Family-friendly holiday rentals in Road Town

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Popular amenities for Road Town family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favourite
Apartment in East End
4.99 out of 5 average rating, 71 reviews

Sunkissed Serenity -Island Chic Home at Cowpet Bay

AmandaRating, 5 stars8 months ago
We traveled to St. Thomas for a wedding and had a lovely stay. The unit was comfortable and pristine with a beautiful view. We walked to the adjacent resort for the pool and restaurants. We used the driver, Jeffi, recommended by Keshri and he took great care of us. The condo was close to everything we needed in the East End.
Superhost
Flat in Cruz Bay
5 out of 5 average rating, 19 reviews

GRANDE BAY 1 BR; SPECTACULAR VIEWS

ChrisRating, 5 stars2 weeks ago
We loved this condo. Well appointed kitchen including a dishwasher and all the appliances you could ask for. Washer and dryer were very useful after a day at the beach . Everything was so close that we didn’t feel we needed a car (even tho you get a dedicated parking space). Shared taxis to the beaches are just 5 mins walk away. We appreciated use of the included beach chairs which were easy to carry on trips .
Cottage in Coral Bay
5 out of 5 average rating, 5 reviews

Cottage w/Awesome View, Hot Tub, Solar, sleep 4-6+

NicoleRating, 5 stars38 months ago
One of our best family vacations ever! Cynthia's house is beautiful, super comfortable and has stunning views. The beds were very comfortable and we loved falling asleep to the sounds of frogs and crickets outside. The house was spotlessly clean and we had everything we needed. The property manager even brought us a delicious banana cake warm out of the oven! We loved the location in the more quiet part of the island - a true getaway! But renters should know that there are not many restaurants so cooking at home is best. Also the driving is challenging and the roads are very steep, so you need to be prepared for some challenging driving - but definitely worth the effort!!! The book of tips from the hosts was also very helpful - great tips on best beaches to visit. Thanks for a great stay!
Apartment in East End
4.68 out of 5 average rating, 34 reviews

3-Bed St. Thomas Getaway on the Bay

AndyRating, 5 stars12 months ago
a little tough to find in the rain and dark, but the location is excellent and it's the end unit on the beach next to the restaurant. the convenience and proximity to the east end goings on was excellent. theres also a bunch of snorkeling equipment, bug spray, sunscreen , etc thats left from other guests. again, super handy.
Guest favourite
Home in Great Cruz Bay
4.93 out of 5 average rating, 30 reviews

Luxury Villa with Pool, Privacy, Sunsets

JohnRating, 5 stars4 months ago
I really don’t want to write this review for fear this villa will never be available when I want to come back but… Villa Capiz hands down the best choice we could have made for our honeymoon trip. This Villa has it all from a extremely well stocked kitchen (minus food and drink) to comfortable furniture inside and out including the beds, there are coolers beach chairs/towels, drinkable water from the faucet and so much more. The pool and hot tub clean and inviting. We spent our mornings and nights in the hot tub overlooking one of the most majestic views you will ever see in your life, I promise you the pictures you’re looking at for it, although great, do not do this place or the view justice. The Villa is also completely private to the point you feel your the only ones on the mountain. Even on a rainy day the views are amazing. We loved the Villa so much that most of our stay on the island was spent here. Do not look any further you found your dream place right here.
Guest favourite
Cottage in Cruz Bay
4.95 out of 5 average rating, 73 reviews

Romantic Cottage - Stunning Ocean Views, Hot tub.

carrieRating, 5 stars1 month ago
We loved staying at the Meritage Cottage and enjoyed the sunset views from the porch. It was a great base to explore St. John from. The cottage was comfortable and had everything we needed. It was really helpful having Abby lead us to the house from the ferry!
Superhost
Apartment in East End
4.94 out of 5 average rating, 16 reviews

Blue Water Haven 3 Bedroom Condo Cowpet Bay East

MeganRating, 5 stars2 months ago
The Condo is beautiful and well appointed and the setting was superb! We travelled to different beaches each day and then spent the later afternoons on Cowpet Bay which was a nice break from the crowds.
Guest favourite
Villa in East End
4.87 out of 5 average rating, 84 reviews

On the water, private pool & spa! Stupendous view

JamesRating, 5 stars2 days ago
The Villa at East end is a perfect spot for a week away. The house and views are so beautiful. I could have sat on the balcony all week watching the boats in and out of Red Hook. The house is well equipped with anything you think you have left behind. My entire party would have booked another week had it been available. We will have to stop in again someday.

