Holiday rentals in Castle Harbour

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Top-rated holiday rentals in Castle Harbour

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
Cottage in Smith's
4.98 out of 5 average rating, 115 reviews

Cow Polly: Coastal luxury, featured in CN Traveler

Recently featured in Condé Nast Traveler, Cow Polly is a high-end luxury oceanfront cottage, 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 cottage setting. Along with its sister property, Top Shell (https://www.airbnb.com/h/top-shell)-- conveniently located next door -- It's like no other vacation rental on the island. Come and experience Cow Polly for yourself.

Top guest favourite
Guest house in SMITHS
4.97 out of 5 average rating, 144 reviews

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.

Top guest favourite
A bright turquoise exterior showcases a welcoming entrance with a white door beneath a decorative awning. Vibrant red flowers and potted green plants are situated beside the door, enhancing the inviting appearance of the studio unit's entrance.
Flat in Ferry Reach
4.98 out of 5 average rating, 222 reviews

"By Faith" Vacation Rental Unit

You’ll love our place because of the coziness. It’s a non-smoking studio unit that is suited for two persons or solo travelers. It is about a 6 minute walk to the bus stop and located about 10 minutes by bus from the UNESCO World Heritage Site, a grocery store and restaurants in St. George's town! We are less than 15 minutes by vehicle to beaches in St. George's! It's a 5 minute walk to (BIOS) Bermuda Institute for Ocean Sciences. We are about a 45 minute bus ride to Hamilton. Sofa is a bed

Top guest favourite
A yellow three-story house with a spacious front yard is depicted, featuring a set of stone steps leading to a second-level balcony. Lush greenery surrounds the property, creating a natural border. The sky appears clear, suggesting a bright and sunny day.
Flat in Hamilton
4.94 out of 5 average rating, 131 reviews

Cozy Studio across from beach

This Cozy studio is located directly across from one of Bermudas most family friendly beaches. There is a large field with a walking track and an outdoor basketball court across the street, and bus stops are easily accessible. Eve's pond nature reserve is a two-minute walk away and you can get there along scenic walking trails. A mile away is Flatts Village which is home to restaurants, and the Bermuda Aquarium and Zoo. A mile in the opposite direction are restaurants and a large supermarket.

Top guest favourite
A serene view reveals a modern home illuminated at dusk, showcasing a tranquil pool reflecting the moonlight. The surrounding landscape and distant lights enhance the atmosphere, inviting relaxation. The expansive patio features warm-toned tiles, seamlessly connecting the indoor living space to the breathtaking waterfront scenery.
Flat in St.George's
4.94 out of 5 average rating, 186 reviews

Waterfront Zen Retreat w/ Pool & Airport Pickup

Overlooking the water in historic St. George’s, the apartment offers quiet mornings, a serene pool, and a private garden setting - without the friction that often comes with travel. With airport pickup included and thoughtful touches throughout, most guests tell us the same thing: they feel settled within minutes of arrival. Revitalize all 5 of your senses immediately upon arrival at your NearEscape - a beautiful, modern and well appointed holiday rental. The best part its 2 hours away.

Top guest favourite
A stately gray building sits atop a stone-walled terrace, surrounded by lush greenery and palm trees. A white railing outlines the terrace, and the entrance is marked by steps leading up from the road, showcasing the welcoming exterior.
Flat in St.George's
4.97 out of 5 average rating, 141 reviews

Roxbury Studio - in St. George

Enjoy this affordable studio rental unit near the historic Towne of St. George. Lovely views of St. George's Harbor and a peaceful neighborhood with close proximity to restaurants, shops, bus and ferry transportation. Tobacco Bay Beach and St. Catherine's Beach are a short distance away (20 minute walk). Only 10 minute drive from the L.F. Wade Airport. (Twizzy and Rugged Electric) car rental across the street as well as 'Temptations', a very good breakfast and lunch restaurant

Top guest favourite
Place to stay in St. David's Island
4.99 out of 5 average rating, 216 reviews

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.

Top guest favourite
Flat in Hamilton Parish
4.96 out of 5 average rating, 129 reviews

Oceanfront Romance Haven — Poolside Bliss + Kayaks

This is a very quaint unit, and has been well received by guests who have stayed there. As you look out of the front door of the entrance to the unit, you can see the pool which is 5 feet away. You will also be able to see the clear blue ocean from your bed as you look out. It is a very romantic unit with its blue walls which blends in with its environment.

Top guest favourite
Home in Flatts Village
4.96 out of 5 average rating, 335 reviews

Your Own Beautiful Bermuda Cottage

WE'RE OPEN! Dean Hall Nursery is your own charming and welcoming home away from home. Perfectly appointed, stocked full of complimentary extras and well-situated, discover for yourself why this open-plan cottage has consistently been the most highly recommended vacation rental in beautiful Bermuda!

Top guest favourite
A covered porch features a glass-top table surrounded by two white metal chairs. Hanging planters display vibrant greenery. The view showcases the turquoise waters of the bay, boats can be seen in the distance, with a clear blue sky providing a serene backdrop.
Home in Baileys Bay
4.96 out of 5 average rating, 236 reviews

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.

Top guest favourite
An aerial view of Tobacco Bay reveals a sandy beach surrounded by clear turquoise waters and rocky formations. A vibrant gathering of beachgoers can be seen enjoying the sun. A floating obstacle course is positioned in the water, with numerous boats anchored nearby.
Home in St.George's
4.97 out of 5 average rating, 109 reviews

The Beach House at Tobacco Bay + Twizzy Charger

The Beach House is is a beautiful 2 Bedroom house located a stones throw away from Tobacco Bay , a short walk to the Town of St. George, The St. Regis Resort and Five Forts Golf Club. Follow us on Instagram @bermudabeachhouse

Guest favourite
Guest suite in St.George's
4.89 out of 5 average rating, 306 reviews

Casa Colonia Guest Suite

New studio apartment beautifully finished in a quaint St Davids neighbourhood. Access to small beach and within walking distance of some of Bermuda's most breathtaking beaches.

Popular amenities for Castle Harbour holiday rentals

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