
Waterfront vacation rentals in Jamaica
Find and book unique waterfront rentals on Airbnb
Quick stats about waterfront rentals in Jamaica

Total vacation rentals
Explore 20 vacation rentals in Jamaica

Nightly prices starting at
Jamaica vacation rentals start at G$29,282 GYD per night before taxes and fees

Verified guest reviews
Over 1,620 verified reviews to help you choose

Family-friendly vacation rentals
10 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
10 of Jamaica vacation 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 waterfront rentals in Jamaica
Guests agree: these waterfront rentals are highly rated for location, cleanliness, and more.

Lovers Honey Pond Treehouse with hot tub & sauna
Guest Favorite VERY romantic abode…The Honey Pond Treehouse is made for you and yours! It’s constructed of all natural materials, has breathtaking views, and is outfitted with absolutely everything you need! Lifted high over a stocked trout pond way up in the birch trees…Enjoy private hot tubbing, sauna time, swimming & hammock time. Skylight was designed for stargazing in bed!! Just minutes to the slopes or enjoy our own groomed trails for Xcountry & snowshoes & nature walks!! High speed WiFi 🐣

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.

Vermont Mirror House
Escape to our stunning glass house nestled in the Vermont forest. This modern retreat offers breathtaking 360-degree views of lush wilderness and beautiful waterways. Unwind in the hot tub, warm up by the cozy fireplace, or rejuvenate in the sauna. Floor-to-ceiling windows bring nature indoors! Perfect for romantic getaways, small families or simply work away from work with fiber wifi. Experience tranquility during all seasons in this one-of-a-kind hideaway. Book now for an unforgettable escape!

The House of Pi
Hot Breakfast and Lunch INCLUDED every day in your stay. Our general store will make you fresh egg sandwiches and coffee. Subs or pizza lunch. Welcome to Pi π aka Lakefront Loft. One of a kind custom built 34 foot high raised container home overlooking a beautiful southern VT lake with direct lakefront property with your own private dock. Our spacious home custom designed and built with 8 shipping containers boasts every amenity you want. 3 master bedrooms designed with amazing panoramic views.

~Luxury Tiny Cabin~
Enjoy an intimate weekend escape in our 400 sq ft Tiny Cabin, located in Southern Vermont! This Home overlooks gorgeous hardwoods and seasonal foliage. Listen to the sound of the brook bustling by while nestled on the spacious front porch, sipping a hot cup of coffee or cocoa! 'Tis the season for glamping and our luxury tiny home experience is just what the doctor ordered! Make sure to cross this off your bucket list; about 45 minutes from Mts Okemo and Killington, 5 minutes from local stores!

Cozy Riverfront Home in beautiful Jamaica
. Surrounded by tall pines and mountains, with the tranquil sound of the West River outside, here you can escape into nature while still enjoying all the cozy comforts of home. Our newly renovated home has been transformed into a getaway spot for romance, friends or family. The deck, set on the waterfront, is a beautiful, serene space to dine or take a soak in our wood burning hot tub. Put on some records, make a meal and cuddle up in front of the fire after a long day of playing outdoors.

West Wing at Mantana Meadows on the West River
Welcome to Mantana Meadows! This 1970's contemporary is able to allow large families and friends a great space to enjoy VT. We are centrally located in Vermont within a half hour of five great ski resorts and all of the shopping Manchester has to offer. The grounds are scenic and peaceful, and the back of the house is 25' away from the West River. Great for Spring, Summer, Fall and Winter recreation and relaxation. We've also got a high speed 50 amp 240 Volt outlet for EV charging!

50 Acres of solitude & 1/2 mile on the West River
A private oasis escape. Prindle Cottage is a 1,400sqft rustic countryside cottage nestled on 50 acres of historic farmland, offering captivating views that will impress first-time visitors. Cozy up by the fireplace with your furry friend, soak up the warmth in the sunroom, or explore the many trails along the West River. There are stunning long-range valley views that overlook the pastures, this pet-friendly cottage is the ideal retreat for both intimate getaways and grand gatherings.

Hillside Cottage @ The Mettawee Retreat
The Hillside Cottage is a luxury cabin with views of the Mettawee River. Located on 26 acres on a back road, it is peaceful & private. Enjoy fishing, swimming, kayaking or relax on the deck. This riverside retreat includes a king bed, jacuzzi tub & a kitchenette. Sitting around the fire pit with dinner cooked on the grill is the perfect ending to a long hike. Whether it’s a quick get-away or an extended vacation, the Hillside Cottage is a simple solution from a complicated life.

