Vacation rentals in Woodlands

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Top-rated vacation rentals in Woodlands

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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.

Top 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.

Guest favorite

A two-story villa is surrounded by lush green hills, featuring a sunlit outdoor basketball court. The property includes multiple verandas with railing details and large windows allowing for ample natural light. A well-maintained lawn with stone pathways adds to the inviting exterior.

Home in Old Road

4.94 out of 5 average rating, 47 reviews

The Pearl: Gorgeous, Gated, 3BD/2BTH Villa w/AC

Welcome to The Pearl, your dream Caribbean getaway villa! This gated, air-conditioned sanctuary boasts a large master suite, two spacious bedrooms, modern entertainment, and an outdoor patio with a half-size basketball court. With breathtaking views, The Pearl features a fully equipped kitchen, laundry room, and a modern home office. Keyless entry, complimentary WiFi, and optional chef-prepared local dishes ensure a hassle-free stay. Book today and enjoy both adventure, relaxation, & luxury!

Top guest favorite

The exterior of a charming cottage is framed by vibrant red and pink flowers. A covered balcony extends from the white structure, surrounded by lush greenery. A certification sign indicating adherence to COVID-19 protocols is displayed prominently.

Cottage in Saint Mary

4.96 out of 5 average rating, 93 reviews

Sweet Lime Beachside Cottage

!!COVID INSPECTED, CERTIFIED & OPEN!! Agave Landings are affordable, one and two bedroom apartments and a studio cottage less than 165 yards from one of Antigua's best beaches. Located on Antigua’s Southwest coast, they are within minutes of a variety of restaurants, shopping, and entertainment facilities; while allowing easy access to St. Johns, Betty's Hope, English Harbour, and other sites; and providing a relaxing retreat to end your day with beautiful sunsets and star-filled skies.

Guest favorite

A macramé hammock is suspended from a covered terrace, showcasing intricate fringe detailing. A soft yellow towel is casually placed on the hammock. The background reveals a serene twilight sky filled with soft clouds, enhancing the peaceful ambiance.

Villa in Urlings

4.9 out of 5 average rating, 70 reviews

Sugar Moon,spectacular Antiguan Villa with pool

Secluded villa ideal for romantic getaways. Nestled atop Johnson's Point, this blissful house offers spacious, luxury accommodation with breathtaking views of the ocean and the nearby islands. The property is also conveniently located within easy reach of the most beautiful beaches of the island as well as the popular Jolly Harbour with easy access to bars, restaurants and shops. This brand new space is only a short distance from the iconic English Harbour and Antigua's rain forest.

Top guest favorite

A private patio area is accessed through glass double doors, shaded by a sail awning. Potted flowers in vibrant colors frame the entrance, complemented by a small dining table and chairs, creating a welcoming outdoor space.

Home in Crabbe Hill Village

5 out of 5 average rating, 28 reviews

Peaceful Village Beach Apartment

Immerse in the natural beauty of a local Caribbean village just 1-2 minutes walk from Crabbe Hill Beach, one of the best beaches in Antigua. Private double doors take you into a downstairs open plan studio with a fully equipped kitchen, double bed, shower room and A/C. Enjoy a glass of wine and sunset from the patio with a day bed and BBQ. Beach loungers and umbrellas at Crabbe Hill Beach Rentals are also included. Perfect for a creative retreat, solo traveller or romantic getaway.

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, 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.

Guest favorite

An outdoor deck area features a dining table with white chairs and two loungers positioned beside a private plunge pool. An entrance leads into a light-filled indoor space, complemented by greenery from surrounding trees.

Home in Valley Church

4.91 out of 5 average rating, 108 reviews

Shell Cottage with leisure pool, near the beach

Price reduced for 2 guests, 1 room for September On route to your temporary home you will glimpse authentic Caribbean living. Traveling through small villages you will notice colorful chattel homes before arriving at your relaxing retreat. Sugar Fields Holiday Home is Perfect for chilling. We are confident that you will enjoy your air-conditioned bedrooms, with private balconies and cozy, open plan indoor, outdoor living space.

Guest favorite

The exterior of a two-story house features a wraparound balcony with wooden railings and red accents. Multiple large windows are visible, surrounded by lush greenery and rocky terrain. A set of stone steps leads up to the entrance, complemented by potted plants.

Apartment in Saint Mary

4.91 out of 5 average rating, 114 reviews

Darkwood Sea View #1/ Car rentals $45-$55 US

Built from Greenheart lumber, this cozy property boasts views of beautiful Darkwood Beach and the Caribbean Sea, which is just a 5 minute walk away. Restaurants & other amenities e.g. supermarkets, banks & tours are within a 5 - 10 min drive. Our location is scenic with lots of greenery and lush vegetation . Guests can venture around for morning hikes and then stroll down to the beach.

Superhost

A private swimming pool sparkles under the sun, surrounded by a sleek deck with outdoor dining furniture. Scenic views of the Caribbean Sea and rolling hills create a vibrant backdrop, while the clear blue sky complements the tranquil surroundings.

Home in Valley Church Bay

4.67 out of 5 average rating, 3 reviews

Oceanview & Pool 3Bdr Escape

Valley Villa - A Modern Caribbean Escape in Ffreye's Estate Welcome to Valley Villa, a stunning brand-new construction, 3 Bedroom 2 bath house, sleeping 6, nestled in the serene Ffreye's Estate, offering breathtaking views of the Caribbean Sea and rolling hills beyond. Designed with a modern Caribbean aesthetic and earthy tones, this villa is a true oasis of tranquility and luxury.

Top guest favorite

A view from the patio showcases a beautifully landscaped garden, filled with lush greenery and vibrant flowers. The distant ocean can be seen under a clear blue sky dotted with clouds, enhancing the serene outdoor environment.

Condo in Old Road

5 out of 5 average rating, 28 reviews

2 bed apt w/ beautiful views-5 min to the beach!

$135 per night special rate June 1st - August 31st, 2025. $163 per night will resume October 16th, 2025! Ixora Vacational Rental is our 900-sq ft downstairs apartment. The space is completely separate from the upstairs portion where my husband and I reside. There is a separate entrance and patio.