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North Side Rentals with Pools

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187 Houses in North Side with pools

Babylon Reef: Recently Renovated Villa with Backyard Snorkeling and a Crystal

North Side house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 5 minutes

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Price per night from

$602

Conched Out: Island Chic Bungalow w/ Lush Tropical Landscaping,Pool & Backyard

North Side house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 hours 5 minutes

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Price per night from

$315

Kaibo Yacht Club # 29C

North Side apartment

2 bedrooms / 2 bathrooms / sleeps 4

“Great quiet location and beautiful sunsets.” Great quiet location. Very well maintained buildings and grounds. Wonderful pool and beach area, perfect for young children or adults that want a nice quiet getaway... Would go and rent again !!

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$250

Villa Emmanuel

North Side villa

5 bedrooms / 4 bathrooms / sleeps 10

“A fabulous week at Villa Emmanuel” Two families (4 adults 4 children ages 2-8) just returned from a wonderful week at Villa Emmanuel. The house was spacious with a nice pool and sandy beach area. There were some jelly fish and/or sea anemones that were stinging so beware. We tried to stay only on the sandy patch except when snorkeling. Snorkeling from the house we saw lobsters and a lion fish. The majority of homes on the inlet had their hurricane shutters up so we enjoyed privacy & tranquility. The kitchen has everything you need to prepare meals and the pool had rafts and toys. Additionally, there were some beach toys at the beach area. The views from the home are spectacular and the sunsets beautiful. Since it's a rental some of the furnishings are a bit worn, as are the pool and beach chairs but this didn't prevent us from having a wonderful time. The huge screened in porch is terrific and the upstairs master suite is amazing. Highly recommend this home and hope to get back soon!

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Price per night from

$995

Villa La Playa

North Side villa

4 bedrooms / 4 bathrooms / sleeps 9

“Perfect Paradise= La Playa” The perfect place for a family. An open floor plan made life easy to multitask and relax. Management was very responsive. We needed a coffee pot and before we could blink- we had a new machine. We wish we could have remained forever.

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Price per night from

$675

Mahogany Point 2

North Side townhouse

3 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$350

Sea Magic

North Side villa

2 bedrooms / 2 bathrooms / sleeps 7

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Price per night from

$450

Luxury Home near Rum Point w/ Beachfront Pool, Spectacular Views, # 2 Peach

North Side villa

3 bedrooms / 3 bathrooms / sleeps 8

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Price per night from

$526

Villa Bellagio

North Side villa

5 bedrooms / 5 bathrooms / sleeps 12

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Price per night from

$850

"A Mid-Winter Night's Dream" Grand Cayman Oceanfront, Quiet, Secluded, Rum Point

North Side apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Loved it” We loved the Rum Point area. The condo was clean. Pool area was clean. We enjoyed the area enough for us to do. When we wanted to do more drove 45 minutes to Seven Mile Beach. Just a great location

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Price per night from

$252

The Pools #10

North Side apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Celebrating 40th Birthday and 1st Anniverssary” Everything was very relaxing. We enjoyed ourselves. The pool was clean and so were the rooms. Would suggest a bit of an update on the furniture and window shading in the room on the bottom floor. But besides that everything was very nice.

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Price per night from

$260

Beach Plum Villa

North Side villa

4 bedrooms / 4 bathrooms / sleeps 8

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Price per night from

$595

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

North Side villa

3 bedrooms / 3 bathrooms / sleeps 8

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Price per night from

$686

Oceanfront Ground Floor 2 bedroom 2 bathroom sleeps 4-6

North Side condo

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$457

Luxury Home near Rum Point w/ Beachfront Pool, Spectacular Views, # 3 Blue

North Side villa

3 bedrooms / 3 bathrooms / sleeps 8

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Price per night from

$526

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

North Side villa

3 bedrooms / 3 bathrooms / sleeps 8

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Price per night from

$686

Kaibo Yacht Club #9C

North Side apartment

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$245

Great rentals within 20 miles that match your search

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!

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Price per night from

$487

Condo on 7 Mile Beach - Great Location - Ground Fl

Seven Mile Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$201

Cayman Beachfront at 22 Villas Pappagallo

West Bay apartment

1 bedroom / 1 bathroom / sleeps 4

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Price per night from

$258

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 27 minutes

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Price per night from

$487

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.

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Price per night from

$567

Sea Breeze, a luxury SMB beachfront condo

Seven Mile Beach apartment

4 bedrooms / 5 bathrooms / sleeps 10

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Price per night from

$3,435

Seven Mile Beach Ground Floor Unit Great Location

Seven Mile Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$516

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

West Bay condo

4 bedrooms / 4 bathrooms / sleeps 10

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Price per night from

$1,144

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

Rum Point villa

3 bedrooms / 3 bathrooms / sleeps 8

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Price per night from

$686

Sea Breeze 5 luxury 4 bedroom on SMB

Seven Mile Beach condo

4 bedrooms / 5 bathrooms / sleeps 10

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Price per night from

$1,700

2bed (1queen, 2 twin), 2bath, beach, tennis & pool

Bodden Town condo

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 2 hours 27 minutes

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Price per night from

$172

Beach condo with sunset view

Seven Mile Beach condo

2 bedrooms / 2 bathrooms / sleeps 6

“Grand Cayman paradise” Four of us stayed at Bill's place it was a beautiful condo with amazing views and the island had the best snorkeling we have ever seen. We've decided to be back there within the next two years it's a vacation you wouldn't forget !

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Price per night from

$315

Crescent Beach (Sky) at Half Moon Bay

East End apartment

3 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$373

Crescent Beach (Sand) at Half Moon Bay

East End apartment

3 bedrooms / 3 bathrooms / sleeps 7

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Price per night from

$315

SMB-Grand 32. Beachside condo with pool. Remote work from Paradise.

Seven Mile Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 1 minutes

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Price per night from

$201

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.

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Price per night from

$567

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.

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Price per night from

$1,050

First Floor Oceanfront Condo in Top Location!

West Bay apartment

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$344

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.

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Price per night from

$229

Cayman Reef Resort #32 - Steps away from the Beach

Seven Mile Beach apartment

1 bedroom / 1 bathroom / sleeps 4

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Price per night from

$682

4BR Penthouse Boggy Sands Club - Seven Mile Beach

Seven Mile Beach condo

4 bedrooms / 4 bathrooms / sleeps 10

“Best Family Vacation Ever!” We came to Grand Cayman to scuba dive as a family. Our condo was a wonderful place to relax after our dive trips because of its proximity to the beach and the pool. Boggy Sands Beach Club is within walking distance of some great local food. Heritage Kitchen, ALFresco, and Calico Bar. The owner Morne Botes was attentive to all of our needs and great to work with. We highly recommend this place and hope to return very soon.

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Price per night from

$1,144

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