Holiday 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.

0 of 0 items showing

1 of 3 pages

Superhost

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.

Top guest favourite

Villa in Island Harbour

5 out of 5 average rating, 45 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

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 .

Apartment in West End

4.71 out of 5 average rating, 51 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

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 favourite

Home in Blowing Point

5 out of 5 average rating, 7 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.

Top guest favourite

Home in Long Bay Village

5 out of 5 average rating, 9 reviews

Châlet Genesis

Escape to the serenity of Châlet Genesis Villa, an exquisite 3-bedroom, 3.5-bathroom haven nestled in the residential charm of Long Bay. This spacious villa boasts walk-in closets, king-size beds, and modern amenities, creating an opulent retreat for up to 8 guests. Revel in the tranquility of your surroundings while being just moments away from pristine beaches and delectable restaurants. Discover the perfect blend of luxury and accessibility at Châlet Genesis Villa

Guest favourite

Cottage in Seafeathers

5 out of 5 average rating, 5 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

Villa in Blowing Point

5 out of 5 average rating, 16 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 Shoal Bay

5 out of 5 average rating, 8 reviews

Ocean View 1 Bedroom Condo on Shoal Bay Beach!

Safe Environment Certified- Visit Fountain Anguilla Website for more details. Over 1,000 sq ft of oceanfront living space accommodating up to three guests, offers magnificent ocean views from the covered verandah accessible from both the living room and bedroom, private master bedroom retreat with king size bed and premium linens, en-suite double vanity bath with walk-in shower, separate spacious living room and dining area and full upgraded kitchen.

Guest favourite

Villa in Rendezvous Bay

5 out of 5 average rating, 9 reviews

Stunning 4BR Private Villa set in 1 acre with pool

Following an extensive refurbishment completed in 2023, Songbird Villa is delighted to welcome guests again to the beautiful island of Anguilla. This private secluded villa is just a short stroll from the Caribbean's #1 beach, Rendezous Bay (as voted by Caribbean Journal), and is in close proximity to all the amenities needed for a relaxing Caribbean stay.

Guest favourite

Cottage in Island Harbour

4.9 out of 5 average rating, 82 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!