Family- and pet-friendly home rentals

Superhost
Villa in Cruz Bay
4.67 out of 5 average rating, 3 reviews

Starfruit Villa

NateRating, 5 stars21 months ago
This place was awesome. Beautiful views of Cruz Bay and the surrounding islands (for some reason they don’t have any pics of the views in the posting, which they should update!). Very short 5 min drive to the grocery store and all the restaurants and bars downtown. Very short drive to all the incredible north shore beaches. Pool is pretty small but the views from the pool area were great.
Superhost
Cottage in Rogues Bay
4.92 out of 5 average rating, 187 reviews

Lowena Cottage

CathyRating, 5 stars1 month ago
Lowena Cottage is situated allowing for beautiful vistas and sunsets. The interior has lovely decor and the exterior offers a multitude of seating options. Ben and Zac were responsive and helpful to our questions and needs. It was an added bonus to he within easy reach to Rogues Bay. such a pretty and secluded beach. I felt very much at home in our vacation spot. We would gladly visit again and recommend this home to others looking for a peaceful vacation.
Apartment in Saint Thomas
4.78 out of 5 average rating, 135 reviews

The View. Unique ocean, BVI, St. John views.

ChristinaRating, 5 stars4 months ago
This condo and everything was amazing! The host, Chris, was phenomenal. Our arrival was delayed due to Spirit Airlines, so we didn’t make it until the next day. Chris was empathetic and understanding, offering invaluable support throughout our stay. She provided recommendations and checked in with us daily to ensure we were okay. The location was perfect for us—peaceful yet conveniently close to great dining and hangout spots. I’m looking forward to returning and hope to stay at this wonderful place again!
Home in Apple Bay
4.86 out of 5 average rating, 103 reviews

Best rates - Apple Bay, Tortola - Owner Operated

NjriRating, 5 stars6 months ago
Had a great stay, it’s a beautiful place. Loved how private and out the way it was. It matched the pictures perfectly! Would stay again.
Guest favourite
Home in East End
4.99 out of 5 average rating, 100 reviews

Brigadoon: RedHook Villa, (sleeps 6) WOW VIEW!

MontanaRating, 5 stars2 months ago
Beautiful location and loved our time at the Brigadoon. The driveway/road was walkable if you are okay with moderate level hikes and we enjoyed walking down the restaurants and coffee shop. Pat makes check in easy! The view is stunning. Highly recommend if you are planning a stay in Redhook.
Guest favourite
Home in VG
5 out of 5 average rating, 55 reviews

Magical Limeberry House, walk to the best beaches

NancyRating, 5 stars2 months ago
Limeberry is a beautiful house in a great location. Walking distance to a gorgeous , mellow beach. Perfect for swimming and not overrun with cruise ship traffic. The hosts were extremely responsive (responded immediately!) and even offered to escort us to the house if we had any problems finding it on Christmas Day! (We had no trouble finding it.) Only a couple of issues - the driveway is a bit tricky getting out of. Must back up a long way down a tight road. But we took it slow and had no problems. Also, the house is very vertical with a lot of random steps. My elderly mother was with me, and though I loved the house, I wouldn’t recommend it to an older person. The downstairs bedroom was her best option but she had to descend four steep steps with NO railing. Otherwise, for a younger crowd the house is perfect!
Guest favourite
Home
4.99 out of 5 average rating, 81 reviews

Luxury LongView Villa with Stunning Sea views

BruceRating, 5 stars1 month ago
There's not much to add as a review of Nick's wonderful home that hasn't been said already. We just spent 10 days there for the third year in a row, and this is our third review. Because of the 4 king bed rooms (two on each side of the center living area), his place can certainly accommodate four couples with plenty of privacy (our trips have been just my wife and myself), each bedroom and a number of outdoor dining and relaxing spots all having world class views of the Carribean from about 200 feet above the sea. Being right above a nice beach provides a constant sound of waves hitting the beach that adds to the ambience of the villa. The villa is well equipped (we cooked every meal there), clean and comfortable. Has WiFi and TV's for those who need or want Internet access and entetainment. Nick (the owner) and Jon and Jude (the on island management team) are terrific people and very accommodating. We hope to be back again to our personal favorite vacation spot on the planet.
Superhost
Villa in St. John
4.85 out of 5 average rating, 59 reviews

Stunning Views Villa Catalina. Full Generator!

