Charlotte Amalie Rentals with Pools

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230 Houses in Charlotte Amalie with pools

Beauty, Comfort, Value! Your Home in the Caribbean

Charlotte Amalie house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Magical Vacation” Thank You Gail & Curlson for allowing us to rent from you. The instant we got to your place, we felt like we were "home". The location of your property is perfect, a short drive to Red Hook and close to some gorgeous beaches. The villa included many "little" amenities such as beach towels, paper goods, hairdryers, that really made my packing job much easier! The kids had the best time swimming in the pool & hot tub and ask daily when we can go back! I think even breakfast tasted better because we were able to eat it every morning on the patio overlooking St. John and Sapphire Beach. Whenever we had a concern or question, you were a quick phone call or email away. And the place looked exactly as it does in your pictures. This was one of the best vacations our family has ever taken. Thank you from the bottom of my heart - Take Care!

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Price per night from

$543

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

Charlotte Amalie hotel apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$558

Sea Dreams St Thomas Villa near beach with pool

Charlotte Amalie house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

“Peace and privacy with warm, caring hosts!” Peace, privacy and real attention from hosts Joyce and Nick Bailey at their secluded guesthouse---"a place where everyone knows your name." For those fortunate enough to book here, you will find a comfy, airy two-story guesthouse with extraordinary views over the Caribbean, a great pool for lounging, terrific jogging and walking opportunities, a first-rate nearby restaurant and all the comforts of home. A little jewel for families with kids, couples traveling together and older vacationers who like an acive outdoors life.

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Price per night from

$591

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

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Price per night from

$221

Beautiful 2 Bedroom Home with Pool, view Ocean

Charlotte Amalie villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 8

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Price per night from

$573

Live the ‘Suite Life’ - All Inclusive Private Yacht

Charlotte Amalie yacht

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 9

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Price per night from

$5,739

The Wintberg Villa w/ PRIVATE Tennis Court & Pool

Charlotte Amalie villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$1,033

Ocean Front, Beach level Condo "Sapphire Beach"B106

Charlotte Amalie apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$304

Caribbean Sugar Apple Retreat

Charlotte Amalie condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$207

Private Heated Pool, Incredible Views-Quiet, Romantic Luxury on Lush Northside

Charlotte Amalie house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$385

The Hideaway Hull Bay Cottage 8

Charlotte Amalie cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$745

Two Tickets To Paradise Cottage, Pool & Tiki Bar

Charlotte Amalie cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$316

The Hideaway Hull Bay Cottage 3

Charlotte Amalie cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$401

The Hideaway Hull Bay Cottage 7

Charlotte Amalie villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$574

The Hideaway Hull Bay Cottage 5

Charlotte Amalie cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$401

The Hideaway Hull Bay Cottage 4

Charlotte Amalie cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$344

The Hideaway Hull Bay 18 Bedroom Beachfront Estate - Sleeps 36

Charlotte Amalie house

  • 18 bedrooms
  • 16 bathrooms
  • sleeps 36

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Price per night from

$14,386

Castle at Cabrita

Charlotte Amalie villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 10

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Price per night from

$2,238

The Hideaway Hull Bay Cottage 6

Charlotte Amalie cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$401

Villa Elegance - New Modern Ocean View Villa

Charlotte Amalie villa

  • 3 bedrooms
  • 5 bathrooms
  • sleeps 10

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Price per night from

$2,009

Margaritaville St Thomas - Studio, Smith Bay next to Coki Beach,Coral World

Charlotte Amalie condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 3 hours 43 minutes

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Price per night from

$321

The Hideaway Hull Bay Cottage 1

Charlotte Amalie cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$401

The Hideaway Hull Bay Beachfront Villa 2

Charlotte Amalie villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$689

The Hideaway Hull Bay Cottage 2

Charlotte Amalie cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$573

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

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Price per night from

$2,009

Rare Brand New Luxury Beachfront Villa

East End condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 6

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Price per night from

$656

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

Swogjan's Dragon 7A Carolina

Coral Bay house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$401

Charming luxury villa/ Super views/ Sleeps 2-8

St. John house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

“My happy place” A beautiful and well maintained villa with a breathtaking view of Coral Bay and the Francis Drake channel. Not the hustle and bustle of Cruz Bay but still close to great restaurants in Coral Bay. Separate living and sleeping buildings isa great idea.

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Price per night from

$543

Coconuts: Panoramic ocean views and sunsets

Cruz Bay villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

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Price per night from

$459

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.

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Price per night from

$688

Responds fast! avg. 3 hours 57 minutes

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Price per night from

$1,803

“We didn't want to leave!” My husband and I stayed at Mooncottage for too short a time in april 2014. We loved it and will hope to go back one day. The layout of the cottage is perfect for a couple. Separate sleeping cottage allows for one to sleep-in undisturbed while the other makes coffee. The island/asian decor is very attractive and the house was fully equipped with everything we needed. But the very best feature is the view which is absolutely to die for. Once there, you will be happy to skip a day at the beach and just bask in the breezy air, taking an occasional dip in the tiny pool, positioned perfectly between the bedroom and the deck. The drive in is pretty hair-raising, but once you get the hang of the very steep and very rough roads (typical in Carol Bay and much of St. John) and the perilously steep driveway, you'll be so glad you made the journey!

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Price per night from

$820

“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

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Price per night from

$160

VILLA AMOUR ,Romantic , Art Lovers Paradise ,

North Side villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

“Perfect!” Title says it all. PERFECT island vacation home. Better than advertised. We had 7 adults and 2 infants and had plenty of room to relax. Pool, views are incredible. Convenient enough to travel the rest of the island (although you may ask yourself "why leave!". Rick and Steve are great hosts, responsive to any questions you might have. Recommend renting SUV and also that you give yourself plenty of time at the airport when departing. Highly recommend Villa Amour and would definitely return!

Responds fast! avg. 1 hour 0 minutes

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Price per night from

$804

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

East End apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$206

Drake's View: Voted Best View in the Caribbean

Coral Bay villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

“Awesome family vacation” This was our second visit to Drakes View and we again enjoyed everything the property has to offer...views, a well equpped kitchen, hot tub and ample space for our 3 generations to be together for Thanksgiving week. In spite of an abnormally rainy week, we made the best of our beach time and enjoyed the views from the villa when we were forced inside. We lovedbeing able to stay overlooking Coral Bay,our favorite side of St. Johns. We explored several new beaches and snorkeling apots. Thanks to the Roberts family and their wonderful concierge team of Dorothy and Fernando.

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Price per night from

$913

'Billion$ View' New Deluxe 2FL Beachfront Villa

East End apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 7

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Price per night from

$656

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