Vacation rentals with a pool in Anguilla

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Top-rated rentals with a pool in Anguilla

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

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Superhost
A spacious hammock is suspended between two posts on a covered porch, offering views of the ocean and surrounding landscape. Arched openings provide a picturesque frame, with sunlight casting soft shadows on the tile floor.
Home in Seafeathers
4.75 out of 5 average rating, 16 reviews

Beach Front Villa With Swimming Pool

Our home is beachfront with an infinity pool. It is a single-story home which is easily accessible, having only one small step down to access the front entrance. The property is completely fenced and has an electric gate at the driveway entrance making this home a safe, child friendly home. Our home is a perfect getaway for families and elderly couples providing you with the ability to stay in one location and be able to enjoy the beach and a pool. It is also convenient to all island activities.

Guest favourite
A serene swimming pool is nestled at the edge of a rocky coastline, reflecting the vibrant hues of the ocean. Gentle waves are observed in the distance, complementing the peaceful atmosphere surrounding the space. Comfortable loungers are positioned nearby for relaxation.
Villa in Island Harbour
5 out of 5 average rating, 25 reviews

Very Private Ocean Front Villa, Shoal Bay closeby

Vast expanse of ocean front, our villa is open-air living in contemporary design. Verdant gardens, natural stone swimming pool, outdoor jacuzzi (unheated) & seaside gazebo in secluded grounds. Serene, private hideaway. Choice of 5 beaches within 12 minute drive, including world famous Shoal Bay. Try a coastal hike, starting from the property, snorkel & swim from our gazebo (subject to weather conditions). We can arrange a French chef and/or massages at the villa. Subject to availability & fees

Guest favourite
A freshwater pool sits adjacent to the coast, surrounded by a stone patio and lounge chairs. Unobstructed sea views are visible beyond the pool, under a partly cloudy sky. The elegant railing complements the serene outdoor atmosphere.
Home in Shoal Bay Village
4.94 out of 5 average rating, 18 reviews

Shoal Bay Coastal Sanctuary, Anguilla, BWI

Shoal Bay Coastal Sanctuary is located directly on the coast with beautiful unobstructed views of the sea. It's a gracious two story home of 3 bedrooms and 3 full bathrooms--the lower level is comprised of 2 bedrooms on either side of an open plan "kitchen / dining room / living room" with the penthouse bedroom on the upper level. All rooms face onto the Caribbean and overlook the freshwater pool--every room is fully screened and air conditioned and graciously decorated in a Caribbean motif .

Guest favourite
A modern lap pool displays clear blue water reflecting the sky, bordered by a spacious deck. Two light blue chaise lounges are positioned nearby, accompanied by a large umbrella. The ocean and lush greenery form a picturesque backdrop under a partly cloudy sky.
Home in Blowing Point
5 out of 5 average rating, 9 reviews

Newly Renovated 2 Bedroom Villa

Peace & Happiness Villa is a perfectly situated 2 bedroom villa in the peaceful neighbourhood of Cul De Sac, Anguilla which is within 5-10 mins to many beaches, restaurants, premier golf, the port/airport and activities. With comfort and luxury in mind, the villa is fully equipped with the amenities and features to suit, like a marble accented gourmet kitchen, a 40ft lap pool, an outdoor dining patio perfect for entertaining, and a large sundeck lined with chaises and umbrellas.

Guest favourite
A private fresh water pool is framed by tropical plants and palm trees, overlooking the ocean. Lounge chairs are placed around the pool, with a shaded seating area visible nearby. The bright blue sea and sky create a serene backdrop.
Villa in Island Harbour
4.82 out of 5 average rating, 22 reviews

Villa Bianca Oceanfront 3BR with Private Pool

Wake to endless sea views, relax by your private pool, and savor calm rhythm of island life at Villa Bianca. Your oceanfront home away from home. From the moment you arrive, the turquoise Caribbean stretches before you, and the sound of the waves invites you to slow down and breathe. Located in a laid-back fishing village, the villa features a gourmet kitchen and a veranda perfect for sunset cocktails. Steps from fresh seafood, artisan pastries and fine French dining.

