Vacation rentals in Isle's Bay Beach

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Top-rated vacation rentals in Isle's Bay Beach

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Superhost

A private pool is set within a spacious outdoor area, surrounded by lush greenery and mountains in the background. Comfortable lounge chairs line the poolside, with a patio dining area visible behind. Sunlight filters through the trees, creating a serene atmosphere.

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

The exterior of the apartment is presented, featuring a vibrant yellow facade. A covered porch area is visible with green railings, providing an inviting entrance. Windows are fitted with shutters, and landscaped greenery lines the ground, enhancing the overall charm of the space.

Apartment in Barzeys

4.88 out of 5 average rating, 26 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.

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

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.

Guest favorite

A sheltered patio area features a dark wooden table surrounded by four black plastic chairs. Lush green foliage can be seen in the background, providing a natural ambiance. Bright sunlight illuminates the space, enhancing the inviting setting for outdoor relaxation.

Apartment in Davy Hill

5 out of 5 average rating, 26 reviews

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.

The villa is set against a backdrop of lush green hills, perched elegantly on a gently sloping lot. The panoramic pool extends towards the horizon, while vibrant tropical landscaping surrounds the property, enhancing its natural beauty and inviting atmosphere.

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.

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

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.

Superhost

The bungalow is surrounded by lush greenery, featuring a combination of palm and other tropical plants. A wide driveway leads to the staircase, which ascends to an elevated porch that offers outdoor seating. The structure is complemented by a inviting red roof under a cloudy sky.

Home in Woodlands

4.82 out of 5 average rating, 11 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!

Top guest favorite

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 St Peter's Village

5 out of 5 average rating, 20 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.

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 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!

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

4.85 out of 5 average rating, 20 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.

Guest favorite

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's

4.93 out of 5 average rating, 27 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

A spacious pool deck features a clear blue swimming pool surrounded by several lounge chairs. Lush greenery and ocean views are visible in the background, while the sunlight reflects off the water's surface, creating a tranquil outdoor space.

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.