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Vacation rentals with a pool in Saint Mary

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Top-rated rentals with a pool in Saint Mary

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

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Guest favorite
An open-air pavilion overlooks the calm sea, featuring a large infinity pool with a wooden deck. A single blue bean bag chair rests on the edge, facing the expansive horizon. Lush palm trees frame the serene view under a clear sky with distant clouds.
Villa in Jolly Harbour
4.95 out of 5 average rating, 41 reviews

Unique Caribbean Secluded Open Air Villa 1 Bedroom

Perched at the very tip of Reeds Point, this open-air villa offers a unique escape for non-luxury seekers who value privacy, natural beauty and true seclusion. From sunrise to sunset, enjoy uninterrupted sea views on both sides of the coastline and distant islands. Spread across multiple levels, the villa offers intimate in/outdoor spaces designed to make most of the views. Stairs lead to the rocky shoreline, offering private access to the sea for swimming and snorkeling just outside your door.

Guest favorite
A modern living area is highlighted by a large, L-shaped white sofa adorned with decorative pillows. A round gold coffee table sits on a light-colored rug. The space features a sleek ceiling fan, elegant lighting fixtures, and an open layout leading to the dining area.
Apartment in Jolly Harbour
4.92 out of 5 average rating, 26 reviews

Stella Vista - Luxury Jolly Harbour Condo

Nestled on the north finger in Jolly Harbour, sits this amazing newly renovated waterfront villa. Stella Vista boasts scenic views of the mountain range, Harbour Island and is ideally located within walking distance to the North Beach. Jolly Harbour is a gated community with 24 hour security, 2 beaches, restaurants, hair salon, supermarket and countless other amenities to make your holiday stress free. Included with your stay is an electric golf cart for added convenience. Adults Only. No kids.

Guest favorite
Villa in Urlings
4.91 out of 5 average rating, 76 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 and zip line

Superhost
A two-story villa is situated by the water, featuring balconies adorned with colorful towels. A wooden dock extends from the patio, leading to the calm, reflective water. Lush greenery and decorative plants enhance the outdoor space, providing a serene retreat.
Home in Jolly Harbour
4.63 out of 5 average rating, 8 reviews

Few Minutes walk to Jolly Beach!

Relax with your family & friends at this tranquil villa on the water in gated Jolly Harbour. Three minute walk from Jolly Beach you will find this comfortable two storey, two bedroom villa. Pool, gym ($) and tennis courts are available on the resort for keeping fit. There is a golf course for avid golfers ($). There are a number of restaurants with nightly entertainment to enjoy. Walk the beach as the sun sets for a magical experience. Rent a car to explore the island. Adventure awaits!

Top guest favorite
An infinity pool extends toward the horizon, reflecting the bright blue sky. The turquoise waters blend with the Caribbean Sea, framed by lush green hills in the background. Clear vistas and serene surroundings create a tranquil outdoor space for relaxation.
Villa in Hermitage
5 out of 5 average rating, 38 reviews

Luxe Panoramic Sea View - near Hermitage Bay Beach

Amazed Sea View Villa This luxury holiday villa is located high up on the beautiful Sleeping Indian hills. Sitting on half an acre of tropical land, the location allows for spectacular vistas across the turquoise waters of the Caribbean. A stunning infinity pool, open terraces, tropical gardens, luxurious, peaceful, and private. Amazed is a must to experience! Just a 10 min walk to stunning Hermitage Bay beach and a 10 min drive to Jolly Harbour, for the grocery store, restaurants, and shops.

Guest favorite
The spacious pool glows in blue lighting at dusk, surrounded by palm trees and lush greenery. Red loungers are positioned along the deck, offering a comfortable space to relax while enjoying the serene sunset views.
Villa in Saint John's
4.95 out of 5 average rating, 19 reviews

Villa Lazy Daze - Private villa with large pool

This recently renovated 4-bed, 3-bath vacation home comes equipped with all the modern amenities, perfectly suited for a relaxing holiday.​​ Secluded in the residential community of Harbour View, you are within walking distance of Jolly Harbour Marina featuring restaurants, bars, banks (ATMs), shopping, supermarket, water-sports and a host of vacation activities. The property is also < 8 min walk from Jolly Beach, a mile long stretch of powdery white sands, turquoise waters and cool winds.

