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Grand Cayman Rentals with Pools

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Grand Cayman Rentals with Pools

266 vacation rentals

Three Little Birds -2BR+ Villa, Private Beach

Rum Point house

2 bedrooms / 2 bathrooms / sleeps 6

“Gorgeous, peaceful- perfect island setting!” We rarely saw any other guests while staying at Three Little Birds. The place is well appointed, clean, comfortable, with a fully stocked kitchen; lovely sitting room overlooking the little beach. Swimming

Price per night from

$573

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2 BR MoonLight Kai condo at Kaibo Yacht Club, ph.2

Rum Point apartment

2 bedrooms / 2 bathrooms / sleeps 4

“Perfect in every way!” Hubby and I just returned from our 2 week stay in the Moonlight Kai condo. We had no concerns at all after reading all the wonderful reviews. The condo is and has almost everything listed (I'll explain further in my review) and

Price per night from

$207

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Cayman Islands Divers Paradise 1st Floor Oceanfront Condo

Seven Mile Beach condo

2 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 58 minutes

Price per night from

$184

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SMB-Grand 32, renovated 2Bd/2Bath,

Seven Mile Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 16 minutes

Price per night from

$175

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3 Bed Condo with Huge Patio on Seven Mile Beach

Seven Mile Beach apartment

3 bedrooms / 2 bathrooms / sleeps 6

“Excellent Condo With Very Attentive Owner” This is an excellent condo with wonderful view and large terrace. Its spacious and well worth the climb of three stairs. The apartment was probably the best equipped rental we have EVER stayed in (and we have

Responds fast! avg. 1 hour 51 minutes

Price per night from

$369

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Laguna del Mar: Prime Seven Mile Beach location ground floor beachfront

Seven Mile Beach condo

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 50 minutes

Price per night from

$674

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Fishbones by Grand Cayman Villas and Condos

Gun Bay house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$687

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Beachfront Cayman Island Condo on 7 mile beach

Seven Mile Beach apartment

3 bedrooms / 2 bathrooms / sleeps 7

“A DREAM COME TRUE” We are the type of people who always look for affordable alternatives to the fancy hotels and the condo we rented from Anandi was just what we needed. Comfortably spacious and well stocked, No 329 Sunset Cove became our home from

Price per night from

$420

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'Sun Cloud' Oceanfront Villa in Rum Point!

Rum Point house

5 bedrooms / 5 bathrooms / sleeps 10

“Perfect Sunrises & Sunsets” Our second trip to the island, however this property made it a remarkable stay. A perfect location, tranquil, close to a small store, 4 minutes drive to Rum point and Cayman Kai. The house is beautiful, a view from every

Responds fast! avg. 41 minutes

Price per night from

$831

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Cayman Beachfront at 22 Villas Pappagallo

West Bay apartment

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$247

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2 BR condo on Seven Mile Beach with ocean views

Seven Mile Beach condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$315

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Coconut Beach by Grand Cayman Villas and Condos

Rum Point house

5 bedrooms / 5 bathrooms / sleeps 12

Price per night from

$1,140

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"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

Responds fast! avg. 2 hours 48 minutes

Price per night from

$258

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Amazing beach villa, with free electric car to explore the island

West Bay villa

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$1,144

1 / 48

Beach or Pool

East End villa

3 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$366

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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. 59 minutes

Price per night from

$326

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Oceanview/Poolside Condo on Seven Mile Beach

George Town condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 16 minutes

Price per night from

$229

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Christmas Palms by Grand Cayman Villas and Condos

Old Man Bay house

4 bedrooms / 4 bathrooms / sleeps 10

“Wedding Week Stay” In a rare occurrence these days, Christmas Palms actually exists as it is portrayed in both photos and video. Everything aspect of our rental was as we hoped for and expected and would have no reservation in staying there again. T

Price per night from

$802

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Two Rainbows by Grand Cayman Villas and Condos

Rum Point house

5 bedrooms / 4 bathrooms / sleeps 10

“Two Rainbows is a peaceful, secluded and affordable villa perfec” Our stay at Two Rainbows was our fourth visit to Grand Cayman. Check-in was absolutely painless. We had great instructions and were able to walk right in a get settled in a matter of

Price per night from

$1,260

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Sea-Esta Beach Front Kaibo Condo

Rum Point apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$206

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Kai Kotch, #17 Island Houses of Cayman Kai, Rum Pt

North Side apartment

2 bedrooms / 3 bathrooms / sleeps 6

“Tranquility” Traveled to Grand Cayman with a couple girlfriends and chose Kai Kotch based on reviews here and was not disappointed! We wanted a peaceful vacation and that's exactly what we got. Kai Kotch #17 was spacious and clean and we really enjoye

Price per night from

$275

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Cayman Stead, 2 BR, 2 bath,BEACH condo,sleeps 6

North Side apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Perfect paradise” This was perfect for my family of 2 teenage girls, my wife and I. We wanted the hot Caribbean vacation without the resort. We dove and explored everyday. This condo had everything we needed, pool, right on the sea, internet, full kit

Responds fast! avg. 3 hours 51 minutes

Price per night from

$286

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Surfers Paradise Oceanfront on the "New Seven Mile Beach"...come and relax !

