Pet-friendly holiday rentals in Jamaica

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Top-rated pet-friendly home rentals in Jamaica

Guests agree: these pet-friendly homes are highly rated for location, cleanliness and more.

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Top guest favourite
An outdoor tub is situated on a wooden deck, surrounded by vibrant autumn foliage. A red faucet provides a natural flow of water, while a small bowl of floating objects rests nearby. In the background, a glimpse of a serene lake can be seen through the trees.
Cabin in Stoddard
4.99 out of 5 average rating, 150 reviews

Boulder House - Extraordinary Luxury in the Woods!

From its unique interior wall of huge boulders to the soaring post and beam construction, Boulder House is bolder in every way. It's a rare combination of peace, solitude, and luxury in a beautiful and secluded setting within the 250-acre Lakefalls estate. The very private deck overlooks "Chandler Meadow" and 11,000 acres of conserved land and water, with stunning views from the sunken tub and outdoor shower. The interior appointments and amenities provide extraordinary comfort and aesthetics.

Guest favourite
The custom home features warm wood siding and a welcoming porch with flower boxes. A spacious deck with rustic railings extends from the second floor, while a covered area includes seating. Surrounding greenery enhances the natural setting, creating a serene outdoor ambiance.
Cabin in Wardsboro
4.86 out of 5 average rating, 177 reviews

Mountain side acres

10 years of love and affection went into building our 2 bedroom custom home. Sticking with natural products to blend together the beauty of the surrounding area. Lay in bed at night and listen to river that runs the entire length of the property. The house has a full kitchen with seating for 6. Spacious living room for relaxing or admiring one of the many birds that visit all year round. Two upstairs bedrooms and office space. Walkout basement with full entertainment area, hot tub,exercise room.

Guest favourite
The inviting living room features a modern wood-burning stove against a backdrop of light wooden walls. A comfortable dark sofa is arranged around a round wooden coffee table, complemented by a decorative plant. Natural light filters through the windows, enhancing the cozy atmosphere.
Cabin in Londonderry
4.95 out of 5 average rating, 248 reviews

Summit View Cottage:Ski | Hot tub|Fireplace3bd 2ba

Summit view cottage boasts 3 acres in the beautiful green mountains, we are 1,700 feet up in elevation . At this brand newly built PET FRIENDLY cabin you will have 3 bedrooms and 2 full bathrooms, which will sleep 7 comfortably. We have a brand new 6 person HOT TUB! You will find yourself within 15 minutes to the world famous Stratton mtn, 15 minutes from Bromley mtn and a close 4 minutes to the local Magic mtn.Very close proximity to the town of Manchester, which has great shops and restaurants

Top guest favourite
Cabin in Stratton
5 out of 5 average rating, 191 reviews

Log Cabin King Beds AC Near Hike Bike Swim Golf!

Kick back and relax in this calm, stylish, newly built log cabin which was finished in early 2022. Fully equipped with stainless steel appliances, soapstone counters, central a/c, all new furniture, mattresses and bedding. First floor master bedroom leads into a large, covered, screened in porch, which is perfect for your early morning coffee or evening cocktails. Starlink high speed Wi-Fi and a smart tv in the living room and bedroom. 7 Minutes from Stratton Mtn, 15 from Mt Snow. Nearby lakes!

Guest favourite
A charming treehouse is nestled in a snowy landscape, elevated on stilts with a wraparound deck. Soft white lights illuminate the exterior, while snow gently falls around it. A wooden staircase leads up to the entrance, highlighting the inviting ambiance.
Treehouse in Londonderry
4.88 out of 5 average rating, 158 reviews

Riverbed Treehouse @hot tub & a new sauna & views!

The beautiful & brand new Riverbed Treehouse with private sauna and a stunning new hot tub! Views all day long and wildly awesome sunsets!! Stratton mountain is right at your toes with a babbling brook turned raging river in the Spring! Beautiful woods & trails to explore. Stunning ridge line off the ski trails of Magic Mnt!! Close to town for quick shopping & coffee shops! Xcountry ski or snowshoe or walk our groomed trails!! FAST WiFi, nature lovers & a birdwatchers paradise!! @bentapplefarm

Guest favourite
A rustic cabin built on stilts is surrounded by snow-covered ground and tall trees. The structure features a pitched roof and a spacious deck. Sunlight filters through the branches, casting shadows on the snow, highlighting the natural beauty of the winter landscape.
Cabin in Winhall
4.88 out of 5 average rating, 110 reviews

Chic Cabin with Fireplace at Stratton Mountain

Originally built as a corn crib in the 1800s, this 2 bedroom, two bath cabin has been lovingly maintained and features many original details from wide pine floors to a brick fireplace. This beautiful post and beam cabin is nestled in the Green Mountains of Central Vermont with convenient access to some of the best skiing, hiking, & sightseeing: 10 min to Stratton Mountain and Bromley, 15 min to Manchester, 20 min to Magic Mountain, 30 min to Mount Snow, 40 min to Okemo, and 1 hour to Killington

Guest favourite
The A-Frame cabin is set amidst a lush forest, featuring a prominent triangular structure with a textured wood exterior. A spacious deck is adorned with red railings, and firewood is neatly stacked beside the entrance. Soft light filters through the trees, enhancing the serene atmosphere.
Cabin in Jamaica
4.95 out of 5 average rating, 101 reviews

