Vacation 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...

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.

Caribbean Rhapsody Oceanfront Villa

Beautiful 4 bedroom 4.5 bathroom resort style home features breathtaking ocean views overlooking Scilly Cay and Island Harbour. Only a 5 minute drive to world famous Shoal Bay East beach or Captains Bay. The Villa offers three levels for big families and ultimate privacy. Main level infinity pool that appears to melt into the ocean. Top level with unbelievable views and bottom level with direct access to the water with amazing snorkeling! Caribbean Rhapsody is a true Anguilla gem!!

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

Romance and relaxation - visit Gardenia Villa

Steps from West End Bay and a five-minute walk from Shoal Bay West. This private villas’ French doors open onto a sheltered private dining area surrounded by private gardens. The rooftop patio boasts an unobstructed 360 view of Anguilla and St. Martin. High, airy ceilings, purple heart floors, and a mahogany four-poster king size bed make Gardenia Villa the perfect romantic retreat. A large pool and common lounge area is just 50 ft away, shared by 2 other villas.

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.

Turtles Nest Beach Resort - direct Beach access 2 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 take two steps and you are on 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.

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.

Oceanfront Studio Villa w/Kitchen By Shoal Bay #10

Enjoy the seaside panoramic Caribbean views. Enjoy your oversized comfy king bed with kitchen, private terrace, fiber-optic internet, Smart TV, AC, club bar area, and complimentary paddle boards and kayaks. Scilly Cay is a 5 minute paddle away. Explore nearby beach bars and restaurants, with world famous Shoal Bay beach just 10 minutes away. On demand house keeping included if needed. We know you’ll love your stay.

Villa Oasis in Shoal Bay

Welcome to Villa Waves, a luxurious 3-bedroom villa on the shores of Shoal Bay East, Anguilla. With views over one of Anguilla’s finest beaches, and a location within driving distance to the restaurants and beach bars of Shoal Bay Village, this property combines its fantastic location with peerless privacy and island luxuries.