George Town guest house

5 bedrooms / 5 bathrooms / sleeps 10

Responds fast! avg. 3 hours 55 minutes

Price per night from

$1,374

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Ocean Pearl Beachfront Townhome Vacation Rental

North Side house

2 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$286

1 / 27

Just For Fun by Grand Cayman Villas and Condos

Rum Point house

3 bedrooms / 2 bathrooms / sleeps 6

“Great Cayman Experience!!” We just finished our 1-week vacation at Just For Fun. The cute cottage certainly lived up to our expectations. Our family cooks three meals a day at home. The kitchen and new grilling area work perfectly. The kitchen has lot

Price per night from

$630

1 / 24

Starboard Kai Beachfront Home Rum Point Cayman Kai

Rum Point house

2 bedrooms / 3 bathrooms / sleeps 6

“Paradise Found” This was our first time to Grand Cayman Island. We were very excited to go as a family for the first time to the Caribbean. We usually like to vacation at destinations that are not too “touristy” so we decided to stay away from the

Responds fast! avg. 3 hours 21 minutes

Price per night from

$315

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Coral Kai by Grand Cayman Villas and Condos

Rum Point house

5 bedrooms / 5 bathrooms / sleeps 10

“Wonderful Spring Break for 2 families” Outside deck was perfect place to relax, great lounge furniture, plenty of space, perfect size pool for kids, large beach area, sea weed visible but not an issue its the ocean there's always going to be some, but

Price per night from

$1,260

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Direct Beachfront Condo,quiet,with pool and tennis

George Town apartment

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 3 hours 11 minutes

Price per night from

$228

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Sea Breeze, a luxury SMB beachfront condo

Seven Mile Beach apartment

4 bedrooms / 5 bathrooms / sleeps 10

Price per night from

$1,031

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Palm Heights Residents #5

Camana Bay villa

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$260

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Kai Conut by Grand Cayman Villas and Condos

Rum Point house

5 bedrooms / 3 bathrooms / sleeps 12

“picture postcard sand beach and beautiful blue waters with soft” Twelve persons arrived at the Kai Conut villa and it was ready for relaxed living.Weather was tropical rainy but did not keep us down. Used the time to tour the island and went to Turtl

Price per night from

$974

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Kai Vista by Grand Cayman Villas and Condos

Rum Point house

4 bedrooms / 4 bathrooms / sleeps 9

“The best vacation I have ever had!” We had the most fantastic vacation ever. Kai Vista has it all - a beautiful and very spacious villa that accomodates your every need and is so family friendly. It is perfectly designed for comfort, relaxation and en

Price per night from

$1,140

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CoCoCondo - Your Home Away from Home in the Caribbean

West Bay apartment

3 bedrooms / 4 bathrooms / sleeps 6

“Great Place To Stay” The condo has everything we need. We are a family of six with two grown children and smaller children as well. This condo is nicely decorated and clean. The pool is just outside the patio which is so convenient especially with sm

Responds fast! avg. 49 minutes

Price per night from

$344

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Heritage House by Grand Cayman Villas and Condos

Rum Point house

4 bedrooms / 4 bathrooms / sleeps 10

“Wow! What a great time” We had the pleasure of staying at the Heritage House for a week at the end of april/beginning of May. The house is not centrally located to the the main part of the island, it is beautifully secluded on the North End of the is

Price per night from

$813

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Villa Caymanas by Grand Cayman Villas and Condos

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 y

Price per night from

$813

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Cayman Sunset, Coconut Bay Oceanfront 3BR near SMB

West Bay apartment

3 bedrooms / 4 bathrooms / sleeps 7

“A wonderful place to stay” We had three generations staying in Cayman Sunset including grandparents and two teenagers for 8 days, It was a great location, with wonderful snorkeling just steps from the patio. Duncan next door was most helpful, and we h

Price per night from

$344

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Ocean Kai by Grand Cayman Villas and Condos

Rum Point house

5 bedrooms / 5 bathrooms / sleeps 10

Price per night from

$1,432

1 / 28

Fantasea by Grand Cayman Villas and Condos

Rum Point house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$539

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