Family-friendly vacation rentals in Jamaica

Find and book unique family-friendly homes on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for Jamaica family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favourite
Home in Plymouth
4.95 out of 5 average rating, 251 reviews

Top of the World! Jacuzzi! Private Hiking Trails!

MichaelRating, 5 stars2 months ago
Nice place thanks Mike
Guest favourite
Farm stay in Valley Falls
4.89 out of 5 average rating, 224 reviews

Country Getaway Lodge / Ranch

TrevorRating, 5 stars4 months ago
Fantastic space for a large group. We had 10 people for a New Year’s Eve ski weekend, and this was the ideal spot for it. Hot tub was a great treat. Be warned - the floors are squeaky, so if you’re a light sleeper in a large group bring ear plugs.
Guest favourite
Condo in Killington
4.95 out of 5 average rating, 105 reviews

⭐️Cozy Ski On/Ski Off 2-Bed/Bath w/Fireplace

PatriciaRating, 5 stars1 month ago
This space was perfect for our family. With walking distance to the entrance of the slopes, this location was ideal for our ski getaway. I appreciated the small touches that made this experience feel luxurious, the provided coffee, wine, wood for the usable fire place. The beds were comfortable and the space was spacious. We would definitely visit Jim’s place again!
Guest favourite
Chalet in Ludlow
4.94 out of 5 average rating, 127 reviews

Okemo Ski Chalet with Hot Tub

KatieRating, 5 stars1 month ago
Bob’s place is great for several families. Many bedrooms, multiple bathrooms, great amenities and close to skiing!
Guest favourite
Condo in Ludlow
4.93 out of 5 average rating, 110 reviews

One Bedroom Suite Near Okemo

ChristopherRating, 5 stars3 weeks ago
Excellent apartment in a resort hotel. Well staffed and the property is kept in excellent condition. Highly recommend this host.
Superhost
Farm stay in Londonderry
4.82 out of 5 average rating, 136 reviews

Cozy Award Winning Farmhouse - hot tub and sauna!

JumanaRating, 5 stars12 months ago
Very beautiful home and lovely host! Would recommend!
Top guest favourite
Home in Newfane
4.98 out of 5 average rating, 136 reviews

Peaceful cabin close to skiing & Brattleboro

MarinaRating, 5 stars1 month ago
This house is incredibly comfortable and well equipped. The location is lovely and private. We came for relaxation and with the fire pit and the hot tub we got our money's worth. My friends who are great cooks enjoyed the gas stove and some very well seasoned cast iron pans. Come here and enjoy the natural light and comfy space.
Guest favourite
Chalet in Killington
4.87 out of 5 average rating, 248 reviews

Large Chalet; Sauna, Hot Tub; Walk to Trail

AudreyRating, 5 stars1 month ago
We could not have found a better home for our Killington ski week. The ski in ski out directions were perfect and so easy. The home comfortably accommodated 8 adults and provided privacy for each of us as well. Fabulous dining area for our family that provided many happy memories. We've never rented a home where every single bed was so luxurious either. Each night we slept so soundly. On days we did not ski there was plenty to do at the house, a beautiful neighborhood to walk in and such close proximity to Killington Rd with so many dining options.

Family- and pet-friendly home rentals

Guest favourite
Cabin in Jamaica
4.88 out of 5 average rating, 112 reviews

Cozy Log Cabin near Stratton/Mt. Snow-pet friendly

JamesRating, 5 stars2 months ago
Christina was an excellent host who ALWAYS responded to any of my questions or concerns immediately and courteously. Her space was exactly as described and very spacious as well as a fantastic environment for a group to get together and have a great time! I highly recommend Christina’s place for a great time with a large group, she is the ideal host who works tirelessly to provide an amazing space for her guests!
Top guest favourite
Guesthouse in Stephentown
5 out of 5 average rating, 410 reviews

