Vacation rentals with a pool in Southampton

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

'Ripple Waters' More 4 Les$ Studio B!

HAPPY BOOKING! Enjoy this cozy and vibrant 'more for le$$' studio. It may be small, BUT it mostly has it all! This unit is stocked with most of your essential needs! Relax in the refreshing 20'x40', salt water pool (shared) after a long day of exploring the island. Directly above the studio, on the upper patio deck, there's a separate BBQ grill, loungers & dining area for studio guests. Chill whilst basking in the sun or watching the beautiful sunset! Your suntan will look fantastic!

Pool House #2 - 2 Bedrooms near beaches-sleeps 6

This is truly home-away-from-home for our guests. Main bedroom with Great Sound view, has a new king sized bed, and second bedroom upstairs has queen bed. A blowup mattress is available if needed. Bedrooms share bathroom which has a walk-in shower, no tub. Downstairs are the living room with full-sized sofa bed, fireplace, a powder room, dining room, and the fully equipped kitchen. The back dining patio has an awning and bbq, and there’s a covered porch by pool. Quiet and private location.

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, BBQ 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.

Natalia Pool Cottage

This is great for a weekend getaway or even a week or two!! With quick flights from NYC, Boston, and the East Coast No children under 18 years old or those who cannot swim. You can now rent a TWIZY from currentvehicles !! TWIZY – a four-wheeled, two-seater, battery-powered little car – contact them for details and to book. Drive all day – charge it overnight at Natalia!! Please note there is no Available Parking - other than for Scooters or Electric Vehicles. i.e., No Car Parking.

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

Oceanview Cottage w/ Private Pool & Poolside bath

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 take in the picturesque view of Bermuda homes and sunsets from the rooftop deck. Perfect for singles, couples or small groups. Sleeps up to 6. This private home awaits you!

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.

Royal Heights | Panoramic Views & Island Comfort

Perched atop one of Bermuda's highest points, Royal Heights offers breathtaking panoramic views of the Great Sound and its crystal-clear turquoise waters. Relax on your private balcony as sailboats drift by, or unwind by the shared pool. With a private entrance, comfort, and an ideal location, Royal Heights is the perfect retreat for couples, families, or friends exploring the very best of Bermuda.

Private studio cottage with pool near beaches!

Bright, clean and private cottage with full kitchenette, air conditioning, pool, private laundry and plush queen sized bed. Cottage is located within 5 min walk to South Shore beaches, golf course, popular restaurants, picturesque Railway Trails and iconic insta worthy Gibb’s Hill Lighthouse. Bus stops and Twizzy rentals also within walking distance.

Studio w/ pool & Twizy charge by the Reefs & beach

Our apartment is across the street from the Reefs Resort and close to Church Bay and Horseshoe beaches and has great views. You’ll love staying because of the location near beaches, restaurants, buses and resorts, full kitchen, amenities, pool and BBQ. The studio is good for couples, solo adventurers, and business travelers.