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Ski-in/Ski-out holiday rentals in Caribbean

Find and book unique ski-in/out homes on Airbnb

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Popular amenities for Caribbean ski-in/out rentals

Ski-in/out house rentals

Superhost
Home in Punta Cana
4.78 out of 5 average rating, 18 reviews

Villa Lovely with Private Pool

ArgenisRating, 5 stars2 months ago
Great place to stay!!
Superhost
Home in Monteverde
4.85 out of 5 average rating, 200 reviews

Natural Wonders House: Where nature awaits you!

LynsieRating, 5 stars2 weeks ago
Great space for a visit to Monteverde. The surroundings are great. The distance to the downtown area is not far, but it is very hilly. So not walkable if you are not able to walk many steep hills. But the drive is easy enough. We enjoyed the wildlife around the house as well. Daniela was a great host and very helpful with recommendations.
Guest favourite
Home in Cape Coral
4.97 out of 5 average rating, 161 reviews

“Cape Paradise”Waterfront.GulfAcc.Jcuzi.Heat Pool.

MelissaRating, 5 stars3 weeks ago
We had a great week at Marcella & Mo’s house. Plenty of room for 6 adults (3 couples), kitchen was well stocked with pots & pans, plates, glasses etc. We enjoyed the lanai with the pool and hot tub a lot. We went for bike rides and took the kayaks out, all in good condition. We had fun exploring the area and most things are just a short drive away. We wouldn’t hesitate to rent again!
Superhost
Home in Las Terrenas
4.72 out of 5 average rating, 139 reviews

Villa El Esfuerzo Las Terrenas 10 minutes from the beach

WilliamRating, 5 stars1 month ago
We had a very good experience in this stay. Very good location, about 10 minutes from the different beaches, a spacious and cozy place, excellent host, always available and attentive. I recommend it 100%
Guest favourite
Home in Alajuela
4.93 out of 5 average rating, 348 reviews

Casita Tio Juan Airport Int. a 15 minutos

JacquesRating, 5 stars2 weeks ago
Perfect accommodation super equipped and comfortable and very good communication with Rodney
Superhost
Home in Bradenton
4.86 out of 5 average rating, 14 reviews

Now Booking for Summer! Pool/Close to Beach!

MandyRating, 5 stars1 month ago
It was spring break so traffic time to beach was a lot longer than expected. House was great. Pool wasn’t warm but weather was great so not a big deal. Communication was great.
Top guest favourite
Home in Fort Lauderdale
4.96 out of 5 average rating, 46 reviews

Tropical Heated Pool Home,Welcome to Palm Terrace!

AnnetteRating, 5 stars2 weeks ago
My mother died and her funeral was Easter Weekend. My daughters and I needed a place that would fit us all and cozy enough to stay around. The pool was gorgeous and clean and the house had so much room. Lots of essentials we needed to cook with. We loved staying there as sad as the occasion was and felt right at home. We would stay there again.
Guest favourite
Home in TC
4.9 out of 5 average rating, 20 reviews

Harbour House - 2 Bed Waterfront; 7 Min to Beach

EricaRating, 5 stars2 months ago
This place was beautiful my husband and I stayed here for Valentine’s Day the view was beautiful and the people friendly

Family-friendly, ski-in/out home rentals

Superhost
Guest suite in Havana
4.94 out of 5 average rating, 31 reviews

Cojimar Le Garage, Habana, Cuba.

Brenda And OrlandoRating, 5 stars12 months ago
Too bad we only stayed one night. Felipe and Roxana were very flexible to authorize us 11 am the check-in time that is usually at 3:00 pm. When both Felipe and Roxana arrived, they gave us the key and made us feel right at home. We loved the place. It is very cozy, spacious and extremely clean in all areas. The photos are as posted and the place is very private separate from the hosts house, but next door. They were immediately available to us to have any need. We will truly come back to stay immediately we return to Cuba!
Superhost
Cottage in Hatillo
4.59 out of 5 average rating, 110 reviews

Holiday Villa in Bahia de Ocoa

ElerisRating, 5 stars2 months ago
Excellent place …super nice for the price !!
Superhost
Apartment in Havana
4.67 out of 5 average rating, 9 reviews

Calixto and Judith excellent service and cleanliness.

