House holiday rentals in Hamilton

4.98 out of 5 average rating, 252 reviews

A vibrant green lawn stretches towards the water, framed by lush trees. A tall palm tree towers above, while the shoreline and ocean are visible in the background under a clear blue sky scattered with fluffy white clouds.

Home in Southampton

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.

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A spacious terrace is depicted, featuring two lounge chairs adorned with black and white stripes. A large umbrella provides shade, while a hanging chair is positioned nearby, overlooking the tranquil waters of the bay and the lush surrounding landscape under a bright blue sky.

4.97 out of 5 average rating, 70 reviews

Oceanfront "Dock of the Bay" Retreat

Escape to the stunning island of Bermuda and experience a truly tranquil getaway at our exquisite oceanfront property nestled in the picturesque Somerset, one of Bermuda's most charming and peaceful villages. Immerse yourself in the beauty of nature and the soothing rhythm of the waves at our Dock of the Bay Retreat – an idyllic haven where relaxation and rejuvenation become a way of life. Relax with the whole family at this hidden gem that promises a serene escape from the bustling world.

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4.91 out of 5 average rating, 306 reviews

A bright bedroom features a wooden bed with a decorative quilt. Nightstands with lamps flank either side of the bed, providing soft illumination. A textured artwork is displayed above the headboard on the vibrant green wall, with warm wooden accents enhancing the space.

Home in Hamilton

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.

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5.0 out of 5 average rating, 75 reviews

A peaceful waterfront scene captures a charming yellow cottage surrounded by lush greenery. The cottage features a white roof and large windows, with palm trees gently swaying nearby. The vibrant blue waters of Harrington Sound reflect the serene atmosphere.

Home in Smith's

Coral Palms Boathouse - Waterside Cottage

Take it easy at this unique and tranquil getaway, nestled on the shores of Harrington Sound. This studio cottage is just a stones throw from the charming village of Flatts. Enjoy a serene sanctuary where you can unwind and immerse yourself in the beauty of nature. Step inside our cozy studio cottage and be greeted by its intimate charm and inviting atmosphere. The focal point of the cottage is the sweet four-poster double bed, promising a restful nights sleep after a day of exploration.

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The outdoor area features a stone walkway leading towards a grassy space, bordered by white walls. A clear view of the water is presented, with trees visible in the background. The sky is filled with clouds, creating a serene atmosphere.

4.94 out of 5 average rating, 89 reviews

Paradise Found! Spacious Oceanfront Near Hamilton

This spacious lower waterfront apartment has spectacular views from one end of the Island to the other, all within walking distance to the city of Hamilton! Plenty exterior spaces to lounge, BBQ and soak up the sun, and then venture into a private unique natural cave where you can swim, fish and snorkel from the dock as you watch cruise ships entering and leaving the Island. It has off-street parking for mopeds and EV chargers for rental cars. A bus stop is outside the gate.

ValueFamilyBathroom

5.0 out of 5 average rating, 31 reviews

Home in Sandys

Private Oceanfront Escape | 3 BR | Beach + Dock

Sky Lark is a serene and secluded 3-bed, 3-bathroom retreat in Sandys Parish, offering panoramic ocean views from every room. Set on a private 1.4-acre estate, it features a private dock on the South Shore, plus access to a private beach on Ely’s Harbour. With air conditioning, WiFi, and a fully equipped kitchen, Sky Lark combines comfort with oceanfront access. Explore local beaches, marinas, and historic sites, or relax in this peaceful, scenic haven.

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4.93 out of 5 average rating, 15 reviews

Home in Smith's

Top Shell: Oceanfront luxury with stunning views

Top Shell is a high-end luxury oceanfront home with spectacular views of Bermuda’s North Shore in a contemporary, beautifully decorated space. Guests enjoy premier amenities and elegantly appointed furnishings in an airy beach house setting. Along with its sister property, Cow Polly (https://www.airbnb.com/h/cowpolly) – conveniently located next door and recently featured in Condé Nast Traveler – it's like no other vacation rental on the island.

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A charming cottage, adorned in soft pink, is surrounded by flourishing gardens and palm trees. The porch, supported by stone pillars, invites relaxation, while lush greenery frames the walkway leading to the main entry, creating a peaceful outdoor atmosphere.

4.98 out of 5 average rating, 181 reviews

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

Take a step back in time for a refreshingly sophisticated island holiday at the Ledgelets Cottage Colony. 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.

ValueFamilyOutdoor spaces

4.99 out of 5 average rating, 308 reviews

Two Adirondack chairs face the ocean, positioned on lush green grass. The vibrant blue water stretches into the horizon under a clear sky, creating a serene and inviting outdoor space.

Home in Southampton

Contemporary Oceanfront Apartment with shared pool

A contemporary oceanfront apartment located at the end of a quiet lane on the south shore between Whale Bay and Church Bay. Ideal for those looking to relax, with great ocean views from every room We also have a 3 Bed Contemporary Oceanfront Villa with private horizon pool approximately a mile down the road perfect for larger groups and family gatherings! Can be booked together for groups up to 8! https://www.airbnb.com/rooms/23767162

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4.94 out of 5 average rating, 18 reviews

Home in Hamilton

Chic 3BR w/ Dock + Hot Tub + Lounge Vibes

Welcome to Banana Cottage, your private island hideaway nestled on a lush, private estate in Hamilton Parish. This beautifully designed 3-bedroom, 2-bathroom home offers the perfect blend of comfort and coastal charm, with stunning views of Harrington Sound, a private dock, and a hot tub shaded by swaying palms. Just minutes from Bermuda’s best natural attractions and fine dining.

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5.0 out of 5 average rating, 36 reviews

A modern loft bedroom features a spacious queen bed, positioned beneath a sloped ceiling. Large windows flood the room with natural light, showcasing unobstructed ocean views in tranquil turquoise. A minimalist dresser and accent lighting enhance the room's clean lines and neutral palette.

Home in Smiths Parish

Ocean front Loft living with unobstructed view

OCEAN LOFT BERMUDA Newly built, bright and spacious loft living in a desirable neighborhood. Our drinking water goes through a 3-stage filtering system. Public transit is just steps away from the property. Ample parking with an EV charger available for guests preferred car rental. Restaurants and Bermuda’s nature railway trails are minutes away from the property.

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A charming Bermuda house sits amidst lush greenery, featuring a pale green exterior and a welcoming front porch with white railings. Surrounding the property, well-maintained lawns and tropical foliage provide a serene setting. A parked vehicle is visible in the driveway.