
Vacation rentals with a pool in Anguilla
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Top-rated rentals with a pool in Anguilla
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Beach Front Villa With Swimming Pool
Our home is beachfront with an infinity pool. It is a single-story home which is easily accessible, having only one small step down to access the front entrance. The property is completely fenced and has an electric gate at the driveway entrance making this home a safe, child friendly home. Our home is a perfect getaway for families and elderly couples providing you with the ability to stay in one location and be able to enjoy the beach and a pool. It is also convenient to all island activities.

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

Fountain Anguilla 1 Bedroom Garden View Condo
Safe Environment Certified- Visit Fountain Anguilla Website for more details. Fountain Anguilla Garden View 1 Bedroom offers intimate accommodations at an exceptional value with lush tropical landscape and pool views, private covered verandah with outdoor living and dining. This well appointed residence also features an upgraded full kitchen and expansive living area. The private bedroom has an en-suite bathroom featuring walk-in shower with dual vanity and king size bed with premium linens.

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.

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.

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.

Cozy Garden Studio with Pool – Suite #1
Property Summary: Relax in your inviting garden-view studio at Arawak Beach Club, featuring a unique bar area perfect for morning coffee or evening cocktails. Enjoy lush tropical surroundings from your private deck, a fully equipped kitchen, and cozy living space. Stay connected with high-speed fiber internet, cool off with air conditioning, or lounge by the pool with sunbeds. Complimentary kayaks and stand-up paddleboards (SUPs) are ready for your island adventures!

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.

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.

South Hill Oasis · Complimentary Breakfast + Pool
Take it easy at this unique and tranquil South Hill escape. Guests enjoy complimentary breakfast each morning at the iconic Tasty’s Restaurant, known for its authentic Anguillian flavors. After exploring the island, relax with access to a refreshing shared pool, making this stay the perfect blend of comfort, convenience, and local charm.

Villa Bianco Oceanfront Luxury Retreat
Wake up to endless sea views and the soothing sound of waves in this luxurious oceanfront villa. Nestled in a laid-back fishing village, the home features a gourmet kitchen, elegant coastal design, and a veranda perfect for sunset cocktails. Steps from fresh seafood, artisan pastries, and fine French dining.

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!
Popular amenities for Anguilla rentals with a pool
House rentals with a pool

Swim, Sun, Fun Central Location

Asha’s Place

Home & Apartment at Lions Rock

Villa Zirok 3 bedroom

Your Anguilla Home! Homeaway from home-AI

Kiki Residence Shoal Bay East

Lockrum Point Villa Oceanside 2bdrm/2bath w/ Pool

Panarea Pool-Gym Villa, Maundays
Condo rentals with a pool

Fountain Anguilla Partial Ocean View 2 Bed 2 Bath

Ocean View 1 Bedroom Condo on Shoal Bay Beach!

Fountain Anguilla Oceanside Penthouse Studio Suite

Sapphire Sea Penthouse Condo

Ocean View Shoal Bay 1 Bedroom Condo

Anguilla Two Bedroom Condo in The Farrington

Ocean View 2 Bedroom Condo- 2 Private King Suites!

Fountain Anguilla Garden View Studio Suite
Other vacation rentals with a pool

Driftwood Haven - Villa 1

Dream Weaver Villa In Rendezvous Bay

Jasmine Villa,Meads Bay, Anguilla, BWI

Peaceful Garden-View Studio – Suite #2

Stunning Oceanfront Villa ~ Pool, Jacuzzi & Kayaks

Turtle Dove Villa

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

Dolphins Villa
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