Holiday houses in Old Town

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Top-rated holiday rentals in Old Town

Guests agree: these stays are highly rated for location, cleanliness and more.

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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

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

ValueLocationWalkability

4.75 out of 5 average rating, 4 reviews

A vibrant green villa is framed by lush palm trees and tropical foliage. The entrance features a set of steps leading to the inviting porch, with a driveway visible on one side. A clear blue sky enhances the tropical setting.

Home in Old Town

See Forever Villa

See Forever Villa: Your Tropical Sanctuary Breathtaking views of Soufriere Hills Volcano meet luxury living. Dive into a half-acre wellness haven with pool, gym, and fruit-laden trees. Coconuts and mangoes at your fingertips. Nearby beaches (Old Road, Isles Bay & Lime Kiln Bay), fine dining and local cuisines just moments away. More than a stay – an experience that reconnects you with nature's magnificent rhythm. Escape the ordinary. Embrace the extraordinary. Your volcanic paradise awaits.

LocationOutdoor spacesHiking

4.67 out of 5 average rating, 3 reviews

Guest favourite

A sandy beach scene features sheltered loungers under green and red umbrellas. Gentle waves lap at the shore, and a rocky coastline is visible in the background, framed by a clear blue sky.

Cottage in Saint John's

TURNER'S BEACH - 2 Bedroom Beachfront Cottage

Quite literally one minute walk from your cottage to the beach Turner's Beach Cottage #1 is the perfect beach cottage of for a family of 4 Follow us on IG @starfishantigua This two bedroom cottage can comfortably fit a family of 4, maximum. Main bedroom: queen size bed, Second bedroom: Two twin beds Separate living and kitchen area with outdoor patio WIFI and cable tv available on site, but we are better suited to a DIGITAL DETOX. Beach loungers and umbrellas available on site Free parking

ValueLocationCleanliness

4.89 out of 5 average rating, 18 reviews

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

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.

LocationOutdoor spacesSleep quality

4.89 out of 5 average rating, 9 reviews

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

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.

LocationValuePool

4.85 out of 5 average rating, 26 reviews

Guest favourite

An open living space features a high vaulted ceiling with exposed beams. A cozy seating area is arranged around a coffee table, while a dining table and chairs sit to the side. Bright tropical accents are visible throughout the space.

Home in Johnson's Point

Reef Cottage

Right on your very own private beach, with views over the ocean to our neighboring islands. This is a one of a kind location, exclusively private, centrally located close to restaurants, bars the biggest grocery store on island. You can spend the day snorkeling the vibrant coral reef, spotting turtles or collecting shell around the coastline, all without leaving the property. Watching the sunsets on the beach with your feet in the sand is the most magical way to end a day.

LocationFamilyGetting around

4.88 out of 5 average rating, 16 reviews

Guest favourite

A villa is set amidst lush greenery, with palm trees surrounding its edges. The house features a light-colored exterior and a sloped roof. Large windows invite natural light, creating a connection with the tropical environment.

Villa in Saint Peter

Lucy's Sunshine Villa Palm Loop, 3 Bed 2 bathroom

Bring the whole family over, with lots of room for fun & Surrounded by nature this villa is approximately ten minute walk to the closest beach. this villa offers the best for both worlds for the sea lovers or for those who prefer to simply relax at home on the veranda and take in the warm sunshine and take in beautiful Sunsets the Caribbean offers? then this is sure to meet your holiday needs. As a self-catering villa, you'll find all the amenities needed for a perfect stay.

FamilyValueAccuracy

5.0 out of 5 average rating, 10 reviews

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

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!

LocationFamilyPool

5.0 out of 5 average rating, 4 reviews

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

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.

LocationFamilySleep quality

5.0 out of 5 average rating, 15 reviews

Home in Woodlands

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.

HospitalityAmenitiesCleanliness

5.0 out of 5 average rating, 3 reviews

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

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.

FamilyLocationTV

4.87 out of 5 average rating, 23 reviews

A clear blue pool reflects the sky, surrounded by vibrant foliage and decorative seating. A white staircase leads to the upper level, complemented by a sun-drenched patio featuring loungers and umbrellas, providing inviting outdoor spaces for relaxation.

Guesthouse in Salem

Hibiscus Suite - Private 1 Bed | Pool | Wifi | AC

Retreat to your own private room and bathroom in a peaceful slice of paradise designed for total relaxation and tranquility. Enjoy the privacy of your own space, complete with thoughtful amenities to make your stay comfortable from check-in to check-out. The property also offers many amenities such as two grand pools, pickleball court, roof decks and much more.

ConditionComfortWalkability

4.86 out of 5 average rating, 7 reviews