Cruz Bay Rentals with Pools

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251 apartments in Cruz Bay with pools

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

Cruz Bay villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$2,295

White Seagull -Just For Two- POOL SALE NOW

Cruz Bay villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“Spectacular View and Wonderful Hospitality!” We just returned from a wonderful 8-day stay in the White Seagull, at "Just For Two" on St. John. This was a return trip for us, having stayed there, last May, as well. We rarely return to the same location, preferring to seek new adventures. This was a rare exception and a testimony to the wonder of this place - both St. John and Jacqueline's hospitality. The room is wonderfully decorated and comfortable, with 270 degree views of the Caribbean. We overlook Great Cruz Bay and Chocolate Hole from our windows, with views of St. Thomas from the Sky Lounge. It's amazing to wake to the early sunrise and see the ocean view, by simply sitting up in the bed. We took wonderful photos of the sunsets from the rooftop Sky Lounge and our location near the top of a mountain, overlooking the island. Jacqueline readily gave us access to her private patio, as well, providing wonderful views of Great Cruz Bay and relaxing surroundings to talk or simply play cards, in paradise! The room is well decorated with antiques and personal items. There was good Wi-Fi access and a TV with limited channels, but we rarely used them. A fireplace was available, but we can't imagine using it, except in the dead of "winter"! The room offers a small kitchenette, suitable for simple breakfasts or lunch preparation. There is access to a grill in the courtyard, as well. However, we mostly enjoyed the wonderful food at all the restaurants on the island. You definitely need to rent a car and we have had great experience with Courtesy Rental. The roads are steep, somewhat narrow and you get the challenge of driving on the left side. It's a challenge, but quickly becomes comfortable. The roads Just For Two are steep, but enjoyable. There is a back way that allows a "less steep" option, if it is rainy. Next year is our 25th anniversary and we are planning to return, yet again. It's hard to argue with perfection - especially for a milestone date.

Responds fast! avg. 3 hours 17 minutes

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Price per night from

$603

Poi Pu St John Villa - great views & total privacy

Cruz Bay house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“St John is just the best little island around.” The villa is wide open, very spacious. Open the big doors and you let the cool breezes in. There are always breezes at Poi Pu. It's great to have your own pool right there, even if you have spent the day at the beach. It's close to town for shopping and dinning, but there is nothing like dinning right there on the deck with the breezes and all those stars. I will be going back it's just the best place to be with friends. Carol

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Price per night from

$395

“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: Swimming pool

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Price per night from

$327

Responds fast! avg. 3 hours 57 minutes

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Price per night from

$1,803

“A little slice of paradise!” When we were deciding on a rental in St. John I was fixated on having a great view...I can't imagine there's a much better view paired with a beautiful and clean house on the whole island! The pictures can't possibly do it justice. We couldn't stop taking pictures in hopes of capturing it the best we could. The house is very clean and well-equipped. We were able to eat some dinners in, using both the grill and the stove. We had Meredith at St. John Provisions shop for food for us and stock the house before we got there so that we didn't have to go back out once we got in the first night. Very convenient! The kids loved the pool. The beds are super comfortable and it seems that our host had thought of everything we might need - soap, shampoo, hair dryers, beach towels, chairs and coolers, etc. Our favorite beach was Cinnamon Bay since we were able to rent paddle boards and skim boards for the kids. All around it was an awesome vacation. Thank you, Michael!!

Responds fast! avg. 1 hour 21 minutes

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Price per night from

$624

Waterklip

Cruz Bay house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$351

Pink Conch Villa

Cruz Bay villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

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Price per night from

$560

Starvilla--Walk to Cruz Bay!

