Vacation rentals with a pool in Anguilla

Find and book unique homes with a pool on Airbnb

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Popular amenities for Anguilla rentals with a pool

House rentals with a pool

The exterior of the building features a bright yellow façade with white railings and arches along the balcony. Lush greenery surrounds the property, and a clear blue sky with scattered clouds provides a vibrant backdrop.
Home in Island Harbour
4.89 out of 5 average rating, 9 reviews

Your Anguilla Home! Homeaway from home-AI

KarsheRating, 5 stars3 months ago
Akira was very responsive, the place was clean & very well put together. Was very pleased with the hospitality and would recommend to those seeking to visit Anguilla! 5/5
A private pool features a clear, inviting surface, surrounded by patterned tile. The pool area is complemented by a stone structure and a wooden terrace with glass doors providing access to the indoor living space. Lush greenery is visible in the background.
Home in South Hill Village
4.79 out of 5 average rating, 33 reviews

Beautiful 3 bed Villa

AdeleRating, 5 stars1 month ago
We had a fabulous stay at Splash again this year! Love the location and the space is very comfortable for us. It’s great to have a pool, and the house is close to a couple of our favorite beaches. Communications with the owner and the local caretaker were great, they are very responsive and helpful. Looking forward to returning again next year.
A spacious outdoor area features a large pool surrounded by multiple lounge chairs. The villa's modern architecture reflects an open design, with sliding glass doors offering views of the inviting pool area. Lush greenery and a clear blue sky enhance the tranquil atmosphere.
Home in Shoal Bay
4.2 out of 5 average rating, 5 reviews

Zirok Villa Shoal Bay

RimahRating, 5 stars14 months ago
Beautiful villa and pool! Very peaceful and private. Had so many thoughtful amenities, everything you would need for an easy stay. Extra towels, beach towels, everything you would need in a kitchen. Professionally done! Sparkling clean! This is a new villa so all furniture and linens were in great shape. Beach and few beachside restaurants are a 10min walk away. Definitely glad we rented a car to explore the rest of the island, would definitely recommend a rental car. Host was super responsive and accommodating. Would definitely come back and recommend to my friends and family.
The exterior of the villa features a spacious wrap-around veranda with multiple seating areas, surrounded by lush greenery. A private freshwater pool is visible in the foreground, complemented by a shaded gazebo. Beach chairs are arranged by the pool, inviting relaxation.
Home in Island Harbour
4.81 out of 5 average rating, 21 reviews

Ocean Front Villa in Island Harbour, Anguilla BWI

JigarRating, 5 stars28 months ago
Awesome place with breathtaking views ! With a car you can get to anywhere on the island, and make the most of the your time exploring the many beaches, shacks, restaurants, and we also were able to buy some lobster at the local pier and prepare a meal that everyone enjoyed. Richard is a great host, and was there to support and make this trip as pleasant as possible. Thanks Richard !
A sunlit outdoor area features a private pool surrounded by a smooth stone deck. Comfortable lounge chairs with soft cushions are positioned nearby. A sturdy table with chairs offers a space for dining or relaxation, while the lush scenery is visible in the background.
Home in Shoal Bay Village
4 out of 5 average rating, 7 reviews

Roy’s Place-3 Bedroom

DustinRating, 5 stars3 months ago
Last minute family trip. Couldn’t have asked for a better spot. Always stay in Shoal Bay East at a hotel but was sold out for our dates. This was our first experience at an AirBnB in Anguilla and would definitely do it again.
Top guest favorite
A private pool area features two lounge chairs with bright orange umbrellas, surrounded by lush greenery. The tranquil water reflects the blue sky and nearby trees, creating a serene outdoor space ideal for relaxation.
Home in Long Bay Village
5 out of 5 average rating, 7 reviews

Châlet Genesis

NishanRating, 5 stars9 months ago
We truly enjoyed our stay here. It’s convenient and close to the major hotels (4 seasons and cap Juluca) as well as local restaurants. The place was flawless with everything you need. The place was cleaned everyday which is something hotels don’t do much of anymore. The AC worked perfectly in all the rooms and although the common area doesn’t have an AC, the fans definitely sufficed. I would 1000% stay here again.

