Road Town Rentals

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32 Houses

Modern 3-bedroom villa with pool

Road Town villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Heated pool

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Price per night from

$1,025

Great rentals within 20 miles that match your search

Swogjan's Dragon 7A Carolina

Coral Bay house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Heated pool

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Price per night from

$401

Coconuts: Panoramic ocean views and sunsets

Cruz Bay villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

Match: Heated pool

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Price per night from

$459

Responds fast! avg. 3 hours 57 minutes

Match: Heated pool

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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!

Match: Heated pool

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Price per night from

$820

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.

Match: Heated pool

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Price per night from

$913

Westin St. John 3 Bdrm/ 3 Bath Thanksgiving Week

Cruz Bay villa

  • 4 bathrooms
  • sleeps 10

Match: Heated pool

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Price per night from

$987

Villa Mirino, Ocean front, Intimate East End Home

East End villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

“Beyond Expectations” I would not stay anywhere else on the island. The house itself is in immaculate condition with huge sliding glass doors in every room allowing for amazing views of the Caribbean from every room. I loved waking up to the breathtaking sunrise every morning and the house's beautiful décor encourages complete relaxation. Whether watching TV, playing Xbox/Playstation or listening to music via the surround sound system, it felt like our every whim was met. The kitchen is stocked with gourmet appliances and cookware which made my ability to create fantastic meals for us easy and fun. When we tired of laying by the pool, the beach was less than a mile away and the Red Hook night life was right down the street. This villa is truly one of the premier locations on the island. I cannot wait for the next trip back

Match: Heated pool

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Price per night from

$861

Chateau Margot

St. John villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 14

“Wonderful” Chateau Margot was perfect for a family celebration and holiday. The three seperate buildings gave privacy and comfort for the three different families on this trip. The terrace was perfect to enjoy the spectacular views and get together for breakfast and afternoon cocktails. The house is very well appointed, tastefully furnished and very quiet.

Match: Heated pool

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Price per night from

$1,060

Prettyview Villa

Sage Mountain National Park villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Heated pool

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Price per night from

$316

Ritz Carlton Residence for 12/24/22-12/31/22, 2/18/23-2/25/23

Red Hook villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Heated pool

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Price per night from

$1,640

Match: Heated pool

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Price per night from

$1,067

Coral Rays - Stunning Island Style Headquarters

Coral Bay villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 9

Match: Heated pool

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Price per night from

$861

Match: Heated pool

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Price per night from

$458

Dahlia Villa

Cruz Bay villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

Match: Heated pool

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Price per night from

$746

Exclusive Peter Bay rental, now renting to the public

Maho Bay villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

Match: Heated pool

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Price per night from

$3,271

Responds fast! avg. 16 minutes

Match: Heated pool

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Price per night from

$1,279

The Westin St. John Resort Premier Villa 2BRM Sleeps 6 with 2 Balconies

Cruz Bay villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Heated pool

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Price per night from

$804

Villa Del Mar - Ocean views from every room & heated infinity pool

Lovenlund villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 10

Match: Heated pool

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Price per night from

$1,664

Sheraton Steamboat Resort Villas

Virgin Islands National Park villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Heated pool

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Price per night from

$426

Cheerful 3 -bedroom villa with Pool

Mount Healthy villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Heated pool

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Price per night from

$1,025

Isla Vista

Cruz Bay villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Heated pool

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Price per night from

$3,443

Match: Heated pool

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Price per night from

$217

Match: Heated pool

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Price per night from

$746

Luxury 3BR Residence –With ocean beachfront view

Nazareth apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Heated pool

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Price per night from

$1,239

Newly refurbished Longview Villa with Heated 40ft pool and stunning views

West End villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

Match: Heated pool

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Price per night from

$573

Villa Bali - Waterfront Villa - 100% Brand New!!

East End villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Heated pool

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Price per night from

$201

Mount Healthy Villas 6- bedrooms with spa & pool

Mount Healthy villa

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 16

Match: Heated pool

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Price per night from

$1,736

Beachtime! Top Floor End Unit Studio

Red Hook condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Heated pool

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Price per night from

$206

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!

Match: Heated pool

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Price per night from

$1,033

Point Pleasant - USVI - Villa East - Best Location

East End studio

  • Studio
  • 1 bathroom
  • sleeps 4

Match: Heated pool

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Price per night from

$189

Breathtaking Views from Sapphire Village II

Red Hook condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 13 minutes

Match: Heated pool

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Price per night from

$184

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