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Old Man Bay Rentals

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269 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 5 minutes

Price per night from

$630

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

$326

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 5 minutes

Price per night from

$859

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 5 minutes

Price per night from

$516

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 5 minutes

Price per night from

$287

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 5 minutes

Price per night from

$487

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 5 minutes

Price per night from

$865

Villa Spirit

Old Man Bay house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$440

Great rentals within 20 miles that match your search

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

$229

Cayman Reef Resort #1 - Renovated Seven Mile Beach

Seven Mile Beach apartment

1 bedroom / 1 bathroom / sleeps 4

“Excellent 1BR on SMB” My wife and I just spent six night in this great one bedroom condo on SMB. It was our first stay in the Caymans. The unit was exactly as advertised. Ample towels were provided, including beach towels. The unit has a full kitchen, with every appliance that you could ever want. The screened in patio, which was great for dinners, also has a nice electronic grill that I used to cook a beautiful red snapper that I purchased from a local fisherman in downtown George Town. The bed was comfortable, the bathroom large, the hot water VERY hot and plentiful, and the AC worked very well. The unit is reasonably stylish, with several nice finishes throughout. The condo building has a mix of vacationers and residents. The pool isn't huge, but more than adequate if you want to take a quick dip. There is a tennis court in very good condition in front of the building. The private beach has several recliners and umbrellas. We never had to fight anyone for use of these, but that may be different during peak travel times. The location of the unit was IDEAL. The resort is on the beach, which is obviously a big plus. Additionally, there are TONS of great food options within a quick 5 minute walking radius. To quickly name a few, Chicken Chicken, Al La Kebab, and several restaurants at Camana Bay were all excellent. We rented a car, which we found useful to get to the grocery store several times. In hindsight, could we have done this by taking cabs or buses? Yes. But we liked the flexibility. The owners provided us with ample suggestions and guides to help make our first stay on island more pleasant. Marc was very responsive to emails and was on top of everything. All in all, the unit worked out great. We didn't spend a whole lot of time there, as we were out every day diving. But the time that we did spend there was very pleasant. We would certainly consider renting this unit again.

Price per night from

$565

Beachcomber on 7MB Corner #17 Ocnfnt near Ritz-Great Snorkeling and Sunsets!

Seven Mile Beach apartment

3 bedrooms / 3 bathrooms / sleeps 7

“Stunning Beachcomber Condo 17 with a stunning view of stunning Seven Mile Beach!” My family and I have travelled to Cayman during March break in the past because we could always count on the amazing weather. This year however, we chose to stay at The Beachcomber Unit 17 instead of a hotel. We were delighted in the upscale environment of condo 17 with its beautiful extended balcony, and we loved the wall of windows enabling us to view the gorgeous water wherever we looked. The view is spectacular, and because it is an end unit, very private too. This unit's third floor balcony is the best in the entire building. It's over sized outdoor area is awesome, and having the option to sit in an optional screened in area is also nice, but with this view, we always remained outside. The decor is fresh, and the building is very well maintained and current. It is spacious with three comfortable bedrooms and three clean ensuites as well. Having laundry within this unit was also a bonus, plus daily cleaning service too makes it even better. It is also an easy trip from the airport and also within walking distance to the grocery store, malls, excellent restaurants and even theatre. We have already booked for next year. We travel a lot, and this condo and luxuries it provides will ensure our return. You will not be disappointed and I would recommend Unit 17 to all of our family members and friends.

Price per night from

$847

Cayman Reef Resort #32 - Steps away from the Beach

Seven Mile Beach apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$679

4BR Pool View at Boggy Sands Club, Seven Mile Beach

Seven Mile Beach condo

4 bedrooms / 4 bathrooms / sleeps 10

“Heaven on Earth in Grand Cayman” The reviews and pictures don't begin to do this Boggy Sand Road property justice! We rented the ground floor unit,which was absolutely spotless, elegant, roomy, well-equipped and only a few steps to the most beautiful beach. The area is residential, private and quiet - like we had somehow privately rented Seven Mile Beach! The grounds of the property were garden-like and the pool was lovely and clean. Our rental car was nice to have but not necessary - there is a Foster's Market within a short walk of the condo, as well as a few great little restaurants (Alfresco's, Timbuctuu and Heritage Kitchen). The bus service is great - more like hailing a cab with pick-up right at the foot of the driveway. But back to the beach...the unit is equipped with 2 kayaks and a paddle board, which we enjoyed tremendously on the calm, crystal-clear waters. Cemetery Beach is right next door for some of the best snorkeling we had ever experienced. The Kittiwake Shipwreck is directly off shore for another fantastic snorkeling experience. We even enjoyed swimming with our own resident sea turtle every day! The condo unit itself was spacious and fully equipped with everything you need - beach towels, chairs, umbrella, rafts and cooler;fully-equipped, gorgeous kitchen with granite counter tops, beautiful and spacious bathrooms, and super-comfortable beds. Although our "kids" were 15, the unit would be wonderful for families with smaller children as well. I must say, the absolute best part, however, was our gracious host Morne, who made us feel like pampered family members visiting from out of town. He picked us up from the airport, made sure we had everything we needed, made great recommendations for activities and restaurants, was never intrusive but always available for anything we needed. I would (and will) vacation here again in a heartbeat, and make the highest recommendation to anyone to enjoy the vacation of a lifetime at this property! Just please don't take the week I want! ;)

