Beachfront holiday rentals in Old Man Bay

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Top-rated beachfront rentals in Old Man Bay

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Guest favourite

Home in Rum Point

5 out of 5 average rating, 26 reviews

Beachfront Retreat w/ Pool – Rum Point Paradise

Sea Charm is a beautiful spacious beachfront house with panoramic sea views and sunrises, located steps from Rum Point. The villa boasts a large and pristine beach front with excellent snorkeling outside the doors. Family friendly or romantic vacation at this large beachfront home is great for adventure, fun and relaxation. It’s only a 3-minute walk from Rum Point which hosts a bar, restaurant and beach with water sports. Starfish Point, Kaibo and Bioluminescence Bay are also just minutes away.

Guest favourite

Flat in Grand Cayman

4.97 out of 5 average rating, 145 reviews

Adorable Boho-Style Beach Villa

This adorable studio apartment has been fully renovated & has everything you need to enjoy the perfect Caribbean getaway. Calypso Cove is directly across from the famous Seven Mile Beach, where you can swim in the crystal clear blue sea every day. The studio has a balcony so you can enjoy the sunset or a morning coffee. Walking distance to supermarket, restaurants, bank and pharmacy, this apartment is in the perfect location. Keurig coffee machine, deck chairs, fins and mask and beach umbrella.

Guest favourite

Flat in West Bay

4.91 out of 5 average rating, 102 reviews

Beachside Boutique Villa Steps to Seven Mile Beach

Enjoy the conveniently located yet quiet and peaceful end of Seven Mile Beach with private beach and beach access just steps away. Enjoy short sunsets and beach walks to some of the islands best snorkeling , diving and restaurants or walk the whole of seven mile beach from right outside your front door . Make some memories at this unique , fully equipped cosy cottage with a real beachy vibe and tranquil private patio garden . We hope you will love Beach Love at Calypso as much as we do. :)

Top guest favourite

Flat in Cayman Kai

4.93 out of 5 average rating, 216 reviews

Rum Cove on the Bioluminescent Bay with Ocean View

Welcome to Rum Cove – your private escape on the bioluminescent bay, just steps from the world-famous Rum Point. This bright & breezy 1-bedroom retreat is part of a charming triplex and offers stunning 360° views. Whether you’re relaxing on the patio, kayaking under the stars, or sipping coffee at sunrise, Rum Cove surrounds you with natural beauty & peace. A perfect space for couples, solo travelers or small families looking for a quiet getaway with the best of Cayman Kai on your doorstep.

Top guest favourite

Cottage in East End

4.98 out of 5 average rating, 104 reviews

Hidden Gem Cottage on the Beach

Hidden Gem is a Traditional Cayman Style cottage located at Grapetree Cove on a beautiful beach area in sleepy fishing village of East End. The property is filled with trees that gives it a dreamy Island ambiance. The Cottage has been fully renovated with modern amenities that makes is very comfortable and homey. Hidden Gem offers a unique CaymanKind experience from a Caymanian host that knows the area well. Located minutes away from local dinning places and many key attractions in the area.

Guest favourite

Villa in West Bay

4.93 out of 5 average rating, 121 reviews

Luxury villa right across 7mile Beach + Bed Swing

1 bedroom with King size bed and Queen size sofa bed to comfortably sleep up to 4 guests. Adorable small boutique community of 7 villas a few short steps from the white sand and crystal clear water of Seven Mile Beach. Includes all the comforts of home, 50” Smart TV, FREE high-speed WiFi, Keurig Coffee Machine, AppleTV, Apple HomePod, New AC in all rooms and Walk-in closet. Condo is recently remodeled w/ new furniture. There is also custom made outdoor swing bed on the patio to relax on.

Guest favourite

Apartment in Rum Point

4.94 out of 5 average rating, 143 reviews

Nature's View: Pools of the Kai #2

Discover the peaceful Caribbean paradise of Cayman Kai. This secluded oasis will put you at ease as soon as you walk through the door. Our beach front property features stunning views across the Caribbean Sea to an unspoiled nature reserve. The double story screened in private pool deck can't be beat. Perfect for family holidays or a romantic getaway. Savor heavenly mornings and sundowners on your master bedroom balcony. Stroll down the beach to Kaibo, true barefoot living!

Top guest favourite

Cottage in East End

4.99 out of 5 average rating, 109 reviews

Piece of Mine, Beachfront Villa #3

Private & Tranquil BEACHFRONT Cottage offers all the conveniences of a luxury home. KAYAKS and SNORKELING GEAR, daybed & smart TV on the SCREENED PORCH, beach chairs, beach swing, and beautiful SUNSETS. Hammocks are throughout the property. Modern walk-in Shower, Towels, and bathrobe. Full Kitchen, Keurig & regular coffee maker & Blender, Extra-large bedroom, Antique four-post bed, Desk + smart TV. Enjoy paradise & experience "True Caymanian Hospitality!!"

Top guest favourite

Home in George Town

4.96 out of 5 average rating, 70 reviews

Paradise Beach House in South Sound, George Town

Paradise Beach House in South Sound, George Town Paradise Beach House is a beautiful vacation rental property located in South Sound, George Town, Grand Cayman. The house offers a spacious and luxurious living experience with its very own paradise beach and a view of the reef and famous wreck of South Sound! Please note the "Resort Fee" is the Government Tourist Tax that is charged to all international guests staying in the Cayman Islands.

Guest favourite

Apartment in George Town

4.98 out of 5 average rating, 116 reviews

Beach condo with sunset view

This luxury penthouse condo has everything for your perfect vacation. Enjoy stunning views of the sun setting over the Caribbean Sea from your private balcony. Located in a resort style complex with a great amenities. This includes bike use, large pool with swim up bar, kiddie pool and hot tub. Great snorkeling off our beach.