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LolliPop Nantucket: A Thoughtfully Designed Island Home for Families and Friends

Family-friendly holiday home in Nantucket with an outdoor pool

Photo gallery for LolliPop Nantucket: A Thoughtfully Designed Island Home for Families and Friends

Pool
Private kitchen
Private kitchen
Miscellaneous
Miscellaneous

Reviews

10 out of 10
Exceptional
4 bedrooms3 bathroomsSleeps 9

Popular amenities

  • Dryer
  • Parking available
  • Washer
  • Pool
  • Kitchen
  • Barbecue grill

Explore the area

View map
Nantucket, MA
  • Place, Nantucket Historical Association
    ‪4 min drive‬
  • Place, Nantucket Atheneum
    ‪4 min drive‬
  • Place, Nantucket Ferry Terminal
    ‪4 min drive‬
  • Airport, Nantucket, MA (ACK-Nantucket Memorial)
    ‪5 min drive‬

Rooms & beds

4 bedrooms (sleeps 9)

Bedroom 1

1 King Bed

Bedroom 2

1 King Bed

Bedroom 3

1 King Bed

Bedroom 4

2 Single Beds

Office 1

1 Single Bed

3 bathrooms

Bathroom 1

Soap · Towels provided · Toilet · Shower only · Shampoo

Bathroom 2

Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer

Bathroom 3

Soap · Towels provided · Bathtub or shower · Bathtub · Toilet · Shampoo · Hair dryer

Spaces

Kitchen
Separate dining area
Outdoor play area
Dining area

About this property

LolliPop Nantucket: A Thoughtfully Designed Island Home for Families and Friends

Stylish Nantucket Escape with Pool, Cabana & Private Backyard

Welcome to your private Nantucket oasis—beautifully appointed, spacious, and thoughtfully designed for effortless island living. This 4-bedroom, 3-bathroom home offers refined style, resort-like amenities, and an unbeatable location close to town and the beaches.

Sleeping Arrangements
This home comfortably sleeps 8–9 guests across four spacious bedrooms plus a flexible cabana space:

- Bedroom 1: King bed
- Bedroom 2: King bed
- Bedroom 3: King bed
- Bedroom 4: Two twin beds (can be converted to a king upon request)
- Pool Cabana: Private, air-conditioned studio with sleeping space for one additional guest

Whether you’re a group of couples or a family with children, the sleeping layout offers flexibility and privacy for everyone.

Bathrooms
There are three full bathrooms:

- Two with luxurious steam showers, ideal for post-beach relaxation
- One with a traditional bath tub
- Plus, an outdoor shower near the pool for rinsing off sandy feet or taking in the fresh air

Outdoor Living
The fully fenced, landscaped yard feels like your own private resort:

- Heated saltwater pool
- Stone patio with loungers and dining area
- Fire pit for evening gatherings
- Expansive yard ideal for games, sunbathing, or simply relaxing under the trees
- Outdoor shower adds convenience and charm

Poolside Cabana
The detached air-conditioned cabana offers a versatile retreat. Use it as:

- A quiet reading room or yoga space
- A fun hangout area for teens or kids
- A private sleeping area for one guest
- A poolside lounge for napping or relaxing out of the sun

Chef’s Kitchen & Living Area
The heart of the home is a chef’s kitchen equipped with:

- Miele and Thermador appliances
- Ample prep space and premium cookware
- Open layout that flows into the dining and living areas

The décor blends upscale coastal design with comfort—think curated art, plush furnishings, and natural light in every room.

Location & Convenience
- Located on a quiet corner lot just minutes from Nantucket Town
- Quick access to beaches, shops, restaurants, and bike paths
- On-property parking available for multiple vehicles
- Easy bike rides or short drives to explore the island at your pace

Perfect For...
- Families seeking a safe, relaxing space with room to spread out
- Couples or friends on a luxury getaway
- Multi-generational groups needing both comfort and flexibility

This home was designed for effortless gathering and memorable moments—whether that’s poolside, biking into town for dinner, or curling up for movie night after a long beach day.

