Road Town Rentals with Pools

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223 Houses in Road Town with pools

Ocean Beach Suites and Villas Bedroom 2

Road Town villa

2 bedrooms / 1 bathroom / sleeps 2

Match: Swimming pool

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Price per night from

$401

Ocean Beach Suites and Villas Bedroom 5

Road Town villa

1 bedroom / 1 bathroom / sleeps 2

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Price per night from

$401

Ocean Beach Suites and Villas Bedroom 9

Road Town villa

1 bedroom / 1 bathroom / sleeps 2

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Price per night from

$401

AnaCapri Estate

Road Town villa

4 bedrooms / 6 bathrooms / sleeps 12

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Price per night from

$655

Ocean Beach Suites and Villas Bedroom 10

Road Town villa

1 bedroom / 1 bathroom / sleeps 2

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Price per night from

$401

Ocean Beach Suites and Villas Bedroom 12

Road Town villa

1 bedroom / 1 bathroom / sleeps 2

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Price per night from

$401

Ocean Beach Suites and Villas Bedroom 3

Road Town villa

1 bedroom / 1 bathroom / sleeps 2

Match: Swimming pool

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Price per night from

$401

Ocean Beach Suites and Villas Bedroom 7

Road Town villa

1 bedroom / 1 bathroom / sleeps 2

Match: Swimming pool

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Price per night from

$401

Ocean Beach Suites and Villas Bedroom 11

Road Town villa

1 bedroom / 1 bathroom / sleeps 2

Match: Swimming pool

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Price per night from

$401

Ocean Beach Suites and Villas Bedroom 6

Road Town villa

1 bedroom / 1 bathroom / sleeps 2

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Price per night from

$401

Ocean Beach Suites and Villas Bedroom 8

Road Town villa

1 bedroom / 1 bathroom / sleeps 2

Match: Swimming pool

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Price per night from

$401

Ocean Beach Suites and Villas Bedroom 4

Road Town villa

1 bedroom / 1 bathroom / sleeps 2

Match: Swimming pool

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Price per night from

$401

Ocean Beach Suites and Villas Bedroom 1

Road Town villa

1 bedroom / 1 bathroom / sleeps 2

Match: Swimming pool

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Price per night from

$401

Modern 3-bedroom villa with pool

Road Town villa

3 bedrooms / 3 bathrooms / sleeps 8

Match: Swimming pool

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Price per night from

$1,022

Great rentals within 20 miles that match your search

Great Expectations St. John vacation rental villa

Cruz Bay villa

8 bedrooms / 9 bathrooms / sleeps 20

“Great expectations helped us have the perfect vacation.” We traveled here for spring break - 8 kids and 8 adults. The house was perfect. The views, the pools and the layout made an ideal getaway for our families. Hoping to return soon.

Match: Swimming pool

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Price per night from

$1,464

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

Match: Swimming pool

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Price per night from

$933

Luxury 5 Bedroom Waterfront Villa

Virgin Gorda house

5 bedrooms / 6 bathrooms / sleeps 10

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Price per night from

$12

Westin St. John 3 Bdrm/ 3 Bath Thanksgiving Week

Cruz Bay villa

/ 4 bathrooms / sleeps 10

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Price per night from

$985

Anam Cara Villa - Secluded Luxury Beachfront Home

South Sound villa

5 bedrooms / 6 bathrooms / sleeps 14

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Price per night from

$859

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. 2 hours 2 minutes

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Price per night from

$819

Villa ValMarc, Mahoe Bay,Virgin Gorda, BVI villa 4 bdrm 4 bath with pool

Virgin Gorda villa

4 bedrooms / 4 bathrooms / sleeps 8

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Price per night from

$638

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

$2,290

LOBLOLLY VILLA VIRGIN GORDA BVI

Virgin Gorda villa

6 bedrooms / 7 bathrooms / sleeps 14

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Price per night from

$743

Eco Friendly Beachfront Villa

Virgin Islands National Park villa

4 bedrooms / 4 bathrooms / sleeps 8

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Price per night from

$744

Waterklip

Cruz Bay house

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$375

Eco Serendib Villa & Spa - Call for Specials!

Cruz Bay villa

8 bedrooms / 9 bathrooms / sleeps 18

“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!

Responds fast! avg. 2 hours 41 minutes

Match: Swimming pool

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Price per night from

$6,296

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: Swimming pool

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Price per night from

$344

View of Paradise (Fully Renovated Condo)

East End apartment

1 bedroom / 1 bathroom / sleeps 4

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Price per night from

$457

TreeTops Villa - Red Hook, Gated, Pool, Spectacular View Perfect 2-4 guests!!