Dog Friendly Studio

JihanRating, 5 stars2 weeks ago
This was our sixth visit to Maple Hill Farms — we just can’t get enough of it! Philip truly the best host, and his home is pure magic. We’re so grateful to have met him and to experience his incredible hospitality and a property filled with the most amazing creatures.
Superhost
Farm stay in West Brattleboro
4.94 out of 5 average rating, 132 reviews

Lilac Ridge Farm House

MatthewRating, 5 stars4 months ago
We had a great stay at Lilac Ridge! The house was near and spacious, plenty of room for our family. We stayed in quite a bit and enjoyed the farm (including a visit with the calves!) and the house. The little farm stand had some nice things, including fresh eggs, maple syrup, honey, and soap, all local. Ross and Amanda were super responsive and took care of all our needs. Thanks so much!
Guest favourite
Cabin in Danby
4.89 out of 5 average rating, 296 reviews

April/May special So Vt Cabin Mt Tabor Treasure

MelissaRating, 5 stars1 month ago
A great escape. We enjoy our stays here. We are booked again in June. Lori is so attentive. She is always one step ahead. Thank you! 😀
Guest favourite
Tiny homes in Jamaica
4.94 out of 5 average rating, 1,259 reviews

Apple Blossom Cottage: A Tiny House

AveryRating, 5 stars2 days ago
I found this listing years ago while scrolling for tiny houses and it stayed in the back of my mind. I finally had the opportunity to visit as a getaway for my birthday. It was SO peaceful and lovely. I really enjoyed walking the grounds with my dog in lieu of taking a hike nearby, since there was so much rain during my stay. Dominic even let me take a walk to his other property, which was so spacious and pretty as well! I spent most of my time journalling and getting clarity while sitting in the swing on the porch, listening to the rain. I also took a brief voyage to Manchester Center, which was a darling town with lots to explore. I recommend Depot 62 for super tasty Turkish food. The cottage had all the essentials and clear instructions. It could use a deep clean in some of the nooks and crannies, but was overall very tidy and well-kept. I would 100% come back. The vibe up there in the misty mountains of VT is just so high and so freeing. Such a re-aligning stay.
Top guest favourite
Home in New Salem
4.89 out of 5 average rating, 215 reviews

Stone n' Sky Lodge

JasonRating, 5 stars5 months ago
I genuinely don't know what to say other than the fact that this may be one of the greatest places I've had the honor to lodge at. I did a lot of vetting across New England to find a wonderful place that could sleep a decent amount of people, provide a scenic and comfortable escape, and keep us entertained. Sarah's wonderful Stone and Sky Lodge exceeded every expectation I just listed. It's cozy, warm, and feels like a hidden nook! The scenery and nature couldn't be more beautiful. I never got the pleasure to meet Sarah, though I wish I did. Over messages and from what my friends told me, I just know that Sarah is the most hospitable and kind host that I've talked with in a while, and I hope that next time I can thank her personally. From my friends and I, we thank you for sharing your home with us. If you think that the excellent reviews are too good to be true, don't. This IS the truth, and I can't wait to have another reason to come back to this wonderful treasure of a place.
Top guest favourite
Chalet in Wells
4.9 out of 5 average rating, 143 reviews

Views! Entire Chalet, FAST Wi-Fi, All 18 Acres

TomRating, 5 stars2 months ago
Rita’s chalet is really clean and the view around it is amazon. The place is well stocked with games for fun and firewoods for warmth. Upon request, Rita was able to accommodate our late checkout request with a reasonable surcharge. We have enjoyed our stay at Rita’s place and would definitely come back next time when we are around
Top guest favourite
Home in Newfane
4.95 out of 5 average rating, 183 reviews

Adorable home in Newfane

ChrisRating, 5 stars4 days ago
We had a great stay at Saskia's house. Directions were perfect and everything was as described. The home is on a dirt road (but you only have to drive on the dirt road for less than a minute), our non-4 wheel drive car handled it with no problem. We loved the secluded and relaxing atmosphere and the bed was really comfortable too. Saskia was a great host, very communicative and welcoming, she left a great guide to the house and area. Highly recommended if you’re looking for a private getaway. We would definitely stay again. A+++

Family-friendly home rentals with a pool

Guest favourite
Townhouse in Dover
4.96 out of 5 average rating, 148 reviews

Bear's Den - Mt Snow Townhome w/ Heated Pool!

