Vacation Rentals & Villas in North Side

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Captain's Quarters Inviting YOU to make Memories in Paradise

North Side apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

Match: Shared outdoor pool (unheated)

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Price per night from

$248

The Hideaway Hull Bay Beachfront Villa 1

North Side villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Shared outdoor pool (unheated)

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Price per night from

$2,766

Great rentals within 20 miles that match your search

Escape Winter at Westin St. John Resort, USVI

Cruz Bay villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Shared outdoor pool (unheated)

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Price per night from

$2,012

Rare Brand New Luxury Beachfront Villa

East End condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 6

Match: Shared outdoor pool (unheated)

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Price per night from

$657

An Enchanting Caribbean Interlude affordable 4 you

Cruz Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Shared outdoor pool (unheated)

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Price per night from

$167

Studio Condo on Bolongo Bay

Bolongo Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Match: Shared outdoor pool (unheated)

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Price per night from

$190

Stunning Newly Renovated 1BR Beachfront Condo

East End condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Shared outdoor pool (unheated)

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Price per night from

$575

Antillean Yacht Charters

Water Island yacht

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Shared outdoor pool (unheated)

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Price per night from

$1,656

⛵ Sail charter Catamaran NEW! Caribbean BVI's

Brewers Bay yacht

  • 1 bedroom
  • 3 bathrooms
  • sleeps 2

Match: Shared outdoor pool (unheated)

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Price per night from

$2,281

Sapphire Beach Front (Fully Renovated)

East End condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Shared outdoor pool (unheated)

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Price per night from

$459

Match: Shared outdoor pool (unheated)

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Price per night from

$218

Starfish Studio on Crystal Cove Sapphire Beach

Smith Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Shared outdoor pool (unheated)

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Price per night from

$225

Sweet Wind Villa overlooking Hurricane Hole

Coral Bay house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

“Sweet Wind is outstanding” We just returned from 9 wonderful days at Nina"s Sweet Wind Villa. The view is spectacular, the trade winds always kept the villa very comfortable and the location to great snorkeling and beautiful beaches is a big plus. Nina is a great hostess and close by if you need any hints on where to go or places to eat but she is never in the way. She even was so kind to fillet a Mahi Mahi I bought in Cruz Bay!! The "Pod" set up of the Villa makes it really nice. The living, dinning and kitchen area is separate but right next to two pods that are the sleeping and bathroom areas. Great for 3 couples or a family. The East end of the Island is also very peaceful and quiet. We certainly plan to return.

Match: Shared outdoor pool (unheated)

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Price per night from

$689

Relax 4 Us at Bolongo Bay ~ USVI

Charlotte Amalie apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Excellent property and great destination!” Our stay here was wonderful! We just came back a few weeks ago (Jan 7-14) from our trip and we are ready to book for the next year! We had such a great time: Accommodations - The apartment is very clean and modern. It has nice comfortable beds and lovely décor in every room. The kitchen is stocked with all necessary utensils and appliances. Bathrooms are clean and modern. I loved the cherry wood doors and marble countertops all around. There is a large balcony that you can eat or relax out on. Beach chairs, towels etc. is also provided for you. Beach - you can go downstairs and you are at the Bolongo Bay beach, its lovely, you have all the water sports options that you would find at a typical resort right there. If you walk past the restaurants and the hotel (5 minute walk along the beach), there is a great snorkeling spot past the rocks, very cool! We had a rental car so we also drove (about 15 min) to Smith Bay. This beach is pure heaven! It seems to be mainly visited by locals and is not crowded with perfect white sand and beautiful calm blue waters. Pool - There are a couple of pools that you can use. We used the one by the beach; it had a tap to wash off the sand as well. The pool was nice and clean and the water was pretty warm. Food - Like I mentioned you have everything you need to prepare your food 'at home' if you are on a budget or have specific dietary needs. There are many supermarkets that deliver or you can shop in a warehouse type place (CostUless) or a supermarket (Pueblo) or some local stands that are all around. There are three popular restaurants directly in the Bolongo Bay area so you don't ever have to leave the area if you choose not to: • Iggys - casual burger type place• Mims - fancier place that serves sea food• Lobster Grill - very fancy There is a lot to do on the island and its neighbors, but we have small kids so we took it easy this time and just enjoy the water. Next time we rent this apartment, we will explore the island.

Responds fast! avg. 2 hours 12 minutes

Match: Shared outdoor pool (unheated)

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Price per night from

$221

“Absolute Paradise!!!!” Thanks to Tom we had the perfect getaway!!! Fast booking, we were provided with tons of information before we even left and the deposit returned asap. This condo was in the best place - you were in your own world yet so close to everything. We had privacy, everyone was pleasant and perfect weather. All that was needed was right there. The view was beautiful, the pool 2 minutes away - walking and Sapphire Beach 5 minutes away - walking. And lets not leave out the Off the Grid food truck at the top of the hill. We are early risers so we snorkeled in the morning, walked the beach in the afternoon and made good use of the pool 7am to 10pm with cocktails and appetizers at the Sapphire and Grill. The ferry to St. Thomas is a 5 minute drive too!!! This is the place you want to be and we will definitely be booking this amazing place again. Thanks to you Tom and your condo - you rock!!!!