East End villa

2 bedrooms / 2 bathrooms / sleeps 4

“TreeTops has it all” We are from Minnesota and make a warm weather getaway every winter. We have been to a number of different places but this was our first time to the USVI. Both the destination generally and our stay with June and Steve exceeded our expectations. June called shortly after our arrival and gave us directions that were easy to follow. She was there to greet us on arrival (along with her dogs Buddy, Fred and Ginger) and walked us through the property so we knew beforehand where everything was located. While walking around, she also went through a running list of things to do and see on the island as well as nearby St. John. The best place to get groceries if we wanted to dine in, the best places nearby to go out for dinner, the best places to go to get away from "the tourists" and mingle with the local islanders, and on and on. Way too much to digest at one time. Fortunately, she and Steve were around most of the week so we could ask a second and third and fourth time when we couldn't remember. They were quite accomodating when it came to providing the "extras" like a cooler, snorkel gear and beach chairs so we didn't have to rent when we got to the beach; and we loved the "furry extras" when Buddy, Fred and Ginger periodically came up to visit during our stay. All in all, the convenient location, the wonderful view, the warm breeze making its way up the hill, the comfortable accomodations, and especially the attention we received from June and Steve made this an exceptionally wonderful break from the Minnesota winter!

Match: Swimming pool

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Price per night from

$190

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 38 minutes

Match: Swimming pool

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Price per night from

$487

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: Swimming pool

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Price per night from

$1,057

Hart Bay Great House

St. John villa

4 bedrooms / 4 bathrooms / sleeps 9

“Our vacation was wonderful.” This was my fourteenth trip to St. John, tenth stay at Rendezview, excellent as always. Island Getaways always does a great job. The island of St. John is a wonderful place, as with the people of St. John.

Match: Swimming pool

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Price per night from

$714

The Pink House

Jost Van Dyke house

8 bedrooms / 8 bathrooms / sleeps 22

“Pink Paridise” We absolutely loved our vacation here. The house is beautiful & well equipped. The sunsets are phenominal from the porch! We had 6 adult family members & there was plenty of space for privacy, as well as plenty of room for gatherings for dinners, etc. Frankie is an excellent contact for whatever you might need & is very resposive to your needs. A short walk down the beach delivers you to great beach bars & resturants. The beach is secluded with rarely anyone there. We even had a beach wedding right in front of the house! We highly recommend the "pink house"!!

Match: Swimming pool

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Price per night from

$921

OCEANFRONT LUXURY! 109 5-STAR REVIEWS ~ Perfection & Luxury & WELCOME DINNER!

Spanish Town villa

5 bedrooms / 6 bathrooms / sleeps 14

“Best group travel experience for family and friends” A Dream Come True is a well fitting name to describe the trip I took for my 50th birthday celebration. The villas owner, Germaine, let us know from the initial contact that she was willing and eager to help us make this trip a memorable and smooth one for our large group of family and friends. After our short ride from the ferry station to our villa, we were met by the courteous and helpful Geno in the Maho Bay office, literally steps away from the entrance to our villa. When we opened the gate and stepped in, we all gasped at how beautiful the villa, pool and views were... The rooms were clean, spacious and each had a great view. It didn't take the adults long to pick our rooms because all the views from the bedrooms are fabulous! The location near sapphire and pond bay was very nice and their were no crowds- it was like having our own succluded island. In the late afternoon, a few beautiful boats and yachts would park in the cove and made our picturesque view even prettier. The kitchen was well stocked with top of the line knives and lots of glassware and plates to accomate our big crew. The pool is not huge but all you really need to float around in after a fun day at the nearby Baths or eating in the great nearby restaurants. The kayaks that come with the property gave our college age kids the perfect vehicle to take off on snorkel adventures within our view. The best part was that although we had 13 in our group, we all felt like we had plenty of room for privacy. We read lots of books off the shelves, took naps in the sun or shade by the pool and swam in the warm water. What I liked the least was that we weren't smart enough to book puck, the chef who made our delicious welcome dinner, more than one other time. What a character and fantastic chef. His concoctions and fusions of the food he prepared made the kids and adults alike very happy.

Match: Swimming pool

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Price per night from

$814

Crystal Cove Deluxe Suites on Sapphire Bay Beach

Smith Bay apartment

2 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 1 hour 22 minutes

Match: Swimming pool

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Price per night from

$441

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!

Match: Swimming pool

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Price per night from

$630

Pelican Peak Villa, Panoramic Island Views - Only minutes to the best Beaches.

West End villa

3 bedrooms / 3 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$556

Bellamare at Mahoe Bay, Virgin Gorda

Spanish Town villa

4 bedrooms / 5 bathrooms / sleeps 8

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Price per night from

$802

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