BélaRating, 5 stars22 months ago
I am very happy that we were able to find a place where we had a great time in Havana, Cuba. And our host Calixto was particularly appealing. Looks like it really provided a nice, memorable moment. Spending a good time in a home is extremely important and Calixto's hospitality skills contributed a lot to that. Their kindness, kindness, and availability were probably critical to making us feel at home and find everything we needed. The accommodation was of high quality where all our basic needs were met and we were able to relax and recharge between explorations. Havana in Cuba is an exciting city and I'm sure you found a lot of interesting sights and experiences. The excellent location of the property allowed us to easily explore the city and access cultural and historical sites. We thank Calixto and his wife for everything.
Superhost
Flat in Aguadilla
4.79 out of 5 average rating, 29 reviews

Caribe Apt

DavidRating, 5 stars2 months ago
love this place. hope to visit again real soon to this apartment.
Top guest favourite
Casa particular in viñales
4.96 out of 5 average rating, 524 reviews

Casa Omar y Mayra,the best option

SamRating, 5 stars3 weeks ago
We are so incredibly happy we stayed here, with Omar, Mayra and their daughter Laura. They were very generous, kind and friendly. You feel instantly comfortable and welcomed amongst them. You can book all activities and taxis through them, and have fantastic meals. The accommodation is very well located and well kept. This casa is top quality, and we highly recommend staying with this lovely family!
Guest favourite
Casa particular in Vinales
4.77 out of 5 average rating, 118 reviews

Complete 3 Bedroom House Gilbe & Maicela.Wifi Free

ElizabethRating, 5 stars4 weeks ago
I was at Don Gilberto's house for the second time I returned to try the satiation of his wife Maricela the installation very clean the surroundings and exterior always leave you fascinated with that beautiful view that has the countryside that makes you contemplate a delicious Cuban coffee I recommend that they pass and meet these people so humble transparent and exceptional 100% recommended

Ski-in/out cabin rentals

Cabin in Juan de Acosta
5 out of 5 average rating, 4 reviews

Cabaña el Atardecer (Juan de Acosta)

Dominga IsabelRating, 5 stars2 weeks ago
Hello… Definitely the Accommodation of my Family in the El Atardecer cabin and with the Host Lizbeth was a wonderful EXPERIENCE, regarding the location it was very easy to find, the place was found clean, neat and very organized, the place met our expectations as it was the same as the public photographs, communication and telephone interaction with the host was always proactive, the area, the neighborhood and the safety of the cabin was safe, private/quiet and finally the value for money was worth it, you also have all the kitchen, utensils and appliances to meet the needs of a full family and including small children, so much so that I would return to the place!!! Recommended.
Cabin in Guachaca
New place to stay

Bobinsana Cabin. ancestral medicine ambiwasi

LeonRating, 5 stars3 weeks ago
German treated us as brothers. thousand thanks for the time in your house!
Guest favourite
Cabin in Sierra
5 out of 5 average rating, 6 reviews

cabin costa del yugo

MommoRating, 5 stars1 week ago
We booked this little house before going to Monteverde NP and it was very much worth it. The location is on a hill so a decent car is advised, the views are amazing, Mari was there to welcome us and show us the lock for the gate, the views are amazing, there is a bit of street noise but it didn't bother us too much, and also: the views are amazing! Really!
Superhost
Cabin in El Porvenir
5 out of 5 average rating, 4 reviews

San blas Sunken Boat Island Private Room

AdrianaRating, 5 stars2 months ago
The island is really very small, but just as advertised it was possible to stand on the side a little hectic or totally isolated. All were polite and helpful, including Omaira asked if they wanted to make the available tours on the other islands. The food is simple but delicious, everything was exactly as I wanted. Omaira advised me to stay in Panama City due to the arrival time of my flight and it was great, as I met Panama viejo and I really liked it.

Destinations to explore