Vacation rentals in Bailey's Bay

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Top-rated vacation rentals in Bailey's Bay

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Top guest favorite

A serene outdoor scene features a curved pool surrounded by lush greenery and palm trees. The clear, blue waters of Harrington Sound are visible in the background, enhancing the tranquil setting under a bright sky.

Apartment in Hamilton Parish

4.89 out of 5 average rating, 149 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.

Top guest favorite

A sandy beach curves along the shore, with people enjoying the turquoise waters. Gentle waves lap at the sand, while distant hills and trees frame the scene. The cloudy sky adds a soft backdrop to the vibrant beach environment.

Guest suite in Southampton

4.95 out of 5 average rating, 374 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! *Another studio above for other 2 guests.

Superhost

Apartment in Southampton

4.91 out of 5 average rating, 193 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 favorite

Apartment in Warwick

4.95 out of 5 average rating, 99 reviews

Private Beach & Pool at The Cliffs of Marley.

Stunning Studio with ocean views of Bermuda's iconic South Shore. Watch the whales from your window, the pool, or your own private balcony. (Whale Season is March through April) BBQ on your porch or wade in the aqua blue waters of your own, private pink sand beach. Fully Furnished unit with Kitchenette. Beach Towels and Chairs available. Laundry on site. Private Beach & Pool for all units. Scooter and twizzy parking on site, no charge. Infants and children are welcome. Concierge avail.

Top guest favorite

A vibrant blue vacation home is situated on the edge of a rocky coastline, surrounded by lush greenery. The property features multiple outdoor spaces, with loungers placed on a grassy area overlooking clear turquoise waters. Nearby, the colorful buildings of the neighborhood can be seen.

Apartment in Pembroke Parish

5 out of 5 average rating, 63 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 favorite

A scenic view captures the azure waters of a beach, dotted with umbrellas and sunbathers enjoying the sun. Rocky formations peek from the turquoise surf, creating a natural contrast to the soft, sandy shore where visitors gather in the gentle waves.

Home in Hamilton Parish

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.

Top guest favorite

A tranquil coastal scene is visible, featuring clear turquoise waters gently lapping against smooth rocks and a sandy shoreline. Lush greenery lines the beach, framing the water's edge, while distant land can be seen with a mix of trees and buildings under a bright blue sky with scattered clouds.

Apartment in Sandys

4.98 out of 5 average rating, 129 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

Apartment in Smiths FL07

4.95 out of 5 average rating, 86 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.

Top guest favorite

Loft in Pembroke Parish

4.97 out of 5 average rating, 187 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.

Superhost

Aerial view showcases a spacious outdoor deck adjacent to clear turquoise waters. Several loungers are arranged on the deck, while a shaded area under an umbrella offers a spot for relaxation. The surrounding space features seating options and vibrant greenery, enhancing the coastal setting.

Apartment in Sandys

4.94 out of 5 average rating, 18 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.

Superhost

A serene beach scene is depicted, featuring two dark rocks surrounded by gentle waves. The water transitions from clear to a soft turquoise, meeting a sandy shoreline that showcases a subtle blush hue. Coastal vegetation peeks from the edges, enhancing the natural beauty.

Townhouse in Ord road

4.9 out of 5 average rating, 78 reviews

Townhouse Close To Beaches/Golf Perfect for Groups

The Village Outback :This attractive townhouse style property consists of 2 bedrooms which both contain full en suite bathrooms, it sleeps 6. The vacation home is good for family and group vacations. The property is located minutes away from a variety of wonderful restaurants, the closes golf course is 5 mins away and there is also the near by "railway trail" where you can walk for miles admiring the beautiful island scenery.

Superhost

A spacious outdoor patio is furnished with dark wicker chairs and a low table, offering a great view of the ocean. The area is bordered by tropical plants and features a large umbrella for shade, creating a relaxing atmosphere.

Apartment in Sandys Parish

4.79 out of 5 average rating, 61 reviews

Paul's Oceanview Private Cozy Studio+ Twiz Charger

"Newly Renovated" Modern, very private, cozy, quaint, self-catering, self-check-in, fully furnished studio apartment with reverse cycle AC and everything you need for an amazing, relaxing Bermuda vacation! Guest accommodations located downstairs of a private Bermuda home. This tranquil apartment provides all the necessary amenities and more for your home away from home. Look at our pictures! We Speak Spanish!