Vacation rentals with a pool in Southhampton

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

Oceanview Cottage with Private Pool

Welcome to Sunset View Cottage-Nestled on a hilltop in Sandy's Parish with perfect water views for a sunset retreat that is exclusively yours. This contemporary-styled home offers a unique ensuite, well-appointed kitchen, laundry and outdoor gathering spaces. Relax by the pool or enjoy the vibrant colors of Bermuda homes and breathtaking sunsets from the rooftop deck. Perfect for couples, friends, families, golfers and digital nomads. Accommodates up to 6. This private home awaits you!

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.

'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!

Luxury Views Hospitality Transformational Retreats

Escape to peace and comfort, enjoy quality... Our Retreats with Accommodations, Bed and Breakfast along with airport pick up/drop off and island excursions. Sacred Waters Retreat in Bermuda is a retreat that focuses on your wellbeing. Available for yoga groups, teachers of various arts, couples, church groups, fitness groups, couples/groups who are in search of healthy wellness travel for a 5 - 28 day retreat. Lets honor our feminine energy by connecting with wellness, movement & nature.

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.

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

Spacious one bedroom apartment with pool

Spacious one bedroom apartment, fully equipped, in central location near beaches, hotels, golf, transportation, and all Bermuda attractions. Pool. Charging station for 220V and 110V electric cars (now available for rental in Bermuda!). We provide all linens, towels, hair dryer, etc. Fully-equipped kitchen, covered patio (shady and cool in the hot summer afternoons) with fireplace for cool spring/winter evenings, barbeque (gas) with dining table and cozy outdoor room.

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.

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.