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Vacation rentals with a pool in Road Town

Find and book unique homes with a pool on Airbnb

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Popular amenities for Road Town rentals with a pool

House rentals with a pool

Top guest favorite
Home in Chocolate Hole
5 out of 5 average rating, 49 reviews

Down Yonder Pool Villa / Full Solar & Battery

LeahRating, 5 stars2 months ago
We had a great week at Down Yonder! Easy access to supermarkets and restaurants. Beautiful view. Private. Great pool for our kids. Extremely clean and nice layout.
Guest favorite
Home in Coral Bay
5 out of 5 average rating, 68 reviews

Casa Tua St John

PaulRating, 5 stars1 week ago
We really enjoyed our stay at Casa Tua. The property felt so secluded by all the surrounding plants and trees but we loved how conveniently located it was to restaurants and a grocery store that we could walk to. The inside spaces were very comfortable and we enjoyed the screened in porch area with the Weber grill for cooking. James was very responsive host and helpful during our stay.
Guest favorite
Home in St. John
5 out of 5 average rating, 30 reviews

La Sirena Secluded Villa w/Pool+NEW Solar backup!

AshleyRating, 5 stars3 weeks ago
A stunning location with gorgeous views, this house is an absolute gem! Thank you, Eileen, for all of your local recommendations, responsiveness to all of my questions (we had a lot!), and for sharing your beautiful home with us. Perched on a hill and down a very unassuming road you find this oasis with ocean breezes, sounds of nature, and all of the necessities you could need. Perfect for my family of four, with two young kids. While the location is "on the other side of the island," we didn't mind the drive to Coral Bay or to the main beach area (Trunk, Maho)--- there was so much scenery to take in! We appreciated the beach chairs and towels, along with cooler bags, to make those trips easy. We also loved the beaches near the house, along with hiking the Ram Head Trail. The beds were super comfortable, we slept beautifully. We used the loft and the AC made for an easy sleep. Thank you so much, we will be back!
Guest favorite
Home in Cruz Bay
4.88 out of 5 average rating, 41 reviews

4 bed/4 bath. Pool/Beautiful Ocean views. Cruz Bay

EmilyRating, 5 stars1 week ago
We had a wonderful stay at Meritage house! The layout was spacious with beautiful views - better than the photos in all regards. A perfect house for a multigenerational trip - we had grandparents, parents, and teens (6 people). Location was very convenient. We had a few minor issues that arose and Linda and Abby coordinated quickly to address them. Highly recommend!
Superhost
Home in Central
5 out of 5 average rating, 3 reviews

Casa Del Palmas ~ SOLAR + pool.

RhondaRating, 5 stars1 month ago
I highly recommend Rosanne's home. Tiffany, a member of the Anteres crew, met us in town after picking up our jeep rentals. We followed her to the house. Super welcoming and answered all of our questions. Casa Del Palmas was in pristine condition and beautifully decorated. Rosanne has put great effort and thought into decorating and stocking her entire home from top to bottom with everything you will possibly need for a perfect vacation. The amazingly beautiful views off the back porches will be greatly missed.
Guest favorite
Home in Great Cruz Bay
4.94 out of 5 average rating, 31 reviews

Luxury Villa with Pool, Privacy, Sunsets

SarahRating, 5 stars3 days ago
We absolutely loved our stay in St. John. We were greeted and welcomed and helped every step of the way! We loved the view and the deck and the pool and hot tub were perfect for our teenage daughters. We made special memories together and we will be back!
Superhost
Home in Cruz Bay
4.8 out of 5 average rating, 5 reviews

Jasmine Villa

JustinRating, 5 stars65 months ago
Absolutely wonderful experience. Been to St. John several times and these accommodations were the best yet - will stay again! Amazing view of Cruz Bay, too. Marble floors, custom kitchen with plenty of utensils and whatnot for cooking, even a grill. The continental breakfast in the morning was a lifesaver and Cathy, the server was personal and very cheery. Maintenance had a malfunctioning AC unit fixed in just a few hours. I would absolutely recommend this location to anyone looking for a luxury stay in St. John. We’ll be back next December!
Superhost
Home in Road Town
4.94 out of 5 average rating, 102 reviews

Kerensa Villa

Julie Dee AnnRating, 5 stars1 month ago
The most idyllic retreat with a phenomenal view! A serene, private escape with all the amenities one could need.

