Vacation rentals in Old Man Bay

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Top-rated vacation rentals in Old Man Bay

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Guest favorite

Villa in Old Man Bay

4.97 out of 5 average rating, 33 reviews

Old Man Bay Villa #2

Tucked away in a corner of Northside, Grand Cayman, is the quaint little community of Old Man Bay, where time has stood still. This is the authentic Cayman, no crowds and the only thing you'll hear are the ocean waves. The 2 side-by-side 1 bedroom villas are identical in layout. The main floor has a living room with queen size sofa bed, flat screen TV, fully equipped kitchen with Dishwasher & powder room. The spacious bedroom is on the 2nd floor and has a full ensuite with a large shower.

Apr 14 – 21

G$32,750 GYD per night

Guest favorite

Townhouse in Old Man Bay

4.92 out of 5 average rating, 53 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.

Dec 3 – 10

G$73,305 GYD per night

Guest favorite

Guest suite in Grand Cayman

4.98 out of 5 average rating, 46 reviews

Studio 1 @ Fort Rocks, Forest King near beach!

STUDIO 1 has amazing natural rock & forest views, WiFi, electricity, water, AC, King bed, seating area, dining area, SMART flat screen TV, portable induction hot plate, coffee maker, toaster oven w/air fryer, microwave, bread toaster, dishwasher, fridge/freezer, compact washer/dryer, private back patio & large two level deck (with deck net) perfect for yoga, morning coffee or just relaxing. Fire pit & BBQ grill. 1 parking space. Close to beaches, restaurants, local attractions, shops & schools.

Nov 6 – 13

G$28,467 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 17 – 24

G$35,611 GYD per night

Guest favorite

Apartment in KY

4.98 out of 5 average rating, 107 reviews

Rum Haven villa on Bioluminescent Bay & Ocean view

Rum Haven is located at 75 Sand Point Road in the beautiful, tranquil district of North Side, across the street from the world famous Rum Point Club. 10 minutes by boat to Stringray City with the Bioluminescent at the end of the cove by this unit. Kaibo Yacht club is located 1 mile away with the beautiful Crystal Caves and Botanic Park only 7 miles away. Kayak and hammocks available for guests to use. The Red/Orange kayak belong to Rum Haven and the paddles are on the screen porch.

Aug 28 – Sep 4

G$49,669 GYD per night

Guest favorite

Condo in North Side

4.89 out of 5 average rating, 38 reviews

Spacious 2-Bedroom 2-Bathroom Beachfront Condo wit

The two 2-bedroom condominium located in Old Man Bay on the North Side of Grand Cayman is nestled in a prime oceanfront location. Step into this expansive unit boasting over 1,685 sq ft of living space, including a generously sized balcony that offers panoramic and uninterrupted vistas of the magnificent Caribbean Sea. Immerse yourself in the breathtaking views not only from the balcony, but also from the comfort of the living room and kitchen, creating a truly mesmerizing experience.

Sep 13 – 20

G$34,264 GYD per night

Guest favorite

Condo in Savannah

4.94 out of 5 average rating, 17 reviews

Clarke’s Cove Residence

Welcome to Clarke's Cove Residence, a newly built modern haven completed in early 2024. Our Airbnb offers a self-sustaining one-bedroom unit where privacy meets comfort. Enjoy exclusive access to your own bedroom, a spacious living/dining area, a fully equipped kitchen, and the convenience of a washer and dryer. With a separate entrance and dedicated parking, Clarke's Cove Residence provides a seamless blend of modern living and complete independence for a delightful stay.

Aug 11 – 18

G$25,178 GYD per night

Guest favorite

Guesthouse in Grand Harbour

4.98 out of 5 average rating, 129 reviews

Heavenly Suite 2 - The M @ The Edge

Heavenly Suíte #2 at The M @ The Edge is a studio apartment with sleek & modern furnishings, smart HD TV, sound bar, chandeliers, state of the art kitchenette with quartz counter-tops, Delta faucet, and under counter lights. The chic bedroom fashioned in white crisp tiles, scones and recessed lighting mimics the luxurious bath styled in porcelain & Carrera tiles, Delta faucets, mirrors. . The patio enlivened by red/white accents, greenery, bar, pergolas, and Jacuzzi.

Dec 12 – 19

G$28,362 GYD per night

Guest favorite

Cottage in East End

4.99 out of 5 average rating, 95 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!!"

Oct 26 – Nov 2

G$81,005 GYD per night

Guest favorite

Apartment in GRAND CAYMAN

4.94 out of 5 average rating, 185 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 22 – 29

G$53,997 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 16 – 23

G$94,713 GYD per night

Guest favorite

Cottage in Savannah

4.97 out of 5 average rating, 132 reviews

John John's Hideaway

Cozy 1 bedroom cottage with en-suite bathroom, sitting area, full kitchen, washer and dryer. Located in a quiet neighbourhood, a 2 minute walk away from Pedro St. James Castle. 3 minute drive from a supermarket and local restaurants. 5 minute drive to snorkel at the picturesque Spotts Beach. 20 minute drive from other popular destinations, including shopping centres and other local attractions.

Oct 15 – 22

G$32,371 GYD per night