Vacation rentals in Old Road Bluff

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Top-rated vacation rentals in Old Road Bluff

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Guest favourite

Guesthouse in Old Town

4.89 out of 5 average rating, 45 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.

Jun. 12 – 19

$116 CAD per night

Guest favourite

Apartment in Barzeys

4.9 out of 5 average rating, 20 reviews

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.

Jan. 7 – 14

$81 CAD per night

Apartment in Cudjoe Head

5.0 out of 5 average rating, 7 reviews

Luxurious Penthouse with Breathtaking Views

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.

May 29 – Jun. 5

$235 CAD per night

Villa in Woodlands

5.0 out of 5 average rating, 17 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.

Apr. 9 – 16

$305 CAD per night

Guest favourite

Home in Woodlands

5.0 out of 5 average rating, 5 reviews

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!

Nov. 2 – 9

$165 CAD per night

Guest favourite

Home in St Peter's Village

5.0 out of 5 average rating, 8 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.

Nov. 25 – Dec. 2

$324 CAD per night

Villa in Old Town

4.88 out of 5 average rating, 8 reviews

The Taj - Breathtaking Panoramic Vistas

Enjoy stunning views of the Caribbean Sea, valley and volcano from the Taj's expansive deck. Swim in the large pool, or walk 10 minutes to swim at secluded Isles Bay Beach. Our huge villa and new kitchen makes cooking delightful and a large family group fun! Explore the charming local bars and restaurants. Walk among the almond, coconut and banana trees. Study the wild iguanas, agoutis, geckos and rare birds in their habitat. Hike on jungle paths. Free wifi.

Nov. 10 – 17

$787 CAD per night

Guest favourite

Villa in Woodlands

5.0 out of 5 average rating, 9 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.

Apr. 4 – 11

$448 CAD per night

Cottage in Old Town

5.0 out of 5 average rating, 6 reviews

Oceanfront Luxurious Villa Stunning Sunsets Avalon

Very well appointed luxurious villa. Bedrooms with comfortable Kingsize bed and private ensuite. Well equipped kitchen with coffee maker, toaster, microwave, gas cooktop, wall oven, dishwasher. Linen all included. Laundry room with washing machine and dryer. Iron and ironing board. Private swimming pool, spacious sunbathing deck, great views of the mountain and the beach. Walking distance to beach ( 5 min ).

Apr. 7 – 14

$625 CAD per night

Guest favourite

Apartment in Saint Peter's

5.0 out of 5 average rating, 12 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

Jan. 28 – Feb. 4

$133 CAD per night

Apartment in Old Town

4.81 out of 5 average rating, 26 reviews

Lime Cliff

Ideally located in the quiet area of Old Town, overlooking the caribbean sea, this newly nuilt house is at a walking distance from Lime Kiln Beach. You can enjoy the cool breeze and the great view on the Centre Hills, the cliffs and the sea, while liming in the hammock on the covered terrace ! You will have access to the neighbour pool, owned by the family and serving 3 independent buildings.

May 13 – 20

$107 CAD per night

Villa in Garibaldi Hill

4.9 out of 5 average rating, 21 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.

Dec. 9 – 16

$272 CAD per night