Vacation rentals with a pool in Southampton Parish

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Popular amenities for Southampton Parish rentals with a pool

House rentals with a pool

Superhost
An inviting outdoor space reveals a swimming pool bordered by a well-maintained garden. Comfortable seating options are provided under the sun, with a light-colored house featuring expansive windows and a bright exterior. Clouds float in a blue sky, enhancing the serene atmosphere.
Home in Smiths
New place to stay

Sweet Dreams around the Pool

PhilippeRating, 5 stars1 week ago
Nice place and nice host. I recommend
Top guest favorite
A serene pool area is surrounded by lush subtropical gardens, featuring a sparkling pool with lounge chairs and striped umbrellas for shade. Tropical palm trees and vibrant potted plants contribute to the calming atmosphere in this private outdoor space.
Home in Sandys
4.98 out of 5 average rating, 156 reviews

The Pool House w/ Heated Pool (Nov. 1)

SteveRating, 5 stars3 days ago
Our stay at John & Alison’s place was peaceful, cozy, and full of charm. The cottage, filled with decor from John’s family who’ve owned the property for over 250 years, had a deep sense of history. A highlight was discovering a 1935 book, Bermuda in Three Colors, signed by John and Helga Young, with an old letter tucked inside from a guest in the 1950s? The book is fragile, with a dust jacket that’s a map of Bermuda — I hope future guests handle it with care. Tana, their cat, joined us for coffee each morning and enjoyed treats from the jar John provided. Bo, their dog, signaled when John was nearby. The bathroom was newly renovated, the EV chargers on-site were incredibly convenient, and island cable TV and pool access added comfort. We’d gladly return — and hope to do so as long as the Youngs continue to welcome travelers like ourselves who love to connect with local Bermuda and not stay at corporate resorts. Bermuda is our most favorite place in the world outside our home in Maine.
Top guest favorite
A clear blue pool is surrounded by palm trees and colorful flower pots. Sun loungers are positioned on one side, inviting relaxation. Two playful statues of children are situated at the pool's edge, adding a charming touch to the serene outdoor area.
Home in Sandys Parish
5 out of 5 average rating, 63 reviews

Sunrise Cottage w/ Heated Pool (Nov. 1)

MeredethRating, 5 stars3 weeks ago
We could not be happier about our stay at Sunrise Cottage. The cottage was comfortable and charming with personal touches to just the right degree. Beds and linens were so comfy and we loved the cozy robes. We made ample use of the outdoor seating and enjoyed looking out on (and wandering around) the beautiful grounds. We found bus and ferry to be the best way around the island and bus stops were very close to the bottom of the island. We also loved that the Railway Trail was easily accessible from the property so we could get out and do some walking. Almost as soon as I booked, John made himself available with suggestions, tips, and recommendations. From arranging transportation from the airport, to sharing activity and dining suggestions, he couldn’t have been more helpful. One we were onsite, John was so welcoming. He has a rare ability to be friendly and available without ever feeling even a little intrusive. And he makes a mean pitcher of Swizzle. We hope to return before long!
A bright pool area is framed by a pink house and lush greenery. The pool features a smooth surface reflecting the sky and is complemented by a white slide at one end. A fenced patio ensures privacy and a safe environment.
Home in Sandys Parish
4.93 out of 5 average rating, 14 reviews

Lavender Dreams - 3 bedroom home with pool

ThomasRating, 5 stars10 months ago
We stayed a full week for our family vacation. The house was exactly as described and shown. Very nice, quiet and peaceful location. House was clean and well maintained. The pool was also private, clean and easily accessible. The location was easy to find and in a quiet neighborhood. We rented scooters for our transportation and were on the go most of the week. However, if you are not into renting mopeds the house is very close to the local grocery store, rail trail and bus and taxi stop for easy transportation purposes. All withing a 2-5 minute walk. Leila was easily contacted, very friendly and helpful. She is a great host and we would definately recommend this place for your stay. We will definately keep this place on our favorite places list and look forward to coming back again!
A tranquil pool sits surrounded by a stone wall, with vibrant turquoise water reflecting the sky above. In the background, views of the ocean and distant palm trees are visible under a partly cloudy sky.
Home in HM01 Bermuda

Architect’s Bermuda home and pool house

JeanRating, 5 stars11 months ago
Beautiful house, good for a medium-sized group. Separate pool and pool house space were great to have, and secret little beach was fun as well. Great views. A little tricky to find / get picked up from without a car, but worth it if you want something out of town for a little more space.
Home in Warwick Parish
5 out of 5 average rating, 29 reviews

❤️Privacy, Pool & View "Finesse-Lucky 7"⭐Twizzy

CatherineRating, 5 stars64 months ago
We loved this house, clean and spacious with an amazing view of the ocean from the second floor. The best part was the short walk to beautiful beaches and the bus stops - so easy to get around and explore. We will definitely be going back!
An infinity pool is set against a backdrop of a pastel sky, reflecting the colors of sunset. The pool's edge overlooks a scenic view of the harbor and a distant lighthouse, surrounded by lush greenery and charming homes.
Home in Southampton

Pool House at Far Vistas

PatrickRating, 5 stars14 months ago
Erica was a top tier host! Super host level. I stay at air bnbs often but this was honestly one of the, if not thee best one I’ve stayed at. The pics do the place no justice, because it is a beauty! It’s about a 30 min drive from the airport, but 15 min. drive to rent the electric buggies m (only island residents can rent gasoline vehicles). Then 15 min ride to the residence. It has a private entrance and shared pool area but she makes sure you feel right at home and doesn’t bother you. I felt like I was bothering her asking for help or recommendations but she was always willing and able to help. She gave amazing recommendations and went above and beyond to make the place feel like home. The views of the Gibbs Hill Lighthouse is the icing on the cake. Just respect her home, and space as if it’s yours and your stay will be top tier.
Guest favorite
A warm orange exterior of the house is complemented by a spacious back patio featuring a heated pool. Comfortable seating arrangements, including lounge chairs and tables, provide inviting spaces for relaxation. An umbrella offers shade, while steps lead to the upper level of the property.
Home in Hamilton
4.9 out of 5 average rating, 279 reviews

Studio Apt w/ pool - quick walk to town

KimRating, 5 stars3 weeks ago
My second stay here, different unit, and won’t be the last. Chris and Susan are extremely generous with their time and attention, and exceptionally kind. I had a medical emergency and it was huge peace of mind benefit to have them supporting me. I find this a peaceful place to stay, lovely outdoor spaces to relax in evening under the palms. Ten minute walk past gorgeous gardens to Hamilton core. New healthy bakery and a pizza place around the corner past the grocery. Perfect combination of private units but hosts to chat or converse with as you prefer. Top notch restaurant just a couple hundred feet down the road and plenty in town. Recommended absolutely.

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