Vacation rentals with a pool in Southhampton

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Top-rated rentals with a pool in Southhampton

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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The image shows a tranquil pool area featuring a rectangular swimming pool with clear blue water. Surrounding the pool are several white lounge chairs, with pink cushions, positioned invitingly. In the background, a pink structure is visible, blending harmoniously with the lush greenery.

Apartment in Southampton

4.71 out of 5 average rating, 94 reviews

Poolside Oceanview Studio Suite

Discover serenity in our Oceanview Studio Suite at Bermuda Connections, perfectly situated just steps from our private pool. This charming studio features a cozy queen-sized bed, a well-equipped kitchenette, and a modern en-suite bathroom, offering everything you need for a comfortable stay. Relax on your private patio while taking in breathtaking views of the ocean and lush Port Royal Golf Course. Located in a peaceful residential estate, the studio is a haven for relaxation and adventure, with

Guest favorite

A spacious pool area is surrounded by tropical greenery, featuring loungers positioned around a clear blue pool. A shaded pavilion with a pointed roof provides a relaxing space. Views of distant homes and a bright sky enhance the outdoor setting.

Apartment in Southampton

4.98 out of 5 average rating, 172 reviews

Panatola Studio 2 - Pool and Close to Beach

"Panatola Studio 2-The Lookout” Private studio with spectacular vistas of the Great Sound and Jews Bay. An ideal holiday retreat located in a desirable neighbourhood of Southampton, within walking distance to Horseshoe Bay Beach, Lighthouse, Turtle Hill golf course, restaurants and the Fairmont Southampton Hotel. Mini Electric car charger available! If traveling with family or friends and looking for another accommodation nearby, there is also another studio below this one that takes 2 guests.

An aerial view captures the lush greenery surrounding a private pool area, with white lounge chairs positioned neatly around the turquoise water. The home, with its white roof and blue accents, is set against natural foliage, creating a tranquil atmosphere.

Home in Warwick

4.57 out of 5 average rating, 49 reviews

Tropical Estate, Large 4 Bedroom, Views

Ease House is a beautiful 4-bedroom, 3.5-bathroom home located in Warwick Parish overlooking historical sites in the Hamilton Harbor like Bermuda's first airport and the Great Sound, sailing grounds of the Americas Cup hosted in 2017. This home sits on a large, private estate completely enclosed by Bermuda's indigenous and rich foliage and fauna. With its westerly central location getting to South Shore beaches like Horseshoe Bay and multiple restaurants ranging in style and theme is a breeze.

Top guest favorite

A spacious outdoor area features a swimming pool with a slide, surrounded by tropical plants. The pool house, visible in the background, contains a lounge area and outdoor kitchen. The ocean can be seen in the distance, adding a calming backdrop to the setting.

Apartment in Southampton Parish

5 out of 5 average rating, 27 reviews

1 bedroom apt w/ Saltwater Pool & Laundry

Ground level apartment with unlimited access to the pool and pool house which boasts an outdoor kitchen, BBQ, Bar, bathroom and outdoor shower. Private laundry on site. Walking distance to The Reefs Hotel (restaurants, spa, scooter and electric car rental), Church Bay beach, Gibb’s Hill Light House, and Turtle Hill Golf course/ Boundary restaurant, and bus stops. We have a dog which will be contained in the main house. Note: unfortunately we are not walking distance to any grocery stores.

Top guest favorite

A clear view of the glistening pool is presented, surrounded by lounge chairs and colorful umbrellas. The expansive lawn leads to scenic ocean views, framed by coastal vegetation and nearby homes under a blue sky.

Apartment in Southampton

5 out of 5 average rating, 79 reviews

'Ripple Waters' - More for Les$ 1 Bdrm Pool House

Guests can choose from the ONE BDRM POOL HOUSE (spacious living room) and/or Studio B (new listing). Relax and enjoy 'Ripple Waters' home away from home. This unique and tranquil 'more for le$$' getaway offers a peaceful, relaxing and rejuvenating experience for couples! Wade in the 20' by 40' glistening pool or sunbathe on the semi-panoramic, upper patio deck. Listen to the melodious, chirping birds as you read a book or gaze at the beautiful views of South Shore. Sit back, relax and enjoy!

Guest favorite

The pool area of Sea Glass Cottage features a sparkling blue pool surrounded by a spacious deck. A lookout tower is positioned nearby, with shaded seating areas under large umbrellas. Lush palm trees and greenery frame the scene against a bright blue sky.

