
Kid-friendly holiday rentals in Jamaica
Find and book unique family-friendly rentals on Airbnb
Top-rated family-friendly rentals in Jamaica
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Popular amenities for Jamaica family-friendly rentals
Kid-friendly house rentals

2-Bedroom Home, 7 Minutes From Stratton Mountain
Ariana’s place was great after a day of snowboarding at Stratton. Great location, the home was cozy and we had a great time relaxing at the house. Ariana was responsive to our question and the home was well equipped to enjoy a meal at home after being out all day.

Stunning Okemo Views - 3BD 3BA on 10 Private Acres
I can only say wonderful things about this property! Everything was beautiful both inside and out. The house was very clean and organized and was also extremely well stocked. Anything that we needed we found in this house. And everyone in our group said the beds were very comfortable… which is very important to me! Erik was great with communication and very proactive. He sent us a note about a week before we checked in that had everything we needed to know; it was quite helpful. I highly recommend this home….and as an added bonus, the view is spectacular! You will not be disappointed if you stay here!

Vermont Botanical Studio Apartment
I’ve returned to the Vermont Botanical studio on an annual basis for several years, since I always find it peaceful and comfortable—off the beaten path, but not lonely. It has everything I need, including a dirt road through the fields for a daily walk, tall windows looking out on lovely trees, a very healthy songbird population, and a nearby farm store where I always go to buy cheese as soon as I arrive. I especially appreciate the comfortable bed, reading chair and couch, and the perfectly serviceable kitchen. The induction range makes for very quick cooking, and it’s nice to have the use of a full-sized fridge, too. For my writing retreats, the studio feels like a home away from home.

The Grafton Chateau
The Grafton house was perfect for our multi-family with the big space, bedrooms, and bathrooms. We loved the living room area where we could all sit together for family games. The property and house are beautiful and the perfect Vermont vibes. As a skiing family, we liked the location between our favorite ski resorts. Raphael was a wonderful host in providing instructions before our arrival and helpful advice. We really enjoyed our stay at the Gafton house.

Wild Blossom Farmhouse - a lovely family getaway
We had a wonderful weekend in Vermont! The Airbnb was beautiful, clean and in a great location!

Birdie's Nest Guesthouse
Sarah was a fantastic host and the property was an absolute gem. It was the perfect place to get a little respite from a crazy-busy weekend. Thank you!

Cheerful 1 bedroom cottage
Glenn was incredibly kind and responsive, and the cottage was exactly like the pictures. The space was perfect for a couple-day getaway before starting my MFA! Also, if you need good local recommendations, Glenn has you covered.

Waterfront Vermont Lake House w/ Canoe/Kayak/SUPs
A great stay at the Lake House. Gorgeous views, fully stocked kitchen, and canoes/SUPs/kayak for everyone. Andrew was very responsive and a great host. We hope to return soon!
Family-friendly apartment rentals

Private two-bedroom suite within a two-story house
Dimitry and Lana’s house was beautiful! The bedrooms were large and cheerful, and each had a window unit AC. The beds were so comfortable, I didn’t even move all night, just zonked out. The bathroom was large and had lots of choices of toiletries to use. The kitchen was small, but had a full sized fridge, coffee maker, microwave, and hot plate. Everything was spotless. We ate so much one evening that we decided to stroll the neighborhood before turning in, and it was beautiful and peaceful. We loved our stay at this cute house. The yard is lush with flowers everywhere, just a beautiful mountain setting. Manchester was fantastic, a “wow” everywhere you looked. We especially loved the Lincoln estate, “Hildene.” Overall, you could not go wrong spending a couple of nights here!

Gorgeous 1-Bedroom Space in Historic Bellows Falls
Photos didn’t do this place justice. So beautiful and unique, but also comfortable. Wunderbar downstairs is not to be missed—absolutely fantastic food. Great location and a lovely stay!

Walk To Wilmington Village
We had a great weekend here! The listing was accurate and the place was cozy and quiet. Just what is needed after a long day at the mountain. Shawn was super helpful and very nice! I highly recommend Shawn and this location.

HeART Barn Retreat
We had a great stay at the HeART Barn and will definitely be looking to book again in the future! Such a beautiful, comfortable, and homey space located on a beautiful property. Brianna is incredibly kind as well. Highly recommend!!

Apartment with a view
Excellent place, great hosts. Easy. Just what we wanted.

Apartment on Main Street
We have family in Springfield so staying at Whitney and Alex’s place is perfect for us. It’s spacious and comfortable. This was our second stay and we will definitely be returning.

