Vacation rentals with a pool in Anguilla

5BR Modern Caribbean Luxury with Pool & Bay Views

Songbird Villa is a newly refurbished 5-bedroom luxury retreat with sweeping views of St. Martin and Rendezvous Bay. Perfect for families or groups (sleeps 10), the villa features spacious ensuite bedrooms (Rms 3, 4 & 5 available as king or twin beds), a private infinity pool, a modern kitchen with outdoor BBQ grill, Sonos sound system and smart TVs throughout, daily housekeeping and concierge service. Just a short walk to Rendezvous Bay & minutes from Anguilla’s top beaches, dining & nightlife

Value · Location · Accuracy

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

Value · Family · Hospitality

Sea View Pool Villa, Sleeps 8 – West End, Anguilla

Cambie Villa is a newly furnished 3-bedroom, 2-bathroom retreat in Anguilla’s West End, just 10 mins walk from the Four Seasons and 15 minutes walk to Meads Bay and Barnes 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. Pls note: there is some nearby daytime construction so we’ve adjusted rates.

Family · Location · Decor

Ocean View House with Gym Sauna & Plunge Pool

Ultimate luxury at a fraction of the price! Because the estate's main house is currently undergoing interior design work, we are offering this guest house separately for a limited time. You will enjoy private access to a world-class amenities building that is usually reserved solely for the $15,000-per-night main house rental. (that only you will have access to!) Large Gym, Pilates Reformer, Sauna, Small Indoor Pool, Cinema Room, Bar, Arcade Machines, Pool Table. Large Ocean View Balcony

Family · Value · Indoor spaces

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. *Now also available as 2bed/2bath

Location · Value · Outdoor spaces

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.

Location · Bathroom · Decor

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

Value · Location · Cleanliness

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.

Location · Value · Bathroom

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!

Location · Family · Check-in

Oceanfront 2BD Villa - Arawak Beach Club #6&7

Start your getaway at Arawak Beach Club's 2BR villa with Caribbean vistas. Private entrance, 2 terraces, beach steps away. Dining 5 min, Shoal Bay 10 min. Fiber Internet, Smart TV, AC bedrooms. Ocean breezes, 2 oceanfront patios, DIY bar. Paddleboards, kayaks. Optional rental car.

Location · Family · Quiet

Swim, Sun, Fun Central Location

The Pool House is your perfect affordable island getaway. Enjoy views of St. Martin to the south while you lounge in a great inner island neighbourhood. Gated yard with lots of shade, full kitchen, cable TV, queen size bed.

Location · Accuracy · Check-in