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Old Man Bay Rentals

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331 Houses

Villa Caymanas: Caribbean Villa w/ Fabulous Snorkeling, Pool, & Panoramic

Old Man Bay house

4 bedrooms / 5 bathrooms / sleeps 8

“A perfect vacation!” The second spring time vacation we had at villa caymanas. When arriving, the view entering the front door blows me away each time I arrive. Property is well maintained and everything was super clean. Private ocean side back yard made it great for relaxing. House has everything you need and some extras. We drove most days to Rum Point Beach( 10 minute drive) to relax, great beach. Spent a few days never leaving the property as we grilled fish we bought from local fisherman at the docks. With the big group we had, the villa suited us perfectly as there was plenty of room inside and out. I liked best the privacy and location of the house, we enjoy getting away from it all and this place gave us that. Worst part about the house is saying good bye.

Responds fast! avg. 3 hours 21 minutes

Price per night from

$616

YOU'VE Arrived! Beachfront 3BR condo w/ Pool-Relax... North Side near Rum Point

Old Man Bay condo

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$338

Cayman Sands: Secluded Beach Villa with Pool Atrium & Guest Cottage

Old Man Bay house

5 bedrooms / 5 bathrooms / sleeps 14

“A wonderful, relaxing paradise” I recently stayed at Cayman Sands with my husband, my in-laws, and our 2 young girls, ages 4 and 6. This home is everything we could have asked for - as gorgeous as the pictures, but even fresher (the larger bedrooms have been painted since the online photos). It was very spacious and clean, and the location was great for us - quite private (even with folks staying in the neighbouring home) but a quick drive to Rum Point, which is a great beach for families with young kids with its calm water, extended shallows and sandy bottom. We had the pool heated - well worth it - as our daughters spent long hours in the pool. The beach area is nice - although it is true the water in this area is more suited to snorkelling than swimming or wading, it was fine for us with the pool right there for the girls, and snorkelling convenient for us. There is washed up plastic garbage if you walk off the property down the beach - which is not the fault of the property managers or the island, but an unfortunate consequence of garbage mismanagement elsewhere and tides/storms washing debris onto the shore. The villa is well stocked with kitchen items, pool toys, beach towels, etc... We took a great glass-bottom boat tour from Rum Point with Red Sail Sports - to Stingray City and for a bit of snorkeling. This was a nice way to go as the boat is smaller, so fewer people and plenty of time for everyone to handle the stingrays and get photos and video without feeling rushed at all. Did some nice diving off Macabuca near the Turtle Farm - can rent gear right there. I would recommend this villa without hesitation, and hope to stay here again in the future. Cayman is a beautiful, safe island, and easy to explore since it's not too big. Jim Leavitt and his staff were wonderful to deal with throughout our searching for and booking of this villa, and provided great information to us before we arrived. The cleaning lady who came mid-week (Sharon) was friendly and efficient.

Responds fast! avg. 3 hours 21 minutes

Price per night from

$733

Coral Cottage Pink: Cozy Old Man Bay Cottage with Infinity Pool Perfect for

Old Man Bay house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 3 hours 21 minutes

Price per night from

$393

Northern Lights #5: 2-Story Beachfront Oasis in North Side w/Pool, Dock

Old Man Bay condo

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 3 hours 21 minutes

Price per night from

$264

Coral Cottage Yellow: A Scuba Diver's Paradise with Infinity Pool & Ocean Reef

Old Man Bay house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 3 hours 21 minutes

