
Pet-friendly holiday rentals in Jamaica
Find and book unique pet-friendly homes on Airbnb
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 $51 NZD 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 and kid-friendly amenities

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wi-Fi availability
90 of Jamaica holiday rentals include Wi-Fi 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!
Top-rated pet-friendly home rentals in Jamaica
Guests agree: These pet-friendly homes are highly rated for location, cleanliness and more.

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.

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

Reillys Rest -GreenMtns! Secluded-Pet-Kid friendly
Reilly's Rest is a private home located on its own 6 acres in a prime location to SKI, HIKE, FISH, SWIM, KAYAK, WALK, + RELAX in the Green Mtns! 11/19 New floors-windows-appliances! The home is just 7 miles to Magic, 10-Bromley, 15-Stratton , and under 20 to both Okemo & Manchester. Reilly's Rest provides a peaceful + cozy stay on 6 acres with Mtn. views. Our Vermont contemporary-style home is sure to impress with warm wood interiors and an upstairs with open floor plan and beautiful views!

7min-Stratton Dogs OK Fire Pit EV Charger Arboreal
7min drive to pickleball, tennis, pool, golf, mountain biking and skiing @Stratton Resort. Soak up 13 acres of arboreal views from your private chalet. Light-filled w/ southern exposure. Deck and fire pit for stargazing, mid-century modern furnishings, new appliances, and 300Mbps Wi-Fi and a Mini Split AC/Heat. Convenient to ski areas, restaurants, shops, and swimming holes, yet secluded and quiet. Walk to Pikes Falls 29min to Bromley and Mt Snow AWD required for spring/winter. Pet fee $187.

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!

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

10 min from Stratton! Log Cabin w/ Beautiful Views
Spectacular views of Stratton Mountain! This cozy log cabin is set on 10 acres of land offering a quiet year round Vermont getaway. The home offers 3 bedrooms (all with mountain views), 2 baths and comfortably sleeps 7. Located 10-15 minutes from skiing (Stratton, Bromley and Magic), 25 minutes from shopping and dining in Manchester, and ½ mile from Gale Meadows Pond for hiking and water activities in the summer. If you’re looking for the ultimate Vermont experience, you’ve found your spot!

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

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.

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

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.

Cottage-7 min to Ski Stratton-Woodstove-View-DogOK
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
Pet-friendly house rentals

Clark Farm-2 Master-Suites, Great kitchen, views!

Hot Tub & Game Room - Ski Mt. Snow/Stratton

Modern 3-bedroom A-frame in Londonderry w/ Pond

MOUNTAIN NEST, views, Manchester, hot tub,

Comfortable farmhouse with stunning views

The Grafton Chateau

Wild Blossom Farmhouse - a lovely family getaway

Stylish Vermont Cabin | Views · Trails · Luxe
Pet-friendly home rentals with a pool

Magical Farm Getaway - a must visit!

Moon Valley Country Retreat no clean fee pets yes

Leonard’s Log - Private Hot Tub, Fire Pit, A/C

Beautiful rustic woods and fields retreat.

Cozy Vermont Antique Sugar House with Fireplace

“Sugar Maple” Rustic 4x4 Cabin Getaway, Fireplace

Mt Snow Chalet: Peaceful Escape w/Hot Tub

Hollywood Bungalow in the Berkshires #C0191633410
Private, pet-friendly home rentals

Stratton; 6 min. King beds. Game rm. Dog friendly

The King's Cottage

The Birchwood Cabin - Stunning Mountain Views

Shakespeare’s Folly Side Farm and AirBnB.

~Serene Barn Retreat~

2-Bedroom Home, 7 Minutes From Stratton Mountain

Private Hilltop farm apartment

Serene & Stylish Chalet w/ HOT TUB near Manchester
When is the best time to visit Jamaica?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $555 NZD | $598 NZD | $474 NZD | $366 NZD | $370 NZD | $339 NZD | $394 NZD | $395 NZD | $383 NZD | $424 NZD | $392 NZD | $554 NZD |
| Avg. temp | -5°C | -4°C | 1°C | 8°C | 14°C | 18°C | 21°C | 20°C | 16°C | 9°C | 4°C | -2°C |
Destinations to explore
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- Pet-friendly rentals Windham County
- Pet-friendly rentals Vermont
- Pet-friendly rentals United States
- Okemo Mountain Resort
- Stratton Mountain
- Saratoga Race Course
- Killington Resort
- Pats Peak Ski Area
- Berkshire East Mountain Resort
- Jiminy Peak Mountain Resort
- Monadnock State Park
- Magic Mountain Ski Resort
- Stratton Mountain Resort
- Six Flags Great Escape Lodge & Indoor Water park
- Pico Mountain Ski Resort
- Mount Snow Ski Resort
- West Mountain Ski Resort
- Fox Run Golf Club
- Bromley Mountain Ski Resort
- Hildene, The Lincoln Family Home
- Dartmouth College
- Montshire Museum of Science
- Emerald Lake State Park
- Mount Sunapee Resort
- Mount Greylock
- Southern Vermont Arts Center
- Camp Plymouth State Park




