Family-friendly vacation rentals in Montserrat

King Bed Studio Chess Apartments

Experience peaceful, family-friendly comfort in our unique, stylish and spacious retreat. We're centrally located, just a 1-min walk from banks, restaurants, supermarkets, and more, plus a short walk to the beach! Free parking, Breathtaking views of Montserrat's landscapes and beaches. Refreshing Breezes (no AC needed here!). Ideal for singles, couples, friends, and small families. King Bed/Two Twin Bed, plus a sofa bed. We offer airport/seaport transfers, car rentals, tours, pool access

Lovely two bedroom apartment

Welcome to your Caribbean bolthole. This is a lovely two bedroom apartment set in the hills of beautiful Montserrat. The apartment is set on the edge of a valley (Ghaut ) with unblocked views of the sea towards Redonda and Nevis and a cool breeze in the evenings. You will have exclusive use of our apartment, with a separate entrance for you to come and go at your leisure. The Host lives in the apartment above, and will therefore be on hand by phone or email if you run into any difficulties.

NEW Stylish Caribbean 3 Bdrm Villa

This incredible 3 bedroom Villa's garden grounds stretches over 100 yards of unobstructed panoramic views, abundant in colour with blooming florals and lush with towering mahogany trees under which hammocks swing in the ever present view of the Caribbean Sea. From corner to corner, this estate has one of the most beautiful, vistas with the sound of waves lapping on its shoreline below -plus views of neighbouring islands Nevis, Redonda & the tip of St. Kitt's - a constant reminder of paradise.

Relax-In 2BR | Central Location + Jeep Rental

Our property is centrally located and just a short walk from everything you need—supermarkets, cookshops, bars, salons, and variety stores are all within 2–3 minutes. The beach is only a 10-minute walk away! We offer free airport/seaport pickup, high-speed Wi-Fi, and thoughtful amenities like a coffee machine to make your stay comfortable. Need help exploring? We can arrange local tours, hiking adventures, or taxi services for you. A rental Jeep is also available for an additional daily rate.

Family Beachside Living with Oceanviews & Pool

Pristine Caribbean beaches, lush palm trees, and exhilarating island breezes await at this gorgeous 3-bedroom, 3-bath Montserrat stay. The bungalow is nestled in the secluded paradise of the West Indies, offering unbeatable panoramic views of Woodlands Bay and is just steps to the yellow sands of Woodlands Beach. Endless adventure awaits on this heavenly island, where you can explore volcanoes, tropical rainforest hiking trails, and local restaurants, all within arm's reach!

Providence: Paul McCartney's former hideaway

Providence Estate House, a unique historic Caribbean house, was the home of Paul McCartney and his family when he recorded "Tug of War" and "Ebony and Ivory" with Stevie Wonder in 1981. Originally built in 1918, it was rebuilt following 1989's Hurricane Hugo. Completely private, set in 10 acres on a breezy hilltop with sunset views overlooking the Caribbean from almost 600 feet, you will love the space, peace and serenity of this classical home and its beautiful setting.

Oasis Villa

Oasis is a beautiful secluded caribbean villa, built in a lush green garden in woodlands, Montserrat. Its a two bedroom villa with two bathrooms. Master suite is steps away from pool , laundry room, kitchen, dining room, living room, large porch overlooking the ocean, garden and a forty foot swimming pool. Oasis is also approximately a ten minute walk to the beautiful, picture perfect and secluded woodlands beach.

Oceanfront luxury, king bed,AC,WiFi,4beds,3bedroom

Private, gated luxury villa leaves Nothing between you and the Carribean blue sea. You can view turtles and dolphins from the comfort and privacy of your pool deck. You will never get tired of the sunsets and the moonlight views. Wake up to the sound of waves and birds every morning. Free WiFi, cable tv and fire stick. 5 minutes to 3 of the island’s premier restaurants, supermarkets, and the village rum bars.

Lucy's Sunny Villa Studios ll

Take an early evening stroll to Bunkum Bay and enjoy the Sunset in the warmth of the Caribbean sea, we are ideally placed for those with a fondness for nature a perfect place to stay for couples. This spacious studio apartment will also accommodate up to 3 adults if required, with all modern amenities stylish shower room and furnishings, Come kickback and relax with us at any one of Lucy's Sunny Villa Studios

Cozy Apartment w/ Jeep & Prime Locatio

The VIP Queen Suite is a fully furnished private unit in a prime location, featuring a queen-size bed, kitchenette, living area, and optional AC (not included in base rate). Located on the ground floor of VIP Penthouse & Suites, guests enjoy full access to a courtyard with a pool and dining area. Walking distance to supermarket, pharmacy, restaurants, bars & more. Jeep rental available at an additional cost.

Camie's Apartment

One of 2 new fully furnished units with Refrigerator, Cooker, Washing Machine, Cable Ready Television and Wifi Access. Within walking distance from two supermarkets and at least three restaurants if you desire to dine out at any time. There is also access to a Bus or Taxi service if prefer not to drive yourself. However, parking is available if you chose to drive.

Old Town Studio w/Separate Affiliated Pool House

We require a USD$50 damage deposit [Fully refunded if no damage] A 1 bedroom with 3 beds and 1 bathroom downstairs Flat. Access to pool from affiliated pool house with advanced notice. [The pool house is a completely separate property. 2 minutes walk from the advertised one]