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Holiday rentals with a pool in Jamaica

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Jamaica

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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Guest favourite
Apartment in Dover
4.89 out of 5 average rating, 111 reviews

SKI IN/OUT @ Mount Snow (Hot Tub & Pool)

Escape to Seasons on Mount Snow & stay in our fully equipped 2 bedroom (ski in/out) condo. Our location is the best on the mountain ... right between the main face & Carinthia Freestyle Park! Enjoy the log burning fire (wood provided), smart TV & boardgames plus the fabulous Seasons on Mount Snow facilities where you can relax in a hot tub, pool or sauna. See below for info on activities in the warmer months including hiking, biking, scenic rides, lakes, golf, camp, a spa & the fall colors!

Guest favourite
Apartment in Dover
4.91 out of 5 average rating, 116 reviews

Base of M.S. All Seasons Fun. Deck/HotT/Pool/Sauna

Sunsil Loft @ MountSnow, your ideal Getaway. Walk to the Base. Unbeatable access to skiing, hiking, biking. Vermont never stops to surprise you with its outdoor adventures, great food and views. The loft offers a cozy gas fireplace, private deck. The kitchen has all you need to prep meals. You also have access to the pool (Summer), sauna, hot tub and GYM. Whether you’re skiing, hiking and biking in summer, or enjoying the fall foliage, our loft is your perfect home base in the Green Mountains.

Top guest favourite
The image displays a serene winter scene of a dark-green chalet nestled among snow-covered trees. Two sections of the interior show a cozy living space with modern leather furniture and a spacious dining area, both featuring large windows that bring in natural light.
Cabin in Wilmington
5 out of 5 average rating, 105 reviews

Mid-mod VT Dream Chalet near skiing, lake & forest

Surround yourself in nature and cozy modern comfort. The romantic mid-mod-styled chalet backs to 10 acres of peaceful forest yet is just 12 min drive to Mount Snow for great skiing. 3 min. to the boat launch of gorgeous Lake Whitingham where you can rent jetskis & boats or go swimming & fishing. Hike trails to the charming town of Wilmington with its coffee shops & restaurants. Pools & hot tub up the road at clubhouse. Just steps away from iceskating, pickleball, hiking & snowmobile trails.

Top guest favourite
The exterior of the chalet is shown in twilight, with soft light emanating from a window. The rustic wooden structure features a sloped roof and is surrounded by snow-covered ground and trees in the background.
Guest house in Granville
4.91 out of 5 average rating, 954 reviews

Moon Valley Country Retreat no clean fee pets yes

Unique centrally located, peaceful country chalet between the Adirondack and Green Mountains on 60 acres. Starlink available if your phone doesn't work here. Near Lk George, Lk Champlain, & VT. Hike, fish, swim nearby. Air conditioners on the main floor for the summer months. Our 9120 watt solar array powers our property. During the cold months enjoy the wood stove. All wheel drive a must in winter. We have a spacious deck by the shared pool, pergola, and a shady deck by the stream.

Top guest favourite
Apartment in Stratton
4.97 out of 5 average rating, 190 reviews

Premier Stratton Village Location - Pool & Hot Tub

-- Walk across the street to Stratton Ski Lifts -- Conveniently located near the Stratton Village, this condo places you at the center of all the mountain activities - skiing, mountain biking, events, weddings, shopping & dining. This updated studio includes gas fireplace, AC, stainless appliances, and nice décor. Long Trail House condos boasts underground heated parking, year-round outdoor pool with patio and multiple hot tubs, and sauna. Come visit and relax in the Vermont mountains.

Top guest favourite
Exposed wooden beams frame the room, complemented by warm brick walls. A cozy fireplace sits centered against the wall, with decorative art above it. A comfortable chair and lamp are positioned nearby, while a television and small dresser provide functional elements in the living space.
Cottage in Newfane
4.99 out of 5 average rating, 262 reviews

Cozy Vermont Antique Sugar House with Fireplace

Enjoy a peaceful and unique stay at this beautiful 1796 Sugar House. Luxury bedding, cozy fireplace, soaring timbers to a cathedral ceiling make this a special place. There is a Queen size bed on the main floor and twin beds in the sleeping loft accessible by a ladder. Try some of our wonderful local restaurants and shops. Lots of hiking trails to explore. Winter sports all around, or just enjoy some hot chocolate, a fire, and a good book. You are sure to enjoy the “Sugar House”.

