Vacation rentals with a pool in Pembroke

Chequers Garden- Paradise at the edge of Hamilton

Come & stay where tree frogs sing you to sleep & the birds serenade you awake. A 15min walk to the heart of Hamilton; situated in a private garden & pool setting. A ground floor, south facing, open plan unit; separate foyer & sitting area- converts to 3rd person sleep area. The kitchen: full fridge, microwave, toaster oven & kettle. If you have children, we can add a single bed or pack'n'play, high chair, some toys, books & accessories. We look forward to welcoming you to our little paradise.

Studio Apt w/ pool - quick walk to town

The perfect edge of town apartment for two. For those who prefer to walk, this is the perfect spot with restaurants and shops within close proximity. We are a very short walk to all the shops, restaurants and bars along Front Street in Hamilton. This unit is a self-contained apartment within our house. We have 3 apartment like this within our home. This means with a total of 3 studios, we have accommodation for up to 6 guests. Head to the back patio and enjoy the heated pool year round.

Architect’s Bermuda home and pool house

Mid Century Modern 3 bedroom home with separate studio on elevated pool terrace with 180’ of sweeping Bermudaful ocean views in an exclusive private estate just 5 minutes from town. A magical peaceful haven with access to secluded cove for swimming. Perfect for musicians - multiple pianos and guitars. Please note - our 2 friendly cats Nova and Nala come un-negotiably with the house and don’t yet know how to open their daily tins of food but know how to get you to help them.

Upper Apt w/ pool, short walk to town

Simple, chic, bright and airy. A private patio overlooking the pool deck and gorgeous island views. This second floor apartment is brand new and finished to a very high standard. Rent all 3 apartments to host your party of 6. The large studio has a 55" LED TV, AC and Wifi. The kitchen includes a fridge/freezer, microwave, induction cooktop, coffee maker, kettle, toaster, wine glasses and all needed plates and cutlery. Transportation from the airport can be arranged.

Smuggler's Cove - Walk to City of Hamilton

** Early check-in is guaranteed on flight arrival with Bermuda Covid entry requirements. ** Fully furnished, newly renovated, Bermuda themed, one bedroom, one bathroom, two story townhouse located on Rosemont Avenue. Interior Queen bed Bath with shower Split unit air-conditioning and heating Full kitchen with Nespresso machine All dining and cookware Laundry Desk 2 Flat screen TV’s Cable, Wifi and local phone Exterior Private patio/BBQ/outdoor dining Shared pool

Chequers - ocean views at the edge of Hamilton.

Chequers Upper Ocean unit offers a comfortable room with glimpses of the North Shore and the combination of a garden and pool setting on the edge of Hamilton City. The pool is shared with 2 guest units and the owner, who lives in the main house. The entrance to Chequers Ocean is seperate, to the side of the main house. Come and stay where the tree frogs sing you to sleep and the birds serenade you awake.

Smuggler's Cove Skyesil Unit

Private one bedroom in a central location within minutes of the town of Hamilton. The fantastic restaurant, Ascots, is immediately next door. Unit has a spacious living room, dining area, and fully equipped kitchen. There is a small garden as well as use of a shared pool with only 5 other units on the property. Ideal for business guests, printer available for use in the unit with fast internet.

ED 9 King bed Hamilton and pool access

Private spacious unit located in the heart of Hamilton Bermuda. Walking distance to restaurants, retail/ groceries shops, night life and public transportation.

ED 12 - Pool, king bed, Hamilton Bermuda

Private spacious unit located in the heart of Hamilton Bermuda. Walking distance to restaurants, retail/ groceries shops, night life and public transportation.

ED 11 Pool, Queen bed, Hamilton Bermuda - Unit 11

Private spacious unit located in the heart of Hamilton Bermuda. Walking distance to restaurants, retail/ groceries shops, night life and public transportation.

ED 10 Pool, Queen bed, Hamilton

Private spacious unit located in the heart of Hamilton Bermuda. Walking distance to restaurants, retail/ groceries shops, night life and public transportation.

ED 13 Pool, King bed, Hamilton Bermuda - Unit 13

Private spacious unit located in the heart of Hamilton Bermuda. Walking distance to restaurants, retail/ groceries shops, night life and public transportation.