Cayman Islands Vacation Rentals & Condos - 99 Rentals Available

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Little Cayman Condo
3 BR / 3 BA / Sleeps 6 3 6 No min stay
Condo / 3 Bedrooms / Sleeps 6
3 bedrooms 3 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
"We stayed at this idyllic beach cottage in Little Cayman. With two separate cottages there was enough room and privacy for all of us (4 adults). You stepped out every morning on to your own private beach. Walking distance from all amenities. Quiet,..."
- Tracie Watler, Grand Cayman, Cayman Islands
(2) Excellent (2 reviews)
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Seven Mile Beach Condo
4 BR / 4.5 BA / Sleeps 10 4 10 Min stay varies
Condo / 4 Bedrooms / Sleeps 10
4 bedrooms 4.5 bathrooms Sleeps 10
High Speed Internet • Dishwasher • Microwave
"This was our fourth time to the island. We travelled with 4 other couples. This was one of the few places we could find where we could all stay together. This condo was beyond perfect for our group. Every detail of the condo was perfect. We enjoyed having..."
- Whitney Edwards Hokett, Oklahoma City, OK
(6) Excellent (6 reviews)
1 / 100

Rum Point Villa
3 BR / 3.5 BA / Sleeps 6 3 6 3 night min stay
Villa / 3 Bedrooms / Sleeps 6
3 bedrooms 3.5 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
"My family rented 2 condos at Rum Point Retreat and both condos were very nice. The Point is great for both sunrise and sunset and the beach is lovely, especially if you walk out to your left. If you stay close to the water you can walk in front of some..."
- Karin Clarke, London, Ontario
(1) Excellent (1 review)
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Rum Point Condo
2 BR / 2 BA / Sleeps 4 2 4 Min stay varies
Condo / 2 Bedrooms / Sleeps 4
2 bedrooms 2 bathrooms Sleeps 4
High Speed Internet • Dishwasher • Microwave
"The title says it all. A wonderful 3 week stay in this condo. The condo is very clean and has everything you need for a self- catering holiday. The location is a bit remote but well worth it. Beautiful views and a very quiet part of the island. Beautiful..."
- Laurie Clayton, Walla Walla, WA
(1) Excellent (1 review)
1 / 41

George Town Villa
6 BR / 5 BA / Sleeps 17 6 17 Min stay varies
Villa / 6 Bedrooms / Sleeps 17
6 bedrooms 5 bathrooms Sleeps 17
High Speed Internet • Dishwasher • Microwave
"Seascape is everything a big group could want. An absolutely beautiful house, right on Seven Mile Beach. Yuri, the on site manager, is wonderful. You can walk to a beach bar, and some of the most wonderful restaurants are also within walking distance...."
- Mary Grilliot, Suburban Dayton Ohio
(1) Excellent (1 review)
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Rum Point Apartment
1 BR / 1 BA / Sleeps 5 1 5 4 night min stay
Apartment / 1 Bedroom / Sleeps 5
1 bedrooms 1 bathroom Sleeps 5
High Speed Internet • Dishwasher • Microwave
"Mi Casa, Su Casa does exactly what it says on the tin! This beautiful Caribbean hideaway has captured the perfect balance between the stunning tropical picture perfect location, luxurious accommodation and vacation activities. We loved this intimate..."
- Anna Keating, Ireland
(1) Excellent (1 review)
1 / 7

