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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Guest favourite

Home in Seafeathers

4.73 out of 5 average rating, 15 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

Villa in Island Harbour

5 out of 5 average rating, 25 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 favourite

Townhouse in Blowing Point

4.9 out of 5 average rating, 20 reviews

White Sands Sand- spacious clean, 5min walk2 beach

Nestled in the quiet historic-tourism neighborhood of Cul De Sac - 5 minutes walk to one of the worlds best beaches (Rendezvous Bay), White Sands Anguilla is a Villa-Home with all modern amenities focused on providing you with the comfort and cleanliness of home with access to all Anguilla has to offer. Rendezvous offers access to popular restaurants such as The Place, Garvey's Beach Shack, The Dune, Tokyo Bay and more. Come relax and enjoy your stay at White Sands. We are happy to host you.

Superhost

Home in North Hill Village

4.86 out of 5 average rating, 14 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.

Superhost

Condo in Shoal Bay

5 out of 5 average rating, 4 reviews

4 Bedroom/ 4 Bath- Sleeps 12 Pool View Condo Combo

Safe Environment Certified- Visit Fountain Anguilla Website for more details. Featuring 4 bedroom suites and 4 full bathrooms offering double vanities and walk-in showers, this lush tropical garden view residence offers lavish comfort along with ample space. This is a combination of 2 residences, side by side with separate entrances. With accommodations for up to 12 guests, 2 upgraded full kitchens and 2 expansive living areas, as well as pool and garden views from the patios.

Villa in Seafeathers

4.91 out of 5 average rating, 11 reviews

Oceanview villa with private pool, 5 mins to beach

Southern Comfort Villa is the perfect place for those looking for a laid back, cottage-like retreat. Our 2 bedroom, 2 bath villa sleeps 4-5 guests. The great room boasts 20 ft vaulted ceilings, a fully equipped kitchen and comfortable furnishings. Take a dip in the pool while enjoying unobstructed views of the Caribbean Sea and neighbouring islands of St. Martin and St. Barth. Enjoy a relaxing morning coffee or afternoon drink with a view on the wrap around veranda.

Superhost

Villa in AI

4.88 out of 5 average rating, 34 reviews

Villa Amor Overlooking the Ocean

Villa Amor, is perched on Harbour Ridge in the charming village of Island Harbour, exudes romantic elegance and contemporary panache. This villa offers the comfort of home and the tranquil ambience found only on Anguilla. Villa Amor is close to beaches, nightlife, and restaurants. You’ll love the villa because of the views, the location, the people, and the outdoors space. Villa Amor is good for couples, solo adventurers, business travelers, and families (with kids).

Home in South Hill Village

4.77 out of 5 average rating, 31 reviews

Beautiful 3 bed Villa

A fantastic, spacious villa in a secluded location which feels very safe and close to everything you need. It is an opportunity to get away from the world. Spend your time touring the island, at the nearby beaches or lazing by the private pool and patio which is exclusively for you to relax or enjoy the sunset in the evening. There is WIFI, and an open living and dining area. Many of our guests have said it is a home away from home

Home in AI

5 out of 5 average rating, 4 reviews

Lockrum Point Villa Oceanside 2bdrm/2bath w/ Pool

Welcome to our retreat, Lockrum Point. This amazing two-level Seaside villa sets the stage for luxurious relaxing and entertaining. Enjoy incredible views of the sea and St. Martin, a private pool, and a gazebo perched on the sea. Each of our bedrooms have ensuite baths, hair dryer, spa bath robes and slippers, Caribbean Sea views and air conditioning.