Beachfront vacation rentals in Old Man Bay

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Top-rated beachfront rentals in Old Man Bay

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Guest favorite

Townhouse in Old Man Bay

4.91 out of 5 average rating, 54 reviews

Your Oceanside Retreat Awaits!

Welcome to On The Bay Condo, located on the ocean’s edge in Old Man Bay, Grand Cayman Island. This is a truly private and tranquil resort, with a lovely white sandy beach, private swimming cove, pool and, of course, the magnificent aqua-blue water of the Caribbean all at your convenience. As pristine as the location is, this condo is only 30 minutes from the International Airport in George Town, and just minutes from various restaurants, water sports, snorkeling, scuba diving and sailing trips.

Aug 10 – 17

G$73,481 GYD per night

Guest favorite

Apartment in East End

4.98 out of 5 average rating, 40 reviews

Beautiful one bedroom beach view unit with cabana

Welcome to the unique and tranquil Rea’s Vista in the Seafarers district of East End in the beautiful Cayman Islands! Enjoy the beach life, the marine life or just swimming at your own private beach where you can also see sunrise! Sunset! Moon rise! in a relaxing atmosphere enjoying the Caribbean Sea. The one bedroom unit offers WiFi, TV, washer and dryer, surveillance cameras and comes fully stocked with utensils to manage your own meals or one may choose to visit nearby local restaurants.

Nov 10 – 17

G$33,830 GYD per night

Guest favorite

Home in North Side

4.94 out of 5 average rating, 35 reviews

Oceanfront “Dreamsicle” Villa with Kayaks

Oceanfront “Dreamsicle” Villa is a 3 bedroom/3 bath vacation getaway located on Northside of Grand Cayman. The ocean is a few steps from the back door. Mahogany Point is a secluded beach front property and you'll enjoy sunshine in this tranquil location. The amazing view of the Caribbean Ocean from the master bedroom balcony; community pool, gazebo, lounge chairs, stocked kitchen, new appliances, granite countertops, and WiFi. Outdoor charcoal Weber grill located in private Villa courtyard.

Apr 27 – May 4

G$126,260 GYD per night

Guest favorite

Guest suite in Savannah

4.97 out of 5 average rating, 196 reviews

Paradise Escape-Charming Oceanfront Guest Suite

A tranquil oceanfront escape for couples and solo adventurers... Ours is a unique community with quaint freehold condo cottages on a vast tract of oceanfront land. Wake-up in bed to a lovely view of a luscious green landscape that melds with the emerald green and blue ocean, sip a hot cup of coffee on the porch, enjoy a sunset cocktail by the ocean front pool, break a sweat in a friendly game of tennis, or take a blanket out to the lawn under the palm trees for breathtaking star gazing.

Apr 3 – 10

G$35,697 GYD per night

Guest favorite

Vacation home in Bodden Town

5.0 out of 5 average rating, 85 reviews

Art Beach House, boutique style luxury.

Private getaway for couples or singles perfect for honeymooners situated at beautiful frank sound. 25 mins from George town so car essential, many attractions nearby include the crystal caves 5 mins botanical gardens and rum point, and the beautiful east end. we also boast some of the the best dining on island. So lots to do or just chill on your private beach away from the crowds. the apartment is situated on ground floor level with art studio/Gallery above. with exclusive use of pool,

Feb 28 – Mar 7

G$93,537 GYD per night

Guest favorite

Condo in Rum Point

4.92 out of 5 average rating, 115 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!

Nov 1 – 8

G$96,816 GYD per night

Guest favorite

Apartment in East End

4.91 out of 5 average rating, 11 reviews

Spacious Oceanfront Studio

Take a break and unwind at this peaceful studio overlooking the sea from your private patio. The studio boasts unparalleled views with a bathroom, king size bed and a kitchenette. Set within the Reef Resort, enjoy lazing the day on the beach, snorkelling or diving. The property boasts a lively bar, restaurant with daily menus, coffee shop, spa, and fitness centre. You also have a small market and adult beverage store just across the street! Come join us in Cayman!!!

Oct 14 – 21

G$36,805 GYD per night

Guest favorite

Cottage in East End

4.99 out of 5 average rating, 96 reviews

Piece of Mine, Beachfront Villa #3

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 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!!"

Nov 22 – 29

G$84,964 GYD per night

Guest favorite

Apartment in GRAND CAYMAN

4.94 out of 5 average rating, 186 reviews

Rum Cove on the Bioluminescent Bay with Ocean View

Beautiful Rum Cove is located next to two one bedroom Villas and it's nicely decorated to suit our Island living, which is quiet and friendly to all who come to live amounts us. Rum Cove sit's in the beautiful Cove where the famous Bioluminescent Bay sits in your backyard. We welcome you to Rum Cove and want to offer you our Cayman Kind. Rum Point Beach Bar and Fine Dining Restaurant is located across the street from Rum Cove.

Mar 13 – 20

G$66,164 GYD per night

Guest favorite

Home in North Side

5.0 out of 5 average rating, 33 reviews

Private oceanfront one-level home w/screened porch

Breezy Bay is an oceanfront, private, single-level 3 bedroom home in North Side (Old Man Bay) perfect for your relaxing Grand Cayman vacation. Enjoy panoramic oceanfront views from this beach house with a bright, open concept. Relax on the 360 degree wraparound screened porch which has two seating areas both boasting oceanfront views of the Caribbean Sea. Over 175 ft of private oceanfront living.

Sep 25 – Oct 2

G$94,940 GYD per night

Guest favorite

Condo in West Bay

4.92 out of 5 average rating, 130 reviews

Villa Steps From The Sand

Ocean view Villa steps from the sand is on its own private beach with all the activities of 7 Mile Beach a short drive away. The best diving, snorkeling, are outside your door. The finest food and cocktails just across the street! Come enjoy!

Jul 20 – 27

G$106,543 GYD per night