Holiday rentals with a pool in Jamaica

Find and book unique homes with a pool on Airbnb

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Popular amenities for Jamaica rentals with a pool

House rentals with a pool

Top guest favourite
Home in Wardsboro
5 out of 5 average rating, 59 reviews

Hot Tub, Game Room, Minutes to Mt. Snow & Stratton

DanielRating, 5 stars1 week ago
We had a great vacation at Whitley’s Airbnb. The house was very clean, spacious, and provided lots to do. It was also great being so close to Mt. Snow. I highly recommend this house and would love to come back!
Guest favourite
Home in Salem
4.98 out of 5 average rating, 192 reviews

Magical Farm Getaway - a must visit!

BriannaRating, 5 stars2 weeks ago
We had a wonderful & relaxing weekend here with a large group for my sister's lowkey bachelorette party. Even with a day of non-stop pouring rain, we were perfectly content with staying in and enjoying the coziness of the house. We had a blast watching the chickens roam around and hanging out with the overly-friendly barn cats while we sat outside. The goats & pigs were happy to greet us at the fence every time. The hot tub and pool were perfect! Highly recommend staying here if you're looking for a beautifully scenic and peaceful getaway. Thanks, Sarah & BBVF team!
Guest favourite
Home in Colrain
4.9 out of 5 average rating, 129 reviews

The 1770 House

CatherineRating, 5 stars1 month ago
Historic house on a beautiful property. Kitchen had all the equipment you could need along with top of the line stove and oven. Make cooking for a large group easy and enjoyable!
Guest favourite
Home in Dover
5 out of 5 average rating, 15 reviews

Private chalet tucked in the green mountains

CarolineRating, 5 stars1 month ago
We had a wonderful weekend at Liz’s cabin. Everything was clean. Hot tub was awesome. Would recommend to anyone looking for a beautiful cabin getaway.
Guest favourite
Home in Keene
4.93 out of 5 average rating, 211 reviews

The Brick House on Washington Street

PaulRating, 5 stars1 week ago
Great stay and was exactly what we needed for our entire family for a weekend wedding!
Guest favourite
Home in Jamaica
4.96 out of 5 average rating, 25 reviews

Ski and tennis house by Stratton Ski Resort.

BillyRating, 5 stars4 months ago
We spent our winter break at Adam's condo. This condo experience had all the important Cs: Clean Condo - it was very clean upon arrival. Convenient Condo - the Stratton shuttle stops right outside the door. Communicative Condo Owner - any questions we had were answered in a timely manner. Cost effective Condo - great value Okay I went overboard with the Cs but honestly it was such a great experience. Adam is great host and the condo worked out perfect for us! Hopefully we get a chance to stay here again!
Guest favourite
Home in Plainfield
4.89 out of 5 average rating, 139 reviews

Historic Home on 17 acres of land. Go escape!

BrandieRating, 5 stars3 months ago
Staying here is always a joy for the entire family! It has become an annual tradition that we all look forward to in winter. Thank you for being so accommodating with our schedule and a special thanks to Mitchell for going the extra mile to snow blow a waking path for me and the dogs to keep our daily routine of visiting the horses, after the last storm brought over 13” of snow. P.S. the new stove/oven is amazing!! 🤩
Guest favourite
Home in Granville
4.94 out of 5 average rating, 105 reviews

Historic 1850’s Renovated Farmhouse w/ Pool!

KimberlyRating, 5 stars3 weeks ago
9 adults and 3 children all met up for a family weekend! We came from NY, NH and Maine! The house was perfect! Plenty of room to gather or separate! Even tho it was a chilly rainy weekend the kids managed to get in plenty of pool time! Tanya was very responsive and Melvin was the greatest! Our first morning he came right over to fix a slow drain. Highly recommend!! Kim and family

Apartment rentals with a pool

Guest favourite
Apartment in Killington
4.96 out of 5 average rating, 131 reviews

Dog-Friendly Mtn Escape/AC/Pool/

CarlaRating, 5 stars3 weeks ago
Great place! We enjoyed our stay so much that we extended it an extra day. Hosts made it super easy to extend.
Guest favourite
Apartment in Dover
4.83 out of 5 average rating, 108 reviews

Mount Snow Ski Chalet

BarryRating, 5 stars3 months ago
Great place to stay. There are no Ubers the week we stayed there and we should have rented a car. But the place was great.
Guest favourite
Apartment in Dover
5 out of 5 average rating, 17 reviews

Slopes N Seasons | Trailside Condo at Mount Snow

ConoRating, 5 stars2 days ago
I had a great experience at Erin's place. Everything about the experience was enjoyable. The home was well-stocked and beautifully decorated. Great little touches like a Bluetooth radio and record player were appreciated. The gym and pool amenities were pristine. We look forward to staying there again.
Guest favourite
Apartment in Dover
4.91 out of 5 average rating, 110 reviews

Seasons on Mt Snow Condo - Ski/Hike/Bike/Swim

MichaelRating, 5 stars3 months ago
We stayed at Julia's vacation rental for a 3-day weekend with our four children under the age of 12. The things that were great: 1) the unit is 150 foot walk in ski boots from a ski trail that will take you to the Mount Snow lift, which was great because we didn't have to shlep 4 kids ski gear, 2) the four kids loved the bunk bed room and were comfortable, 3) there are two large shelves of board games the kids enjoyed, 4) the access to the Sports Center which has a heated indoor pool and hot tubs were a great way to end the day after skiing, 5) the outdoor locker was a great place to dump all the ski gear (much better storage location than inside the car or inside the unit) and 6) very nice fluffy towels and bed sheeting was comfortable. A combined liquid shampoo and body soap is provided in each bathroom, which is the same that we use to bath our kids at home.
Guest favourite
Apartment in Dover
4.87 out of 5 average rating, 239 reviews

Mt Snow Ski In/Out at Seasons

MarkRating, 5 stars2 months 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.
Top guest favourite
Apartment in Stratton
5 out of 5 average rating, 44 reviews

Your Vermondo awaits: Steps to Lifts & Village.

ErinRating, 5 stars2 months ago
We really enjoyed our stay here with our 3 kids! The second bedroom was perfect with the trundle and the bunk beds. The condo was well maintained and exactly as described. The heated pool and hot tubs were great after a day on the slopes. We enjoyed the close walk to the lifts at Stratton as well as the walk to the village. Would highly recommend!
Guest favourite
Apartment in Stratton
4.9 out of 5 average rating, 20 reviews

Stratton Duplex Condo Steps to Lifts, Village!

NathalieRating, 5 stars2 months ago
Great walkable location. Loft space granted nice privacy for 2 couples or extended family. Fireplace and living room were cozy.
Guest favourite
Apartment in Peru
4.99 out of 5 average rating, 81 reviews

Summer in the mountains!

VincentRating, 5 stars3 months ago
Just as described in the listing, clean and comfortable, no surprises. We loved the how the slopes were literally right outside the back door. Made it really convenient both at the beginning and end of two great days of skiing!

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