Holiday 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.

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Guest favourite

Villa in Rendezvous Bay

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

LocationValueKitchen

4.91 out of 5 average rating, 23 reviews

Top guest favourite

A serene swimming pool is nestled at the edge of a rocky coastline, reflecting the vibrant hues of the ocean. Gentle waves are observed in the distance, complementing the peaceful atmosphere surrounding the space. Comfortable loungers are positioned nearby for relaxation.

Villa in Island Harbour

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

LocationFamilyComfort

5.0 out of 5 average rating, 29 reviews

Top guest favourite

Guest house in West End

Ocean View House, Private 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!) Private Gym, Pilates Reformer, Sauna, Small Indoor Pool, Cinema Room, Bar, Arcade Machines, Pool Table. Large Ocean View Balcony

LocationFamilyHot tub

5.0 out of 5 average rating, 14 reviews

Guest favourite

Home in West End Village

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.

FamilyLocationBack garden

5.0 out of 5 average rating, 8 reviews

Top guest favourite

A private pool is surrounded by landscaped gardens, with a sun lounger positioned nearby. The pool's clear blue water reflects the bright sky and surrounding greenery, creating a serene outdoor space for relaxation.

Villa in Blowing Point

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

LocationValueQuiet

5.0 out of 5 average rating, 34 reviews

Guest favourite

A bright and airy living space features large windows that offer expansive ocean views. Light-colored furniture complements the open layout, while a ceiling fan provides airflow. The fully equipped kitchen is visible in the background, with neutral cabinetry and countertops.

Apartment in West End

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.

FamilyLocationKitchen

4.73 out of 5 average rating, 75 reviews

A private fresh water pool is framed by tropical plants and palm trees, overlooking the ocean. Lounge chairs are placed around the pool, with a shaded seating area visible nearby. The bright blue sea and sky create a serene backdrop.

Villa in Island Harbour

Villa Bianca Oceanfront 3BR with Private Pool

Wake to endless sea views, relax by your private pool, and savor calm rhythm of island life at Villa Bianca. Your oceanfront home away from home. From the moment you arrive, the turquoise Caribbean stretches before you, and the sound of the waves invites you to slow down and breathe. Located in a laid-back fishing village, the villa features a gourmet kitchen and a veranda perfect for sunset cocktails. Steps from fresh seafood, artisan pastries and fine French dining.

FamilyLocationComfort

4.81 out of 5 average rating, 27 reviews

Top guest favourite

Home in Long Bay Village

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

FamilyLocationBathroom

5.0 out of 5 average rating, 16 reviews

Guest favourite

Villa in Island Harbour

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.

ValueLocationBathroom

5.0 out of 5 average rating, 8 reviews

Guest favourite

Cottage

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.

LocationValueIndoor spaces

4.83 out of 5 average rating, 58 reviews

Superhost

Apartment in Shoal Bay

Fountain Anguilla- Poolside Studio- 2 Queen Beds!

Fountain Anguilla Ocean View Studio Suite Fountain Anguilla by Refined Retreats- This hotel-style suite offers intimate luxury accommodations at an exceptional value with magnificent ocean views, private covered verandah with outdoor living, en-suite bathroom featuring walk-in shower with dual vanity and 2 luxurious queen size beds with premium linens.

LocationValueDecor

4.69 out of 5 average rating, 13 reviews

Superhost

An outdoor terrace overlooks the ocean, featuring a private pool surrounded by a sun-drenched patio. Comfortable wicker seating is arranged around a glass-top table, ideal for relaxation. A roofed area provides shade, with views of the blue sea and clear skies in the background.

Home in Shoal Bay Village

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.

LocationOutdoor spacesQuiet