Vacation rentals in Old Man Bay

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Top-rated vacation rentals in Old Man Bay

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Guest favorite

A pool area is shown with lounge chairs arranged around a clear blue pool. The deck is paved with light-colored bricks and surrounded by greenery. In the background, a covered seating area with multiple chairs can be seen, alongside colorful buildings under a sunny sky.

Condo in Grand Harbour

4.93 out of 5 average rating, 266 reviews

Waterfront Sanctuary Serene | 2BR | Pool & Porch

Cool clean contemporary Sanctuary with water views; a two bedroom/two bathroom condo with a full kitchen and living room packed with all popular amenities (wifi, cable television, Apple TV, Netflix, Playstation game console, central A/C, iron and ironing board, washer and dryer, outdoor patio, pool and free parking) - conveniently located in Grand Harbour. The Shoppes at Grand Harbour, & Harbour Walk are next door. Perfect for exploring and enjoying all that the Cayman Islands has to offer.

Top guest favorite

A charming traditional cottage is partially obscured by vibrant tropical foliage. The light blue exterior, framed by lush green palm leaves, creates a serene and inviting backdrop. Natural sunlight enhances the warmth of the atmosphere, while wooden railings suggest a welcoming entryway.

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 favorite

A spacious bed is centered against a soft blue wall, complemented by two bedside tables with decorative lamps. A wall-mounted TV is visible in the corner, and natural light filters through sheer white curtains, creating a welcoming atmosphere.

Apartment in North Side

4.89 out of 5 average rating, 19 reviews

Apartment in Frank Sound

Welcome to our home!! Situated in Frank Sound, North Side. This apartment provides accommodation with free private parking. Small apartment attached to the main house, for added privacy, the accommodation features a private entrance. One room with 1 small closet and with one bathroom and kitchen with utensils. The apartment includes TV, wifi, hot water, beach chairs, cooler and much more! A short drive to tourist attractions; Kaibo, Rum Point, Crystal Caves, Blow holes & Barefoot beach.

Top guest favorite

A tranquil swimming pool is framed by palm trees and a rocky outcrop, with clear blue water inviting relaxation. The ocean is visible in the background, where waves gently meet the shore. Lounge chairs are arranged around the pool area, creating a serene atmosphere.

Guest suite in George Town

4.98 out of 5 average rating, 250 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.

Superhost

A private oceanfront saltwater pool is surrounded by lounge chairs and a gazebo. Palm trees sway gently in the breeze, and the clear blue water of the ocean is visible in the background, creating a serene atmosphere for relaxation.

Home in Old Man Bay

5 out of 5 average rating, 3 reviews

The Bay with 500 Feet of BeachFront and 2 Cottages

The Bay is a private home with 500 Feet of beach front over 5 acres in the laid-back Old Man Bay community on the North Side. 3 Acre protected beach next door. Beach Access: Nearby sandy shallow water cove at On the Bay condos and excellent sandy coral reefs 100 yards down the beach. Large screened-in patio, private oceanfront saltwater pool, gazebo with twin hammocks and lounge chairs. White sand beach adjoining an extended beach along the North Side. Countless activities.

Guest favorite

A serene beachfront scene features clean white sand gently sloping to a clear turquoise sea. Lush palm trees provide shade along the shore, while a rocky outcrop is visible in the water. Beach chairs are arranged invitingly, offering views of the tranquil coastline.

Apartment in North Side

5 out of 5 average rating, 15 reviews

On The Bay 310 - Enjoy the View

Pristine beachfront condo with large bedrooms and master bath. On the Bay is one of the nicest condo complexes on the Northern Coastline of Grand Cayman. It has beautiful and lush tropical landscaping, which is maintained daily, and a beautiful beach located in a cove directly in front of the apartment complex with clean white sand. Enjoy the large pool and cabana with BBQ area for your convenience. Restaurants, diving, water sports and grocery stores are a 10 min drive away.

Top guest favorite

The exterior of the studio apartment is framed by lush greenery and flowering plants. An outdoor dining set with an umbrella is positioned on a blue deck. The building features large windows and light-colored walls, complemented by stone accents and manicured landscaping.

Guesthouse in Grand Harbour

4.98 out of 5 average rating, 166 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.

Guest favorite

A cozy sleeping area is presented with a queen-sized bed, dressed in soft, muted bedding. Textured wall art made of natural materials is displayed above the bed, contributing to the room’s tropical theme. A small kitchenette is visible in the background.

Guesthouse in Bodden Town

4.93 out of 5 average rating, 15 reviews

Cozy Guesthouse in Middle of The Island

Welcome to our charming tropical-themed studio, a hidden gem nestled behind the inviting House on The Hill in the heart of Grand Cayman. This cozy studio retreat is perfect for those seeking a comfortable, inviting space to rest after exploring the island. The home is located in the center of the island and is located off the main arterial road, providing easy access to all sides of the island. It is close to beaches and 5 minutes from supermarkets and restaurants.

Top guest favorite

A cottage exterior is presented with a coral and green color scheme, surrounded by a landscaped yard with gravel pathways. The screened porch offers views of the inviting outdoor space, while lush greenery and palm trees enhance the peaceful atmosphere.

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!!"

Guest favorite

An aerial view captures the beachfront condo complex, showcasing its green exterior surrounded by lush landscaping. A tranquil pool is nestled among palm trees, with the white sand beach leading to clear waters in the foreground. The serene ocean adds to the inviting coastal atmosphere.

Condo in North Side

5 out of 5 average rating, 7 reviews

Penthouse 2 Bd/Bth Beachfront Condo w/ Heated Pool

Experience the Ultimate Beachfront Getaway and truley find your Happy Place at On the Bay # 312. Discover unparalleled luxury and serenity at this expansive 2-bedroom, 2-bathroom beachfront condo, nestled within the prestigious On the Bay complex in Old Man Bay, North Side, Grand Cayman. Renowned for its immaculate tropical landscaping and pristine white sand beach, On the Bay stands as one of the premier condo developments along the northern coastline.

Guest favorite

A cozy bedroom features a spacious bed with a patterned blanket. A small television is positioned on a dresser against a wall. Natural light filters through textured window treatments, complementing the earthy tones of the decor. A comfortable chair is located nearby, adding to the inviting space.

Guesthouse in George Town

4.88 out of 5 average rating, 147 reviews

Zen Den 3, cozy private studio in George Town

Welcome to this private cozy studio in the vibrant heart of George Town! Lokated 10-15 minute walking distance to Smiths Cove Beach, this is separate unit with an independent entry. Has a bedroom, kitchenette, washer dryer, bathroom and designated parking spot. Located in George Town near hospitals, pharmacy, gas station and restaurants. Bedroom has queen bed, split A/C, smart TV and Internet. Private outside patio with seating and a hammock.

Guest favorite

A charming white cottage features a wooden front door with a cross design, flanked by blue potted plants. Lush green foliage surrounds the stone pathway leading to the entrance, while large windows provide a view of the inviting interior.

Cottage in Savannah

4.96 out of 5 average rating, 195 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.