Guesthouse in Warwick Parish

4.95 out of 5 average rating, 173 reviews

Sea Glass Cottage with EV charging station

Your own private pool house + tower on a lush 5-acre estate Sea Glass Cottage—ranked the #6 best Airbnb in Bermuda by Condé Nast, and the #1 spot that’s not right on the water Spacious 1,400 sq. ft. pool house: Open-plan living + dining with exposed beams, soaring ceilings, separate bedroom, with AC + comfy queen bed Well stocked kitchen with full-sized fridge Updated bathroom, walk-in shower. TV, washer/dryer, ceiling fans, dedicated Wi-Fi The only thing you’ll share? The gorgeous pool.

Guest favorite

A clean and spacious outdoor area features a pool surrounded by manicured grass. A shaded umbrella stands next to the pool, while a covered balcony offers seating options. An inviting view of the ocean and sky can be seen through large sliding glass doors.

Guest suite in Southampton

4.98 out of 5 average rating, 45 reviews

Cedar Palms - PRIVATE POOL AND VIEWS!!!

Encompassing over 1000 SF of interior space, this guest suite is completely private from the main house, occupying the entire first floor. Everything is new, a full reno was completed in 2017. It opens up to a pool (for guests' exclusive use during their stay) by way of a 300SF covered balcony with dining and deep seating. Think of this as the pool house, we do. The home features sweeping views of the great sound with a direct view of the sun creeping below the horizon in the evening.

A private pool is set within a walled garden, featuring clear blue water and steps for easy access. Two lounge chairs are positioned alongside the pool, while potted plants are visible, adding greenery to the serene setting.

Guest suite in Southampton

4.98 out of 5 average rating, 46 reviews

Rose Hill View - near Golf Course and Whale Bay

The guest suite is a self-contained air-conditioned unit attached to a typical Bermuda built house that sits high on a hill with stunning views of the ocean and is a 5 minute walk (par 4 away) to the Port Royal Golf Course and a 15 minute walk to nearby Whale Bay. There is a pool for guests to enjoy at their leisure. The location is in a friendly neighborhood with public transport including bus (5-10 minute walk) and ferry (15 minute walk) nearby as well as a moped rental business.

Top guest favorite

A clear blue pool is seen, reflecting the surrounding area. A lounge chair is positioned nearby, and a farm-style table and chairs are set up on the poolside deck. The yellow house with palm trees and a white railing is visible in the background.

Guesthouse in Southampton

4.99 out of 5 average rating, 143 reviews

The Pool House at 'Lemon Tart'

The Pool House at 'Lemon Tart' is the perfect escape in paradise! Set in a private garden near the sea and pink sand beaches, this delightful guest rental is in an excellent location to begin exploring beautiful Bermuda. https://www.gov.bm/coronavirus-travellers-visitors Tourism info, bus route (see # 7) https://www.gotobermuda.com Ask questions on ‘Bermuda Bound’ fb page Grocery delivery: www.dropit.bm Take-out App: Sargasso Public transport app: PinknBlue Taxi app: Hitch

A bright blue swimming pool is surrounded by a spacious deck featuring patterned tiles. Poolside, a wooden dining table with matching chairs is positioned for outdoor meals. Lush greenery is visible in the background, enhancing the tranquil atmosphere.

Apartment in Southampton Parish

5 out of 5 average rating, 29 reviews

Royal Heights - Royal Views, Comfortable Stay

Gem on the hill, our place has spectacular views of the Great Sound. Located at walking distance from restaurants, public transportation, the Fairmount Southampton Princess, Port Royal Golf Course, Gibbs Hill lighthouse, and south shore beaches including Horseshoe Bay. After a day of exciting action, relax at the pool with a drink. Comfortably furnished, the apartment can accommodate people travelling alone, couples and even a family of four.

Superhost

Apartment in Southampton

Scenic Southampton Stay w/ Pool + Views

Welcome to Riddlesview, a beautifully situated upper-level home nestled in Bermuda’s sought-after Southampton Parish. With sweeping views of the Great Sound and a location just moments from iconic landmarks like the Gibbs Hill Lighthouse and Church Bay Beach. Outdoors, enjoy your own private pool, complete with a lounge deck, BBQ area, and small backyard space. This is your gateway to island adventure and restful retreat.

Guest favorite

A charming residence is set against a bright blue sky, featuring a spacious veranda supported by palm trees. Comfortable seating is arranged on the exterior, and the shimmering pool reflects the surrounding greenery and architecture.

Apartment in Warwick

4.85 out of 5 average rating, 268 reviews

Natalia Studio & Pool

We offer a low cost alternative to Bermuda's hotels. By staying here you can choose to eat in or dine out at the nearby 5 star restaurants and still play golf on our world class courses and visit all the tourist attractions across the island. No children under 18 years old. Please note there is no Available Parking - other than for Scooters or Electric Vehicles. I.E. No Car Parking.