Vacation rentals with a pool in Montserrat

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Top-rated rentals with a pool in Montserrat

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

Guesthouse in Old Town

4.88 out of 5 average rating, 52 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.

Superhost

Home in Saint Peter's

Caribbean Island Getaway

11,000 sq ft Villa nestled on 1.5 lush acres with the Caribbean Sea in your back yard and Mountains of Montserrat in your front yard . Relax in the private pool or walk in the gardens while enjoying the fruits from the many trees on the property when in season. Conveniently located to several restaurants and beaches .10 min hike or 4 min drive to Woodlands beach . Dine in the indoor or outdoor dining area .Watch the sunset from several different patios. This is how the Caribbean used to be.

Superhost

Home in Woodlands

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.

Home in Garibaldi Hill

5 out of 5 average rating, 4 reviews

Beautiful Caribbean Villa with spectacular views

Ranked one of the safest Islands in the Caribbean, Montserrat is a hidden gem of the Caribbean, where emerald hills cascade to pristine beaches. Montserrat beckons adventurers & serenity seekers alike to uncover its enchanting beauty. Dive into azure waters, explore volcanic landscapes, & immerse in vibrant local culture. This 3 bedroom private villa offers breath taking views of the sea, the valley & Volcano. The Villa is beautifully furnished, features great dining areas & a stunning pool.

Villa in Old Town

5 out of 5 average rating, 8 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.

Villa in Woodlands

4.83 out of 5 average rating, 24 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.

Top guest favorite

Home in St Peter's Village

5 out of 5 average rating, 19 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.

Home in Old Town

5 out of 5 average rating, 3 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!

Home in Woodlands

5 out of 5 average rating, 3 reviews

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.

Guest favorite

Villa in Woodlands

4.89 out of 5 average rating, 19 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.

Villa in Garibaldi Hill

4.77 out of 5 average rating, 26 reviews

Isles Bay Villa

Exclusive three bedroom villa overlooking the Belham Valley and Old Road Bay. Our villa overlooks the beach where Hank's Beach Bar is located. You can see and hear the waves breaking on the beach from the pool deck. You’ll love the views, the private location, and the trade winds cooling the house. Our villa is perfect for up to three couples or a family vacation.