Condo rentals with a pool

Superhost
A spacious swimming pool is surrounded by sun loungers and lush tropical landscaping. The ocean can be seen in the background, with a two-story building showcasing arched windows beneath a white roof. Palm trees add a refreshing touch to the serene setting.
Condo in Shoal Bay
4.67 out of 5 average rating, 3 reviews

Fountain Anguilla Partial Ocean View 2 Bed 2 Bath

MadeleineRating, 5 stars69 months ago
Amazing location, short walk and even shorter drive to Shoal Bay Beach. Stay included beach passes for 2 lounge chairs and an umbrella at Tropical Sunset, which was a delicious and very friendly beach bar and grill. The space itself was beautiful and spacious for a group of 6 26- year olds. Also great location for families. I do recommend renting a vehicle to travel the island but it is not needed to the beach, unless you’re traveling with someone who can’t easily walk. Overall, HIGHLY RECOMMEND!
Superhost
A tropical swimming pool is surrounded by vibrant greenery and lounge chairs with blue cushions. The property features a three-story building in the background, with palm trees and a clear blue sky completing the scene.
Condo in Shoal Bay
5 out of 5 average rating, 6 reviews

Ocean View 1 Bedroom Condo on Shoal Bay Beach!

DavidRating, 5 stars2 months ago
It was a spectacular stay. Great views from the very large balcony. There is a wonderful group of people taking care of the condo. Easy walk down to the water. Not more than six minutes and private. Renting a car will give you options to explore. Keep in mind that it is left side driving. Not a problem, just requires some focus. We will definitely book with Sherri the next time we are in Anguilla.
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.
Condo in West End
4.69 out of 5 average rating, 48 reviews

Turtles Nest Beach Resort - Beachfront 1 bedroom condo

DavidRating, 5 stars2 months ago
Turtle’s Nest Beach Resort on Meads Bay is the ultimate hidden gem for travelers seeking luxury, comfort, and an unbeatable beachfront location. Nestled on one of Anguilla’s most spectacular stretches of sand, this boutique condo-style resort offers spacious, well-appointed accommodations with breathtaking ocean views. Whether you’re sipping coffee on your private balcony or stepping directly onto the soft white sand, every moment feels like paradise. One of the highlights of a stay at Turtle’s Nest is the lively yet relaxed atmosphere. The beachfront pool is the perfect spot to unwind, especially during happy hour, when guests can enjoy complimentary rum punch as the sun begins its golden descent. The impeccable beach service from the nearby Straw Hat restaurant elevates the experience even further—expect chilled drinks and gourmet bites delivered right to your lounger. With warm hospitality, unbeatable views, and direct access to Meads Bay’s crystal-clear waters, Nest is great
The image features a private terrace overlooking a serene ocean view. A clear blue pool is framed by a sun-drenched patio with white lounge chairs arranged nearby, creating an inviting space for relaxation. The distant shoreline is visible against the backdrop of a bright sky.
Condo in The Valley
4.86 out of 5 average rating, 7 reviews

Sapphire Sea Penthouse Condo

YanaRating, 5 stars4 months ago
Lisa's condo was very spacious and meticulously clean. It is quiet with incredible ocean views. Kitchen had a complimentary 5 gallon water jug and starter kitchen basics. Lisa was very responsive to our questions and even found a reputable children's agency that would rent a pack n play for our son. The only negative is a terrible bumpy unpaved 0.5 miles of a back road leading to the condo: use a high profile SUV if you must. Otherwise, we loved staying in this home away from home.
A clear blue pool surrounded by striped lounge chairs and a view of distant mountains and ocean. Lush palm trees sway gently in the breeze near the edge of a balustrade, providing a tranquil ambiance.
Condo in George Hill
5 out of 5 average rating, 3 reviews

Anguilla Two Bedroom Condo in The Farrington

KathleenRating, 5 stars76 months ago
Beautiful view with amazing sea breeze and super sweet and helpful on site management.
Superhost
A clear view of the tropical swimming pool surrounded by lounge chairs is presented. Lush greenery and palm trees frame the area, while the ocean is visible in the background under a bright sky with scattered clouds.
Condo in Shoal Bay
4.8 out of 5 average rating, 5 reviews

Fountain Anguilla Studio Suite

ShayRating, 5 stars8 months ago
Can’t say enough about this beautiful property. The staff are knowledgeable and hospitable. The room was spotless and equipped with every amenity you may need including a super cold AC unit. There is easy access to one of the most beautiful white sand beaches on the island, Shoal Bay. I could go on and on but I encourage you to book and experience it for yourself.

Destinations to explore