Cruz Bay house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$487

Coconuts: Panoramic ocean views and sunsets

Cruz Bay villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

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Price per night from

$459

Comfortable Cruz Bay Condo with Awesome Views and Convenient Walk

Cruz Bay condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$402

Calicaribe--hill top villa with views of Caribbean

Cruz Bay house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Fantastic Villa” Your Review is Pending Please read and confirm your review for Property #284227 below. Review #4627412 Fantastic Villa Our family spent two unforgettable weeks in late July and early august at Calicaribe, celebrating our 50th wedding anniversary, We can't say enough about Calicaribe. We loved the villa -- its layout and tasteful decor. The views of St Thomas, other islands, and Cruz Bay from the property, especially the guest house and the pool area, are breathtaking. Although the heat and humidity were high during the peak hours of each day, temperatures and humidity lowered late in the afternoon so that we could enjoy wine and cheese and the view, including spectacular sunsets, on the patio and dinner on the verandah. Pictures of the property on various websites don't do it justice. Calicaribe is much better than we expected. It is clean and very well maintained. Calicaribe is blessed with an excellent local property manager, Steve Black, who has lived in Cruz Bay for 25 years and is a constructive civic activist. Whenever we needed anything, Steve was prompt in his response. St John is truly paradise. We were fortunate to have a rental jeep to get around the island and to have our daughter and her partner do all the driving. The roads are challenging because the island is very hilly and the roads have very sharp turns, which means that one does not need to worry about exceeding the 20 mph speed limit. Opportunities for snorkeling and scuba diving abound. The beaches (St John has 39 of them) are beautiful. We swam at four of them: Trunk Bay, Little Lameshur Bay, Hawksnest Bay, and Maho Bay. We ate out only three times because my daughter's partner loves to cook, and having dinner on the verandah was a pleasant experience. The Fish Trap and Zozo's are excellent restaurants in Cruz Bay, although the latter may be too expensive for some folks. We highly recommend a sojourn at Calicaribe. You'll get plenty of bang for your bucks.

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Price per night from

$1,148

Spectacular Sunsets & Ocean Views Remodeled Villa

Cruz Bay villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 10

“Awesome View” We recently stayed here and it was perfect. The villa was very clean and well maintained. They have everything you need there (beach towels, cooler, chairs, pots, pans, appliances, wifi). There is a/c in both bedrooms and it cools the place off very nice at night. It has a large glass door that opens up to the deck where you have one of the best views of the island. The view is simply breath-taking. Relaxing in the evening on the deck with the view was one of my highlights of the vacation. The property is about 5 minutes from town. Their property management company met us at ferry dock and gave us tour of the town and villa. This is an awesome property and wouldn't hesitate to stay there again. I don't have one complaint about this villa. Highly recommended!

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Price per night from

$1,030

Eco Serendib Villa & Spa - Luxury in Harmony with Nature

Cruz Bay villa

  • 8 bedrooms
  • 9 bathrooms
  • sleeps 16

“Want for nothing -- and I mean nothing!” From the incredibly spacious and luxurious suites to the world class swimming pool to the on-site massage therapy sanctuaries to the full on-site gym with sauna, steam and soaking tub to the Epicurean theater to the on-site fruit, vegetable and herb garden to the meeting facilities and beyond -- all served up astride one of the most amazing views on St. John -- it's not only possible to spend several weeks here without the need to leave the grounds, it's actually desirable. Still, see the parks and head downtown for some amazing cuisine just to round out the stay. And enjoy one of the best support staffs on the island. Well done, all!

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Price per night from

$3,436

Sky-Sea

Cruz Bay house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$366

“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.

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Price per night from

$263

Dahlia Villa

Cruz Bay villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

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Price per night from

$746

Westin St. John 3 Bdrm/ 3 Bath Thanksgiving Week

Cruz Bay villa

  • 4 bathrooms
  • sleeps 10

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Price per night from

$987

Westin St. Johns, 2 Bedroom Bay Vista Villa Loft, April 21-28

Cruz Bay villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$1,017

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Price per night from

$746

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Price per night from

$686

An Enchanting Caribbean Interlude affordable 4 you

Cruz Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$167

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Price per night from

$1,066

Great Expectations St. John vacation rental villa

Cruz Bay villa

  • 8 bedrooms
  • 9 bathrooms
  • sleeps 20

“Re-impressed” I spent time at Great Expectations for one month, each, in 2010 and 2011 with family and friends. We had an amazing time. Its really a beautiful property, and its true, everything you need, they supply. in 2013 we tried a new place on a different island. What a mistake. the place did not live up to its on line review or pics. This year we went back to G E and were even more pleased (which none of us thought was possible)! The new pool is amazing. Infinity in style, large, with amazing views. Can't wait for next year!

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Price per night from

$1,468

Fantastic Ocean Views and Breezes

Cruz Bay villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

“Can't wait to go back!” We loved Villa Mar de amores from the moment we got there. Amazing views, great vibes, lovely decorations, high ceilings, comfy beds, great kitchen, just perfect. It's even nicer than the pictures. We all started smiling when we climbed to the top of the hill in our Jeep. Perfect amount of space for the five of us. Could sit on that deck any time of day and be totally entranced. The owner is great, and the on island managers were also great. We booked the house again for next year before we left!