Guest favourite
Apartment in Dover
4.92 out of 5 average rating, 105 reviews

MountSnow ski on/off condo in Vermont

Ski seasons just began Pool and Sports Center is open. Hours vary by day BBQ available for use by the outdoor pool pavilion On Mount Snow, Across from the Tin Lizzy trail leading to the Sundance Base Lodge and access to the Seasons Pass trail leading back to the condo. Very unique Condo in seasons as it has high vaulted ceilings. Condo is a 2 bedroom, 2 bathroom with 2nd bedroom on 2nd floor. Plenty of tennis and pickleball courts Best parking on the mountain

Guest favourite
A spacious log cabin home is showcased amidst a lush green landscape. The A-frame structure features large windows allowing natural light to enhance the interior. The wrap-around deck provides outdoor space for relaxation, while steps lead down to an area with garage access.
Cabin in Wardsboro
4.9 out of 5 average rating, 237 reviews

Log Cabin w/ Hot Tub & Fire Pit - Stratton/Mt Snow

Large Log cabin home located midway between Stratton Mountain and Mt Snow and near the town of Dover. There is plenty of space for you and your nearest and dearest in this 4 bed/4 bath home. Whether you are entertaining friends and family in the open-concept living and dining space, quietly curled up with a book in front of the cathedral fireplace, or enjoying a relaxing soak in the outdoor hot tub after a long day on the slopes—this place has something for everybody!

Guest favourite
A charming red cabin is nestled among lush green trees, surrounded by moss-covered ground. The exterior features multiple windows, allowing natural light to fill the space. A small shed is visible to the left of the cabin, enhancing the serene woodland setting.
Cabin in Guilford
4.95 out of 5 average rating, 180 reviews

Silver Brook Cabin

Waterfront setting in a relaxing, but convenient, location in southeastern Vermont. Photos and captions do the best job of describing our cabin, adjacent brook, and very nearby Green River with its covered bridge and swimming holes. The cabin is 20 minutes from Brattleboro with its many restaurants, shops, movie theater, and galleries. Not only is the immediate area wonderful for swimming, biking, and hiking, you can also simply relax with a good book or two.

Guest favourite
A living room features a large stone fireplace with a wood storage basket beside it. A comfortable sofa with decorative pillows faces a wooden coffee table. Natural light floods the space through a large window, complemented by a nearby area rug.
Apartment in Dover
4.87 out of 5 average rating, 247 reviews

Mt Snow Ski In/Out at Seasons

Directly on the mountain. Minutes walk to 2 trails. Full kitchen, dishwater, washer/dryer, microwave. Fireplace with free wood. Large screen TV in living room and tv in each bedroom. Plenty of board games. King size bed in Master. Free parking for 2 cars. Ground floor with deck with tables and chairs for relaxing. Free parking. The pool (indoor & outdoor) and hot tubs are free to renters as is fully equipped gym (all year) and tennis courts in summer.

Top guest favourite
A red wooden cabin nestled among trees, showcasing a welcoming front porch. Air conditioning units are situated to the side. Natural light filters through the foliage, creating a serene and shaded outdoor atmosphere.
Barn in Newfane
4.98 out of 5 average rating, 166 reviews

Beautiful rustic woods and fields retreat.

Within the Fritz Conference Center, tucked into the beauty of the Vermont Countryside, is this charming apartment/ mini house. Part of a renovated 19th century barn it is the perfect getaway. It sits on over 33 acres of fields, woods, apple orchard and Mountain View’s. 2 miles from historic Newfane Vermont, you are able to enjoy privacy, while close to the many attractions of the area. We are also dog friendly. There is an extra fee of $50 per trip per dog

Top guest favourite
A spacious living area features a large sectional sofa adorned with cozy throw pillows, complemented by a textured area rug. Natural light pours in through expansive windows, enhancing the inviting atmosphere. A side table and a plush armchair add to the comfortable seating options.
Apartment in Dover
4.99 out of 5 average rating, 125 reviews

Winter Dream! The Handle Lodge at Snowtree Condos

The Handle Lodge at Snowtree Condos is a modern 1BR condo at the base area of Mount Snow. Comfortably sleeps 6 adults and is fully equipped with everything you'll need for a fun getaway with friends and family. Make a meal in the beautiful kitchen or step out on the balcony for stunning mountain views. Our modern and cozy decor, the lovely views, and proximity to the mountain make it a great place to relax and recharge.

Popular amenities for Jamaica rentals with a pool

Quick stats about holiday rentals with a pool in Jamaica

  • Nightly prices starting at

    Jamaica holiday rentals start at € 212 per night before taxes and fees

  • Verified guest reviews

    Over 120 verified reviews to help you choose

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Jamaica rentals

  • 5 Average rating

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

Destinations to explore

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  4. Windham County
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