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Villas Cayman Islands

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60 villas

3 Bedroom Plus Den Beach Front Home in West Bay - Sleeps 10!

West Bay villa

3 bedrooms / 3 bathrooms / sleeps 10

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$1,489

“Everything about this place is first class!” 3 King Bed Beachfront Villa

Cayman Brac villa

3 bedrooms / 5 bathrooms / sleeps 8

Responds fast! avg. 31 minutes

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$403

Beautiful Sea Dreams Villa

Cayman Brac villa

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 hours 8 minutes

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$206

Gorgeous Beachfront Villa, Azure Breeze #5

North Side villa

3 bedrooms / 2 bathrooms / sleeps 6

“What We Were Hoping It Would Be” No, really, we were hoping there would be oregano -- there was. We were hoping the knives would be sharp and that the dishwasher really washed dishes -- yup. We were hoping you really could snorkel out the back door and see fish you've only seen on TV and in aquariums -- absolutely. What we couldn't have hoped: that the cable would be wonky, I'd send an email, and ten minutes later the owner would call me personally to walk me through fixing it. That on a day too windy to go in the water, there would be so many things to do on the island (turtles, hikes, eating and eating and eating) that we wouldn't even care. Hopes exceeded. Such a great place to stay. Such a great owner. Clearly this is not a money-making investment. This is their second home that they let a few other lucky people use. I hope they rent this property as much as they can but always save some time for us.

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$444

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

Rum Point villa

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 52 minutes

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$227

Lovely 'Sea Dreams Villa' w/ Private Beach & Deck!

West End villa

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 46 minutes

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$167

Queen Room + Bath (Hibiscus Room)

George Town villa

1 bedroom / 1 bathroom / sleeps 2

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$155

Palm Heights Residents #5

Camana Bay villa

3 bedrooms / 3 bathrooms / sleeps 6

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$260

Morning Glory

Savannah villa

7 bedrooms / 6 bathrooms / sleeps 14

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Price per night from

$1,450

Lime Tree Villa

Camana Bay villa

4 bedrooms / 3 bathrooms / sleeps 10

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$595

6 Bedroom Dramatic Oceanfront Estate with Private Beach

Breakers villa

6 bedrooms / 6 bathrooms / sleeps 16

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$2,729

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

West Bay villa

2 bedrooms / 2 bathrooms / sleeps 6

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$503

Addison & Lee Cayman Villa

George Town villa

6 bedrooms / 6 bathrooms / sleeps 14

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$1,203

Sea Magic

North Side villa

2 bedrooms / 2 bathrooms / sleeps 7

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$335

6-Bedroom Beachfront w/ 150' Pool, 2 Hot Tubs and 2 Fire Pit

George Town villa

6 bedrooms / 6 bathrooms / sleeps 16

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$3,359

Ultra-Cool 6-Bedroom Beachfront Mansion in Rum Point

Rum Point villa

5 bedrooms / 5 bathrooms / sleeps 18

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Price per night from

$2,729

Present Moment

Bodden Town villa

4 bedrooms / 4 bathrooms / sleeps 12

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Price per night from

$755

4-Bedroom Private, Modern Family Bungalow on Seven Mile

West Bay villa

5 bedrooms / 3 bathrooms / sleeps 12

“Private & Well Maintained” This is the second time we've rented Serenity Now, so that speaks for itself. We travel with another family, so there are four children under age eight between us. The house is extremely kid-friendly, especially the pool, sandy area to play, spacious kitchen and safety measures that have been taken throughout the house. The house is located at the end of Seven Mile Beach, which provides privacy and quiet. Yet, you are still conveniently close to a grocery store and several tourist attractions. The on-island contact, Sonya, is easily accessible, as she lives down the street. She was nice and attentive to us throughout our stay. The house is bright and comfortable. There is plenty of seating both inside and on the patio if you like to enjoy a few meals while you're there. We were pleasantly surprised at the addition of a new grill, fridge and cabinet area on the patio. It was fabulous! We only had a couple small frustrations...the ocean has encroached upon the small walk path along the sea wall that existed the last time we stayed, so it's impossible to get down to the beach from the back patio stairs. You have to walk a few hundred feet down the street to get beach access. Also, there is a new structure that is being built next to the house on the pool side. It obstructs the views we enjoyed last time we visited. By no means did these minor things ruin our week. It's heavenly to wake up to the sound of waves in the morning in a home that only enhances the paradise of Grand Cayman.