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Price per night from

$574

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!

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Price per night from

$798

Villa L'Agave

Cruz Bay villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$660

Rhapsody: Luxury! Sunset Views! Full AC! Pool!

Cruz Bay villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

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Price per night from

$2,000

Sunset Ridge Villas, Unit D

Cruz Bay villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 53 minutes

Match: Swimming pool

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Price per night from

$689

Ballena Blue: Panoramic Views! New Pool!

Cruz Bay villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$1,017

Estate Rose: Luxury Villa! Full AC! Pool! Hot Tub!

Cruz Bay villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

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Price per night from

$1,586

Villa Adagio: Newly Renovated! Indoor Pool! Sunset Views!

Cruz Bay villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Home away from home...but with a view!” I don't know where to begin. This was our first, but definitely not our last, visit to Villa adagio. We have rented several homes on St. John over the past years and they all pale in comparison. Let's start with the pool in the middle of the great room. It's amazing! There is no smell from the chlorine which was my initial concern. It is not heated, which is great, because who needs a heated pool in St. John and the view cannot be beat. Speaking of the view, you will have prime seats for sunset...get your cameras ready. Next, let's talk about the outdoor showers in 2 of the 3 bathrooms. I loved this. What an indulgence coming from a rough winter in the Northeast! Third, the furnishings are lovley. It is very homey and there are so many places both inside and outside to relax with a cocktail and enjoy the surroundings. If you want a change of scenery from the stunning views of the water, head to the front yard which has a lovely lawn and garden. Lastly, if convenience is important to you, then you will be happy here. It is 10 minutes to Cruz Bay and within 5 minutes of the car ferry and grocery store. I have already checked availability for this fall. Don't hesitate...reserve it now!

Match: Swimming pool

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Price per night from

$1,077

Blue Tang: Spectacular Sunset Views!

Cruz Bay villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Very Much Enjoyed The Villa” We didn't know what to expect arriving with two two-year olds and my wife, but we very much enjoyed the Villa. It is two bedrooms connected in the middle by the living room/dining area/kitchen. It was more than enough room for the four of us. Not sure if it could fit much more without having to use the middle area. Villa was nicely outfitted and had lots of extras such as deck chairs and a barbecue as well as beach towels and even sun screen. We went to the beach in the morning and then used the small pool in the afternoon -- which was perfect for young kids. Deck has a great view of grand cruz bay and you can spend all day under the shaded part. The bedrooms are air conditioned but not the main part -- we didn't mind because we just kept the screen doors open. It is just beyond the Westin -- so we drove into town and to the beaches with a rental car which you will definitely need. The villa is on a hill -- very steep so you basically have to drive everywhere which is the one down side. We also bought our food on St. Thomas at the Cost-U-Less (Costco equivalent) which saved us a lot of money. It was a great vacation and we would go back.

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Price per night from

$1,357

Seas Edge: Waterfront! Breathtaking Views! Newly Renovated!

Cruz Bay villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

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Price per night from

$2,071

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Price per night from

$631

Ami La Vita: Views of Rendezvous Bay! Sun all day!

Cruz Bay villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$1,126

Vista Caribe: Sunset Views all Year! Full A/C! Amazing Pool!

Cruz Bay villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

“Spring Break in the islands!!!” Vista Caribe was perfect for us! Had everything we could have imagined and incredible views. We had 8 adults on our trip, 6 of which were making their first trip to St. John. Could not have gone better and we will be back. Thank you to Catered To for doing an excellent job!

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Price per night from

$1,329

Altagracia: Stunning Sunsets! Endless Decks! Huge Pool!

Cruz Bay villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

“Paradise” This was our 3rd visit to St. John and will not be our last. Altagracia was wonderful. The house was so comfortable. Everything was perfect, the pool, the bedrooms, the decks, everything!!! The kitchen is fully equipped with everything one needs. The bedrooms are spacious. The views from the deck were breathtaking. We loved the fact that the home was close to Cruz Bay. Catered To Management is a very professional group of people, especially Jason. We needed something and he took care of it immediately. Our greeter Michelle was a very special person. Not only did she recommend us to take a day sail on Kekoa, but she followed through with a call to tell us the schedules and who to contact. We all have very special memories from that sail! All in all, we will definitely return to St. John and would love to stay at altagracia! Thanks to all of you for a very special vacation.

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Price per night from

$1,200

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