Family-friendly holiday rentals in Road Town

4.99 out of 5 average rating, 158 reviews

Cottage in Central

Caribbean Style Cottage

The 500sq. Tortuga Cottage is located in Fish Bay, St. John in the US Virgin Islands. The property is privately owned and adjacent to the National Park. This charming cottage places you within a 5 minute walk to Reef Bay beach and gives you access to many of St. John's greatest hiking trails. By car, we are 3 miles from town (Cruz Bay), where you will find all of your necessities. This is the ideal cottage for a couple or two friends. We have a full kitchen, a king Casper mattress, and much more

5 out of 5 average rating, 183 reviews

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

"H2Oh What a Beach!" condo Building A of Sapphire Beach Resort & Marina: ground floor unit with direct access to one of the most beautiful beaches in the Caribbean. Steps away from Sea Salt fine dining restaurant, Sapphire Beach Bar, Paradise Pie pizza, and Beach Buzz coffee shop. A mile from Red Hook featuring many restaurants & island ferries. Great beach, swimming, snorkeling, parasailing, and relaxing right outside your door. Be among the many visitors who LOVE this totally renovated condo.

4.99 out of 5 average rating, 111 reviews

Guest house in Coral Bay

A House of Open Arms Cottage with AC

Lovely Cottage with 180 degrees of white water views. You can see and hear the crashing waves below. A/C, Private , Romantic with a gorgeous outdoor shower. Spoon into a nest of intimacy. Immerse yourself in island breezes. Take in the views of the rising sun and moon as they glisten across the crystalline waters of Hurricane Hole. Settle into the rhythm of Island life with solar energy and purified rainwater, resourceful recommendations, advice and insider tips. Welcome to simple elegance.

4.97 out of 5 average rating, 146 reviews

Family Friendly 3BR with a Killer View!

STOP! Look no further than this 1,470sf condo, with a TOTAL MAKEOVER. Everything is Brand New. Professional interior designers transformed this gorgeous condo to "OMG"! Open the LR doors to a fully-screened lanai for additional living space & enjoy the plentiful island breezes blowing through. As our reviews consistently say, you won’t regret booking this condo for your St. Thomas vacation! Sherri, your AirBnB Superhost has lived in STT for 20 years & can answer all of your VI questions.

4.89 out of 5 average rating, 232 reviews

Flat in Road Town

Trunk Bay Spring - downstairs self-contained room

Hi! We paused this listing after being badly damaged by Hurricane Irma, and then due to Covid 19, but we're back – repaired and upgraded! The outdoor shower that our guests loved is still there, only now it has hot water. There's also a new kitchen made of hardwood we were able to salvage after Irma. Great news! The beach is still there, too, and still a just ten minute walk away. Always popular for being simple and beautiful in a fantastic location, now it's the same, but even better!

Superhost

4.87 out of 5 average rating, 104 reviews

Paradise Beach Haven with Spectacular Ocean Views

The great thing about this place is, that is right on the beach,plenty shade by the seagrape trees, and palm trees, snorkeling right outside the patio as well swimming, kayaking, and plenty activities, marina to rent boats or take excursion is right there as well, restaurants and dining, great views, nightlife, and family-friendly activities. You’ll love my place because of the comfy bed and the coziness, the easy in and out to the water for swimming or snorkeling. free *wi/fi

4.99 out of 5 average rating, 107 reviews

Home in Coral Bay

Paradisea 2 Bedroom w/ Pool & Backup Solar Power

2 cozy bedrooms, fully equipped kitchen, large decks, pool, solar and backup battery power. Everything you need for a day at the beach: chairs, umbrella, coolers, toys, towels all provided. Close to Coral Bay restaurants and shops. North Shore beaches and hiking trails are only a short drive away. Quiet setting in the hills above Coral Bay. Close to it all with a far away feel. good for couples, solo adventurers, and families with children over the age of 8.

Superhost

Guest suite in Tortola

4.88 out of 5 average rating, 146 reviews

Cane Gdn Villa 2 bd 2 bath for 2-6

Beautiful new 2 bdrm villa in Cane Garden Bay, steps to beach, restaurants & taverns. Villa has been totally renovated including split air conditioning in bdrms, fresh new baths kitchen w granite n stainless. Beach chairs. Price based on 2 guests using 1 bedroom, $40 per person per night extra using 2nd bedroom. Comprises upper level right side of house in pic, we have self contained water system and power if needed. WiFi working most of time.

4.98 out of 5 average rating, 111 reviews

Home in East End

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

Brigadoon! This recently built villa commands a bird's eye view over “the city” of Red Hook to St. John all the way to the British Virgin Islands. Breezes abound. Enjoy a full kitchen, grill and all the comforts of home. Choose between 6 beaches all within 5 minutes drive. There are 2 king beds, 2 single sofas, and an additional downstairs studio should you need the extra space. Pricing is based on the number of guests.

4.93 out of 5 average rating, 101 reviews

Your Perfect Beachfront Condo in Paradise

Highly Desired Corner Unit right on Gorgeous Sapphire Beach. It's all here: Warm weather, White sand, Fun and Relaxation. Sapphire Beach is considered to be one of the most beautiful beaches in St Thomas. Your second floor beachfront condo in Building C is just 7 easy steps to the beach and in a perfect central location for quiet relaxation and convenient access to the facilities.

4.93 out of 5 average rating, 119 reviews

Beachfront Condo #13802083- October Savings!

Imagine waking up in the morning to the most amazing down island view of the British Virgin Islands! Turquoise waters, blue skies, white sands. You can sip your morning coffee or have cocktails on a spacious porch and lower deck while enjoying the incredible views and ever present breezes. Located right on the beach & only a few footsteps away from the multi-tiered pool and ocean.