Entire home
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





Reviews
10 out of 10
Exceptional
4 bedrooms3 bathroomsSleeps 9
Popular amenities
Explore the area

Nantucket, MA
- Place, Nantucket Historical Association4 min drive
- Place, Nantucket Atheneum4 min drive
- Place, Nantucket Ferry Terminal4 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.
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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10.0 out of 10, (65 reviews)
House Rules
Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
Children
Children allowed: ages 0–17
Pool is not fenced—supervision is required.
Events
No events allowed
Pets
No pets allowed
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.

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
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
About the host
Hosted by Kirby Joseph
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.
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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