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 Pool House is surrounded by lush greenery, showcasing a private pool with a shaded deck area. A red roof complements the neutral exterior, and the inviting space is framed by a white railing. Scenic views of the surrounding landscape extend in the background.
Home in Little Harbour
4.89 out of 5 average rating, 9 reviews

Swim, Sun, Fun Central Location

LinhRating, 5 stars14 months ago
We had a hard time finding the place but Samuel was very helpful and responsive. He stayed with us on the phone until we arrived. The pool house is listed in Google maps if you need to find it more easily. When we arrived the property is beautiful! Acres to the pool from the bedroom was wonderful. We loved our stay and would definitely come back!
An expansive outdoor deck is featured, overlooking a refreshing pool surrounded by a tiled surface. A gazebo provides shaded seating, and a dining table accommodates several chairs. Lush greenery and a clear blue sky create a serene setting for relaxation and gatherings.
Home in Island Harbour

Home & Apartment at Lions Rock

IanRating, 5 stars10 months ago
It was great to be back in Anguilla after many years and the house felt like a luxurious way of doing it. As we gradually filled the house with our party, the joy of being able to swim in the pool or the sea was complete and we didn't miss not having a TV as we entertained ourselves with games etc. Don't get me wrong, Anguilla's infrastructure can fail sometimes, power went out once or the internet drop but that's not the host's fault and the house was back up and running within two hours. Food prices are quite expensive, coming from the UK, but if you know that and come prepared then all is good. We intentionally came out for Carnival Week and are glad we did, as there was so much to see and do. Our host Peter was not on the island but we were very well looked after by Oris who gave us a very warm welcome and dealt with issues swiftly and often went out of his way to help. My family will have very fond memories of their holiday and would definitely go back to Lion's Rock. Thank you.
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 stars5 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 spacious vacation home is shown, featuring an outdoor pool surrounded by a deck with lounge chairs. The two-story structure boasts multiple balconies and large windows, with greenery visible in the background and a clear blue sky overhead.
Home in Seafeathers
4.8 out of 5 average rating, 5 reviews

Luxury Vacation Home with Pool!

KimRating, 5 stars3 months ago
Felicia was a very warm and accommodating host. We had a problem with one of the beds the first night and she had it resolved quickly. One of the teens in our group got very sick on our last day and she couldn't have been more gracious and accommodating. The place was spacious and the beds were very comfortable. Seafeathers is a beautiful part of the island.
A private pool is framed by lounge chairs under blue umbrellas, creating a relaxing space for guests. The Caribbean Sea stretches into the distance, with a gazebo visible on a rocky outcrop. Lush greenery complements the scenic coastal view.
Home in AI
5 out of 5 average rating, 4 reviews

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

JodiRating, 5 stars15 months ago
Lockrum Point is a beautiful home with everything you need for a comfortable vacation. The pictures really don't do it justice. The house is beautiful and the view is spectacular. It is set off the main road, but well-marked (by Caribbean standards) and it is very private and secluded. We felt very safe at all times. Sue was very responsive and answered all of my (many) questions. Her manager, Marcia, is wonderful as well. Thank you for the "goodies" upon check-in. We loved the pool and the outdoor shower and sitting on the pool deck at night counting stars.
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 stars3 months 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 stars15 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
4.82 out of 5 average rating, 22 reviews

Ocean Front Villa in Island Harbour, Anguilla BWI

MaryRating, 5 stars2 weeks ago
Richard was an excellent host, very communicative before and during our stay, extremely accommodating and kind when we had a last minute scheduling issue due to illness...definitely one of the best hosts we've had in our many airbnb stays! The villa was also great, top floor suite is wonderful with a private rooftop balcony overlooking the water, and balcony and views from the main floor are also amazing!! The kitchen is very well stocked, had everything we needed and more. This villa was the perfect place to start and end each day in Anguilla. There is also a great little spot that makes delicious fresh seafood pasta right up the street (called Lime Keel, perfect for takeout to enjoy at the villa), and other good restaurants hidden in plain site in the town of Island Harbour and throughout the island.

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 stars71 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 large swimming pool is surrounded by lush greenery and lounge chairs, creating a serene outdoor space. The two-story building in the background is framed by palm trees under a clear blue sky, offering a tranquil atmosphere for relaxation.
Condo in Shoal Bay
5 out of 5 average rating, 4 reviews

4 Bedroom/ 4 Bath- Sleeps 12 Pool View Condo Combo

LeidyRating, 5 stars22 months ago
excellent place I would definitely go back
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
4.7 out of 5 average rating, 50 reviews

Turtles Nest Beach Resort - Beachfront 1 bedroom condo

JessicaRating, 5 stars1 month ago
Beautiful space and the most perfect location on meads bay. It’s quiet, super nice guest and staff too. Unit is on 4th floor with no elevator (we knew in advance). The steps are worth the incredible views. We will be back!
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 stars6 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.
Superhost
A tropical swimming pool is surrounded by sun loungers with blue cushions and small tables. Lush greenery and palm trees frame the area, while a multi-level building stands in the background under a clear blue sky, creating a serene outdoor retreat.
Condo in Shoal Bay

Ocean View Shoal Bay 1 Bedroom Condo

CassandraRating, 5 stars2 months ago
Loved Anguilla and the Fountain property! Perfect location! The host and Fountain management and staff were attentive and informative; and made our stay completely enjoyable. Would go back there in a heartbeat.
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 stars78 months ago
Beautiful view with amazing sea breeze and super sweet and helpful on site management.
Superhost
The tropical swimming pool area features a spacious pool surrounded by lounge chairs with blue cushions. Lush greenery and palm trees provide shade, while the two-story building stands in the background under a clear blue sky, creating a serene ambiance.
Condo in Shoal Bay

Ocean View 2 Bedroom Condo- 2 Private King Suites!

Toni Rating, 5 stars6 months ago
The place was really nice. It was easy to get around and our host was super responsive and helpful.
A vibrant sunset fills the sky with shades of orange and pink, casting a warm glow over the horizon. The serene landscape in the foreground features rolling hills and a glimpse of water in the distance, evoking a sense of tranquility.
Condo in The Valley

Ocean Terrace Condo

BiancaRating, 5 stars91 months ago
One of the best vacation lodging decisions we've ever made. Sam's condo with a private pool is immaculate and adorable. This is perfect for a couple or family with kids. We had a great stay. We felt safe and the house was exactly as pictured. A complete kitchen gives you the option to cook although with all of the good food on the island - it is tempting not to cook. The grounds are lovely with beautiful flowering trees and palms. Paula was a great host! We have nothing but praise for this beautiful place. And we hope to return soon.

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