Vacation rentals with a pool in Anguilla

Find and book unique homes with a pool on Airbnb

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 favorite

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

Superhost

A private pool is situated beside the ocean, surrounded by lounge chairs facing the water. The tranquil surface of the pool reflects the morning sunlight, while the Caribbean sea extends into the horizon, highlighting the serene atmosphere of the villa.

Villa in Island Harbour

4.96 out of 5 average rating, 50 reviews

Stunning Oceanfront Villa ~ Pool, Jacuzzi & Kayaks

Your 5 star Airbnb guest favorite oceanfront villa includes a private pool, hot tub and panoramic Caribbean views. Scilly Cay is right out front and only a 5 min drive to famous Shoal Bay. Wake up to the glowing turquoise sea from the master King Bed. Relax on the spacious lower & upper decks. Full kitchen, private office and outdoor shower. Enjoy kayaks, stand up paddleboards, additional club pool, decks & fire pit. Perfect for families or romantic getaway in paradise. Read our 5 star reviews!

Guest favorite

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 .

A bright and airy living space features large windows that offer expansive ocean views. Light-colored furniture complements the open layout, while a ceiling fan provides airflow. The fully equipped kitchen is visible in the background, with neutral cabinetry and countertops.

Condo in West End

4.71 out of 5 average rating, 52 reviews

Turtles Nest Beach Resort - Beachfront 1 bedroom condo

Turtle's Nest stands in the middle of Meads Bay, the most iconic beach of Anguilla. A supermarket is nearby, as well as many dining options. You can enjoy the view from your oceanfront balcony overlooking the beach. Free WIFI, beach towels along with beach chairs and umbrellas are offered. From car rental to babysitting, our friendly staff will insure all your needs are catered. Every afternoon a complimentary rum punch is brought to you by our lovely staff on the beach or in the pool.

Superhost

An aerial view captures the villa, surrounded by lush greenery, with the coastline of Anguilla visible in the background. The vibrant turquoise waters contrast with the white sands along the shore, showcasing the natural beauty of the secluded landscape.

Home in North Hill Village

4.83 out of 5 average rating, 18 reviews

Cloud Cottage- Cliffside villa

Villa Cloud Cottage, is a newly-renovated 4-bedroom villa located in peaceful North Hill with some of the best views in Anguilla. A short walk down the hill is Katouche Bay; a secluded beach where you're likely to have the white sand and turquoise water all to yourself. Hammocks, loungers, and chairs dotted around the property, providing endless spots to enjoy the expansive views of the island's Northern coast. Chef-designed and professional grade kitchen, with an expansive island.

Guest favorite

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, 8 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 favorite

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 favorite

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

New place to stay

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

The sleeping area features two luxurious queen beds with premium linens and decorative pillows. A spacious closet is visible in the background, and large glass doors open to a private covered verandah with views of palm trees.

Apartment in Shoal Bay

4.6 out of 5 average rating, 5 reviews

Studio- 2 Queens, Partial View!

Safe Environment Certified- Visit Fountain Anguilla Website for more details. Fountain Anguilla Ocean View Studio Suite Fountain Anguilla by Refined Retreats- This hotel-style suite offers intimate luxury accommodations at an exceptional value with magnificent ocean views, private covered verandah with outdoor living, en-suite bathroom featuring walk-in shower with dual vanity and 2 luxurious queen size beds 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 harbor

4.88 out of 5 average rating, 85 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!