Holiday rentals with a pool in Southhampton

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.

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.

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.

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.

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.

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.

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

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.

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.