River House Apartment - Dog friendly
Entire downstairs of a house with one double bed. There is nice bathroom with shower. There is a microwave, coffee, massage chair, outdoor grill and picnic table. Internet and cable provided with fire stick for the TV. Fire pit and hot tub are shared by other guests. Up to three and all size dogs or pets are allowed and welcome. The three acres has a lovely place for them to run and has been sprayed for ticks and mosquitos. Please note: key replacement $30 if lost or taken

Kingsley Grist Mill Waterfall & Private Beach OMG
One of the "World's Most Amazing Vacation Rentals " as seen on the exciting NetFlix series, s.2, ep.7 and on HGTV's "You Live in What?, s.2, ep.1. Join us this season for the romance, the history, the breakfast, the natural mineral spring tap water, the concert, the rafting, the architecture and the legacy of the KGM, Vermont's Wright-esque falling water masterpiece. No cleaning fees added. Come make history with us ! Near Killington & Okemo Mtns.

The Writer's Retreat: A Sweetwater Stay
Located on the shore of Tully Pond, The Writers Retreat is a newly designed 325sqft lake side cottage with breathtaking views of Tully Mountain. This 4-season cottage is built with salvaged barn wood; up-cycled maple floors and custom built furniture and lighting. It's the little sister to The Fishing Cottage. You'll find this intimate home has everything you need to relax, write the next Great American Novel, connect with a lover, or just plain chill.
Popular amenities for Jamaica waterfront rentals
Waterfront apartment rentals

Cozy Brookside Getaway

**Happy Hour! Gorgeous & Modern Downtown Retreat**

49 River Street

Suite 23 - Spacious Sunny 2-BR with Mountain view

River View apartment

Globetrotter Retreat - Minutes to the Mountain

Unique historic remodeled Pub

River View Apt in Shelburne Falls Historic Village
Waterfront house rentals

Green River Cottage-A Peaceful Country Retreat

Cozy Riverfront Home, 1mi to Mt Snow, On Moover

Historic Mill • Near Okemo • Fireplaces • Wi-Fi

VT Cabin sitting above the West River and Village

Scenic Lake Front Home near Saratoga/Lake George

Vermont lake house near Mt. Snow-fab 360 views!

Lakefront A-Frame Home Emerald Lake, NY

Waterfront Cabin • Dock • Fire Pit • Kayaks & SUPs
Other waterfront vacation rentals

Stratton Summer House | Trails + Swim Holes + AC

Lakefront gem

Willow Tree Cottage on Peaceful Mountain Lake

Wishing Well Cabin

Cozy Cottage Loft and Retreat

Brook Haven Retreat - Minutes to Mt Snow&Stratton

Historic Riverfront 3BR Farmhouse, Pet-Friendly

Fjällstugan - 2 br cozy log cabin
When is the best time to visit Jamaica?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$66,513 GYD | G$65,886 GYD | G$56,473 GYD | G$44,760 GYD | G$50,199 GYD | G$49,571 GYD | G$51,872 GYD | G$48,525 GYD | G$47,061 GYD | G$52,290 GYD | G$50,617 GYD | G$59,402 GYD |
| 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
- Plainview Vacation rentals
- New York Vacation rentals
- Tuckahoe Vacation rentals
- Long Island Vacation rentals
- Montreal Vacation rentals
- Boston Vacation rentals
- East River Vacation rentals
- Hudson Valley Vacation rentals
- Jersey Shore Vacation rentals
- Philadelphia Vacation rentals
- South Jersey Vacation rentals
- Pocono Mountains Vacation rentals
- Chalet rentals Jamaica
- Family-friendly rentals Jamaica
- Cabin rentals Jamaica
- Rentals with a hot tub Jamaica
- Fitness-friendly rentals Jamaica
- House rentals Jamaica
- Rentals with a fireplace Jamaica
- Rentals with a fire pit Jamaica
- Rentals with a patio Jamaica
- Rentals with an EV charger Jamaica
- Rentals with outdoor seating Jamaica
- Pet-friendly rentals Jamaica
- Rentals with a sauna Jamaica
- Villa rentals Jamaica
- Rentals with a washer and dryer Jamaica
- Rentals with pools Jamaica
- Waterfront rentals Windham County
- Waterfront rentals Vermont
- Waterfront rentals United States
- Okemo Mountain Resort
- Stratton Mountain
- Saratoga Race Course
- Killington Resort
- Berkshire East Mountain Resort
- Pats Peak Ski Area
- Monadnock State Park
- Magic Mountain Ski Resort
- Mount Snow Ski Resort
- Pico Mountain Ski Resort
- Six Flags Great Escape Lodge & Indoor Water park
- Stratton Mountain Resort
- Jiminy Peak Mountain Resort
- West Mountain Ski Resort
- Hildene, The Lincoln Family Home
- Fox Run Golf Club
- Dartmouth College
- Bromley Mountain Ski Resort
- Mount Sunapee Resort
- Montshire Museum of Science
- Emerald Lake State Park
- Mount Monadnock
- Camp Plymouth State Park
- Southern Vermont Arts Center