Price per night from

$393

Grand Cayman Northern Lights Beachfront Villa

Old Man Bay condo

2 bedrooms / 3 bathrooms / sleeps 6

“A piece of heaven in the Carribean” We arrived at Northern Lights after a long, cold, snowy winter to find a place that exceeded our expectations. Many times during the week, we spoke about how happy we were that we chose Northern Lights. The setting is quiet, serene and peaceful. The trade winds made the air-conditioner a useless item. The sound and smell of the ocean was soothing and enticing. The pool was delightful and clean. Our primary goal, other than relaxing and warming up, was snorkeling. Other than the day we went to Stingray City, all of our snorkeling was immediately in front of our condo. A short swim brought us to a great barrier reef. Our favorite "finds" were scorpion fish[very hard to see], a yellow spotted ray, and a lion fish. Although the lion fish is an invasive species, it was very interesting to see it, none the less. The condo had everything we needed, and we elected to prepare most of our meals in the full kitchen. We ate our meals on the lanai, and actually spent most of our time out there. The other residents were friendly and pleasant. None of them were noisy or intrusive. Bo, the condo owner, was delightful: warm, friendly, helpful and informative. We learned a lot about the island from him, something that we really appreciated. Both couples were very satisfied with our bedrooms and private baths. The beds were very comfortable. The bathrooms separate the two bedrooms so there was plenty of privacy. We could not hear the downstairs TV at all if the other couple were watching it. All in all, this was the perfect place for us. We totally recommend it for those people who prefer peace and quiet, rather than the noise and frenetic activity that seems to abound in other parts of the island. We would love to return to Northern Lights.

Price per night from

$259

Coral Cottages: Two Oceanfront Villas with Infinity Pools in a Scuba Diver's

Old Man Bay house

6 bedrooms / 6 bathrooms / sleeps 12

Responds fast! avg. 3 hours 21 minutes

Price per night from

$698

Villa Spirit

Old Man Bay house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$442

Great rentals within 20 miles that match your search

Seascape - A Luxury Villa on Seven Mile Beach on Grand Cayman, Cayman Islands

Seven Mile Beach guest house

6 bedrooms / 5 bathrooms / sleeps 17

Price per night from

$3,529

Seaing Spotts Coral Bay Village Beachfront Rental Grand Cayman

Savannah condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$472

OCEANFRONT LUXURY RENTAL REGAL BEACH CLUB UNIT 121 CAYMAN ISLANDS

Seven Mile Beach condo

3 bedrooms / 3 bathrooms / sleeps 9

Price per night from

$590

Perfect Cosy 1 Bedroom, Beachfront

Seven Mile Beach apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$266

Cayman Reef Resort #33 - Personal Lanai Overlooking Beach & Ocean

Seven Mile Beach apartment

1 bedroom / 1 bathroom / sleeps 4

“Wonderful Stay, Beautiful Condo and Grounds, Easy to Work With” Condo is beautiful and exactly as described in the listing and in all communications with Marc. Very close to beach and water. Even closer than looks in pictures. Literally few steps out the door. Also close walk to great restaurants, stores and Camana Bay. Unit well equipped with towels, umbrella. Beach is gorgeous with beautiful turquoise warm water. Pool and grounds immaculate. Well maintained. Pretty landscaping. Enjoyed the screened porch with ceiling fan for morning coffee. Most gorgeous sunsets on the island right outside of the door. Marc was easy to work with ..... from the time of booking and throughout our stay. He touched base by email and phone upon our arrival to ensure we were doing ok. We would not hesitate to book again .... amazing experience.

Price per night from

$584

On the Beach -- As Good As It Gets

George Town house

5 bedrooms / 5 bathrooms / sleeps 10

Price per night from

$4,222

Morritt's Tortuga Club: 1-BR, Sleeps 4, Full Kitchen

East End condo

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 33 minutes

Price per night from

$207

Oceanview/Poolside Condo on Seven Mile Beach

George Town condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 8 minutes

Price per night from

$444

Heart of Seven Mile Beach

Seven Mile Beach apartment

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 1 hour 28 minutes

Price per night from

$473

4BR Seven Mile Beach - Boggy Sands Club - Parrot 1

West Bay apartment

4 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$1,181

Kaiku: Gated Estate w/Guesthouse, Private Pool, Heated Spa, and Private Dock

Rum Point house

7 bedrooms / 6 bathrooms / sleeps 15

Responds fast! avg. 3 hours 43 minutes

Price per night from

$2,188

SUMMER/FALL RATES DISCOUNTED!/OCEANFRONT VILLA ON PRIVATE SANDY BEACH!!

