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Allesandra - Expansive Views - All A/C - 4 Bedroom villa. Pool-Spa!

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Dates still open!! All A/C- 4 bdrm pool villa w/ spa, views and privacy
Views of Chocolate Hole, Great Cruz Bay, the St james Islands and St Thomas.
The private allows plenty of parking. Stairway to 3rd bedroom suite.
Views from Allesandra over Flamboyant Tree.
Air-conditioned great room on pool deck level. Master bedrooms on opposite sides

Reviews

10 out of 10
Exceptional

Highlights

  • The great outdoors
    Guests love the outdoor space here.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
4 bedrooms4 bathroomsSleeps 8

Popular amenities

  • Private pool
  • Onsite parking available
  • Kitchen
  • Washing machine
  • Air-conditioning
  • Barbecue

Explore the area

View map
Cruz Bay, St John

Rooms & beds

4 bedrooms (sleeps 8)

Bedroom 1

1 King Bed

Bedroom 4

1 Queen Bed

4 bathrooms

Bathroom 1

Toilet · Shower only

Bathroom 2

Toilet · Shower only

Bathroom 3

Toilet · Shower only

Bathroom 4

Toilet · Shower only

Spaces

Deck or patio
Porch or lanai
Kitchen
Balcony
Garden
Dining area

About this property

Allesandra - Expansive Views - All A/C - 4 Bedroom villa. Pool-Spa!

Villa Allesandra has a level floor plan with 2 air-conditioned King Master bedrooms in the main house and a separate air-conditioned Garden cottage with 2 more bedrooms.

The rates are determined by the number of bedrooms needed.
(i.e. 4 guests using 3 bedrooms - the 6 person rate applies).

The greatroom has AC and the villa has 4 flat screen TV's, 20' x 16' pool, 6 person spa, lower level has a 20' x 20' covered play area with ping-pong table, games and sky bar. Separate laundry room. Luxurious tropical plantings including orchids, lime trees, bananas, jasmine, hibiscus, tai, flamboyant, ferns and many more. Peaceful setting, great views!
Please note rates are; Jan. 2 - April 30 2 pp $4900/ 4pp $5600/ 6 pp $6300/ 8pp $7000 May 1 - Dec. 18 2 pp $3500/ 4 pp $4200/ 6 pp $4900/8 pp $5600.

Add dates for prices

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House Rules

Check in after 3:00 PM
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted

Important information

You need to know

Property # 729405vb
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has not indicated whether there is a smoke detector on the property

About the area

St. John

Located in St. John, this villa is in the city centre. Blackbeard's Castle is a notable landmark, and the area's natural beauty can be seen at Virgin Islands National Park and Cruz Bay Beach. Discover the area's water adventures with jet skiing and kayaking nearby, or enjoy the great outdoors with hiking/biking trails and mountain climbing.
View more Villas in St. JohnOpens in a new window
Map
Cruz Bay, St John

Getting around

  • St. Thomas (SPB-St. Thomas Seaplane Base) - 60 min drive

Restaurants

  • ‪Woody's Seafood Saloon - ‬7 min drive
  • ‪Cruz Bay Landing - ‬7 min drive
  • ‪The Longboard - ‬7 min drive
  • ‪Morgan's Mango - ‬7 min drive
  • ‪Greengo’s - ‬7 min drive

Frequently asked questions

Does Allesandra - Expansive Views - All A/C - 4 Bedroom villa. Pool-Spa! have a pool?

Yes, this property has an outdoor pool.

How much does it cost to stay at Allesandra - Expansive Views - All A/C - 4 Bedroom villa. Pool-Spa!?

As of 17 June 2026, prices found for a 1-night stay for 2 adults at Allesandra - Expansive Views - All A/C - 4 Bedroom villa. Pool-Spa! on 3 August 2026 start from NZ$1,421, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Is Allesandra - Expansive Views - All A/C - 4 Bedroom villa. Pool-Spa! pet-friendly?

No, pets are not allowed at this property.

How much is parking at Allesandra - Expansive Views - All A/C - 4 Bedroom villa. Pool-Spa!?

On-site parking is available at the property.

What time is check-in at Allesandra - Expansive Views - All A/C - 4 Bedroom villa. Pool-Spa!?

Check-in begins at 3:00 PM.

What time is check-out at Allesandra - Expansive Views - All A/C - 4 Bedroom villa. Pool-Spa!?

Checkout is at 10:00 AM.

Where is Allesandra - Expansive Views - All A/C - 4 Bedroom villa. Pool-Spa! located?

