The Allesandra property was beautiful with the absolute best views! It was very well stocked and had everything you might need and then some. Our trip was a family vacation with multiple adults so the availability of the cottage with 2 extra rooms was very convenient. The property management team at Carefree Getaways was fabulous! Cindy truly made our trip Carefree; when we had an issue at the property she took care of it immediately and did not let it interfere with our good time! I would recommend this property and team to anyone looking for a beautiful home with incredible views from every balcony, a great indoor space, an even better outoor space, and a property management team who will do everything possible to give you the best experience on their amazing island!!

We had a fantastic family gathering lasting 8 nights at the gorgeous Allesandra! This house has everything you need for groups as large as 8 adults and the pool area , overlooking Cruz Bay, is a real beauty. Carefree Getaways, the managers of the property, were great to work with. Highest recommendation!

This was an amazing rental more than equipped with everything you would need to make your stay wonderful! So much room and the beds gave us the best nights sleep! The view was breath taking, the sunsets from the balcony was spectacular. The property managers responded very fast with any need also.

This was an amazing rental more than equipped with everything you would need to make your stay wonderful! So much room and the beds gave us the best nights sleep! The view was breath taking, the sunsets from the balcony was spectacular. The property managers responded very fast with any need also.

Absolutely thrilled. Carefree Getaways was very communicative and the young person who brought us to the house was a doll. Nakira was so kind. We will be back to the Allessandra! Having my family with me was perfect!

Great for a group, the kitchen setup suited us well for preparing our meals. We enjoyed dining poolside on the patio at sunset; view was spectacular. Hot tub after hiking was great. Well maintained, well equipped and very comfortable overall.

This was the 26th year for us on island but the first time at Alessandra. We always look for great outdoor space and an amazing view. Alessandra did not disappoint. The view over Great Cruz Bay to St James and St Thomas was amazing and the pool and hot tub were awesome. The villa was clean, the beds comfortable, and the kitchen well stocked. The added bonus of cable TV was mitigated by a remote that was persnickety. The booking and check-in was great, as someone met us at the house. There is ample parking for 2 Jeeps and easy access to Starfish, Cruz Bay, North Shore beaches. We were 3 couples and I would definitely stay here again.

The villa is situated in an ideal location. It was pretty close to Cruz Bay, driving wise. Located up high with a wonderful view to the west. As others have expressed, would recommend a jeep four wheel drive for use on the island. Location is excellent for sunset viewings. It is very private with no neighbors within view and eerily quiet. The views from the infinity style pool as well as the hot tub were marvelous. The whole outdoor area is wonderful and the main selling point for me. The outdoor table area is covered and has a lovely ceiling fan over it. The grill is nearby for cooking out and the door connecting to the outdoor area via the master bath is very convenient for quick showers after pool or hot tub. The master bedroom was very comfortable and having a/c in each room was appreciated as it does get hot inside. There are many ceiling fans throughout that aid in cooling as well. The beds and linens were excellent, however, can only comment on master as there were only two of us using the villa. The kitchen is very serviceable. We cooked all breakfasts, made all lunches, and ate almost all dinners at the villa. Having a refrigerator with an icemaker was a plus. We used the outdoor beach chairs every day, only two have buckles that work to hold the chairs together for ease of carrying. A beach umbrella would however, be a nice addition, as there is not one. There are enough beach towels. The game area on the lower level was also pretty cool. If our kids had been with us, I know they would have really enjoyed this area as well. It was a nice surprise. I would come here again simply because the outside is so wonderful.

What a place.! The view is incredible, the Villa spacious and the staff were wonderful. We had a perfect stay.

Great view over Cruz Bay, located close to supermarkets and restaurants/bars. Beautiful pool and the house had everything you need. 10-15 minute drive to the north shore beaches. Everything you are looking for from an amenity and location perspective.

My wife and I stayed here for a week on our honeymoon, and it exceeded our expectations. The pictures don't do the view justice, it is absolutely stunning and didn't lose any of it's impact as the week went on. The amenities were also impressive for being on the top of a hill in an isolated Caribbean paradise: solid internet, A/C, fairly large pool, hot tub, wireless speakers, and an entertainment center (which we didn't use, but nice to have). Definitely recommended. There were only two of us, but the property is definitely large enough to accommodate larger groups. It also has another small deck underneath the main deck with hammocks, chairs, and a ping pong table. Carefree Getaways did a great job communicating with us and getting us settled in. It's also worth noting that the pool, hot tub, etc. are private and not shared with any other units. The property is quite private, except for some sight lines to the neighboring house through the trees. Bonus: fresh limes in the surrounding trees.