GenieRating, 5 stars2 weeks ago
We loved our stay here for a family of 6, kids 2 and 5yo. Beautiful view, comfortable beds, very clean, the kitchen had everything we needed, chairs and towels for the beach, even workout equipment! Having a pool was amazing, and it was very clean too. Lots of chairs and lounge options outdoors and on the deck. It was so comfortable there we spent half a day there each day relaxing and playing with the kids. One note: we didn’t realize that the two downstairs rooms are completely separate from the house upstairs, you have to go outside and down stone steps to get there. One of the doors doesn’t lock from the outside. So our plan to have small kids sleep in those rooms didn’t work. Also if you need an amenity, be sure to check in advance. The listing had a crib available but only had a pack n play, which our child is too big for.

Family-friendly home rentals with a pool

Guest favourite
Apartment in Smith Bay Road
4.89 out of 5 average rating, 93 reviews

Sapphire Beach Paradise Condo

WendyRating, 5 stars1 month ago
Absolutely beautiful, we will be back for sure. Love accommodations. Loved every minute of our vacation.
Guest favourite
Townhouse in Cruz Bay
4.97 out of 5 average rating, 146 reviews

Ocean Views, Pool, Walk2Town, Backup Generator!

MichelleRating, 5 stars1 month ago
I can’t say enough great things about our stay at Mango Terrace, and our host David. The accommodations were lovely and David was the best host - super communicative, friendly and helpful. The kitchen was so well appointed, including new small appliances. I highly recommend Mango Terrace for your stay in STJ. We’ll be back!
Guest favourite
Apartment in East End
4.88 out of 5 average rating, 34 reviews

Beach, Bed and Beyond! Walk out to beach

JudithRating, 5 stars3 months ago
We had a wonderful stay here. It was exactly as described. Vey clean. Beautiful view! Beautiful beach. We loved being on the first floor, able to walk right out onto the sand. Spent our mornings with coffee on the patio and evenings with our wine! Lots of beach toys, rafts, snorkel equipment (but we had our own), buckets provided. Lots of spices for cooking (but we didn’t do that). Kitchen essentials all provided. Nice binder with area information. Loved being in Building C also. Not too far from anything. We ate at the Beach Bar and Pizza place a lot. Live music on Sundays from 3-6 which was fun . Went to Sudi’s, up the hill. All very good. Also Duffy’s and Tap and Still in Red Hook. (a quick cab ride). We loved the resort and loved our stay. We definitely hope to be back! Thank you for sharing your condo with us Denise.
Apartment in East End
4.81 out of 5 average rating, 117 reviews

Sapphire Outlook Villa: Oceanfront Sapphire Beach

WalkerRating, 5 stars4 weeks ago
Could not say enough wonderful things about our host and their lovely property. They were beyond helpful, responsive, and attentive. The home was lovely, the resort was perfect, the experience was remarkable. 10/10 would book again, 10/10 would recommend you staying at any of Alexander’s properties.
Superhost
Apartment in East End
4.91 out of 5 average rating, 11 reviews

Sapphire Beach Resort Rental

XavierRating, 5 stars12 months ago
Amazing views, just steps from the beach. This condo was equipped with everything we needed. Loved our stay!
Superhost
Apartment in East End
4.83 out of 5 average rating, 214 reviews

Villa in Paradise with Private Pool and Generator

RobertRating, 5 stars2 months ago
I was hesitant to write this review because it is such a hidden gem, but I am willing to share. The accommodations were amazing. The property was easy to locate and private. The unit description was exact. There were no surprises. The outdoor shower was amazing. The host were accommodating and easy to deal with. Always provided quick responses with clear direction and kindness. I would recommend this place to everyone. I look forward to staying here again in the future.
Guest favourite
Guest house in St. John
5 out of 5 average rating, 57 reviews

A House of Open Arms Villa with Pool and AC

HayleaRating, 5 stars1 month ago
The villa at House of Open Arms was the perfect home base for our honeymoon. The views are breathtaking, the grounds and gardens pristine, and the villa was incredibly warm and inviting. We loved how quiet and peaceful the villa and Coral Bay were. Catherine went above and beyond to ensure our arrival to the island and drive to the villa was seamless. She is also a fantastic cook - our welcome dinner was 10/10! We couldn’t have asked for a better hostess or home for a week. I wish we could give Catherine more than 5 stars! Thank you everything, Catherine! We will be back!
Villa in Central
4.92 out of 5 average rating, 12 reviews

Villa Solare -sunsets, private pool

LynnRating, 5 stars11 months ago
The Villa was even nicer than we were expecting from the photos we saw and we Loved the location! Susan was extremely quick to respond to any questions we had and always helpful with suggestions.

Quick stats about holiday rentals that are family-friendly in Road Town

  • Total rentals

    50 properties

  • Nightly prices starting at

    £39 before taxes and fees

  • Total number of reviews

    410 reviews

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with a pool

    10 properties have a pool

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

Destinations to explore