Kid-friendly holiday rentals in Jamaica

Find and book unique kid-friendly rentals on Airbnb

Top-rated kid-friendly rentals in Jamaica

Guests agree: These kid-friendly rentals are highly rated for location, cleanliness and more.

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Top Guest favourite

Home in Whitingham

5 out of 5 average rating, 58 reviews

2.5mi from the lake! Fire pit, arcade, yard games!

Escape to our tranquil countryside retreat, where relaxation meets adventure. Nestled amidst nature, our cozy home offers a haven of tranquility. Breathe in crisp air as you unwind in the peace & quiet. Indulge in outdoor pursuits with skiing, hiking, and foliage just moments away. After a day of exploration, find solace in the inviting warmth of our home. Whether you're curling up with a book or stargazing by the fire pit, every moment becomes a cherished memory. Your idyllic VT retreat awaits.

Superhost

Home in Ludlow

4.87 out of 5 average rating, 139 reviews

1st floor, Okemo contemporary country 3 BR 2 BA

Family-friendly, pet-friendly, clean, comfortable, contemporary country ski cabin on Okema shuttle buss route in Ludlow, VT, a few minutes from mountain. Very easy access to outdoor activities: skiing, hiking, lakes, boating, hunting, snowmobiling, fly-fishing. Updated, comfortable, light filled ambiance. Great location, 10 minute walk to downtown (2 minute drive). Great for groups, couples, families. Recently renovated. New butcher block counter-tops and island, all new kitchen, new bathrooms.

Top Guest favourite

Chalet in Stratton

4.99 out of 5 average rating, 167 reviews

Chalet w/Disc Golf & AC near hike/bike/golf/swim

Cozy chalet awaits your stay. This home sits on just under 4 acres. Sit back and enjoy the heated sunroom and stare out at the woods that surround you. You may be lucky enough to spot one of the moose or bear that visit the property. Kitchen remodeled June 2023! Open floor plan w/wood burning fireplace. Main bedroom has Qn bed & twin bunks. Finished basement with new Qn size bed and twin bunk above. Kid friendly home! Mins to Stratton Mtn & Mt Snow for skiing & golf! Free Disc golf on property!

Guest favourite

Home in Hoosick Falls

4.87 out of 5 average rating, 15 reviews

Enjoy Fall & Experience Beautiful Changing Colors

Nestled on a private 5 acres lot on the border of NY and Vermont this home is just perfect. Just 30-60 minutes from several ski areas. This charming home has everything you need to relax and enjoy . The night sky perfect for stargazing. Have morning coffee on the deck and watch as deer wander in the fields or the cows across the meadow. Enjoy a quiet evening by the fire after a long day on the slopes or soak in the oversize soaking tub! Stroller, changing table and a pack-n-play included.

Superhost

Home in Jamaica

4.75 out of 5 average rating, 57 reviews

Green Mountain A-Frame with HOT TUB near Stratton

Our cozy Green Mountain A-Frame is the perfect place for your Vermont getaway! A perfect combination of modern meets eclectic charm. Newly added deck with 7 person hot tub for your enjoyment. Nestled on a private road in town, you can’t go wrong! Hike from the house or head down the road to Jamaica State Park. High-demand ski resorts are just minutes away - only 6 minutes to the Stratton Mountain access road, 17 minutes to Magic Mountain, 20 minutes to Bromley and 30 minutes to Mt. Snow.

Guest favourite

Home in Mount Holly

4.92 out of 5 average rating, 118 reviews

Modern Farmhouse - 2 kings, minutes to Okemo!

Newly renovated property surrounded by picturesque mountains with views from every bedroom. Relax in our cozy 4 bedroom, 2 bath home, large enough for your whole family to come together. Sleeps 11. Dog friendly. Arcade games and firepit. Large yard. Excellent place to work remotely. Enjoy hiking, fishing, biking, kayaking, skiing & golf nearby. Explore nearby Ludlow, Woodstock, Manchester and Weston. Okemo & Jackson Gore resorts are less than 10 minutes away. Killington Mtn 30 min drive.

Guest favourite

Home in Rutland

4.81 out of 5 average rating, 347 reviews

Home Sweet Home

Single family house within walking distance of downtown Rutland. Many restaurants, bars, movies, bowling, farmer's market, etc to do. 15-20 minute drive to Pico and Killington. 30 minutes to Okemo. Mountain bike parks near by- Pine Hill, Killington and Okemo. Adventure park at Killington. 4 bedrooms, 1.5 baths. House sleeps 8+comfortably. Room for more if needed. Keurig coffee maker in kitchen, microwave, toaster, crock pot. Kitchen is fully furnished. AC units on first floor and second.

Top Guest favourite

Home in North Adams

5 out of 5 average rating, 109 reviews

Berkshires Retreat! in the woods, yet in town!

We are happy to share our piece of heaven in the Berkshires! Newly renovated 4-bedroom 2-1/2-bathroom vacation rental nested in 2.7 acres of woods, yet conveniently located in the city of North Adams. A 5 minute walk from Windsor Lake, a 15 minute walk to MASS MoCA, and a close drive to many restaurants. The house is kid friendly, basketball hoop, soccer goal, and games. We are close to ski resorts, as well hiking and biking trails, including Mount Greylock. PET FEE. PERMISSION NEEDED.

Superhost

Home in Windham

4.87 out of 5 average rating, 113 reviews

Magic Creek

Come enjoy our brand new hot tub! Magic Creek is quintessential Vermont- an antique made modern. The cozy living room with fireplace is an ideal spot to gather at the end of your day. The house has 3 bedrooms and a play room that doubles as a guest room. The house is bordered by a creek with peaceful water falls. Centrally located in the heart of ski country, minutes to Magic Mountain, 20 minutes to Bromley, and 30 to Stratton or Mt Snow, and 40 minutes to Okemo. Come and enjoy it all.

Top Guest favourite

Chalet in Dover

4.97 out of 5 average rating, 113 reviews

Grey Wolf's Den: 5 miles to Mount Snow w/HOT TUB

Charming spacious A-frame with lots of natural light, beautiful scenery and wrap around deck. Property features a long rolling hill perfect for sleigh riding or 75' slip n slide, tennis court, firepit, and 5 acres of Green Mountain Nat'l forest and brook. Home has 3 bedrooms + loft area.. 5 miles to Mount Snow, and minutes to golf course, bars/restaurants and lakes. This house is action packed inside and out with hot tub, 200' zipline and "unlock the box" scavenger hunt.

Top Guest favourite

Home in Plymouth

5 out of 5 average rating, 16 reviews

Luxury Modern Cabin near Okemo & Killington

All-seasons fun for the whole family in this brand-new home with unparalleled privacy! Modern design elements, tranquil scenery, and 21st century comforts set the backdrop for the perfect getaway. Enjoy ski season in this mountainside abode that's 10 minutes from Okemo, 20 minutes from Killington, and close to downtown Ludlow & Camp Plymouth State Park. Golfer-friendly in spring, summer, and fall. In all seasons, enjoy hiking, leaf peeping, brewery hopping, and swimming.

Guest favourite

Condo in Killington

4.78 out of 5 average rating, 176 reviews

Amazing,Ski, Golf, Hike, Bike, Adventures

Killington has become a wonderful 4 season resort area that satisfies many tastes. You can hike, play golf ,swim, bike, ski-snowboard, or just lay back and enjoy the surroundings. You can go to the Killington website to find out what is happening. Please go to the Killington website to get complete information before you go. There is also a Mountain Green website that will let you know which amenities are available during your stay. mountaingreen.com