Holiday 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 up to 10), the villa features spacious ensuite bedrooms (configurable as kings or twins), 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 and minutes from Anguilla’s top beaches, dining, and nightlife.

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!

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 .

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.

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.

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.

Island Hideaway: Pool Access + Daily Breakfast

Discover your private South Hill hideaway—a welcoming one-bedroom retreat with bright living space, full kitchen, and a cozy bedroom for restful nights. Unwind in the private courtyard surrounded by greenery, ideal for morning coffee or a BBQ under the stars. Just minutes from Anguilla’s best beaches, dining, and culture, your stay also includes breakfast for two at Tasty’s POV, blending comfort, privacy, and authentic island charm.

Ocean View Terrace

You'll have the main floor which includes one master bedroom with full bathroom, full kitchen, queen size sofa sleeper, dining room, terrace, laundry room and infinity pool. The rest of the property will be vacant during your entire stay. This level is only rented when the rest of the property is vacant.

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!