Family-friendly vacation rentals in Bermuda

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.

Sea Breeze Mews on the Little Sound

Cozy & compact, this delightful 1 bedroom/2 story waterfront hideaway affords a panoramic view of the Little & Great Sounds. On the water (walk across the lawn and jump in) with a large dock suitable for swimming, snorkeling & spectacular sunsets. "Sea Breeze Mews" is only a 10 minute walk to picturesque Church Bay beach & a short bus ride to all the magnificent South Shore Beaches. Restaurants and award winning Golf courses are only a few minutes away. Public transportation right outside gate.

Pool house in a garden setting (+ EV chargers)

The pool house has a queen bed and its own bathroom + shower. It is next to our house in a spacious yard in a quiet residential neighbourhood. Bus stop is a 3 minute walk, John Smith's Bay beach 5 minutes and grocery store 12 minutes away. We also have a Labrador that roams the property. There's cable tv (includes HBO and Showtime) free wifi. Please see our other rental on the property "Las Brisas apartment with a pool" as an alternative (has a full stove) or if you are travelling with friends.

SOUTH SHORE GEM (Beach, Electric Car Charger)

Located above Church Bay on beautiful South Shore (15 miles of the most beautiful coastline) sits a Modern, delightful studio full of luxuries. Features A/C, king size TEMPURPEDIC bed, Queen sofa-bed, 55" TV, WI-FI(fiber), KOHLER bubble-massage tub, full kitchen, granite countertops, washer/dryer, private patio, EV Car Charge Point/Outlets, Electric Fireplace, partial ocean view and in the unlikely event of power loss - full solar/battery backup and full generator backup if all else fails! .

Centrally Located 2BED Apartment Near Beaches

Our cozy apartment is located in a quiet residential neighborhood , perfectly positioned between the capital of Hamilton and stunning South Shore beaches. We are a 25 minute taxi drive from the airport, 5 minute walk to a grocery store/bus stop and 15 minute walk to stunning Elbow Beach. The apartment has 2 bedrooms, 1 bath with tub/shower, kitchen with full size appliances and washer/dryer. There are air conditioners and ceiling fans in both bedrooms and living room for your comfort .

Modern Ocean Front Studio w/ Panoramic View

Modern, clifftop, ocean front studio with breathtaking panoramic views of the exquisite turquoise waters off the rugged south shore. Bright and airy with a relaxed, minimalist island vibe. Well appointed kitchenette, perfect for prepping morning coffee or small, simple meals to enjoy in the comfort of the studio or on the patio in the fresh ocean air. Central location 10-15 mins drive from the town of Hamilton and close to many of Bermuda's best beaches, restaurants and attractions.

Private apt walk to Bermuda's Best Beaches

Private studio in a quiet residential neighbourhood across from the entrance to Warwick Long Bay Beach. Full kitchen, private patio, and garden. Walking distance to South Shore beaches, dunes, and trails, including Horseshoe Bay. Note: Bermuda is hilly. All South Shore beaches are accessed via steep hills, and there is a steep hill in and out of the neighbourhood. Not an easy walk to a grocery store. Ideal for guests comfortable with hills and a quiet setting.

The Pool House w/ Heated Pool (Nov. 1)

Take a step back in time for a refreshingly sophisticated island holiday at the Ledgelets Cottage Collective. The serene atmosphere instantly lulls you into a soothing, restful state of relaxation. Wake to the chirping birds, and fall asleep to the choral tree frogs. The refurbished cottage interiors and pool terrace have been created with a modern vintage, boho-luxe vibe. To us, nostalgia is a very cool thing. Welcome, Pool House cottage awaits.

Pepper Tree Cottage one bedroom.

This charming newly renovated, one bedroom in Pepper Tree Cottage, is literally a stones throw from beautiful Dolly’s Bay. Your private garden area is the perfect place to enjoy the gorgeous views of the bobbing boats or a paddle in the kayak. Please note, there are many steps down to this unit. The very quaint old town of St. George's where you will find local hangouts and some lovely restaurants, only a 15 minute bus, car or bike ride away.

Little Arches Studio close to town

The unit is within my house, is self-contained, and consists of a bedroom and en-suite bathroom. It has its own entrance via french doors onto the patio and garden. It has a fridge, microwave and Keurig coffee machine. It is air-conditioned, has WIFI and cable TV. Hamilton is only a five minute walk with shops and restaurants, bus station and ferry terminal. The central location makes it a convenient place from which to explore Bermuda.

Ocean Side Studio Cottage - Condé Nast Recommended

"Saltine" is an exquisite cottage overlooking Hungry Bay in Paget. In July 2025 Condé Nast Traveler selected Saltine as one of the top 11 AirBNBs in Bermuda and selected it as the top pick for Local Charm. With stunning views across south shore with magnificent sunrise, enjoy the nature, beauty & tranquility of Hungry Bay, while being a short distance from the City of Hamilton.

Bird's Nest Cottage

Bird's Nest cottage is a historically listed seaside cottage perched at the waters edge, overlooking Bailey's Bay. The cottage has been restored and includes modern conveniences necessary for a comfortable stay. It's the perfect getaway for up to four guests, with 2 bedrooms with double beds.