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$1,489

Serenity Sands

Bodden Town villa

2 bedrooms / 2 bathrooms / sleeps 4

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$285

Caribbean Paradise 9

George Town villa

3 bedrooms / 3 bathrooms / sleeps 6

“Beautiful location and comfortable accomodations” We usually stay at a timeshare on Seven Mile Beach, but this villa on the South Sound was so much more private and intimate. The villa is a comfortable three bedroom, three bath - two of the bedrooms have king beds, which is hard to find! The kitchen is well furnished. The back deck that looks onto the ocean was our favorite spot! The property manager, Bernie, was quite helpful and accessible. We won't be staying at a timeshare ever again when we come to the island! We plan on staying at this villa!!!

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$395

Coral Reef

Seven Mile Beach villa

7 bedrooms / 7 bathrooms / sleeps 25

“This beautiful home has everything you need!” We had a blast staying at Coral Reef. There were 6 adults and 2 kids (ages 9 & 13). There was plenty of room for hanging out, eating breakfast, playing games, swimming and playing on the beach. We never felt crowded or on top of each other. Truly appreciated the kayaks, paddle boards, wake boards and snorkeling gear that was right on site available to use. Didn't have to walk or drive anywhere to do activities - just dragged something out to the water and got going. Also was thankful a washer/dryer was there. The kitchen is stocked - don't worry about bringing spices or basics. The water is a little rough to enter due to the shells but once you get in it is wonderful. The house is just a short walk (5 min) up the beach to the Tiki Bar, a place known on the island for their jerk chicken and rum punch. Would love to return again soon.

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$2,860

3-Bedroom Luxury Villa on a Spectacular Cove Beach

George Town villa

3 bedrooms / 4 bathrooms / sleeps 6

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$1,339

Villa Bellagio

North Side villa

5 bedrooms / 5 bathrooms / sleeps 12

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$675

Little Cayman Escape

South Town villa

3 bedrooms / 2 bathrooms / sleeps 8

“Secluded” Great place to stay for seclusion. Went with 2 families of four with kids 8 to 11. Snorkeling and fishing good from shore. Can only enter water with water shows. Could use some outdoor lounge chairs, but house was great and clean.

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$285

Elegant, Coastal 7-Bedroom Estate w/ Private Beach

Rum Point villa

7 bedrooms / 9 bathrooms / sleeps 18

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$3,359

Queen Room + Bath (Bluebell Room)

George Town villa

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 2 hours 48 minutes

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$155

Morritt's Tortuga Club: 2-Bedrooms, 2 Baths, Sleeps 6, Full Kitchen

East End villa

2 bedrooms / 2 bathrooms / sleeps 6

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$489

Queen Suite (Daffodil Room )

George Town villa

1 bedroom / 1 bathroom / sleeps 4

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$212

Henry's Hideout

North Side villa

3 bedrooms / 2 bathrooms / sleeps 6

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$425

Morris Tortuga One bedroom

East End villa

1 bedroom / 1 bathroom / sleeps 4

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$196

Sprat Bay Luxury Villa

George Town villa

6 bedrooms / 6 bathrooms / sleeps 22

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Price per night from

$1,609

Luxury 4 Bed 4 Bath, Golf View, 5100+sf Villa, Seven Mile Beach Corridor, Cayman

Seven Mile Beach villa

4 bedrooms / 4 bathrooms / sleeps 8

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$1,960

Turtle House

Breakers villa

3 bedrooms / 3 bathrooms / sleeps 6

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$400

Castaway by the Sea - Cottage

Bodden Town villa

1 bedroom / 1 bathroom / sleeps 2

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$228

Kirk Kove

North Side villa

2 bedrooms / 2 bathrooms / sleeps 6

“Wonderful stay on the cove” My wife and I and two children (ages 20 and 15) enjoyed a stay-cation at Kirk Kove. The villa was clean and well appointed with a large sandy beach with volleyball net, an enormous cabana with BBQ, and a boat dock. Despite initial problem with the WiFi not working (resolved after the technician finally turned up), and a few rusty door hinges, we had a glorious time enjoying early morning beach strolls, swims, (rented) paddle boarding and kayaking. We used our car to drive to restaurants at North Side and East End and our boat for trips to Hurley's for shopping and the sandbar for swims with the stingrays and the reef for snorkeling. All in all a wonderful relaxing get-away.

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$225

Queen Suite Deluxe + Kitchen (Marigold Room)

George Town villa

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 2 hours 48 minutes

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$212

Pease Bay House: Luxury Beachfront Estate w/ Infinity Pool & Private Tennis

Bodden Town villa

6 bedrooms / 6 bathrooms / sleeps 12

Responds fast! avg. 2 hours 58 minutes

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Price per night from

$1,712

Maridadi

George Town villa

4 bedrooms / 3 bathrooms / sleeps 10

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Price per night from

$475

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