Guest favourite
An aerial view captures a pool area surrounded by palm trees and colorful buildings. Sun loungers are arranged near the pool, with guests enjoying the water. The ocean extends in the background, meeting a rocky shore under a clear sky.
Cottage in Island Harbour
4.93 out of 5 average rating, 30 reviews

Cozy Garden Studio with Pool – Suite #1

Property Summary: Relax in your inviting garden-view studio at Arawak Beach Club, featuring a unique bar area perfect for morning coffee or evening cocktails. Enjoy lush tropical surroundings from your private deck, a fully equipped kitchen, and cozy living space. Stay connected with high-speed fiber internet, cool off with air conditioning, or lounge by the pool with sunbeds. Complimentary kayaks and stand-up paddleboards (SUPs) are ready for your island adventures!

Guest favourite
The villa entrance is framed by palm trees and tropical plants, leading to a tiled pathway. Arched doorways and wooden shutters complement the traditional West Indian architecture. A view of the sea can be glimpsed in the distance, enhancing the inviting entryway.
Cottage in Seafeathers
5 out of 5 average rating, 6 reviews

Waterfront West Indian Island Villa

Manana is a 3 bedroom, 2 bathroom villa on the southeast coast of Anguilla with views of St. Martin, St. Barts, Statia, and on a clear day St. Kitts and Nevis. Enjoy a dip in a private infinity pool and listen to the birds sing. Built in a traditional West Indian design incorporating gardens planted with a variety of indigenous and tropical plants which create a beautiful setting. The Villa is a 7 min walk to Sandy Hill Beach and a 10 min drive to Shoal Bay East.

Top guest favourite
A private pool is surrounded by landscaped gardens, with a sun lounger positioned nearby. The pool's clear blue water reflects the bright sky and surrounding greenery, creating a serene outdoor space for relaxation.
Villa in Blowing Point
5 out of 5 average rating, 17 reviews

Modern Bungalow With Pool - 3 Min Walk To Beach

Immerse yourself in nature during your stay at The Bungalow, a tropical open-air villa perched amongst the trees on the island of Anguilla. Enjoy breath-taking ocean views from your private pool, take a quick walk down to the beach for a dip in Rendezvous Bay, and wind down while watching the sunset from your expansive roof deck. Nature lovers will delight in the property’s indoor-outdoor feel, surrounded by lush gardens and with visits from native birds.

Superhost
Apartment in South Hill Village

Chic Apartment with Pool Access with Breakfast

Enjoy a relaxing stay at this modern one-bedroom apartment with shared pool and balcony views. The cozy bedroom, full kitchen, and bright living area are perfect for couples or solo travelers. Just minutes from Anguilla’s best beaches, your stay includes breakfast for two at Tasty’s POV, where fresh island flavors and local ingredients create a truly delicious start to the day. Comfortable, convenient, and full of Caribbean charm—your ideal getaway.

Superhost
A clear swimming pool reflects the bright blue sky, surrounded by lush tropical greenery and palm trees. Comfortable lounge chairs are positioned near the pool, while a shaded area is provided by a blue umbrella, enhancing the outdoor relaxation environment.
Condo in Shoal Bay
5 out of 5 average rating, 6 reviews

Fountain Anguilla 1 Bedroom Garden View Condo

Fountain Anguilla Garden View 1 Bedroom offers intimate accommodations at an exceptional value with lush tropical landscape and pool views, private covered verandah with outdoor living and dining. This well appointed residence also features an upgraded full kitchen and expansive living area. The private bedroom has an en-suite bathroom featuring walk-in shower with dual vanity and king size bed with premium linens.

Superhost
A serene outdoor space is featured with two comfortable chairs positioned around a table. The infinity pool extends towards the ocean, with vibrant blue water reflecting the sky. Lush potted plants are placed nearby, enhancing the coastal atmosphere.
Cottage in Island Harbour
4.89 out of 5 average rating, 87 reviews

St.Somewhere Else

Oceanside guesthouse is peaceful, beautiful and gated. Full access to the bacce ball court, pool and ocean! We are located on the eastern end of the island, 5 minute drive to shoal bay and 3 minute drive to island harbor. Walking distance to some of the best local beach bars and restaurants!

Guest favourite
A sunlit pathway is framed by lush greenery and vibrant plants. The steps lead to a well-maintained entrance, showcasing a blend of modern architecture and tropical landscaping. The bright environment reflects a welcoming atmosphere, ideal for relaxing walks.
Villa in Island Harbour
4.96 out of 5 average rating, 25 reviews

Villa Romantica Overlooking the Ocean

My place is close to family-friendly activities, nightlife, beaches, restaurants. You’ll love my place because of the views, the people, the location, the outdoors space, and the ambiance. My place is good for couples, solo adventurers, business travelers, and families (with kids).

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