Vacation rentals in Bailey's Bay

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Top-rated vacation rentals in Bailey's Bay

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Guest favorite

Apartment in Hamilton Parish

4.88 out of 5 average rating, 125 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.

Feb 16 – 23

R4,905 ZAR per night

Guest favorite

Guesthouse in Sandys

4.99 out of 5 average rating, 165 reviews

No Matata Cottage

Welcome ! Come, relax and enjoy our lovely studio cottage, ideally located on the waterside of beautiful Westside road. The property has 140 ft of easily accessible waterfront, perfect for a swim and is also within a 2 minute walk to a secluded beach. The cottage is quiet, airy and is finished to a high standard, offering a very casual luxury. Transportation is easy and the amenities are many. This is a slice of old Bermuda charm, perfect for relaxing and taking in all that is Bermuda !

Nov 18 – 25

R5,637 ZAR per night

Guest favorite

Guesthouse in SMITHS

4.97 out of 5 average rating, 111 reviews

Pool house in a garden setting (+ Twizy charger)

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 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.

Mar 21 – 28

R2,642 ZAR per night

Guest favorite

Apartment in Ferry Reach

5.0 out of 5 average rating, 139 reviews

"By Faith" Vacation Rental Unit

You’ll love our place because of the coziness. It is 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. We are located about 10 minutes by bus from the UNESCO World Heritage Site, a grocery store and restaurants in the town of St. George's! For walkers you can get there on foot. 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.

Oct 4 – 11

R2,603 ZAR per night

Guest favorite

Apartment in Devonshire

4.95 out of 5 average rating, 175 reviews

Spirit House Bermuda

We are a small spiritual community center in the middle of the island of Bermuda. Our cosy bedroom (which consists of a queen bed and two bunk beds, plus desk and love seat) will be solely yours unless you bring friends or family with you. It offers a comfortable retreat where you can choose to spend time on your own or join in and become part of the community if there is an event going on. You are also welcome to attend classes upstairs for a fee directly to the teachers.

Dec 13 – 20

R2,080 ZAR per night

Guest favorite

Place to stay in St. David's Island

4.99 out of 5 average rating, 166 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. 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. Please note that since Covid, breakfast is no longer available.

Sep 18 – 25

R2,276 ZAR per night

Guest favorite

Apartment in Hamilton Parish

4.98 out of 5 average rating, 122 reviews

"Del-Lita"

This apartment is fully furnished and has a 'Queen' size bed + a 'Foldaway' cot + an Air Bed suitable for an extra person. It is located 2/3 miles from the Airport. Has its own private porch in a garden setting. Nearby is the Crystal Caves, Blue Hole Park, The Swizzle Inn, The Grotto Bay Hotel, The Railway /Walking trail, The Ice Cream Parlor, A Cycle Livery, Nearby convenience store and several Scenic Bus routes to the City of Hamilton and popular Beaches.

Sep 15 – 22

R2,632 ZAR per night

Guest favorite

Home in Bermuda

4.99 out of 5 average rating, 233 reviews

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

Feb 18 – 25

R10,766 ZAR per night

Guest favorite

Apartment in Pembroke

4.95 out of 5 average rating, 134 reviews

Chequers - ocean views at the edge of Hamilton.

Chequers Upper Ocean unit offers a comfortable room with glimpses of the North Shore and the combination of a garden and pool setting on the edge of Hamilton City. The pool is shared with 2 guest units and the owners who live in the main house. The entrance to Chequers Upper is seperate, to the side of the main house. Come and stay where the tree frogs sing you to sleep and the birds serenade you awake.

Aug 19 – 26

R2,806 ZAR per night

Guest favorite

Apartment in Pembroke Parish

4.99 out of 5 average rating, 197 reviews

Paradise Awaits on the water’s edge, walk to town!

Welcome to your piece of Paradise, where you can wine and dine under the stars in your private garden with 180 degree unobstructed water views. Snorkel on your private reef directly in front of your apartment. Hamilton is just a 15 - 20 minute stroll away, or a 5 minute bus or cab ride. A convenience store is only a 2 minute walk. You have a full bathroom, fully equipped kitchen, and a king size bed.

Jan 25 – Feb 1

R3,707 ZAR per night

Guest favorite

Home in Flatt's Village

4.95 out of 5 average rating, 286 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!

Dec 14 – 21

R3,937 ZAR per night

Guest favorite

Home in Baileys Bay

4.95 out of 5 average rating, 187 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.

Nov 16 – 23

R6,507 ZAR per night