Guest favorite
An outdoor deck features two lounge chairs with cushions, a small table adorned with potted plants, and a pitcher beside glasses. The setting is illuminated by a warm sunset, creating a serene ambiance over the water.
Townhouse in Jolly Harbour
4.92 out of 5 average rating, 118 reviews

Waterfront Villa – Designer Tropical Getaway

Townhome with 2 bedrooms, 2.5 bathrooms, 1200 sq. feet (111 sq. meters). Water facing private deck and 2 balconies with western sunset views. Fully stocked and equipped kitchen. On-site private parking for smaller cars; parking for larger vehicles a few steps away. Gated community with restaurants, bars and cafes, golf course, marina, supermarket, banks and rental car agencies. 10-minute walk to North Beach and golf course, 20-minute walk to restaurants, shops, other amenities.

Superhost
A table set beneath a large umbrella features two colorful drinks, overlooking the tranquil Caribbean Sea. The surrounding area is adorned with vibrant pink flowers and lush greenery, with gentle hills visible in the background.
Villa in St. Marys
4.94 out of 5 average rating, 32 reviews

Winter Discount! Pool, Panoramic Sea view & Kayaks

PARADISE AWAITS YOU AT ANTIGUASOLEIL. Short walk to beach. NEW saltwater, lap Pool. Kayak. Beach chairs. Cooler. Grill. Hiking. Relaxation. Smart TV's. Wifi. Spectacular, panoramic views of the tranquil Caribbean Sea will take your breath away! This luxurious, spa-like, gated 3-bedroom home is on Sleeping Indian overlooking Jolly Harbour & multiple islands including the volcanic island of Montserrat. All nationalities, cultures & religions are welcome at AntiguaSoleil.

Guest favorite
A large swimming pool is situated at the forefront, reflecting the clear blue sky above. A spacious covered patio with modern seating is visible behind the pool, providing shaded outdoor living. The villa's light blue exterior complements the vibrant atmosphere.
Villa in Jolly Harbour
5 out of 5 average rating, 9 reviews

Spacious Waterfront Sanctuary

Welcome to Blue Haven, a stunning new three-bedroom luxury villa that promises an unparalleled Caribbean experience. Nestled by the water's edge, this stunning property features a large swimming pool, a beautifully crafted wooden deck with loungers, and a spacious covered patio equipped with dining and lounging areas. Complete with a state-of-the-art built-in Bbq, it’s the perfect setting for al fresco living against the breathtaking backdrop of the waterfront.<br><br>

Superhost
A well-equipped kitchen is showcased with wooden cabinetry and modern appliances. Two chairs are positioned at the bar counter, set with plates and cutlery. Light streams in through a door leading to a garden area adorned with colorful flowers.
Townhouse in St. Mary's
4.79 out of 5 average rating, 24 reviews

Comfy Waterfront Jolly Harbour - Villa Beverly

Come and enjoy this comfortable 2 Bedroom, 2.5 bathroom, waterfront villa. Convenient on site access to all amenities including restaurants, shops, and a white sand beach, it is everything you want in a vacation paradise home. As of December 2025, Jolly Harbour offers a brandnew sports center with pool, lounge area, bar, gym, tennis court and pickle ball court to enjoy. You have free access to pool and courts and you can purchase a membership for the gym.

Guest favorite
A two-story villa is positioned on a lush hillside, surrounded by greenery. The building features a vibrant red roof and spacious balconies that overlook the landscape. Various palm trees and other vegetation are visible in the foreground, enhancing the property’s natural setting.
Home in AG
4.97 out of 5 average rating, 33 reviews

Cactus House. Uber Peace, Tranquility & OMG Views

WORLD CLASS AWARD WINNING PROPERTY. Cactus House is situated on lush hillside was built with the intention of providing tranquil luxury accommodation for up to 8 people. Built virtually regardless of cost, this sumptuous Villa is already regarded as one of the best properties in the area. The 270' Caribbean views are stunning & has the largest private infinity swimming pool locally. Beaches are just the other side of the road.

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
4.9 out of 5 average rating, 112 reviews

Shell Cottage with leisure pool, near the beach

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.

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