This family-friendly villa is located in the city centre, within 1 mi (2 km) of Chocolate Hole Beach, Sunset Beach and Great Cruz Bay. Virgin Islands National Park is 1.7 mi (2.7 km) away.

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 25 out of 27 reviews
Rating 8 - Good. 2 out of 27 reviews
Rating 6 - Okay. 0 out of 27 reviews
Rating 4 - Poor. 0 out of 27 reviews
Rating 2 - Terrible. 0 out of 27 reviews

9.6/10

Cleanliness

9.8/10

Check-in

10/10

Communication

10/10

Location

9.6/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Leslie M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Aside from the refrigerator having to be replaced, the villa was very nice. Beds were comfortable and the rooms were clean and spacious. We enjoyed the pool and hot tub every evening! The views were spectacular!! We would highly recommend staying at this property.
Stayed 7 nights in May 2026
Verified

8/10 Good

Lisa H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The view was great. We were met by Nakira and she showed us around the property. The house was clean but needs some maintenance and updating
Stayed 7 nights in Nov 2025
Verified

10/10 Excellent

JOHN C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect stay

The communication was perfect. The house had the best views ever. Saint John is an amazing Island.
Stayed 7 nights in Jan 2025
Response from VrboOwner on 29 January 2025
Glad you enjoyed our island of St John and hope to see you again!
Verified

10/10 Excellent

Alastair I.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing Stay

Can't think of a single negative thing to say about Villa Allesandra. Amazing view, great pool and hot tub, shaded dining area, separate master suites on opposite sides of the house, close to town, private and secluded, fully stocked including beach gear. This was our fourth time on St. John and Allesandra was by far the best rental we've had. We hope to be back!
Stayed 7 nights in Mar 2025
Verified

10/10 Excellent

Maureen H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Awesome property for a memorable vacation

Our family of 6 adults thoroughly enjoyed our week at Allesandra. The view from the home is even better than pictures can capture, and the surrounding gardens make for a beautiful setting. We cooked in most of the time and we found everything we needed in the well equipped kitchen. We loved the pool, hot tub, and long evenings playing cards and games in the air conditioned great room. The staff from Carefree Getaways were super about proving information at every step of the process and responded quickly to any question or need.
Stayed 7 nights in Jun 2025
Verified

10/10 Excellent

Frankie R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing property!

This property exceeded our expectations. It was clean, comfortable, and very well equipped. The views were breathtaking from every room. We totally enjoyed our stay at Alessandra and look forward to staying there again in the future.
Stayed 7 nights in Apr 2023
Verified

10/10 Excellent

Cindy K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fantastic view, great for group, nice amenities

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.
Stayed 6 nights in Feb 2022
Response from VrboOwner on 21 August 2023
We were glad to be your hosts and you enjoyed your stay at Allesandra and our island of St John!
Verified

10/10 Excellent

Caleb B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Christmas Vacation

The house was perfect. Fantastic outdoor space, plenty of comfortable beds. Not too far from town for dinner in the evenings. Would certainly come back.
Stayed 7 nights in Dec 2023
Verified

10/10 Excellent

john k.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We were a group of three couples staying for a week in Jan'26. Host was very good with communication from the start and had lots of suggestions. Property manager met us at house to provide quick summary and answer any questions we had. House was great and the view is amazing. Had lots of beach towels and chairs to use. Nice open kitchen/living area. Two large rooms off the main area and then a wonderful deck and pool area. Another two-bedroom cottage a short walk away from main house. Definitely need a car! Grocery store nearby, and it was a short drive or taxi to Cruz Bay. We drove to beaches mostly but would cab into Cruz Bay for dinner. Definitely take the property manager up on leading you to the house, we had a hard time finding it. During our stay we heard from the property manager a few times to check in. Check in and out process really easy. Quiet neighborhood.
Stayed 7 nights in Jan 2026
Verified

10/10 Excellent

Ralph A.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great location, beautiful home!

Allesandra checked all the boxes for us and our adult children! Very well stocked kitchen, pool floats, snorkel gear, coolers, linens, etc. Loved every minute of our time in St. John, & the house exceeded our expectations 💕
Stayed 7 nights in Jan 2023
Response from VrboOwner on 21 August 2023
It was a pleasure to be your hosts here on St John for your vacation!
Verified

10/10 Excellent

Joseph K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great view

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.
Stayed 6 nights in Jul 2021
Response from VrboOwner on 21 August 2023
So glad to have you as our guests to enjoy Allesandra and our island of St John!
Verified

10/10 Excellent

Donna Z.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fantastic!