Rum Point villa

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 2 minutes

Price per night from

$237

Rum Point Retreat 17

Rum Point condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$337

Cayman Reef Resort 56 - Luxury on Seven Mile Beach

Seven Mile Beach apartment

3 bedrooms / 2 bathrooms / sleeps 7

“Fantastic Condo on a fantastic beach” This condo was more than we could have hoped for. Modern, new, clean and extremely well stocked with kitchen ware, towels and bed linens. Two screened in patios with a view of the sunset. A very clean pool just off the main balcony. Washer, dryer and dishwasher made this unit a very family friendly unit. My kids said that they thought the condo was better than home ! We plan on returning to grand cayman and when we do our first choice for lodging will be Cayman Reef Resort unit 56. Lastly, I can't imagine a more attentive landlord than Marc. His attention to detail and the comprehensive packets of information regarding the condo and Cayman in general wee invaluable. I felt like he was our personal concierge. He gave us advice on private tours, excursions and dining. We recommend this condo and Marc with 5 Stars.

Price per night from

$1,035

Sea Jewel, 2BR, 2BA, oceanview villa

West Bay villa

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$468

At home on Seven Mile Beach

Seven Mile Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$409

Grand Cayman Islands Ocean front Villa with 2 bedrooms and 2 baths

West Bay villa

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$456

Majestic Luxury Private Home On Seven Mile Beach

George Town villa

6 bedrooms / 5 bathrooms / sleeps 17

Price per night from

$3,198

4BR on the Pool at Boggy Sands Club, Seven Mile Beach.

West Bay condo

4 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$1,184

Hidden Gem at Grapetree Cove

East End cottage

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$237

Sea Breeze, a luxury SMB beachfront condo

Seven Mile Beach apartment

4 bedrooms / 5 bathrooms / sleeps 10

Price per night from

$2,961

Grand Cayman/Rum Point area, Beachfront Condo- sleeps 6 comfortably

Rum Point condo

2 bedrooms / 2 bathrooms / sleeps 7

Price per night from

$338

Sunset Cove 2 Bed/2Bath Condo on Seven Mile Beach with Discounted Boat Charters

Seven Mile Beach condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$297

Kaibo Phase 2 - A4, Grand Cayman

Rum Point apartment

2 bedrooms / 2 bathrooms / sleeps 4

“Perfect vacation” My husband and I spent a week in this condo and found it to be perfect for us. It is very clean with nice linen and a well equipped kitchen. The location is great for walking around Kaibo. It is on a sandy beach with a restaurant right next door. We will definitely return to this spot. The beach is not good for swimming but there is a pool and hot tub. There is a beach within walking distance that is good for swimming.

Responds fast! avg. 1 hour 3 minutes

Price per night from

$178

Ocean Views Long Sunsets 25 steps to water Ground Floor, pool outside front door

Seven Mile Beach apartment

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 1 hour 0 minutes

Price per night from

$355

Villa with Ocean Views and 200ft of PRIVATE Beach

East End house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$314

Right on Seven Mile Beach 3 Bed 2 Bath Condo Cayman Reef Resort #58 Grand Cayman

Seven Mile Beach condo

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 30 minutes

Price per night from

$474

GCAYMAN: Your Very Own Private Seven Mile Beach Area Tropical Blue Guest Home

Seven Mile Beach guest house

2 bedrooms / 2 bathrooms / sleeps 6

“Cayman Relaxed” What a great place. Away from the congestion of seven mile beach. Two good restaurants, beach and a grocery store within walking distance. We made good use of the two outdoor hammocks. Nicely appointed kitchen although we just used it for breakfast every day. Six minutes from the governor's beach. 20 minutes from Georgetown. We plan on coming back.

Price per night from

$231

Rum and Kai - TripAdvisor Rum Point Award Winner

Rum Point apartment

1 bedroom / 1 bathroom / sleeps 4

“Perfection on Rum Point” This was our second trip to The Retreat. This time, we were without kids, so we only needed a one-bedroom and Rum & Kai is the perfect choice. The unit is very spacious, and immaculately clean. It's perfect for two or a small family. We had everything we needed and then some. We especially enjoyed the massive movie hard drive! The reservation process was seamless as was communication. The Retreat complex is the island's best kept secret--perfect location, great beach, quiet, wonderful snorkeling, great amenities--the list goes on and on. We will definitely return! Thank you for a great stay.

Price per night from

$237

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rentals in Old Man Bay

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Top Destination reviews

Grand Cayman Northern Lights Beachfront Villa
PERFECT VACATION SPOT....exceeded all expectations!

