Vacation rentals in Bailey's Bay

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Top-rated vacation rentals in Bailey's Bay

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

Guest favorite

Apartment in Sandys

4.99 out of 5 average rating, 139 reviews

Charming Beachfront chill spot

Welcome to our beautiful beachside studio, the Ledges. It’s located on over an acre of property in the rustic west of Bermuda. Take strolls on our country road to the local farm. The bus stop is steps away to take public transportation to Dockyard or to Hamilton. Or spend your days on the property at one of 2 private beaches. The Ledges studio is an architectural gem with exposed beamed ceilings, a cozy fireplace for chilly evenings, and a modern fully equipped kitchen. The studio has its own private, large upper deck for entertaining or relaxing where the sunsets are just stupendous!!! Airport pick-ups and island tours can be arranged through your host.

Mar 16 – 23

G$58,473 GYD per night
Guest favorite

Apartment in Hamilton Parish

4.88 out of 5 average rating, 124 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.

Jan 14 – 21

G$54,032 GYD per night
Guest favorite

Home in Southampton

4.96 out of 5 average rating, 154 reviews

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.

Dec 13 – 20

G$40,063 GYD per night

Popular amenities for Bailey's Bay vacation rentals

Other great vacation rentals in Bailey's Bay

Guest favorite

Cottage in Smith's

4.97 out of 5 average rating, 73 reviews

Cow Polly: Oceanfront luxury with stunning views

Aug 19 – 26

G$140,417 GYD per night
Guest favorite

Apartment in St.George's

4.98 out of 5 average rating, 45 reviews

Roxbury Studio - in St. George

Feb 8 – 15

G$23,895 GYD per night
Superhost

Apartment in Hamilton

5.0 out of 5 average rating, 3 reviews

2br Spacious Bay View Retreat

Jul 1 – 8

G$68,191 GYD per night
Guest favorite

Bungalow in Hamilton Parish

4.95 out of 5 average rating, 19 reviews

Historic Westport on the water in Flatts

Apr 1 – 8

G$85,579 GYD per night
Superhost

Apartment in Smiths

4.94 out of 5 average rating, 18 reviews

Cute Studio w Patio & South Shore Views

Jun 5 – 12

G$25,541 GYD per night
Superhost

Apartment in Hamilton

4.87 out of 5 average rating, 31 reviews

Cozy Studio across from beach

Aug 12 – 19

G$28,779 GYD per night
Guest favorite

Apartment in St.George's

4.83 out of 5 average rating, 81 reviews

Domiche's Apt - Water Front Paradise

Jan 22 – 29

G$28,353 GYD per night
Guest favorite

Cottage in St.George's

5.0 out of 5 average rating, 32 reviews

KC Retreat

Nov 20 – 27

G$62,263 GYD per night
Guest favorite

Apartment in Smith's

4.94 out of 5 average rating, 51 reviews

Las Brisas apartment with a pool (+ Twizy charger)

Nov 12 – 19

G$27,989 GYD per night
Guest favorite

Cottage in Pembroke

5.0 out of 5 average rating, 53 reviews

Palmberry Oceanfront Cottage

Nov 13 – 20

G$90,112 GYD per night
Guest favorite

Apartment in Devonshire Parish

5.0 out of 5 average rating, 28 reviews

Top of The Hill AirBnB

Nov 23 – 30

G$25,806 GYD per night
Guest favorite

Villa in Pembroke

4.93 out of 5 average rating, 45 reviews

Waterlap-Fairylands Little Haven Exclusive

Oct 14 – 21

G$129,661 GYD per night
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