Contemporary forest eco-retreat, mountain views
This cozy apartment in a beautiful, quiet setting is conveniently located close to NECCA and Brattleboro. Millicent and Tony provided numerous thoughtful touches, like local maple syrup in the fridge! They clearly care about the comfort and convenience of their guests, and were even upgrading the walkway lighting while we were there. The gardens right outside our large windows were in full bloom, and we woke to bird songs. I look forward to returning!

Private Hilltop farm apartment
Beautiful property with amazing views! Laura was very responsive and friendly. The apartment was comfortable and cozy for our weekend stay. We would definitely stay here again!
Family-friendly apartment rentals

Mt Snow Ski In/Out at Seasons
The unit is very comfortable for a family and very convenient to Mount Snow. Updated bathrooms and washer/dryer. Great clubhouse and pool facilities at Seasons condo. Andrew was a pleasure to work with.

Summer Dream! The Handle Lodge at Snowtree Condos
Our family enjoyed our stay at Rafael's condo. The space was very clean and comfy, and exactly matched the description and photos posted here. The fireplace was a great draw, too. If you're planning on skiing at Mt. Snow, the Moover shuttle bus stop is located right outside of this building, which made for a very convenient and quick way to get to Mt. Snow for my family of 4. We would certainly stay here again in the future.

Updated Ski in/Ski out Stratton Condo!
Caitlyn An excellent host quick to respond despite moving with her babies the same day as my trip! She was accommodating and provided a clear quick easy in from my late night travel. Her space is large and spacious with great set up lighting and comfortable and clean bedding. Loved the couch bedding set up! The entrance allowed ease to store the ski stuff so roomy keeping the living space free of the typical ski vacay clutter! The bathroom shower temp and pressure with soft towel and wash cloths provided with soap, and shampoo and conditioner gave a nice end of the day relax. Plenty of blankets for layering that may be needed. Kitchen appointed well with a good stove and oven easy to use and to easy prepare with pans and utensils for cooking, plenty of silver ware and plates glasses and plates that i truly appreciated. Couldn't use the ski in/ ski out as that lift was this late int eh season but how easy was it to scoot down in 2 min! Will be my stratton stay always onward!

Okemo Clock Tower Base Ski-in/Ski-out Condo
We loved it. Although it’s not the newest or fanciest condo the location can’t be better right at the Clocktower Base. Our family of for had an amazing time snowboarding and exploring the area. Great restaurants close by and we will definitely be back next year.

Great 2 bedroom condo at Stratton Mountain
Great place to stay conveniently located by the mountain base! We enjoyed walking into the village after skiing. Very clean and cozy and had everything we needed and more. Dana was very responsive! Hope to come again next year!!

Cozy condo within walking distance to the slopes.
You really can’t beat this location. It’s across the steet from the lifts and the village with lots of restaurants/bars/stores. The space was perfect for our family of four. Our two young children stayed on the pullout and we thought the king bed was quite comfy. We would def stay here again!

3 Story Condo - 5 Minutes to Mount Snow!
It was such an easy check in and check out process. He let us check in an hour early since we arrived earlier. Place is spacious and exactly as described. Highly recommend!

Lovely, light-filled condo in Eastman
Lyn’s place was perfect for our girls getaway. 3 full bathrooms was great. Lots of space for everyone. The house was very clean and comfortable! We loved the close proximity to the trail around the lake.
Quick stats about holiday rentals that are kid-friendly in Jamaica
Total rentals
70 properties
Nightly prices starting at
$90 SGD before taxes and fees
Total number of reviews
7.4K reviews
Family-friendly rentals
60 properties are a good fit for families
Pet-friendly rentals
40 properties allow pets
Rentals with dedicated workspaces
50 properties have a dedicated workspace
Destinations to explore
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- Stratton Mountain
- Okemo Mountain Resort
- Saratoga Race Course
- Monadnock State Park
- Six Flags Great Escape Lodge & Indoor Water park
- Jiminy Peak Mountain Resort
- Berkshire East Mountain Resort
- Pats Peak Ski Area
- Pico Mountain Ski Resort
- West Mountain Ski Resort
- Stratton Mountain Resort
- Magic Mountain Ski Resort
- Mount Greylock Ski Club
- Mount Snow Ski Resort
- The Shattuck Golf Club
- Dorset Field Club
- Autumn Mountain Winery
- Mount Sugarloaf State Reservation
- Hildene, The Lincoln Family Home
- Bromley Mountain Ski Resort
- Baker Hill Golf Club
- Pineridge Cross Country Ski Area
- Clarksburg State Park
- Ekwanok Country Club