Price per night from

$1,140

Cayman Conch Quest Beachfront Condo in Rum Point

Grand Cayman apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Great Condo to Rent” We would agree with all of the positive reviews for this condo. We stayed a week in early January. The condo is very comfortable; it is actually even nicer than the pictures. This condo is extremely clean and well maintained. The beds are very comfortable; there are plenty of beach towels, bath towels and linens. There is a TV ( gets all kinds of channels) stereo, Ipod docking; DVD player- more than you need. The artwork in the condo is very nice. The screened in lanai is great for meals and to just watch the ocean. The pool is clean. The complex is small and is kept immaculate by the management company. It was windy the week we were there so we were not able to swim/snorkel out front. Loved having the beach chairs,mats,bags and cooler to use. Bob replyed to all of my emails thoroughly and quickly. There is detailed information Bob emails to you and there are 2 notebooks of information at the condo. It is very quiet and peaceful. The drive is approx 40 minutes from the airport. Bob recommended Marshall's car rental and we found them to be great. This was our first trip to Grand Cayman. We would without a doubt recommend this condo.

Price per night from

$257

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

$999

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

$440

SMB Area Private Villa From $995/wk ($100/ nite*)

West Bay 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

$206

Luxury Home near Rum Point w/ Beachfront Pool, Spectacular Views, # 5 Yellow

North Side villa

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$684

Island Gem

West Bay apartment

2 bedrooms / 2 bathrooms / sleeps 5

“Villas Pappagallo - a real treasure!” My boyfriend and I stayed at Villas Pappagallo in April 2015 for 9 days. What a delight! After booking the apartment, we were supplied with more information by the owner that helped us prepare and plan for our vacation. Sandy greeted us upon arrival. She was happy to answer any questions we had and left us to settle in and explore. At first glance, we were pleasantly surprised by the accuracy of the photos. I have ended up in rental units that often times look spacious and clean from the photos and unfortunately were not. This was NOT the case with this unit. It was large, clean, and well-decorated. The beds were big, comfortable and fresh. The towels were clean and plentiful. The kitchen was better equipped than our own. We immediately felt at home in our “temporary home”! The unit was a treat, but the property at Villas Pappagallo was the real treasure. We were looking to relax and decompress – VP was just the place! We found ourselves fall into a routine early on. Waking up early to the sun peaking through the bedroom windows, breakfast on the balcony, trips down to the pool, and long walks down the beach. Some of the best snorkelling on the island is directly off the VP jetty – we saw plenty of fun sea creatures. In the evenings, we found ourselves back on the balcony with a drink in hand. It was a level of relaxation we had never experienced! When we did decide to travel outside of the property, we were pleased to see that this wasn’t a cliché Caribbean Island. The locals are genuine and you won’t be harrassed while walking down the beach. We took trips to the Turtle Farm and Cracked Conch, Seven Mile Beach, Cemetery Beach and the East End. We felt comfortable everywhere we went and the island was easy to navigate by car. A must do is Stingray City. What majestic creatures! While we ate many meals at home, we did venture out to a couple meals during our stay. We ate Chicken Chicken for take-out, and dined out at Ristorante Pappagallo, Calypso Grill and Cimboco. All fantastic meals! The restaurants on the island provide something for everyone. Overall our experience was unforgettable! Lee has put a lot of thought, effort and care into making this place a home. She was responsive and her advice was extremely valuable. We hope that we have a chance to return to Villas Pappagallo in the near future and we will definitely recommend to all friends and family! Thank you Lee!

Price per night from

$485

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

Rum Point villa

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 17 minutes

Price per night from

$229

Cayman Beachfront at 22 Villas Pappagallo

West Bay apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$257

3 bed 3 bath beachfront penthouse with huge decks, pool & tennis

Bodden Town apartment

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 2 hours 32 minutes

Price per night from

$485

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

$565

Sea Breeze, a luxury SMB beachfront condo

Seven Mile Beach apartment

4 bedrooms / 5 bathrooms / sleeps 10

Price per night from

$3,424

Seven Mile Beach Ground Floor Unit Great Location

Seven Mile Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$269

Luxury Home near Rum Point w/ Beachfront Pool, Spectacular Views, # 4 Green

North Side villa

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$684

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

West Bay condo

4 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$1,140

Luxury Home near Rum Point w/ Beachfront Pool, Spectacular Views, # 1 Cream

North Side house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$524

Ocean Paradise # 5 Yellow - Affordable Luxury Home w/ pool

Rum Point villa

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$684

Sea Breeze 5 luxury 4 bedroom on SMB

Seven Mile Beach condo

4 bedrooms / 5 bathrooms / sleeps 10

Price per night from

$1,695

RUM POINT -Ocean Front Villa

Rum Point house

3 bedrooms / 2 bathrooms / sleeps 7

Price per night from

$343

Crescent Beach (Sky) at Half Moon Bay

East End apartment

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$343

Luxury Condo #1 on Boggy Sand Road-Garden Level

Seven Mile Beach apartment

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$571

Cayman Reef Resort

Seven Mile Beach condo

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$401

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

Rum Point condo

2 bedrooms / 2 bathrooms / sleeps 7

Price per night from

$343

Majestic Luxury Private Home On Seven Mile Beach

George Town villa

6 bedrooms / 5 bathrooms / sleeps 17

Price per night from

$4,573

Coconut Cottage

Bodden Town cottage

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$572

Rum Point Retreat 17

Rum Point condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$326

Viewing 38 of 269
rentals in Old Man Bay

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Top Destination reviews

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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