Responds fast! avg. 3 hours 18 minutes

Match: Shared outdoor pool (unheated)

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Price per night from

$160

Sapphire 1 Bedroom-Free H/S WIFI & No Excessive Owner Fees #257

East End apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Shared outdoor pool (unheated)

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Price per night from

$206

Waterfront Escape: Paradise at a Great Price!

East End studio

  • Studio
  • 1 bathroom
  • sleeps 4

“Amazing Experience” I loved my stay at this condo! Great location! Owner was super friendly and helpful. The condo was very clean and newly renovated, exactly like the photos shows. I could have not asked for a better vacation. Will definitely come back again.

Match: Shared outdoor pool (unheated)

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Price per night from

$317

“Week in paradise!” Our stay in the Little Palm Suite was wonderful! The suite was exactly as described in the posting and was accurately displayed in the photos. The view of Fish Bay off the deck was amazing! It was a beautiful sight to look forward to every morning. The suite was very clean and well-stocked with necessities. Both the inside and outside (grounds) at the suite were extremely well-maintained. We appreciated having beach towels and beach chairs provided for us to use for our daily trip(s) to the beaches. Michael was a wonderful host! The information he provided to prior to our trip was extremely helpful as we made our plans. He was so helpful to us during our stay as well with directions and with restaurant and beach recommendations. We enjoyed all of the restaurants that he recommended. Our personal favorites were the Sun Dog Cafe for breakfast/lunch and the Lime Inn and Fish Trap for dinner. We loved being able to eat every meal outside for an entire week! The ice cream shop at the end of Mongoose Junction was also a favorite. Our favorite north side beaches were Hawksnest (smaller and not very busy) and Trunk Bay (busier, but so beautiful and picturesque). We really enjoyed the laid-back pace on St. John and had a truly relaxing week. I really enjoyed staying a little bit outside of Cruz Bay and the location in Fish Bay was perfect. We would highly recommend Little Palm Suite! Thank you, Michael for sharing your home with us and for helping us enjoy our week in paradise!

Responds fast! avg. 1 hour 21 minutes

Match: Shared outdoor pool (unheated)

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Price per night from

$328

Beachfront Villa with a Down Island View-Priceless

East End apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 6

“Well maintained, quality furnished condo with very helpful owner.” We have stayed in several different condos @ Sapphire Beach in several different price ranges. John's is by far the best maintained despite it not being the highest end priced. It also has a great bar/eating area on the lower deck. Renting from John is like renting from a friend or family member. There were no surprises from John other than I had over paid without realizing & he contacted me to let me know he was sending me a check.

Match: Shared outdoor pool (unheated)

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Price per night from

$403

'Billion$ View' New Deluxe 2FL Beachfront Villa

East End apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 7

Match: Shared outdoor pool (unheated)

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Price per night from

$657

St. Thomas USVI 3 bedroom plus Cottage Villa

Peterborg villa

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

“Truly Exceptional Property!” Villa Sunrose was a truly exceptional property. The villa was exceedingly well appointed, very tasteful and spacious. All the bedrooms were extremely well decorated and comfortable, and the cottage was a once in a lifetime experience. The main living areas and kitchen were spacious and beautiful, and accommodated our group wonderfully. The owners have thought of everything, and make your stay warm and inviting, from having beach chairs and coolers to kitchen supplies ready for your use. Like the inside, the outdoor decks/living areas went far beyond our expectations, and we thoroughly enjoyed our time in the hammocks, glider and chairs, and meals and games at the outdoor tables. The views from all the decks of St. John and the BVIs were breathtaking day and night. The binoculars were a fabulous treat. The decks, like the inside, were so very well appointed and decorated, and we truly enjoyed all the small touches throughout the many decks.The kids loved the pool, and we adults appreciated the ample covered decking to enjoy the outside while taking a break from the sun. The outdoor shower was a hit, the boys and dads especially loved this. Thank you for a truly exceptional stay at your villa. Your graciousness and sharing of your exceptional property have left us all with a trip of a lifetime.

Match: Shared outdoor pool (unheated)

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Price per night from

$501

Studio Condo on the Waterfront at Bolongo Bay

Bolongo Bay condo

  • 1 bathroom
  • sleeps 2

Match: Shared outdoor pool (unheated)

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Price per night from

$190

Westin St. John Luxury -- Three-Bedroom Pool Villa

Cruz Bay villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Shared outdoor pool (unheated)

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Price per night from

$2,300

“Great time at Bliss” Bliss is not large but perfect for 3 to 4 people. We enjoyed the view of Cruz Bay and the proximity to town. Cynthia has all the necessities in Bliss and it was nice to use the cooler and beach chairs. We rented a jeep from amalie at the airport in St Thomas, I would recommend renting a vehicle, as the walk to town and back is possible, but requires a lot of effort. The beaches around the island are beautiful and it is great to be able to explore. I would recommend going to Chateau Bordeaux for lunch, it has a great view of Coral Bay and wonderful food. Thanks Cynthia, you have a great villa and would love to stay again.

