accommodating up to 13 guests
- Two full bathrooms
- Full kitchen
- Comfortable living room
- Outdoor kitchen and bar
- Outdoor fire pit
- Access to the Hummock-side pool and entertaining spaces

CAPTAIN'S QUARTERS | 1 BEDROOM | 1.5 BATHROOMS | SLEEPS 2

Captain's Quarters offers a more intimate and private retreat within the estate.

Filled with personal character and a collection of nautical treasures, this charming one-bedroom home is especially well-suited for a couple, grandparents, or guests who appreciate having their own space while remaining close to the rest of the group.

Highlights include:
- One private bedroom accommodating two guests
- One full bathroom and one half bathroom
- Full kitchen
- Private living space
- Access to the adjacent heated pool and cabana

OUTDOOR LIVING & ENTERTAINING:

One of The Fleet's most exceptional features is its collection of outdoor spaces, designed for making the most of Nantucket's beautiful summer days and evenings.

Across the estate, guests can enjoy:

- Two heated swimming pools
- Swim-up spa
- Pool volleyball
- Three outdoor kitchens
- Cabana bar
- Two outdoor fire pits
- Beautifully landscaped gardens
- Croquet lawn
- Outdoor spaces for gathering and relaxing
- Bikes for exploring the nearby Cisco bike path

Spend your mornings enjoying coffee in the gardens, afternoons lounging poolside, and evenings gathering around the fire with family and friends.

With multiple entertaining areas throughout the property, there's plenty of room to come together while still finding a quiet corner to unwind.

THE PERFECT SETTING FOR GROUP GETAWAYS:

The Fleet was designed for the moments that bring people together.

Whether you're celebrating a special occasion, reconnecting with extended family, or enjoying a Nantucket summer with your closest friends, the estate provides the flexibility of three individual homes with the convenience of staying together.

Gather for meals, enjoy poolside afternoons, host movie nights, or simply relax and enjoy the island at your own pace.

For those planning something extra special, private chef experiences, event planning assistance, and concierge services may be arranged upon request.

EXPLORE NANTUCKET:

Ideally situated between Nantucket's historic downtown and the popular Cisco area, The Fleet offers convenient access to some of the island's most beloved destinations.

Explore charming cobblestone streets, local boutiques, beautiful beaches, and Nantucket's celebrated dining scene. Take advantage of the nearby bike path to discover the island on two wheels, or spend the day enjoying everything your private estate has to offer.

YOUR STAY INCLUDES:

Booking The Fleet means reserving the entire three-home compound exclusively for your group.

You'll have access to all three homes, their included amenities, and the private grounds connecting them. No other vacation rental guests will be staying on the property during your reservation.

Linens and towels are provided, with additional concierge assistance available upon request.

PETS & SPECIAL EVENTS:

Planning to bring a furry friend or host a special event during your stay? We'd love to hear from you!

Please contact us prior to booking to discuss your plans and receive approval. Pets and events are considered on a case-by-case basis and may be subject to additional fees, restrictions, or arrangements.

EXPERIENCE NANTUCKET TOGETHER:

Three distinctive homes. Two beautiful pools. Endless opportunities to make memories.

From intimate mornings in your own private space to unforgettable evenings gathered together, The Fleet offers a truly unique way to experience Nantucket.

One reservation. Three private homes. An entire Nantucket estate, exclusively yours.