Holiday rentals in Bailey's Bay

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Top-rated holiday rentals in Bailey's Bay

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

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Guest favourite

Flat

4.89 out of 5 average rating, 145 reviews

Great Relaxing Pool and Ocean View With Kayaks

Welcome to 'Neston'! Picture yourself on 2 acres of lush property nestled in a serene, tucked-away neighborhood. Immerse yourself in the breathtaking views of Harrington Sound, one of Bermuda's most enchanting inlets. Step into your private paradise with access to a dock – swim to secluded islands or paddle away on kayaks at your leisure. Savor the tranquility as you bask in the beauty of the crystal-clear azure waters. Wander along the longest, safest trail just 8 minutes away from your haven.

Guest favourite

Flat

4.88 out of 5 average rating, 8 reviews

South Shore Gem

Come and experience the best of island living, just a short stroll from one of the islands most popular and stunning beaches. You can soak up the sun, swim in the ocean, or for the avid walker, simply take a walk along the shore or the trails. Our peaceful and centrally located property is conveniently close to a grocery store, public transportation, and dining options. Perfect for a small family or friends looking to enjoy a home away from home experience. Designed with your comfort in mind.

Superhost

Flat

4.91 out of 5 average rating, 184 reviews

SOUTH SHORE GEM (Beach, Electric Car Charger)

Located above Church Bay on beautiful South Shore (15 miles of the most beautiful coastline) sits a Brand New, modern, delightful studio full of luxuries. Features A/C, king size TEMPURPEDIC bed, Queen size sofa-bed, 55" flat screen with HD Dish Network Satellite, WI-FI(200 Mbps fiber), KOHLER bubble-massage tub, full-size kitchen with VIKING stove and microwave, granite countertops, washer/dryer, private patio, dedicated Electric Car (Twizzy) Charge Point, Electric Fireplace, view of ocean.

Guest favourite

Flat

5 out of 5 average rating, 58 reviews

Lovely Majestic Waterfront 1 BR Vacation Home

This unique vacation home has a style of its own with panoramic views from one end of the Island to the other all within walking distance to Hamilton and sandy beaches. The grounds of this spacious upper-level vacation home boasts a private dock inside a natural cave to swim, fish and snorkel. This distinctive home has two cozy rooftop balconies and Bermuda cedar throughout. There are plenty of outdoor spaces to enjoy; a BBQ and lounge, whilst watching cruise ships and Bermuda longtails.

Guest favourite

Flat

4.95 out of 5 average rating, 113 reviews

The Windsor, your quaint and cozy getaway.

Nestled just off Turkey Hill, St. George’s, in the UNESCO World Heritage Site, you will find THE WINDSOR. The Windsor is a quaint and cozy vacation rental unit that is within walking distance to the town center, grocery store, restaurants and shops. It is a short walk to public transportation and beaches. The Windsor, which has been tastefully furnished, is non-smoking, comfortable and cozy and can sleep up to 3 persons. This Airbnb is part of Richard Allen AME Church. Be you and enjoy!

Guest favourite

Home

4.8 out of 5 average rating, 113 reviews

Sunset Paradise Ocean view 1-Bedroom Holiday Home

Oceanview Lower 1 Bedroom Vacation Home, your vacation "Home Away From Home". This stylish vacation home provides all the necessary amenities: fully equipped stocked kitchen, Split system AC throughout, Free Local Calls, Free Fast Internet/WIFI 100mb. We offer much more for an amazing relaxing "Bermuda Vacation". Just a few walking steps from Shelly Bay Beach, the Railway Trail with scenic oceanviews, easy access to Hamilton City. 7-10 min drive to Swizzle Inn or 20 minute walk.

Guest favourite

Flat

4.98 out of 5 average rating, 125 reviews

Little Palms - Charming one bedroom

Immaculate 1 bedroom, while there is no beach view - access to a beach is just steps away! With 2 small islands and their pristine beaches very near to our rugged neighborhood beach a which is a 2 minute walk way- this is a swimmer’s, snorkeler’s and kayaker’s paradise. We also have a 3 bedroom unit which can hold up to 6 people https://abnb.me/o3XBbkctA9 Kayak and land tours available. 10 minutes ride away in Dockyard by bus or car. Close to Port Royal PGA golf course

Superhost

Flat

4.81 out of 5 average rating, 70 reviews

Private & Stunning Large 1 Bed with amazing views

Relax and soak in the stunning Southshore sunsets from all areas of this property. The beautiful front yard and upper balcony are the best seats in the house. The large inviting entrance sets the mood for this uber-spacious 1 bedroom. Newly renovated, it features lovely stainless steal appliances, modern decor and pops of color for fun! This quiet but hilly neighborhood is 5 minutes away from Church Bay and the Port Royal Golf Course and a handful of popular restaurants nearby.

Superhost

Flat

4.95 out of 5 average rating, 84 reviews

Perfect location with Water Views

In the words of our guests, experiences in the unit have been described as 'Spectacular', 'Incredible', Amazing', 'Awesome', 'Excellent' and we have even had a 'Wow'. The unit is spacious wiith beautiful views as the ocean is in your front yard. Many reviews extoll the location of the unit as it is centrally located. Large families (up to 8) with children, couples, and business travelers have all enjoyed the unit. We have never had anyone complain about this unit.

Guest favourite

Loft

4.97 out of 5 average rating, 182 reviews

Harbour views - just outside Hamilton

Great Views over Hamilton Harbour - a bright and funky newly decorated apartment. Walk into town in 5 mins and catch a bus or the ferry or go to one of the many Front Street bars and restaurants. King size loft bed and a pull out (twin) sofa bed. Newly renovated bathroom. Brand new kitchen with stove, sink, refrigerator, microwave and coffee maker. Loads of space outside to just chill out - Hot Tub, hammock - tables and chairs - or just watch Bermuda go by on the water.

Guest favourite

Guest suite

4.95 out of 5 average rating, 367 reviews

PANATOLA STUDIO- Breathtaking Views Close to Beach

Panatola Studio is your own charming home away form home. Consistently been the most highly recommended vacation rental in beautiful Bermuda! Located in a desirable neighbourhood of Southampton with a breathtaking view! Conveniently located within walking distance to Horseshoe Bay beach, the lighthouse, a golf course and wonderful restaurants. Fully furnished with all the amenities you need for a relaxing vacation. Mini Electric car charger available!

Superhost

Flat

4.94 out of 5 average rating, 17 reviews

Oceanfront 3Bed w/ Private Patio & Garden - 5B

Lower apartment on the water's edge perfect for the whole family to enjoy. Self check in. Additional safety measures and deep clean professionally. All high touch areas sanitised. High speed wifi. Located in a private enclave with a dock and ocean swimming and snorkeling access. Dedicated Concierge. Spectacular views of Bermuda’s Great Sound clear turquoise waters. Rent mopeds, bikes or ride the ferry in Dockyard. Twizy (2 seater car) charger on site.