Highly recommend! We were with our 2 sons, ages 10 and 12, and this condo had everything we could have asked for and more. The views were spectacular, snorkeling right off the dock was the best we found.....like dipping your face into a tropical fish bowl. Beach was clean and the dock was a great place to sit with a drink and watch the sunset. Condo was spacious, bright, clean and incredibly well stocked. No need to bring any towels, tons of beach towels too. Kitchen was great, already stocked with many of the staples (paper towels, soaps, sponges, coffee filters, trash bags, etc.) This was our first trip to Grand Cayman and we plan to return and stay here again, it was that great!see more
Cayman Sands: Secluded Beach Villa with Pool Atrium & Guest Cottage
Cayman Sands

My wife and I were searching for a house with 5 bedrooms to accommodate our family of 10. Jim and Didi were great to work with. They made excellent suggestions, and answered all of our questions. Cayman Sands suited us perfectly. The house and property was well maintained, spacious, and very clean. Midweek, someone came and cleaned the house, pool service came and cleaned the pool, and the beach service cleaned the beach. In each case, those who performed the services were professional and courteous. In short, the property met our expectations. The only issue that was a little disappointing was, we didn't feel comfortable snorkeling at the house due to the sea urchins and their spines, but on the website it plainly warns about the issues with the sea creatures. The only issue we had with the house while there was with the alarm, which started beeping in the middle of the night. This happened intermittently during the night. We contacted the property manager the next day, and the problem was corrected promptly when reported. Our experience on the island was nothing short of wonderful, each of us hated to leave. We snorkeled at Rum Point, Smith Cove, Eden Rock, Cemetery Reef on 7 Mile Beach, we went to Stingray City, Dolphin Discovery, the Turtle Farm, and the Botanical Garden, and we enjoyed each of these. We felt very safe in traveling over the island which is not the case in many of the islands, and all we met were very friendly and made every effort to make us comfortable. My wife, daughter, and I had been to Grand Cayman once before. My son and his wife have visited two times before, and I'm sure we would all love to visit again. We rented our 2 vans from Mrs. McCurley, and she was helpful with a number of suggestions. I would like to give a special thanks to Melissa Wolf of Better angle photography for coming to the house and taking our wonderful beach photos for us to relive our trip in the years to come. Thanks for a wonderful vacation, Bruce Lawsonsee more
Villa Caymanas: Caribbean Villa w/ Fabulous Snorkeling, Pool, & Panoramic
Dream Vacation

Recently stayed at Villa Caymanas this home was amazing, it allowed everyone to enjoy the privacy, space and flexibility that you need to experience the full range of all that Grand Cayman has to offer while staying in a spacious, immaculately maintained home. With your own fully stocked kitchen, dining room, private pool and outdoor living areas, the entire family can spread out with room to spare or gather together in the spacious great room and dining room. The home was beautifully decorated and the owners thought of everything for you so you can have a first class experience in Grand Cayman. You can kayak and snorkel just steps from your back door in glass bottom kayaks!! I will definitely plan a return trip to Cayman and will plan on staying at Villa Caymanas again.see more
Villa Spirit
Perfection on the Beach, Inside and Out

This villa is absolutely beautiful from the architecture, which makes you feel part of the outdoors even when inside, sliders open or not, to the gorgeous interior design. The villa is equipped with everything you would need and more. All appliances are top of the line and especially liked having the washer/dryer. You are on the beach and there is great snorkeling in your own backyard. Loved using the kayaks to scout the reefs. When you are tired of the ocean you can relax at the pool/grill deck which has beautiful ambient lighting at night. Very private on the North Side but close to Rum Point, Kaibo and the East End. Quaint and casual Over the Edge Restaurant is minutes away with homey menu, friendly staff and Sushi Sunday. A must is the Bioluminescent Boat Tour with Sweet Spot Watersports. The Concierge Service through Cayman Villas was very responsive and a shout out to the villa manager Mitzi. I could go on (the plush towels and linens, the bathroom out at the pool area, the water sprayer to rinse off sea and sand before hitting the pool deck) but I will end by saying that though the pictures of the Villa Esprit are great they don't do justice to this beach paradise.see more

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