Vacation 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.

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Guest favorite

Villa in Island Harbour

5 out of 5 average rating, 20 reviews

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

Superhost

Cottage in Island Harbour

5 out of 5 average rating, 4 reviews

Arawak Beach Club Studio w/Pool and King Bed #1

Welcome to our oceanfront studio at world famous Arawak Beach Club, where each morning brings a stunning sunrise and the sight of pelicans gliding over the waves. Glowing colors throughout the property. This cozy space features a bathroom, an equipped kitchen, and a private deck. Enjoy the comfort of AC, stay connected with fiber optic internet, or relax by the pool with sun loungers. Private parking is available, ensuring a hassle-free stay. Kayaks and SUP’s included. Come unwind in paradise!

Guest favorite

Home in Shoal Bay Village

4.92 out of 5 average rating, 13 reviews

Shoal Bay Coastal Sanctuary, Anguilla

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.

Guest favorite

Villa in Island Harbour

5 out of 5 average rating, 5 reviews

Caribbean Rhapsody Oceanfront Villa

Beautiful 4 bedroom 4 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 a spacious middle level which rolls seamlessly into the pool deck and 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!!

Condo in West End

4.68 out of 5 average rating, 47 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

4.86 out of 5 average rating, 14 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 favorite

Home in Blowing Point

5 out of 5 average rating, 5 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.

Villa in Seafeathers

4.91 out of 5 average rating, 11 reviews

Oceanview villa with private pool, 5 mins to beach

Southern Comfort Villa is the perfect place for those looking for a laid back, cottage-like retreat. Our 2 bedroom, 2 bath villa sleeps 4-5 guests. The great room boasts 20 ft vaulted ceilings, a fully equipped kitchen and comfortable furnishings. Take a dip in the pool while enjoying unobstructed views of the Caribbean Sea and neighbouring islands of St. Martin and St. Barth. Enjoy a relaxing morning coffee or afternoon drink with a view on the wrap around veranda.

Guest favorite

Home in Long Bay Village

5 out of 5 average rating, 6 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

Superhost

Condo in Shoal Bay

5 out of 5 average rating, 5 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 favorite

Cottage in Island harbor

4.9 out of 5 average rating, 63 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!