Holiday rentals with a pool in Anguilla

Artistic 'Maison Hibernia', 10 mins to Shoal Bay.

Once home to the beloved Hibernia Restaurant & Art Gallery, this tranquil 2-bedroom retreat continues a story that began 38 years ago, when MaryPat & Raoul arrived in Anguilla & created Hibernia Restaurant, a place not only popular for its cuisine but known for art, travel & gracious hospitality. Now 'MAISON HIBERNIA', they carry that same spirit forward with their holiday villa, shaped by their eye for detail, love of design, and quiet appreciation of beauty. 10 minutes to Famous Shoal Bay...

Charming 4 Bedroom Estate w/ Beach Access

Tigh-na-Mara Villa, exudes old world West Indies charm inside and out. This storybook island villa immerses you in a delightful ambiance of days gone by, combined with modern necessities including high speed internet, a recently renovated chef’s kitchen and air-conditioning throughout. The sparkling lap pool is your own private paradise — and you have direct access (via a 2 min path) to Elsie Bay Cove. This unique Villa is nestled in lush landscaping with magnificent views of St. Martin.

3-BR Villa w/ Pool & Sea Views – West End Anguilla

Cambie Villa is a newly furnished 3-bedroom, 2-bathroom retreat in Anguilla’s West End, just a short walk from the Four Seasons and minutes from Meads Bay. Enjoy shaded porches, a private dipping pool, and sea views across to St. Martin. The open-plan living space boasts full AC and plenty of natural light. Two spacious bedrooms feature king-size beds, while the third offers two full-size beds. Please note: there is some nearby daytime construction so we’ve adjusted rates accordingly.

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.

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

Driftwood Haven | 2-Bedroom Villa w/ Private Pool

Enjoy this spacious 2-bedroom, 2.5-bathroom villa in Anguilla’s popular West End. Just a 3-minute drive to Maundays, Meads, and Rendezvous Bays, the villa features an open-plan living and kitchen area that opens to a private deck and small pool—perfect for relaxing or entertaining. Upstairs, both bedrooms offer en-suite bathrooms and private patios. Ideal for families or couples seeking comfort, style, and close proximity to the island’s best beaches and resorts.

Chic Apartment

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 10% off all meals 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.

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.

Villa Grande (Up) Oceanview Escape |2 bed 2.5 bath

Villa Grande is a bright, oceanview upstairs villa with 2 bedrooms and 2.5 baths, just minutes from Anguilla’s best beaches, restaurants, and nightlife. Enjoy stunning sea views from the private balcony, cook in the full kitchen, and relax in the spacious living and dining area. Ideal for couples, families, or friends seeking a peaceful island retreat with modern comfort and easy access to everything Anguilla has to offer.

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

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 10 guests, 2 upgraded full kitchens and 2 expansive living areas, as well as pool and garden views from the patios.

Lush Garden Studio with Pool Access – Suite #3

Welcome to your peaceful island retreat! This charming 1-bedroom suite offers serene views of the lush tropical gardens. Start your morning with coffee on the balcony surrounded by greenery, or unwind in the evening with a glass of wine as you soak in the tranquil atmosphere. The suite is fully equipped with everything you need for a comfortable and unforgettable vacation!

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!