Vacation rentals in Windward Side

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Top-rated vacation rentals in Windward Side

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Apartment in Oranjestad

5 out of 5 average rating, 3 reviews

A Quiet Getaway #2

StephannRating, 5 stars1 week ago

Zevers and Charlisia were excellent at communicating with us, especially given the ferry to Statia broke down and was cancelled on the day of our checkin. Despite this, they were flexible and accommodating. The apartment itself was beautifully furnished and extremely comfortable. We wish we could have stayed longer!

Top guest favorite

Home in Windward Side

4.9 out of 5 average rating, 41 reviews

Beautiful traditional Saba Cottage

EfratRating, 5 stars1 week ago

Great stay at Saba. Exactly as described, clean and comfortable. This Airbnb goes the extra mile with providing 2 sets of towels and beach towels. I highly recommend this stay as an alternative to a hotel - it is located around the corner from a supermarket, restaurants and SeaSaba dive shop. You can organize a dive and get picked up straight from the shop with no extra cost. There are also trails that start close by. Special surprise: there is a museum and a playground adjusted to the backyard with chickens and bunnies running around. This was a dream for our 4 year old and although Saba is not the easiest place to travel with kids, I found that Michal’s place, it’s surroundings and friendly neighbors made it an unforgettable experience for all 3 of us.

Guest favorite

Vacation home in Windward Side

4.93 out of 5 average rating, 54 reviews

Peter Hytte by Althea

ChristopherRating, 5 stars2 weeks ago

Jeff’s place is clean, practical, and perfectly located in Windwardside—just steps away from markets, restaurants, bars, a dive shop, and a trail shop. In less than 2 minutes we were on the trails to Mount Scenery. Jeff is a professional and thoughtful host; he arranged our airport transfers and was always available to answer questions. Saba is a beautiful island, and Jeff’s place was the perfect home base for our stay.

Apartment in Oranjestad

4.8 out of 5 average rating, 5 reviews

George's Petite Studio Apartment - St. Eustatius

ArjanRating, 5 stars26 months ago

Comfortable and clean apartment in a quiet area, but still close enough to shops and not far from the old center. The owner was very helpful. The apartment was well equipped for the almost two weeks I stayed here, with a clean and useful kitchen, washing machine and great airconditioning. I highly recommend staying here.

Villa in The Bottom

5 out of 5 average rating, 5 reviews

Magnificent private hilltop villa on magical Saba

JohnRating, 5 stars2 months ago

Haiku House on Saba is a gem. We stayed a week and with our family and it was fabulous. The view is fantastic and the house has all the amenities you could ask for. Assistance was always available from the property manager who was very responsive. Would highly recommend.

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What guests are saying

2B - EUX. Home Away From Home (St. Eustatius)

4.67 out of 5 average rating, 12 reviews1 month ago

My stay at the airbnb was amazing! At arrival Georgine’s dad picked me up from the airport and helped me to check in. Georgiane is an amazing host. She responds quick and helps where needed. The studio was very clean and well kept. I even got cleaning service during my stay. So it was a very pleasant stay for me!

Private room in Oranjestad

What guests are saying

Safe, Scenic, Serene Getaway!

4.38 out of 5 average rating, 8 reviews124 months ago

The place is very nice, the house is quite sharme and Darlene was very helpful and friendship. It was an opporunity to get a better touch of the island. The house is very near the Quill mountain, and I was climbing it on Saturday. I hope to come back soon. The house is up in the hill so you have to climb a little bit, but you have a very nice view of the Caribbean and the nearby islands

Home in Sint Eustatius

What guests are saying

Townhouse in the historical heart

4.38 out of 5 average rating, 21 reviews1 month ago

I stayed here for 5 nights in Statia and really couldn't have asked for a better place to both get some remote work done and to use as a base for exploring the whole island. It has excellent consistent 21 Mbps download speed wifi which is lightning fast for this part of the Caribbean! It's a spacious house with a bathroom, 3 bedrooms (one has an office), master bedroom with AC, a small kitchen (kettle, microwave, stove, fridge), kitchen table and a living room with TV. The location is perfect, right in the core of Oranjestad - almost any restaurant or tourist attraction is within a 10-15 minute walk. Very easy to find and check in and out with a lock box. I really loved both St Eustatius and this accommodation, and hope to return to both one day!

Home in Oranjestad

What guests are saying

House on The Path

4.62 out of 5 average rating, 29 reviews1 month ago

We loved our stay in a 1500 year old little cottage in the middle of the rainforest. The sink for rushes was outside, which we loved it is like going back in time. We had a torch to walk the stairs to windwardside which is really neccesary. And you have to take something for musquoti’s with you. But we loved the stay, sitting on the veranda hearing the birds seeing the beautiful lush green! Would definetely come back when we are on Saba

Cottage in Windward Side

What guests are saying

Budget Double Room

4.79 out of 5 average rating, 24 reviews2 weeks ago

I had a great time staying at Carmen's/Lollipops and would/will definitely go back. She is super accommodating and friendly and her place is in a convenient location. It might not seem walkable but it actually is. There are trails nearby such as the Crispeen trail which I used to walk over to winward side and back to get dinner with some other divers I met, lots of signage on the trail. The food at Carmen's is great as well, all of my meals there were delicious. Very happy and laid back atmosphere. Great host on a wonderful island! 10/10

Private room in Saint Johns

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Popular amenities for Windward Side vacation rentals

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Other great vacation rentals in Windward Side

Apartment in Oranjestad

4.5 out of 5 average rating, 50 reviews

A Quiet Getaway.

WolfgangRating, 5 stars4 weeks ago

this is a fabulous place...perfect for hiking and enjoying the nature. it is in distance to Oranjestad, but my hosts were angels in helping me. I was picked up from the ferry and we stopped at the local supermarket to get food for my stay...i was instructed what i could see and visit. i walked 29 kms in 3 days. but Zevers also has rental cars to hire....as i was stressed out i gladly enjoyed to hike. the accomodation had a super nice modern and clean kitchen. i made my breakfast there and enjoyed lunch at a local restaurant named SUPER BURGER [offered excellent local lunch]. i loved this place so much....and i have to confess that i came as a stranger and went as a friend. such fabulous people. . i love you and thanks so much for everything

Superhost

Private room in Booby Hill

4.81 out of 5 average rating, 37 reviews

El Momo Cottages (standard cottage)

PaulRating, 5 stars3 months ago

Very nice place to stay. Very quiet and you are surrounded by nature and a great view. We had a good time there.

Private room in Saint Johns

4.82 out of 5 average rating, 17 reviews

Private Double room with Sea View

MarcosRating, 5 stars1 week ago

Excellent service. Lovely family. The atmosphere was very friendly. I recommend them 100 x 100

Apartment in Oranjestad

4.33 out of 5 average rating, 3 reviews

Calypso H2O Suite

IdaRating, 5 stars103 months ago

The apartment was very clean and comfortable with comfortable bed and a very luxurious bathroom. Ilka is very kind and helpful. I would definitely stay here again!