NOTE: This home is undergoing a major transformation this fall (2025). The interior will be painted, an additional bedroom/office will be added, and an additional bathroom will be added making the second bedroom on the first floor ensuite. There will be new furnishings, linens, glassware, artwork and more. The current room photos do not illustrate these changes. See the storyboards for more details.

Add dates for prices

Amenities

Pool
Kitchen
Washing machine
Dryer
Free WiFi
Air conditioning

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
Pool is not fenced—supervision is required.
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Property Registration Number C0553971970

About the area

Nantucket

Nantucket Town, a neighbourhood in Nantucket, is home to this holiday home. Nantucket Lightship Basket Museum and Hadwen House are cultural highlights, and some of the area's landmarks include The Old Mill and Fire Hose Cart House. Travelling with kids? Consider Vestal St Observatory and Loines Observatory.
Map
Nantucket, MA

What's nearby

  • The Old Mill - 17 min walk - 1.5 km
  • Nantucket Historical Association - 4 min drive - 2.1 km
  • Nantucket Atheneum - 4 min drive - 2.1 km
  • Whaling Museum - 4 min drive - 2.1 km
  • Nantucket Ferry Terminal - 4 min drive - 2.5 km

Getting around

  • Nantucket, MA (ACK-Nantucket Memorial) - 8 min drive

Restaurants

  • ‪Handlebar Cafe - ‬4 min drive
  • ‪Cumberland Farms - ‬17 min walk
  • ‪The Chicken Box - ‬12 min walk
  • ‪Yummy - ‬13 min walk
  • ‪The Sea Grille - ‬9 min walk

Frequently asked questions

Does LolliPop Nantucket: A Thoughtfully Designed Island Home for Families and Friends have a pool?

Yes, this property has an outdoor pool. Pool types include heated pools.

Is LolliPop Nantucket: A Thoughtfully Designed Island Home for Families and Friends pet-friendly?

No, pets are not allowed at this property.

How much is parking at LolliPop Nantucket: A Thoughtfully Designed Island Home for Families and Friends?

On-site parking is available at the property.

What time is check-in at LolliPop Nantucket: A Thoughtfully Designed Island Home for Families and Friends?

Check-in begins at 4:00 PM.

What time is check-out at LolliPop Nantucket: A Thoughtfully Designed Island Home for Families and Friends?

Checkout is at 10:00 AM.

Where is LolliPop Nantucket: A Thoughtfully Designed Island Home for Families and Friends located?

This family-friendly Nantucket holiday home is located in Nantucket Town, within 1 mi (2 km) of The Old Mill, Francis Street Beach and Nantucket Lightship Basket Museum. Hadwen House and "Colored" Cemetery are also within 1 mile (2 km).

About the host

Hosted by Kirby Joseph

Host profile image
Hi, we’re Kirby and Jeff! Nantucket has been a part of our family’s story for generations—Kirby’s roots here go back 12 generations, and her grandfather was even born on the island. Over the years, we’ve spent countless summers on Nantucket with our four kids (two sets of twins!) and have made some of our most treasured memories here as a family.

When we recently purchased this home, we saw it as more than just a house—it was a chance to create a space where our family could continue to grow, laugh, and unwind together. With the help of a talented interior designer, we renovated the home to blend the charm of Nantucket with the comfort and ease of high-end coastal living. We named it LolliPop because it captures the fun, light-hearted, and family-friendly vibe we want every guest to feel the moment they walk through the door.

Whether you're a couple looking for a peaceful island getaway or a family wanting a space to slow down and reconnect, we hope LolliPop offers you the same sense of joy, warmth, and belonging it brings to us.

We’re honored to share a little piece of our Nantucket with you and hope it becomes a part of your story, too.
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