
Beachfront holiday rental in Old Man Bay
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Top-rated beachfront accommodation in Old Man Bay
Guests agree: These beachfront homes are highly rated for location, cleanliness and more.

North Side Grand Cayman Beachfront Villa
Spacious beachfront home on Grand Cayman’s peaceful North Side. Walk out to crystal-clear water for snorkeling and paddleboarding — we provide kayaks, paddleboards, and snorkel gear. 4 en-suite bedrooms plus two sofa beds in living room, rooftop with ocean views, fast WiFi, full kitchen, and washer/dryer. Small grocery store and Over the Edge are 1 mile away. Supermarket in Savannah (~20 min). Restaurants & bars @ Kaibo & Rum Point (~15 min). Travel crib and kids’ games available. Self check-in.
ViewBeachHiking
4.99 out of 5 average rating, 117 reviews
Adorable Boho 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.
WalkabilityBeachSleep quality
4.96 out of 5 average rating, 183 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.
WalkabilityViewLayout
4.93 out of 5 average rating, 231 reviews
7 Mile Beach Waterfront-1 Bed Condo. Hidden Gem!
Seven Mile Beach Waterfront Condo overlooking the Caribbean Sea! location,location,location. Staying in this fully equipped one bedroom condo will be a vacation you will never forget. A comfortable sofa bed is a available if you choose to share this experience with family or friends. Relax on a sun lounger, snorkel, scuba dive, paddleboard all available from this location. A new listing exceeding expectations with only 5 star reviews! There are 2 paddleboards available with this rental.
BeachWalkabilityCondition
4.98 out of 5 average rating, 100 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.
ViewBeachFamily
4.98 out of 5 average rating, 124 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,
BeachViewQuiet
5.0 out of 5 average rating, 114 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!
BeachWalkabilityAccuracy
4.94 out of 5 average rating, 171 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, Caribbean Antique four-post bed, Desk + smart TV. Enjoy paradise & experience "True Caymanian Hospitality!!"
ViewBeachAir conditioning
4.99 out of 5 average rating, 121 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.
BeachWalkabilityCondition
4.94 out of 5 average rating, 109 reviews
Oceanview 2BR Condo w/ Big Balcony on 7 Mile Beach
Stylish, spacious, and steps from the sea—Cocoplum 10 is a renovated 2-bedroom, 2-bath condo with ocean views, coastal-modern interiors, and a large private balcony overlooking the Pool and Ocean. Located on the quieter end of Seven Mile Beach, you’ll enjoy calm waters for snorkeling and paddleboarding, a beachfront pool, and easy walks to local restaurants and shops. One of the most popular 2BR condos on the island—book early!
WalkabilityBeachFamily
4.97 out of 5 average rating, 119 reviews
2 Bedroom 2 Bathroom Condo 7 Mile Beach
The apartment was previously used by us as a home. It has everything you need for a relaxed vacation. It is located on the northern side of the complex with a pleasant peaceful garden view yet close to the action on the Seven Mile Beach corridor where Camana Bay, the nightlife and famous Seven Mile Beach are located. The amenities of the complex are a short walk away.
BeachWalkabilityIndoor spaces
4.9 out of 5 average rating, 111 reviews
Swim with Turtles! Uncrowded Oceanfront Retreat!
Imagine waking to the gentle sound of waves, brewing a cup of coffee, and stepping onto your screened beachfront patio as the Caribbean glows shades of turquoise and blue. Just beyond your door lies one of Grand Cayman's best-kept secrets—a quiet white-sand beach where guests regularly snorkel with sea turtles only a short swim from shore.
ViewBeachLaundry
4.95 out of 5 average rating, 108 reviewsPopular amenities for Old Man Bay beachfront rentals
Pet-friendly beachfront home rentals

Seven Mile Beach with Soul
ViewBeachValue
4.94 out of 5 average rating, 186 reviews
The Cottage at Rum Point
ViewWalkabilitySleep quality
5.0 out of 5 average rating, 7 reviews
Deluxe Studio on the beach #9
BeachViewCheckout
4.9 out of 5 average rating, 72 reviews
Ocean/Beachfront-stunning views! Seabreeze Villas
BeachViewParking
5.0 out of 5 average rating, 4 reviews
1BR King Suite w/ Kitchen, Patio & Living Area
WalkabilityBeachPool
4.78 out of 5 average rating, 64 reviews
Island View Apt w/ Kitchen - Near Seven Mile Beach
BeachAmenitiesLocation
4.67 out of 5 average rating, 6 reviews
Luxury villa just a few steps from 7 Mile Beach
WalkabilityBeachAccess
4.89 out of 5 average rating, 139 reviews
ISLAND PINE VILLAS 24 - On Beautiful 7 Mile Beach!
BeachViewOutdoor spaces
4.86 out of 5 average rating, 101 reviewsBeachfront home rentals with a pool

Oceanfront 2bed 2bath Condo Seven Mile Beach
ViewWalkabilityCheck-in
4.94 out of 5 average rating, 113 reviews
Beautiful Beachfront 2BR Condo.
BeachViewNearby
4.91 out of 5 average rating, 104 reviews
Cayman Reef Resort on Seven Mile Beach
WalkabilityBeachFamily
4.95 out of 5 average rating, 211 reviews
On the Bay #103 - Northside 3BR Beach Condo & Pool
WalkabilityBeachHospitality
4.89 out of 5 average rating, 28 reviews
BeachPlumVilla
ViewWalkabilityNearby
4.98 out of 5 average rating, 85 reviews
Yippee Kai Yay Beachfront oasis
ViewBeachParking
4.97 out of 5 average rating, 38 reviews
Private Beachfront Retreat, Pool/Snorkel, 16 Guest
ViewBeachBackyard
4.98 out of 5 average rating, 60 reviews
Beach & Pool in 2BR secluded condo at Rum Point
WalkabilityBeachAccuracy
4.98 out of 5 average rating, 44 reviewsPrivate beachfront home rentals

Next to Ritz | Oceanview 1BR on Seven Mile Beach
BeachViewIndoor spaces
4.98 out of 5 average rating, 117 reviews
Villa at the Sea Front
ViewWalkabilityLocation
4.95 out of 5 average rating, 61 reviews
Beautiful one bedroom beach view unit with cabana
ViewWalkabilityWi-Fi
4.99 out of 5 average rating, 73 reviews
East End Beach House with Private Dock!
ViewWalkabilityHeating
4.96 out of 5 average rating, 79 reviews
Villa on Seven Mile Beach
ViewBeachQuiet
4.98 out of 5 average rating, 86 reviews
Seaing Spotts: Beachfront Seaside retreat! Cayman
BeachViewBathroom
4.93 out of 5 average rating, 70 reviews
Ocean club seaside luxury
ViewBeachQuiet
4.95 out of 5 average rating, 20 reviews
Luxury Penthouse 1 Bedroom Condo Beachfront Resort
BeachViewSleep quality
4.97 out of 5 average rating, 34 reviewsDestinations to explore
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