Oranjestad Holiday Rentals from €444: Search Short-Term Rentals

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Holiday Rentals in Oranjestad

Outdoor pool, pool umbrellas, pool loungers

includes taxes & fees

29 Nov - 30 Nov

includes taxes & fees

29 Nov - 30 Nov

"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,...

includes taxes & fees

29 Nov - 30 Nov

"You can't get a better spot/place in Saba. This quaint cottage has views to die for, as well as everything you need in a vacation rental. Plus it has a pool. No need for AC either since the breezes, along with the fans keep the place quite comfortable. I know some guests stated they walked to Windwardside....quite a hike. We rented a car which worked perfect. Communication with Michael the property manager, and Larry the owner was perfect. "

"We absolutely loved our week at Spyglass! The home has the feel of a traditional Saba cottage, with some of the BEST views in the Caribbean. We love this small island. The hiking is amazing, the diving is world class, and we love the local food. The home is in a private location, very peaceful and quiet. We would definitely choose to stay here again. If you lead an active lifestyle and enjoy walking/hiking, you can easily walk to the main areas in the village of Windwardside where the local...

"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."

"We enjoyed our stay very much. The cottage had everything we needed and more! Appreciate Jeff and all his knowledge. He was always available to answer questions etc. We loved being able to walk right down to Windward side and surrounding areas. We would stay again for sure! "

includes taxes & fees

29 Nov - 30 Nov

"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!"

"The cottage is great, just as described. The beds are comfortable and clean. All of Windwardside is walking distance from this location, the grocery store is steps away. I would definitely stay here again."

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Other types of properties in Oranjestad you may be interested in

2 outdoor pools, pool umbrellas, pool loungers

"Very peaceful! "

includes taxes & fees

29 Nov - 30 Nov

"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!"

includes taxes & fees

29 Nov - 30 Nov

"Quiet and relaxing "

Find out more about Oranjestad

Everything you need to know about Oranjestad holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Oranjestad holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Oranjestad holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Oranjestad holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Oranjestad. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Oranjestad holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Oranjestad holiday rentals we have selected for you start as low as €444 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Oranjestad rentals

At Expedia, we put the best Oranjestad holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Oranjestad rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Oranjestad holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Oranjestad. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Recent reviews of Oranjestad properties

Historic Saban cottage in Windwardside, all amenities only a 2 minute walk away!

5/5 Excellent

Quiet and beautiful property

"We enjoyed our stay very much. The cottage had everything we needed and more! Appreciate Jeff and all his knowledge. He was always available to answer questions etc. We loved being able to walk right down to Windward side and surrounding areas. We would stay again for sure! "

A verified traveller from Aurora stayed at Historic Saban cottage in Windwardside, all amenities only a 2 minute walk away!

Posted 3 days ago

5/5 Excellent

Fun and Eco Friendly

"I had a wonderful visit at El Momo. I was in Saba for hiking and the cottages were nestled into the woods, giving the perfect setting for enjoying the natural surroundings. The view from the cottages was amazing, the pool was a perfect spot to relax after a day out. The staff was helpful and friendly. "

A verified traveller stayed at El Momo Cottages

Posted 2 months ago

Beautiful Gingerbread Cottage - Spectacular View & Pool

5/5 Excellent

Unspoiled Queen of the Caribbean

"You can't get a better spot/place in Saba. This quaint cottage has views to die for, as well as everything you need in a vacation rental. Plus it has a pool. No need for AC either since the breezes, along with the fans keep the place quite comfortable. I know some guests stated they walked to Windwardside....quite a hike. We rented a car which worked perfect. Communication with Michael the property manager, and Larry the owner was perfect. "

A verified traveller stayed at Beautiful Gingerbread Cottage - Spectacular View & Pool

Posted 3 months ago

Spyglass is a Private Villa With 360 View Near Windwardside.

5/5 Excellent

Wonderful home. Amazing location.

"We absolutely loved our week at Spyglass! The home has the feel of a traditional Saba cottage, with some of the BEST views in the Caribbean. We love this small island. The hiking is amazing, the diving is world class, and we love the local food. The home is in a private location, very peaceful and quiet. We would definitely choose to stay here again. If you lead an active lifestyle and enjoy walking/hiking, you can easily walk to the main areas in the village of Windwardside where the local shops and restaurants are. We enjoyed the spectacular views of each sunrise and sunset with a good book in hand. We'll be back soon!"

A verified traveller stayed at Spyglass is a Private Villa With 360 View Near Windwardside.

Posted 6 months ago

5/5 Excellent

"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!"

A verified traveller stayed at The Old Gin House

Posted 8 months ago

Frequently asked questions

Are there holiday rentals in Oranjestad?

Yes, there are holiday rentals close to the most popular sights in Oranjestad, or you can select a more secluded option if you're looking for a relaxing stay. Oranjestad is known for its waterfront and local tours.

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

Home a way from home in the Unspoiled queen of the Caribbean.: This holiday home rental outside of Oranjestad is located in the city centre, and has an outdoor pool, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. You and your friends and family can relax into your holiday with amenities such as a garden.

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, Honem Dalim Synagogue Ruins and Government Guesthouse are other places worth a visit.

What’s a holiday rental in Oranjestad like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Oranjestad. Holiday rentals feature extras such as WiFi and washers and dryers so you'll feel right at home. If you're concerned about cleanliness, holiday rentals can offer a sense of security away from shared hotel lifts and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular option for family trips or small group gatherings.

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Holiday Rentals in Oranjestad

Check Oranjestad holiday rental availability

Holiday Rentals in Oranjestad

Whale Tails Hotel

Forever Young Apartment B

Palm Spring Inn

Forever Young Apartment A

Studio apartment in quiet neighborhood.

Flamboyant Cottage - Spectacular View & Pool

Spyglass is a Private Villa With 360 View Near Windwardside.

Home a way from home in the Unspoiled queen of the Caribbean.

Historic Saban cottage in Windwardside, all amenities only a 2 minute walk away!

Poets and Painters Cottage

Modern Luxury Villa in Flatlands. Pool. Walk to Beach. Sleeps 6. Ocean Views.

Beautiful Traditional Saba Cottage With all the Modern Amenities

Peter Hytte is close to everything at great price!

Your very own cottage

Other types of properties in Oranjestad you may be interested in

Golden Rock Dive And Nature Resort

The Old Gin House

Talk of the Town Inn & Suites

Find out more about Oranjestad

Recent reviews of Oranjestad properties

Historic Saban cottage in Windwardside, all amenities only a 2 minute walk away!

Golden Rock Dive And Nature Resort

El Momo Cottages

Quill Gardens Boutique Hotel

Beautiful Gingerbread Cottage - Spectacular View & Pool

Spyglass is a Private Villa With 360 View Near Windwardside.

Saba Arawak Hotel

The Old Gin House

Talk of the Town

Frequently asked questions