Road Town Rentals

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320 Houses

The Best Caribbean sailing vacations for the best price; No Bad Days Sailing

Road Town yacht

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Price per night from

$1,247

Ocean Beach Suites and Villas Bedroom 2

Road Town villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 2

Price per night from

$401

Ocean Beach Suites and Villas Bedroom 5

Road Town villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$401

105 ft Luxury Trimaran

Road Town yacht

  • 10 bedrooms
  • 10 bathrooms
  • sleeps 20

Responds fast! avg. 2 hours 59 minutes

Price per night from

$490

Ocean Beach Suites and Villas Bedroom 9

Road Town villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$401

AnaCapri Estate

Road Town villa

  • 4 bedrooms
  • 6 bathrooms
  • sleeps 12

Price per night from

$655

Ocean Beach Suites and Villas Bedroom 10

Road Town villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$401

Ocean Beach Suites and Villas Bedroom 12

Road Town villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$401

Ocean Beach Suites and Villas Bedroom 3

Road Town villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$401

Ocean Beach Suites and Villas Bedroom 7

Road Town villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$401

Ocean Beach Suites and Villas Bedroom 11

Road Town villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$401

Ocean Beach Suites and Villas Bedroom 6

Road Town villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$401

Ocean Beach Suites and Villas Bedroom 8

Road Town villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$401

Ocean Beach Suites and Villas Bedroom 4

Road Town villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$401

Ocean Beach Suites and Villas Bedroom 1

Road Town villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$401

Catamaran Lagoon 42

Road Town yacht

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 9

Price per night from

$1,635

Experience BVILOVE at Yonderville Homes

Road Town apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$178

1 Bedroom Vacation Rental

Road Town apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$149

Fort Hill's Hidden Secret

Road Town apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$155

villa jaden #2

Road Town apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$229

Modern 3-bedroom villa with pool

Road Town villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$1,022

Exquisitely Threadfall

Road Town apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$218

Spacious, Sunny, Apartments near Nanny Cay

Road Town apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Price per night from

$194

Great rentals within 20 miles that match your search

Villa in Paradise w/Private Pool! Walk to beach!

East End villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Perfect vacation in St Thomas” Spent end of January, beginning of February at Laverne's place in Pavilions and Pools. Everything was perfect. The condo was clean and very comfortable. It was great having your own pool just outside the door. The property was quiet and peaceful and We really enjoyed our stay here. The girls at the front desk, the maintenance people, everyone at the facility were extremely friendly and very responsive to any of our requests. Vicars, the on site restaurant was excellent. If you go there, order the steamed mussels appetizer. It was fabulous. Every morning there are bagels, muffins, cereal, juice and coffee if you don't feel like making your own breakfast. We also used the grill to cook a few steaks during our stay. The only slight drawback was the walk to the beach, it was approximately 5 minutes long, but seemed worse if you are carrying beach chairs, towels, etc. However, once you get to the beach the walk was worth it. Sapphire Beach is a really nice beach, with changing and rest room facilities and a vendor (Banana Bar) that serves sandwiches, drinks etc. From the beach it's a short walk to the Marina where you can see the Tarpon & Barracudas swimming in the clear waters. Red hook was a great area for restaurants or a trip to St Johns and it's only a few minutes away. We did not have a car and didn't need one. The Safari taxis stop right in front of the hotel, and regular taxis are not that expensive and easy to find. Don't miss the fiddle player at Latitude 18 on the other side of the Red Hook Harbor.

Responds fast! avg. 3 hours 24 minutes

Price per night from

$201

SOUTH SOUND VILLA VIRGIN GORDA Waterfront Luxury villa 7 bedrooms w/pool A/C

South Sound villa

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 18

“Heaven on earth” I want to thank the owner Thursten Cook for another wonderful week at South Sound. The property is located on a private cove with breathtaking views of the Ocean. The property was in great shape with a new refrigerator and a new boat. It is difficult to put into words the feeling of falling asleep at night and hearing the roar of the ocean. As this is our second time at the Villa we are starting to get to know all the citizens. The people on the Island go out of their way to make you feel confortable. Thanks again for an incredible week and hopefully we will see you again next summer. Heaven on earth!!! Michael Vincent John Spaziani Palm Beach, Florida

Price per night from

$933

Responds fast! avg. 1 hour 27 minutes

Price per night from

$342

Ocean View Villa!!! 2 bedrooms, 2 Bathrooms ( sleeps 4 to 6 ).

Jost Van Dyke villa

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$504

Too Blue Villa - Spectacular Caribbean front 3B/3B

St. Thomas apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“A Gem” Too Blue is a Gem!! Having tea every morning while watching Yacht Club activities, or boats coming and going from Cowpet Harbor was soothing. Walking to the beach each day without having to drive, perfect. Being close to Red Hook was nice too. Very good restaurants near by as well. Perfect spot. The unit itself is beyond 5 star's ! The only issue we had was there was no electricity in the bathrooms that is it (you shouldn't blow dry your hair on the islands any way). Every other amenity was thought of (frying pan's on the small side should you want to cook breakfast in the am for the group) The furniture and beds are all comfortable. But wait.... The master bath shower, will be the best shower you ever experience. I had tears in my eyes the day I turned off the water for the last time! I actually waved good bye to the view! Miray has been nothing but great to work with! This is the place to stay!!!

Responds fast! avg. 3 hours 36 minutes

Price per night from

$515

Secret Haven Villa St. Thomas, US Virgin Islands

St. Thomas villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

Price per night from

$1,773

Westin St. John 3 Bdrm/ 3 Bath Thanksgiving Week

Cruz Bay villa

  • 4 bathrooms
  • sleeps 10

Price per night from

$984

Oceanfront secluded villa, walk to private beach

St. Thomas villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$572

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

Price per night from

$801

Allamanda Estate A Dream Villa With Amazing Views

Tortola villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

Price per night from

$1,470

Spectacular VIew in Lush Surroundings

East End cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$258

Anam Cara Villa - Secluded Luxury Beachfront Home

South Sound villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 14

Price per night from

$858

Limin'House Luxury 4 Bedroom Caribbean Villa Fully updated and renovated!

West End villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

“Loved this house!” The layout of Limin house was perfect, lots of private areas to chill and a lovely open air veranda to come together. The attention to detail was noted from the great margarita and ice machines to flashlights in all rooms. Loved to be able to make coffee in the bedroom and the sit on the balcony early in the morning and watch the scene unfold below. We loved the huge outside BBQ and took advantage of having half our dinners in. Pool was fantastic with great views and gardens all around the property were lovely. Outdoor showers were great anytime of day! We had issues with our main fridge, but Deb (Manager) was very attentive and helpful and brought us ice if we needed. The freezer worked and there was a bar fridge by the pool so we all got lots of exercise. We understand things go wrong and it is hard to get parts etc on the island. The house more than made up for this and we didn't really care too much. we hope to be back in 2 years and would definitely stay at Limin House.

Responds fast! avg. 38 minutes

Price per night from

$818

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

Cruz Bay villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$2,288

LOBLOLLY VILLA VIRGIN GORDA BVI

Virgin Gorda villa

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 14

Price per night from

$958

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