Match: Shared outdoor pool (unheated)

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Price per night from

$264

CARIBBEAN Beachfront Condo,Georgeous Views, Elysian Beach Resort

East End apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

“I really cannot imagine any place more enjoyable for us” We recently stayed at Nancy's condos for the first three days of our 10 day stay. All I can say is that I wished we had stayed there the entire time! We headed to a resort and even my 12 and 7 year old boys (who had plenty to keep them busy at the resort) kept saying that they wished we were back at "Nancy's condos." The beach and the water were simply amazing. No having to fight for pool or beach chairs. I was pleasantly surprised at how well appointed the kitchen was with excellent cookware and general supplies with many guests "paying it forward," with items they left. We did the same. There is really nothing negative I can say at all, as evidenced by the fact that we already booked for next year immediately upon arriving home!

Match: Shared outdoor pool (unheated)

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Price per night from

$345

View of Paradise (Fully Renovated Condo)

East End apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Shared outdoor pool (unheated)

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Price per night from

$459

Beautiful Sapphire Beach St. Thomas, USVI

East End apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 5

“Perfect Stay at Sapphire Bay” We just returned from the most fabulous week in St Thomas at the Sapphire Beach condo. The condo location could not be more perfect. Just steps to the beach with the most serine views of the island. It is a quick 2 min drive to Red Hook harbor for great restaurants, bars, grocery store and ferry to BVI or St John. The owners were so accommodating bringing in a full size crib, high chair and pack and play for my 1 YO. The house keeper Norma gave us a complete run down of the area, where to eat and what to do during our stay. Being a family with 2 kids, this was the perfect stay for us. Full kitchen in the unit, washer and dryer, satellite TV, games and movies for the kids--and the convenience of going back and forth between the beach and home when needed. The island was nothing but beautiful and after visiting many beaches on the island, this was by far the best. If you don’t snorkel, you will start on this trip. The water is so calm and clear with amazing fish, turtles and coral. Plus gear is provided at the condo! A trip to the Mountain Top for a banana daiquiri is a must. For dinner, Fish Tails had the freshest seafood and best sushi around. For Caribbean fare, don’t skip Cuzzin's and Glady's in Charlotte Amalie-- absolutely delicious! We cannot wait to return to paradise-- maybe next time without the kiddos!

Responds fast! avg. 1 hour 30 minutes

Match: Shared outdoor pool (unheated)

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Price per night from

$363

Marriott Frenchman's Cove 2/2 Gorgeous, Spacious, Villa - 2 Units available -4BR

Charlotte Amalie hotel apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Shared outdoor pool (unheated)

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Price per night from

$559

Crystal Cove Deluxe Suites on Sapphire Bay Beach

Smith Bay apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 58 minutes

Match: Shared outdoor pool (unheated)

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Price per night from

$443

BEAUTIFUL Beachfront Condo, Elysian Beach Resort, East End

East End apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 8

“Perfect location in St. Thomas” I had the pleasure of staying at Nancy's condo along with my wife, our 2 children, and another couple, 6 of us in total. The condo was the perfect size for all of us, and having a kitchen made preparing for excursions (having a nice breakfast, and preparing picnic lunches) a breeze. There is also laundry facilities in the condo, and with the breeze coming off the water we almost never needed to use the AC. The Location on Cowpet bay was very close to the ferry to St. Johns, restaurants, nightlife and shopping. Although Redhook is only about a mile away, it was not easily walkable due to the narrow streets, so you will want to get a taxi to go into town. My daughter loved playing in the pool, there were many other families around so she always had somebody to play with. My wife and I enjoyed walking on the beach, and the restaurant (Caribbean Fish Market) has amazing sea food, and a wonderful ambiance. At night I loved the ability to sit on the patio, listen to the waves and relax before preparing for another exciting day.

Match: Shared outdoor pool (unheated)

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Price per night from

$345

Sapphire Fully Renovated

East End apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Shared outdoor pool (unheated)

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Price per night from

$459

Sail Away at Sapphire Beach Resort in St. Thomas VI

Smith Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Shared outdoor pool (unheated)

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Price per night from

$403

Sailboat Ragamuffin Floating Bed and Breakfast INCL meals drinks water toys

Water Island b&b

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Shared outdoor pool (unheated)

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Price per night from

$230

AMAZING Beachfront Condo, On the East End at the Elysian Beach Resort,

East End condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Shared outdoor pool (unheated)

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Price per night from

$345

A Place in the Sun

Coral Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Match: Shared outdoor pool (unheated)

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Price per night from

$403

Suite St. John at Gallows Point

Cruz Bay villa

  • 1 bedroom
  • 2 bathrooms
  • sleeps 6

“Beautiful views, quiet and convenient” From the initial reservation to check-out, service was terrific. The property has everything you might need from beach chairs and towels to groceries. The proximity to town is also a big plus. Our condo was spotless and very comfortable. Excellent all around. We will definitely rent again!

Match: Shared outdoor pool (unheated)

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Price per night from

$799

Match: Shared outdoor pool (unheated)

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Price per night from

$1,068

Match: Shared outdoor pool (unheated)

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Price per night from

$275

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