Family-friendly holiday rentals in Montserrat

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Montserrat

Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

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Guest favourite

A charming cottage is situated along a winding path, surrounded by lush greenery and rolling hills. The structure features a bright blue exterior with a yellow door, blending harmoniously with the natural landscape.

Guesthouse in Old Town

4.88 out of 5 average rating, 57 reviews

Blue Lime Cottage

Our cottage is located at a walking distance of Lime Kiln Beach. You will like our cottage because of its privacy and the nature surrounding it. As of October 1st Monserrat welcomes visitors who are fully vaccinated with a WHO approved vaccine and a negative Covid test done within the last 72 hours. In addition visitors are required to quarantine for 5 days upon arrival. During the quarantine you can walk around our property and use the swimming pool in addition. Items can be delivered to you.

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Superhost

A bright living area features a white sofa with contrasting black and white cushions, positioned beside a glass coffee table. A wall-mounted TV displays a selection of channels. Natural light enters through large windows, and an open door leads to a green outdoor landscape.

Apartment in Davy Hill

4.75 out of 5 average rating, 4 reviews

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

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Superhost

The exterior of the villa is framed by lush tropical landscaping, featuring vibrant green plants and colorful flowers. A paved driveway leads up to the entrance, where the two-story white building is highlighted under a clear blue sky.

Home in Woodlands

5.0 out of 5 average rating, 3 reviews

Stylish Caribbean 3 Bdrm Villa Nestled in Nature

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.

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Superhost

A master bedroom features warm yellow walls and an inviting atmosphere. A spacious bed is adorned with neutral linens, complemented by decorative pillows. A large window offers a view of the outside, while wooden furniture adds a touch of elegance to the room.

Apartment in Cudjoe Head

4.91 out of 5 average rating, 11 reviews

Luxurious Penthouse w/ Breathtaking Views & Jeep

Experience the simple luxuries in life in a place that is simply extraordinary. Affordable & luxurious, VIP Penthouse & Suites is one of its kind sitting approx. 900ft above sea level on the hillsides of Baker Hill, Montserrat, WI. We are just 7 minutes away from the airport. Well-kept gardens, sparkling pool, outdoor kitchen w/ dining area & charming pergola. Close to the local bank, pharmacy, supermarket, restaurant/ bars, beauty salon. Jeep rental is available and we also arrange tours.

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The image captures a serene outdoor area featuring a swimming pool with an ocean view. Two lounge chairs sit beneath a large umbrella, surrounded by lush greenery. The calm sea and distant hills create a tranquil backdrop against a clear sky.

Villa in Old Town

4.89 out of 5 average rating, 9 reviews

Oceanfront Luxurious Villa Stunning Sunsets Avalon

Villa Avalon is a well appointed luxurious and rare ocean front property. All bedrooms boast a comfortable King size bed and private ensuite bathroom. The kitchen is well equipped with everything you will need. The main living is outdoors in this villa, with 180 degree ocean view as you lounge, dine or sunbathe. Enjoy beach and mountain view from the main patio and breathtaking mountain and volcano views from the lookout. This villa offers ocean front living at it's best.

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A view from the garden captures the lush greenery framing a panoramic scene of the Caribbean Sea. The villa's architecture is visible alongside vibrant palm trees and tropical foliage, all set against a clear blue sky, creating a serene atmosphere.

Villa in Woodlands

4.85 out of 5 average rating, 26 reviews

Secluded Caribbean retreat with a spectacular view

Nestled in Montserrat's rainforest-covered hills, with breathtaking views over the Caribbean Sea and a ten-minute walk to an often-deserted beach, this secluded hideaway is perfect for those seeking a restorative and utterly peaceful vacation. Because it is west-facing, sunset cocktails on either of the 60ft balconies or pool deck are a must. I can send a drone video of the villa and garden (kindly sent to me by a guest) once a booking has been made and email addresses exchanged.

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Top Guest favourite

An aerial view of a historic Caribbean house highlights its spacious covered verandah and private pool. Lush greenery surrounds the property, with palm trees and ornamental plants creating a tranquil atmosphere. The design features open spaces and direct access to the pool deck.

Home in Saint Peter

5.0 out of 5 average rating, 26 reviews

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.

Indoor spacesFamilyBeach

A vibrant red villa is nestled among lush greenery, showcasing a clear blue sky overhead. A swimming pool is positioned in the foreground, reflecting the surrounding landscape. Steps lead up to the villa's entry, complemented by white railings and tropical plants.

Home in Old Town

5.0 out of 5 average rating, 4 reviews

Bananaquit at the beach!

Wishing to escape to a delightful villa overlooking a lovely beach on the most tranquil island ever? Planning to spend hours poolside soaking up the sun or just taking cool dips? Want to be footsteps from the shores? Bananaquit says yes to all above! This comfy villa in a prime location on Montserrat has stunning views all around. The villa includes 2 bedrooms upstairs and a lower level 1 bedroom apartment. Lush mature gardens surround this perfect getaway! Book Now!

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Top Guest favourite

The cozy clubhouse is situated close to the shoreline and surrounded by lush palm trees. The structure features a porch with seating, offering views of the beach and the nearby rocks. A gentle slope leads from the clubhouse to the water, integrating nature with the living space.

Guesthouse in Little Bay

5.0 out of 5 average rating, 15 reviews

The Clubhouse

Welcome to Montserrat's first eco-conscious clubhouse by the sea. We are located on the northwest coast of our small but incredible island, in the centre of the Little Bay, steps away from the surf. We are only five minutes drive from the the new town “ brades’ , and just 3 mins walk to Marine Village, a collection of small bars, a couple restaurants an a dive shop. The Clubhouse is nestled between coconut trees in the heart of our beach community.

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Home in Woodlands

5.0 out of 5 average rating, 3 reviews

Villa 2860

Nestled in the peaceful village of Woodlands, this charming retreat offers a rare chance to experience Montserrat’s natural beauty. Surrounded by lush greenery and cooled by Caribbean breezes, it’s a quiet escape where time slows down. Just down the street from Woodlands’ black-sand beaches and Runaway Ghaut, the home blends island character with modern comfort—an unforgettable stay that will draw you back to the Emerald Isle.

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Guest favourite

A tranquil scene featuring a shimmering pool reflecting the colors of the sunset. Lush palm trees are visible at the pool's edge, while the calm sea and colorful clouds create a serene backdrop.

Villa in Woodlands

4.87 out of 5 average rating, 23 reviews

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.

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Superhost

A tropical setting is depicted, showcasing the white exterior of a spacious house surrounded by lush green palm trees and foliage. The roof is gently sloped, blending harmoniously with the natural landscape.

Apartment in Saint Peter

4.9 out of 5 average rating, 41 reviews

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

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