Northside Vacation Rentals from CA $284: Short-Term Rentals for 2026

Our top choices for Northside vacation rentals

A balcony with two wicker chairs and a small round table, surrounded by a white railing, overlooking a lush green landscape with hills in the background.

1. Villa Indigo 1BR in Private Gated Estate

St. Thomas

Trent

CA $523 total

includes taxes & fees

Oct 20 - Oct 21

A spacious living area with a sofa, dining table, and chairs, overlooking a scenic ocean view.

2. The Breeze

ST Thomas

CA $1,199 total

includes taxes & fees

Oct 20 - Oct 21

A swimming pool with lounge chairs and a view of the ocean.

3. St Thomas Cliffside Villa With Pool & Hot Tub!

St. Thomas

CA $1,602 total

includes taxes & fees

Oct 24 - Oct 25

A stone building with a staircase leading to an entrance, surrounded by potted plants and a clear sky.

4. Bluebeard's Castle Resort

Charlotte Amalie

Freo

CA $284 total

includes taxes & fees

Nov 18 - Nov 19

A beachfront hotel with multiple colorful buildings, a sandy beach, and rows of sun loungers with umbrellas.

5. Marriott's Frenchman's Cove

St. Thomas

Cathryn

CA $1,001 total

includes taxes & fees

Oct 27 - Oct 28

A resort with a central pool, palm trees, and a view of the ocean.

6. The Westin St. John Resort Villas

St. John

Treacy

CA $560 total

includes taxes & fees

Nov 2 - Nov 3

A room with a TV, wicker furniture, and a view of the ocean.

7. Suite St. John at Gallows Point Resort

St. John

Sean

CA $1,290 total

includes taxes & fees

Oct 23 - Oct 24

A coastal landscape with a beach, clear blue waters, and lush greenery.

8. Villa Island Paradise

St. John

Zach Ezekiel Azurus

CA $774 total

includes taxes & fees

Oct 20 - Oct 21

A bedroom with a bed, a nightstand, a lamp, and a view through a door.

9. Aqua

St. Thomas

Paola

CA $569 total

includes taxes & fees

Oct 28 - Oct 29

A bedroom with a bed, a chair, a nightstand, a lamp, and a window with blinds.

10. The Cottage at Villa Indigo

St. Thomas

Oronde

CA $616 total

includes taxes & fees

Oct 31 - Nov 1

A balcony with a view of a coastal town, a table, and a chair.

11. Little Indigo Apartments

St. Thomas

Lynda

CA $433 total

includes taxes & fees

Oct 20 - Oct 21

A room with two wicker chairs with blue cushions, a small table with a vase, and a door with a keyhole.

12. The Perch at Hawk Hill

St. Thomas

CA $486 total

includes taxes & fees

Oct 20 - Oct 21

A balcony with a table, chairs, and a view of a turquoise sea and green hills.

13. Peter Bay Gatehouse

Maho Bay Quarter

Thomas

CA $1,484 total

includes taxes & fees

Oct 20 - Oct 21

A beach with clear turquoise water, rocky shoreline, and a distant view of a hill with buildings.

14. Oceanview Retreat at Point Pleasant, Virgin Island

St. Thomas

CA $565 total

includes taxes & fees

Nov 1 - Nov 2

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Top Northside Hotel Reviews

Buoy Haus Beach Resort St. Thomas, Autograph Collection

10/10 Excellent

"Amazing place. Clean, pristine grounds and friendly staff. Would definitely stay again."

Secret Harbour Beach Resort

8/10 Good

"The room was nice, a little outdated, but the view of the ocean made up for it. It was very clean though. There was a kitchenette, bathroom, living room and kitchen all in one space. It was all just open (except the bathroom that obviously had a door.) Make sure you really like the person you’re going with because the space is tight! The bed was so comfortable though, we slept like babies when we were there. If you want to use the pool no one tells you that it is up on a hill and you have to climb a million steps to get to it. It is not even attached to the resort itself. It is beautiful though, and huge. So if you cannot climb stairs, you can’t get to the pool. Forget asking anyone for help, they are all so hard to understand so my boyfriend and I just explored everywhere finding things. Also, the workout room is very small and barely has any equipment. Just driving around the island is terrible. First of all, you drive on the left side of the road. Secondly, drivers cut you off and flip you the bird. They are so hostile for no reason. It’s worse than driving in New York City! I recommend not leaving the resort if you don’t have to. You’re taking a chance risking your life by driving on this island! Secret Harbour is the most beautiful beach. Crystal clear water. You can see little fish swimming around your feet. The problem is there is hardly any beach frontage. It’s only a couple hundred feet, so forget those long walks on the beach. Overall a wonderful adventure!"

Bolongo Bay Beach Resort

10/10 Excellent

"This is as small property with a laid back vibe. Not your typical all inclusive resort. It is an older property and dated but that is what gives it charm. The only complaint is the small shower, but we knew about that prior to our visit. No biggie! Rooms are very clean! The staff are great and the food is hands down the best we have ever had at an all inclusive. It is not gourmet, but good food done well! No buffets here! Make sure you meet Big Dog at Iggies. If she does not put a smile on your face, no one will! Then you have Rosie, the resort dog! She is just the sweetest and adds little extra to your stay! Highly recommend Jermaine with Island Life Jeep Tour! He is great, knows the island and it's history. Your day is all customized to what you want to do! We will be back soon for sure!"

Find out more about Northside

Everything you need to know about Northside vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Northside vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, 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 Northside vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Northside vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Northside. 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 Northside vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Northside vacation rentals we have selected for you start as low as CA $284 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Northside rentals

At Expedia, we put the best Northside vacation 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 Northside 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 Northside vacation.

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

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Our top choices for Northside vacation rentals

1. Villa Indigo 1BR in Private Gated Estate

2. The Breeze

3. St Thomas Cliffside Villa With Pool & Hot Tub!

4. Bluebeard's Castle Resort

5. Marriott's Frenchman's Cove

6. The Westin St. John Resort Villas

7. Suite St. John at Gallows Point Resort

8. Villa Island Paradise

9. Aqua

10. The Cottage at Villa Indigo

11. Little Indigo Apartments

12. The Perch at Hawk Hill

13. Peter Bay Gatehouse

14. Oceanview Retreat at Point Pleasant, Virgin Island

Find vacation rentals that suit your style

Top Northside Hotel Reviews

Buoy Haus Beach Resort St. Thomas, Autograph Collection

The Westin St. Thomas Beach Resort & Spa

Bunker Hill Hotel

Secret Harbour Beach Resort

The Ritz-Carlton, St. Thomas

Shibui Cove

The Westin St. John Resort Villas

Hampton by Hilton St. Thomas

Bolongo Bay Beach Resort

Find out more about Northside