The Woodland A-Frame

Welcome to The Woodland A-Frame! Built in 1965, our cozy cabin is located 20 mins from Stratton Mountain & Mt. Snow, and 30 mins from Bromley, & Magic Mountain! Vermont is a four-season state, allowing guests to enjoy the cabin anytime of year. Whether it's for fall foliage, winter activities, spring festivals, or a summer at the lake, we are happy to host you anytime during the year to experience your ideal Vermont getaway! Dogs welcome with a $100 pet fee per pet (two dog max). No cats

Top guest favourite
The chalet is set against a backdrop of trees, showcasing a combination of natural stone and wood siding. Multiple outdoor seating areas are visible, featuring colorful chairs with a fire pit nearby. Dim evening light gently illuminates the home, highlighting the windows and inviting ambiance.
Chalet in Jamaica
4.99 out of 5 average rating, 102 reviews

Designer Chalet w/ Mountain Views close to it all

A perfect little getaway. This stylish 3 bedroom/2 bath chalet is surrounded by endless outdoor activities. Swimming, hiking, biking, visiting the local waterfalls, golf courses, or rent an ATV from local outfit. This beautiful home is perfect for 6-8 people. Situated on 2.5 acres, this private setting with mountain views, has everything you need to feel at home. Multiple restaurants, cafes, markets for food, beer & wine less than a 5 min drive as well to sporting stores for supplies.

Guest favourite
The tiny house exterior features a charming porch with colorful railings and vibrant green doors. Tall trees surround the cottage, and a light dusting of snow covers the ground, adding to the serene atmosphere of the setting.
Tiny home in Jamaica
4.94 out of 5 average rating, 1,347 reviews

Apple Blossom Cottage: A Tiny House

The ABC is located just 15 minutes from the Stratton Mountain Gondola and just 2 miles from the popular Jamaica State Park. Comfortable for up to 5 people. The private tiny house includes fresh linens, dedicated Wi-Fi, a kitchenette, hot shower, flushing toilet, fire pit and porch. The calendar is accurate. Stratton Mountain Resort 10 miles Grace Cottage Hospital 7 miles Magic Mtn 15 miles Bromley 18 miles Mount Snow 15 miles Brattleboro 24 miles Okemo 30 miles Killington 47 miles

Top guest favourite
The cabin features a wooden exterior surrounded by lush greenery, with large windows allowing natural light to enter. A wooden deck extends from the side, leading to a cozy outdoor area and an adjacent structure, contributing to the rustic charm of the setting.
Tiny home in Dover
5 out of 5 average rating, 213 reviews

Rustic Cabin in foothills of Green Mountains

Rennsli Cabin is off grid + nestled on a forested plateau in the foothills of the Green Mountains. You will feel like you are in the middle of nowhere, unplugged and able to regenerate. Kitchen is equipped with cooking essentials, water, coffee, tea, milk, fresh eggs + homemade soap. It has an indoor compost toilet, outhouse + outdoor shower (May-Oct) Most seasons, the cabin is 100ft from parking, but weather conditions may require an 800 ft walk from parking at main house.

Guest favourite
A cozy living area is highlighted by striking geometric windows that allow natural light to enter. Dark wood accents complement the light-colored wooden floor. A comfortable sectional sofa and wooden coffee table create an inviting space for relaxation.
Chalet in Jamaica
4.84 out of 5 average rating, 189 reviews

Artists Chalet minutes from Stratton Ski Resort

One of a kind hand gem…built by the owner in the heart of the Green Mountains. House boasts spacious high ceilings, maple trim sourced from the property and custom windows that reflect the intention of the land. Pikes Falls is one mile down the road. Minutes to Stratton Mountain and Jamaica State Park. Mountain views from the deck! During the winter season, all wheel drive or 4WD is recommended. Pets are welcome on a case by case basis and may be subject to a Pet Fee

Guest favourite
A charming cottage entrance is depicted with natural wood siding and a small porch area. Soft lighting enhances the ambiance. A friendly dog sits on the gravel path, surrounded by lush greenery, indicating a tranquil forest setting.
Cottage in Jamaica
4.85 out of 5 average rating, 614 reviews

Cottage-Swim-View-Firepit-7min to Stratton-Dog OK

Authentic post & beam cottage surrounded by forest. Private location off a quiet road, 3 miles to Stratton Sun Bowl (a 7-minute drive). Nearby swimming hole at brook on property. Fire pit, propane BBQ, picnic table, spectacular Stratton Mountain view. Front porch & back porch with hammock, table & chairs. VCR/DVD & videos, boardgames & puzzles, kids toys, turntable & records, Satellite Internet & WiFi 20-100 mbps, TV & Roku. Gas heat, wood stove. Dog friendly.

Popular amenities for Jamaica pet-friendly home rentals

When is the best time to visit Jamaica?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$443 SGD$467 SGD$324 SGD$275 SGD$278 SGD$255 SGD$296 SGD$297 SGD$288 SGD$319 SGD$295 SGD$416 SGD
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Quick stats about holiday rentals that are pet-friendly in Jamaica

  • Total holiday rentals

    Explore 90 holiday rentals in Jamaica

  • Nightly prices starting at

    Jamaica holiday rentals start at $38 SGD per night before taxes and fees

  • Verified guest reviews

    Over 8,110 verified reviews to help you choose

  • Family-friendly holiday rentals

    80 properties offer extra space & child-friendly amenities

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wifi availability

    90 of Jamaica holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Jamaica rentals

  • 4.9 Average rating

    Jamaica stays are highly rated by guests – averaging 4.9 out of 5!

Destinations to explore

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