Oranjestad Vacation Rentals

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Vacation Rentals in Oranjestad

Outdoor pool, pool umbrellas, sun loungers
Whale Tails Hotel
4.0 star property
The price is CA $240
CA $257 total
includes taxes & fees
May 17 - May 18
Whale Tails Hotel
Suite, 2 Bedrooms | Private kitchenette
Palm Spring Inn
3.0 star property
8.6 out of 10, Excellent, (14)
"Arrived late, well advanced noticed sent to owner. Was met by a man at hotel who showed us suite and gave us keys and wifii password. This man told us the owner will comeby the following day. No show. Apartment was nasty as if the last guest left and we arrived. Used bag of ice in freezer, dish on dish rack, used toiletries. No microwave and no feee bottled water. Shower stank after use because water stayed stagnant for good hour to two or so after use. I emailed owner about microwave,...
Palm Spring Inn
Exterior
Studio apartment in quiet neighborhood.
Studio apartment in quiet neighborhood.
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Exterior
Beautiful Gingerbread Cottage - Spectacular View & Pool
9.8 out of 10, Exceptional, (32)
"This place was beautiful, so peaceful and the views and pool were perfect. A well appointed kitchen and plenty of outdoor spaces to enjoy. Michael was an extremely helpful host coordinating transport easily and even making the occasional dinner reservation for us. Wonderful island, visit if you feel like completely relaxing!"
Beautiful Gingerbread Cottage - Spectacular View & Pool
Outdoor dining
Spyglass is a Private Villa With 360 View Near Windwardside.
9.8 out of 10, Exceptional, (63)
"Very nice villa with some of the most spectacular views you’ll find anywhere in the world. Good hikers can walk into/from the village of Windwardside — be prepared for a steep hill on return. We were 4 adults, though 6 would be very comfortable. All conveniences are in the house. Mgmt: 1 sink awaiting repair parts; we never found the orientation book. We appreciated the mid-week cleaning service, but would like to be notified of that before they intrude on our privacy."
Spyglass is a Private Villa With 360 View Near Windwardside.
Property grounds
Historic Saban cottage in Windwardside, all amenities only a 2 minute walk away!
10.0 out of 10, Exceptional, (6)
"Very pleased with the responsiveness of the owner, and location of the property. Exactly what we were looking for. Hope to stay again."
Historic Saban cottage in Windwardside, all amenities only a 2 minute walk away!
Pool
Modern Luxury Villa in Flatlands. Pool. Walk to Beach. Sleeps 6. Ocean Views.
10.0 out of 10, Exceptional, (4)
"Our stay was fantastic! Cece was awesome and helpful in every way! She arranged a rental car for us at the house so we could get around the island independently. Views were magnificent and hacienda was perfect! Very clean with every amenity you could possibly want! Kitchen is fully stocked with anything you could possibly need to cook a meal. Don’t hesitate to book this magnificent home! You won’t be sorry!"
Modern Luxury Villa in Flatlands. Pool. Walk to Beach. Sleeps 6. Ocean Views.
Property grounds
Beautiful Traditional Saba Cottage With all the Modern Amenities
Beautiful Traditional Saba Cottage With all the Modern Amenities
Exterior
Home a way from home in the Unspoiled queen of the Caribbean.
10.0 out of 10, Exceptional, (2)
"Even though we had to pay for an unused night on account of a canceled ferry, this was a beautiful place in a gorgeous location close to everything in Windwardside. My kids and I enjoyed the private pool with a view."
Home a way from home in the Unspoiled queen of the Caribbean.
Pool
2023 Villa Fairview on Saba. Ultimate privacy.
10.0 out of 10, Exceptional, (3)
"Villa Fairview was gorgeous! The views and the ambiance are unbeatable, and visitors get the full island experience: amazing sunsets, hills, cloud cover, rain, and ocean breezes. Leaving the doors open is magical, but it does come with a side of insects that serve to contribute to the experience. The pool will cool you off on a hot day, and the place has everything you could need, including a great kitchen and laundry room. I’d definitely stay here again!"
2023 Villa Fairview on Saba. Ultimate privacy.
Terrace/patio
Your very own cottage
Your very own cottage
Property grounds
Poets and Painters Cottage
The price is CA $490
CA $552 total
includes taxes & fees
May 18 - May 19
Poets and Painters Cottage
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Oranjestad Vacation Rental Travel Info

Other types of properties in Oranjestad you may be interested in

Outdoor pool
Quill Gardens Boutique Hotel
4.0 star property
9.2 out of 10, Wonderful, (13)
"Second stay at this gem of a property. If you are looking for a quiet relaxing place to stay while you hike Statia, this is your spot."
The price is CA $247
CA $265 total
includes taxes & fees
May 19 - May 20
Quill Gardens Boutique Hotel
Hiking
The Old Gin House Hotel
3.0 star property
8.2 out of 10, Very good, (40)
"The new owners are working hard to refresh this historic property. The seaside location is a gem and the staff members are friendly and attentive (special shout-out to Julia). The full breakfast is a wonderful benefit, and my mahi-mahi dinner was absolutely delicious! An added bonus is the proximity to another excellent restaurant, as well as a scuba center for those who come to Statia to dive. Thanks to Peter and Jeanette and your amazing staff!"
The price is CA $280
CA $300 total
includes taxes & fees
May 22 - May 23
The Old Gin House Hotel
2 outdoor pools, pool umbrellas, sun loungers
Golden Rock Dive And Nature Resort
4.5 star property
9.8 out of 10, Exceptional, (9)
"Golden Rock Resort is truly golden!! An absolute gem on a little known island! The property itself is gorgeous with amazing landscaping everywhere. All accommodations are lovely but we particularly enjoyed our villa for space, convenience, beauty & view. The best part, however, is the people. All of the staff were kind & truly made us feel like family. Sally & Sophie sold us on this property at a travel show and we will be forever grateful - they went above & beyond for us (and all of their...
The price is CA $512
CA $548 total
includes taxes & fees
May 20 - May 21
Golden Rock Dive And Nature Resort
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Oranjestad. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there vacation rentals in Oranjestad?

Yes, you can find vacation rentals near well known local attractions in Oranjestad, or you can choose a secluded option if you're looking for relaxation. Oranjestad is known for its waterfront and local tours.

What are some of the best vacation rentals that Oranjestad has to offer?

Beautiful Traditional Saba Cottage With all the Modern Amenities: You might want to consider this vacation home rental near Oranjestad, which is equipped with a barbecue grill, air-conditioning, and laundry facilities to help you feel comfortable during your stay. Kitchen amenities like a stovetop and a microwave can make your vacation run smoothly.

What’s there to see and do in Oranjestad?

Lower Town Beach and The Quill are a couple of scenic spots to enjoy the outdoors, whereas St. Eustatius Historical Foundation Museum is one of the cultural attractions. While here, Government Guesthouse and Honem Dalim Synagogue Ruins are other places worth a visit.

What’s a vacation rental in Oranjestad like?

Vacation rentals are private properties where you can stay for several days or longer in Oranjestad. Vacation rentals offer amenities such as hot tubs, fire pits, and patios so you'll have a home away from home. If you're concerned about cleanliness, vacation rentals can provide a sense of privacy away from shared hotel elevators and busy reception areas while still allowing you to travel. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental a popular option for family trips.

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