Condo rentals with a pool

Superhost
Condo in East End
4.81 out of 5 average rating, 21 reviews

Beautiful 2BDRM Condo with Stunning Views

GiannaRating, 5 stars1 month ago
Great Location! It took us a little bit of time to find the location. It’s right next to St. Thomas’s yacht club. Once we arrived and checked in, we were pleasantly surprised it looked just like the photos. Me and My Husband stood 30 days. This is the first time I stayed at an Airbnb. I am so thrilled we did. The convenience of having a kitchen, a washer and dryer the freedom to come and go as you please. Nathan’s project manager Brittany was wonderful and took care of any mishap that will occur. The beds were extremely comfortable. He had everything that you could possibly need for a comfortable stay. Thank you again so much, Nathan. We definitely will be back in the future. You can’t beat the Location . the restaurants and so many attractions are endless .
Guest favorite
Condo in East End
4.88 out of 5 average rating, 256 reviews

Ocean View Sapphire Condo-Balcony & King Bed

HannahRating, 5 stars2 weeks ago
We loved staying at Emily’s place. Clean space, very comfortable bed, great restaurants on the property and very close to the beach. Would stay again.
Superhost
Condo in Saint Thomas
4.8 out of 5 average rating, 105 reviews

Ocean View Condo

MariaRating, 5 stars5 months ago
This condo was delightful-just as advertised. It was clean, bright, comfortable and welcoming. The kitchen was well equipped and we thoroughly enjoyed the large patio with views of the bay. The condo community was quiet and well maintained. Overall very enjoyable stay!
Top guest favorite
Condo in Road Town
4.98 out of 5 average rating, 45 reviews

Modern condo with shared pool in Road Town-3 Rooms

SherylRating, 5 stars3 weeks ago
From beginning to end Shan was responsive and helpful. I text him when we left the airport and we were met by a gentleman who opened up the condo. The place was immaculate. Bathrooms very clean. A/C wall units were on and it was nice and cool when we got in. There is a cute porch with a table and 4 chairs outside. Not a great view of the water but peaceful surroundings. Would have loved a couple of lounge chairs but it didn’t really matter…we just brought out two more chairs and had bfast outside. We swam in the pool which was nice and clean also. Very happy with the accommodations and if we find ourselves in Tortola again I wouldn’t hesitate to reach out again.
Top guest favorite
Condo in East End
5 out of 5 average rating, 179 reviews

"H2Oh What a Beach!" condo: Walk-out Beach Access!

SarahRating, 5 stars3 weeks ago
We loved our stay on Sapphire Beach. The place was exactly as described. Perfect location right on the beach. Beautiful views and nice bar and food options right next door. The pool area was also very nice, and there is a taxi service right on the property which was very convenient. Darryl picked us up from the airport and made sure we felt right at home. This was the perfect spot for our Virgin Island getway. Would highly recommend and can't wait to come back!!
Guest favorite
Condo in St. Thomas
4.95 out of 5 average rating, 127 reviews

Oceanfront Condo Perfect Sunsets Backup Generator!

MerissaRating, 5 stars3 weeks ago
Beautiful views, comfortable and clean! Chris and Carol were excellent hosts. Very informative and communicated well. Responsive and friendly! The bed was comfortable and the condo had everything we needed. The AC worked great!!! Definitely follow the recommended temperature, it stays very comfortable. We did not want to leave!!!! We will definitely be back!!!!
Guest favorite
Condo in East End
5 out of 5 average rating, 21 reviews

Villa Miramar - Beachfront 3 bedroom condo, Pool

KevinRating, 5 stars5 months ago
Great condo. Beautiful view of the water and island. We loved the decorations. Appliances and furnishings were generally up to date. Beds and pillow were comfortable. Just like any other beach place, keep your food sealed in ziplocks or containers to avoid ants. We enjoyed having the gym and pool a few minute walk away. Parking was steps away from the stairs up to the condo. The beach at the condo complex is small and rocky, but there were very nice beaches a few minute drive away. A Rental car is helpful for getting to Red Hook and the grocery store. Overall, our stay was excellent. Although the issue may be resolved after our stay, the shower bathroom had some issues with hot water but the other tub/shower bathroom was fine.
Top guest favorite
Condo in Southside
4.99 out of 5 average rating, 82 reviews

Mermaid Hideaway

DeanRating, 5 stars4 weeks ago
The place was as advertised and had a great view of Bologo Bay and the beach below. We enjoyed an afternoon beverage watching the waves roll in! The beach going amenities were great, we used the cooler, beach chairs and a snorkel mask on our beach days. The kitchen was well stocked and worked for our meals; Food City was about a 10-minute drive towards Redhook. We thought the location suited us well, being in between Charlotte Amalie and the Redhook area allows visitors to get to those areas easily. And it was only about a 20-minute drive to Megans Bay/beach. The host offered extensive and clear instruction for entrance and when leaving and allowed us early check-in, which was nice. The grounds were well maintained and the pool refreshing.

Quick stats about vacation rentals with a pool in Road Town

  • Total rentals

    20 properties

  • Nightly prices starting at

    ﺩ.ﺇ257 before taxes and fees

  • Total number of reviews

    300 reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 properties include access to wifi

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