North East Bay Cottage
1 BR / 1 BA / Sleeps 3 1 3 Min stay varies
Cottage / 1 Bedroom / Sleeps 3
1 bedrooms 1 bathroom Sleeps 3
High Speed Internet • Dishwasher • Microwave
"We truly loved our vacation at this wonderful destination. Everything was perfect. My absolute favorite part was listing to the waves at night while going to sleep and feeling the soft sea breeze flow through our beautiful cottage. The mornings I ..."
- Jodi Magrum, Bloomington, Minnesnowta
(1) Excellent (1 review)
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Seven Mile Beach Condo
3 BR / 2 BA / Sleeps 8 3 8 5 night min stay
Condo / 3 Bedrooms / Sleeps 8
3 bedrooms 2 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
"We recently spent the week of New Years at Coconut Bay in this condo and had a great time. It was all we could ask for. Clean, lots of dishes and pots and pans and plenty of beach towels for our many visits to the beach. We were out and about each..."
- Belinda Rude, Kearney, NE
(2) Excellent (2 reviews)
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Seven Mile Beach Condo
2 BR / 2.5 BA / Sleeps 4 2 4 Min stay varies
Condo / 2 Bedrooms / Sleeps 4
2 bedrooms 2.5 bathrooms Sleeps 4
High Speed Internet • Dishwasher • Microwave
"Harbor Heights #6 was great for our January getaway. Updated, clean, well- equipped and the great property location added to the enjoyment of Cayman! The kitchen was so great that we cooked in all but one night! The owners considered all needs ..."
- Amy Rhew Keeter, Greensboro, NC
(1) Excellent (1 review)
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About Cayman Islands

Calm blue waters, white sand, and swaying palm trees are the hallmarks of the Cayman Islands. Located south of Cuba and west of Jamaica, the Caymans are becoming the place to vacation in the Caribbean. Cayman Islands vacation rentals are perfect for families who want the comforts of home as they explore this island paradise. The Cayman Islands have so much beauty and adventure to offer its visitors, and this destination can’t be missed.


The Caymans enjoy a tropical marine climate. Temperatures hold steady around 80 degrees Fahrenheit during the summer and hover around 70 degrees in the winter. Summer is the wet season for the Cayman Islands, and it lasts from May to October. Winters are relatively dry and cool by island standards. The best time to visit the Cayman Islands is between May and June when temperatures are at their best and the weather is calm and clear.

Areas within the Cayman Islands

The Caymans consist of three islands: Grand Cayman, Cayman Brac, and Little Cayman. Grand Cayman is the largest of the three islands. Historic George Town offers fine dining and duty-free shopping among traditional Caribbean-style buildings. Cayman Brac has the most spectacular landscape of the three islands. Book Cayman Island vacation rentals with wonderful views of the limestone outcropping, or “brac,” in the center of the island which gives Cayman Brac its name. Little Cayman is smaller and less developed than its sisters but is world famous for scuba diving and has more than 50 unique dive sights.

Things to Do

The Cayman Islands are a playground for seaside activities and entertainment. On Grand Cayman, enjoy the white sands and crystal waters of Seven Mile Beach, voted one of the world’s ultimate beaches. When you’re not cooling off in the water or strolling along the sand at Seven Mile Beach, you can get up close and personal with the local wildlife at Stingray City and interact year-round with the friendly southern stingray here. Offshore, scuba dive through the warm, cerulean waters, explore man-made reefs like the USS Kittiwake. Visit the South Hole Sound Lagoon or dive at Bloody Bay Wall Marine Park on Little Cayman to see the brilliant underwater landscape.

Away from the sandy beaches, visit the imposing, three-story Pedro St. James Castle in Savannah, learn about the maritime past of the Cayman Islands at East End Lighthouse Park and discover the history of the Cayman Islands at the National Museum. Take the kids to Booby Pond Nature Reserve on Little Cayman, and see red-footed boobies at the largest colony in the Western Hemisphere. Birdwatching is popular on Cayman Brac where visitors can catch a glimpse of more than 200 species that call the island home.

Food & Dining

The cuisine of the Cayman Island is a mix of Jamaican, British, and native culinary traditions often supplemented with international flair. Local dishes contain native fruits, such as coconuts, plantains, breadfruit, and cassava, and reflect the abundance of the islands. Seafood is also prevalent in a variety of chowders and stews that contain conch, lobster, shrimp, and fresh fish. These local and Caribbean ingredients can be found in the dishes served up Upstairs at Kaibo, a renowned restaurant overlooking the serene North Sound. For casual dining with a colorful, Caribbean flair, head to Sunshine Grill, a favorite of the locals in Grand Cayman. For fishing enthusiasts, some restaurants even have “you catch, we cook” options.

Whether you enjoy swimming, diving, learning or simply relaxing, the Cayman Islands have something for every vacationer. Cayman Islands vacation rentals offer the perfect home away from home during your getaway and will allow you to see the island through the eyes of a local. There’s no place quite like the Cayman Islands for an island retreat.