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

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.

'Ripple Waters' More 4 Les$ New Studio B Special!

HAPPY BOOKING! Enjoy this chic experience within a very cozy and vibrant-looking studio. The full kitchen area is stocked with seasonings, pots, pans, coffee, tea, condiments, etc. In addition, the shower bathroom has most of your bathroom needs! A separate BBQ grill is placed on the upper patio deck. Dine there or relax on the loungers whilst basking in the sun or watching the sunset! Your suntan will look fantastic! Relax in the refreshing pool after a long day of exploring the island.

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

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.

Palm Cottages Southampton, Bermuda

Cozy Apartment in Southampton, Bermuda Convenient & Relaxed Base Shared pool/Outdoor area / Dog-friendly Short walk/ride to: -Horseshoe Bay Beach -Church Bay (prime snorkeling spot) -Historic Gibbs Hill Lighthouse -Fairmont Southampton (major $550M renovation, reopening summer 2026) Route #8 bus nearby to Hamilton & Dockyard. Groceries/eateries close.

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.