NikkiRating, 5 stars2 months ago
Had a great time! Within 4 minutes of a stellar breakfast at Trail 87 and within 5 min of mount snow base.
Superhost
Condo in Killington
4.92 out of 5 average rating, 106 reviews

Right at Killington !

CrossanRating, 5 stars2 months ago
Our family had a wonderful stay at the condo in Killington. The location could not be beat! A very short 5 minute walk to the lifts and Snowshed lodge. The complex had an amenity building with pool/hot tub that the kids loved and the condo was quite spacious and clean. Ruslana was a great host and very responsive! There is a solid chance we will be back next year!
Guest favourite
Condo in Dover
4.87 out of 5 average rating, 239 reviews

Mt Snow Ski In/Out at Seasons

MarkRating, 5 stars2 weeks ago
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.
Guest favourite
Guesthouse in Granville
4.9 out of 5 average rating, 896 reviews

Moon Valley Country Retreat no clean fee pets yes

AmberRating, 5 stars2 weeks ago
There is not enough to say about the pristine beauty that is Loraine’s cabin. The instructions were helpful in navigating into the property and lights were turned on as it was dark to assure my comfortable arrival. The cabin feels like a nurturing home and is equipped with comforts and small touches. The bed was neatly made and felt like a picture walking in to see it. The stairs are cabin stairs and there is caution to take your time and step gently. Seemingly every question was answered with small notes around the cabin and a detailed welcome book. The care and attention to detail was perfection in a stay. I only wish I had been on a longer trip to fully enjoy the grounds and the surroundings. It was easy to feel at home and welcome with Loraine and Dean as hosts.
Superhost
Condo in Killington
4.8 out of 5 average rating, 107 reviews

*Killington Summer Rental: 3 Bdrm, 2 Bth*

MikeRating, 5 stars2 months ago
Dray was thorough and the airbnb was clean, comfortable, and close to everything! I hope to stay here next time I visit!
Superhost
Condo in Killington
4.78 out of 5 average rating, 307 reviews

Serene Top Floor Condo (resort style amenities)

JonRating, 5 stars1 month ago
A wonderful place situated close to the mountain. The amenities were fantastic as well. The only issue was getting the right pin to access the apartment...however Scott responded within seconds so it was minimally disruptive.
Guest favourite
Condo in Killington
4.97 out of 5 average rating, 144 reviews

#45 Luxury Ski & Summer Condo with Private Sauna

MichaelRating, 5 stars1 month ago
Great spot near the mountain. nice community pool and hot tub.
Guest favourite
Condo in Hancock
4.86 out of 5 average rating, 152 reviews

Cozy Condo @ Jiminy Peak

ElizabethRating, 5 stars2 months ago
We always book with Dawn! Her place is amazing. We feel right at home. She ensures the house has everything you could need in case you forget something. There are extra details to make your stay more comfortable. Her linens are softer than mine at home! There is plenty of space for my family of five to stay comfortably. I highly recommend booking here! We can’t wait until our next stay here.

Quick stats about vacation rentals that are family-friendly in Jamaica

  • Total rentals

    170 properties

  • Nightly prices starting at

    $97 CAD before taxes and fees

  • Total number of reviews

    8.4K reviews

  • Pet-friendly rentals

    80 properties allow pets

  • Rentals with dedicated workspaces

    90 properties have a dedicated workspace

  • Wifi availability

    160 properties include access to wifi

Destinations to explore