Beautiful property, location and view is amazing, perfect for sunset viewing. Plenty of space, game space is a bonus. Had a great time, can’t wait to go back!
Stayed 10 nights in Mar 2023
Verified

10/10 Excellent

Tina R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Total Paradise

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.
Stayed 8 nights in May 2022
Response from VrboOwner on 21 August 2023
Good Morning Tina, It was a pleasure hosting you at Allesandra and on our island of St John!
Verified

10/10 Excellent

Jody S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fantastic week at Allesandra!

Our group of six spent so much time enjoying the view, pool, and hot tub. We prepared most of our meals in the kitchen and ate all of them outside. The management staff was quick to solve a few maintenance issues. The location was quiet and convenient.
Stayed 7 nights in Mar 2023
Verified

10/10 Excellent

Lillian a.

Liked: Cleanliness, communication, location, listing accuracy

A wonderful villa

Sunset views of Chocolate Hole at night and the harbor during the day. The house was everything and more than we could have hoped for. Well-stocked kitchen, comfortable beds, lots of beach chairs and snorkeling equipment. The pool and hot tub were in use all the time. We spent most of our time at the outdoor table which overlooks the pool. Lounge chairs at the pool were comfortable in both sun and shade.
Stayed 7 nights in Feb 2023
Verified

10/10 Excellent

Christopher D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

What a View!

Our family of seven, ages 18 and up, had a fabulous week here. The house had everything we needed and we spent quite a bit of time lounging by the pool or in the hot tub. The location is great for access to Cruz Bay and the beaches. The beds were comfortable and the kitchen had everything we needed for preparing meals at home. Best of all is the view! Wow! We have rented houses in St. John several times, and Allesandra has far and away the best and most panoramic view we’ve experienced. Highly recommend!
Stayed 7 nights in Aug 2023
Verified

10/10 Excellent

nancy r.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great View

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.
Stayed 8 nights in Jan 2022
Response from VrboOwner on 21 August 2023
We enjoy hosting guests in our villas to enjoy our island of St John!
Verified

8/10 Good

Lynn W.

Liked: Cleanliness, check-in, communication, location
Disliked: Listing accuracy

Million Dollar View

Alessandra is a lovely place for adult couples to come to. The view is to die for. The outside deck area is great because it supplies shade.However, the house is in need of a facelift. there are many things that are corroded, missing or don’t work properly. In all fairness, I did try to reach out to the property manager discuss this with her before posting this, but I never got a call back. Hopefully they will start to address these issues as it is a lovely place to stay and we enjoyed our time very much. If this sort of long in the tooth older type of home doesn’t bother you then you’ll have an absolutely wonderful time. But when you go into VRBO website and it says 10 as the overall rating, as far as the house is concerned that is simply not the case.
Stayed 7 nights in Mar 2025
Verified

10/10 Excellent

Susan W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Delightful vista, amazing sunsets

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.
Stayed 7 nights in Oct 2021
Response from VrboOwner on 21 August 2023
Good Morning Susan, So glad you enjoyed Allesandra and our island of St John! Carefree Getaways on St John
Verified

10/10 Excellent

Rebecca W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Christmas Delight

Our family of 5 had a wonderful vacation! The house was exactly as listed, and the view was breathtaking. Clean, convenient, well-appointed kitchen, comfy beds, plenty of linens, and more! I would love to return again next year!
Stayed 7 nights in Dec 2022
Verified

10/10 Excellent

Stephanie W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Allesandra/St John USVI family vacation

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!!
Stayed 7 nights in Dec 2022
Verified

10/10 Excellent

Matthew W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Gorgeous property, fabulous time!!

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!
Stayed 8 nights in Aug 2022
Verified

10/10 Excellent

Jim A.

Liked: Cleanliness, check-in, communication, location, listing accuracy

It was an amazing experience! Allessandra is a ten! Comfortable and clean with exotic views!

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!
Stayed 8 nights in Apr 2022
Verified

10/10 Excellent

Pat B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Allesandra Villa

What a place.! The view is incredible, the Villa spacious and the staff were wonderful. We had a perfect stay.
Stayed 6 nights in Jul 2021
Archival

10/10 Excellent

Dan v.

Outstanding property

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.

About the host

Hosted by Carefree Getaways

Host profile image

What makes this property unique

Allesandra offers a great location, pool, spa, table tennis and private gardens. Air-conditioned great room and 4 A/C bedrooms. Paved road access. The views are endless and privacy as if you were the only villa in the area.

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English
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