Luxury Vacation Rentals for Families in Jamaica

Luxury Vacation Rentals for Families in Jamaica

Never book a bad vacation home again. Every Wander comes with hotel-grade amenities, inspiring views, pristine cleaning and 24/7 concierge service.
We found 4 family vacation rentals – enter your dates for availability.

Top-rated family vacation rentals in Jamaica

Stratton Ski Haus property photo 1

Stratton Ski Haus

4 bedrooms•2.5 baths
834 US dollars for 1 night•
New

~$70 less than other sites

Winhall Pines property photo 1
Luxury

Winhall Pines

5 bedrooms•4.5 baths
2,299 US dollars for 3 nights•

~$180 less than other sites

Stratton Mountain property photo 1

Stratton Mountain

4 bedrooms•4.5 baths
2,464 US dollars for 3 nights•

~$195 less than other sites

Shred Shack property photo 1

Shred Shack

4 bedrooms•3 baths
1,664 US dollars for 3 nights•
New

~$145 less than other sites

Welcome to family adventures in Jamaica

Welcome to family adventures in Jamaica

Bring everyone together at our luxury family vacation rentals in Jamaica, Vermont. Wander pairs the polish of a five-star hotel with the privacy of a contemporary mountain home, so every generation can settle in with ease. Each stay is expertly managed and always true to the photos.
Spread out in multi-bedroom layouts with bunk rooms, airy great rooms, and chef-ready kitchens for family meals. Expect pristine cleaning, ultra fast WiFi, dedicated workspaces for parents, and kid-friendly touches like blackout shades. Select homes add hot tubs, game rooms, and expansive decks for outdoor downtime. With 24/7 concierge support, you can focus on time together.

Available soon in Jamaica

Stratton Ski Haus property photo 1

Stratton Ski Haus

4 bedrooms•2.5 baths
834 US dollars for 1 night•
New

~$70 less than other sites

Winhall Pines property photo 1
Luxury

Winhall Pines

5 bedrooms•4.5 baths
2,299 US dollars for 3 nights•

~$180 less than other sites

Stratton Mountain property photo 1

Stratton Mountain

4 bedrooms•4.5 baths
2,464 US dollars for 3 nights•

~$195 less than other sites

Featured family vacation rentals in Jamaica

Winhall Pines property photo 1
Luxury

Winhall Pines

5 bedrooms•4.5 baths
2,299 US dollars for 3 nights•

~$180 less than other sites

Stratton Mountain property photo 1

Stratton Mountain

4 bedrooms•4.5 baths
2,464 US dollars for 3 nights•

~$195 less than other sites

Highlights in Jamaica

Discover outdoor adventures, scenic state parks, and family-friendly mountain resorts nestled in the heart of Vermont's beautiful Green Mountains.
Jamaica State Park
Ball Mountain Dam and Lake
Stratton Mountain Resort
Taylor Farm
Magic Mountain Ski Area

IT'S A VACATION HOME, BUT BETTER

The Wander difference

Wander is different because we combine the quality of a luxury hotel with the comfort of a private vacation home. Your best trip ever is just a few clicks away.

Only the best homes

We’ll never not look like the pictures. Every Wander is beautiful and expertly operated, so you can leave any stress at the door.

Hotel-grade amenities

We’ll never leave you with nothing to do. From ultra fast WiFi to gyms and pools, our homes make it easy to blend work and play.

24/7 concierge service

We’ll never leave you hanging. Our chat-based Concierge is always available to help – from trip questions to special requests.

Inspiring and stunning views

We’ll never leave you uninspired. Every Wander has stunning views to refresh and inspire your soul. Adventure awaits.

Meticulous cleaning

We’ll never have you check in to a dirty house. Our cleaning teams are meticulous, and there are no chores at checkout.

Safety and security

We’ll never pass you off to a stranger. Every Wander location meets our industry-leading safety standards to give you peace of mind.

All homes in Jamaica

Stratton Ski Haus property photo 1

Stratton Ski Haus

4 bedrooms•2.5 baths
834 US dollars for 1 night•
New

~$70 less than other sites

Winhall Pines property photo 1
Luxury

Winhall Pines

5 bedrooms•4.5 baths
2,299 US dollars for 3 nights•

~$180 less than other sites

Stratton Mountain property photo 1

Stratton Mountain

4 bedrooms•4.5 baths
2,464 US dollars for 3 nights•

~$195 less than other sites

Shred Shack property photo 1

Shred Shack

4 bedrooms•3 baths
1,664 US dollars for 3 nights•
New

~$145 less than other sites

View all homes

Most popular amenities for family vacation rentals in Jamaica

Jacuzzi (4)
Hot tub (4)
Ev charger (2)
Sauna (2)
Sound system (3)
Gym (1)
Mountain view (3)
Fire pit (4)
Fire place (4)
Pool table (2)
Patio (3)
Garden (3)
Foosball table (1)
Dryer (4)
Bbq area (2)
Washer (4)

More popular family destinations near Jamaica

Family vacation rentals in Johnson
Family vacation rentals in Jay

Other popular amenities & vacation types in Jamaica

Large group vacation rentals in Jamaica
Hot tub vacation rentals in Jamaica
Discover more family fun in Jamaica

Discover more family fun in Jamaica

Set along the West River in southern Vermont, Jamaica is a four-season favorite for families. Wander forested paths in Jamaica State Park, pause at Hamilton Falls, and take in big-sky views from nearby Stratton and Bromley.
Country roads, historic covered bridges, and quiet valley vistas create an easygoing pace, while autumn color and winter snow turn the landscape into a postcard. Clear nights bring remarkable stargazing and a hush that feels restorative. All of this is why Wander’s luxury family vacation rentals in Jamaica, Vermont are the perfect choice, whether you’re traveling for work or leisure.

FAQs: Vacation Rentals in Jamaica

Why should I book a Wander in Jamaica over other family vacation rentals?

Wander offers a level of consistency and quality you won’t find with most family vacation rentals.
Every home in Jamaica delivers the quality of a luxury hotel, paired with the comfort and space of a private vacation home. You get hotel-grade amenities, meticulous cleaning, stunning views, and 24/7 concierge support in every stay. Why would you want to stay anywhere else?

Which are Wander’s most popular family vacation rentals in Jamaica?

Some of our most popular family vacation rentals in Jamaica include Stratton Ski Haus, Wander Winhall Pines, and Wander Stratton Mountain. Guests love the quality of a luxury hotel, the comfort of a private vacation home, and the consistently exceptional experience Wander is known for. Explore the full collection to find the perfect home for your next stay.

How many different family vacation rentals does Wander have available in Jamaica?

Wander offers 4 family vacation rentals in Jamaica, each carefully designed and expertly operated. Browse the full collection to see what’s available for your trip.

What time is check-in and check-out at Wander’s family vacation rentals in Jamaica?

You can check-in to Wander family vacation rentals in Jamaica after 4.00pm and check-out before 10.00am.

Do Wander’s family vacation rentals in Jamaica have WiFi access?

Yes. Every Wander home in Jamaica has ultra fast, reliable WiFi so you can stay connected throughout your stay.

What is Wander’s cancellation policy?

You can cancel your reservation within 24 hours of booking for a full refund.
For stays of less than 15 nights, you can cancel or reschedule up to 14 days before check-in for a full refund. For stays of 15 nights or longer, the cancellation window is 60 days.
For some homes, a 30-day deadline applies; this will be clearly shown before you book.