International+1-514-360-2529

Luxury Cayman Islands Vacation Rentals

Luxury Villa Rentals in Cayman Islands for 2 people

Destination Guide
Coconut WalkCoconut Walk #2Coconut Walk #3Coconut Walk #4Coconut Walk #5Coconut Walk #6Coconut Walk #7Coconut Walk #8Coconut Walk #9Coconut Walk #10Coconut Walk #11Coconut Walk #12Coconut Walk #13Coconut Walk #14Coconut Walk #15Coconut Walk #16Coconut Walk #17
Starting at $5,000 /night.
Point of View VillaPoint of View Villa #2Point of View Villa #3Point of View Villa #4Point of View Villa #5Point of View Villa #6Point of View Villa #7Point of View Villa #8Point of View Villa #9Point of View Villa #10Point of View Villa #11Point of View Villa #12Point of View Villa #13Point of View Villa #14Point of View Villa #15Point of View Villa #16Point of View Villa #17Point of View Villa #18Point of View Villa #19Point of View Villa #20Point of View Villa #21Point of View Villa #22Point of View Villa #23
Starting at $3,100 /night.

Kaia Kamina

Cayman Islands, Caribbean

8 Bedrooms, Sleeps 18

Kaia KaminaKaia Kamina #2Kaia Kamina #3Kaia Kamina #4Kaia Kamina #5Kaia Kamina #6Kaia Kamina #7Kaia Kamina #8Kaia Kamina #9Kaia Kamina #10Kaia Kamina #11Kaia Kamina #12Kaia Kamina #13Kaia Kamina #14Kaia Kamina #15Kaia Kamina #16Kaia Kamina #17Kaia Kamina #18Kaia Kamina #19Kaia Kamina #20Kaia Kamina #21Kaia Kamina #22Kaia Kamina #23Kaia Kamina #24Kaia Kamina #25Kaia Kamina #26Kaia Kamina #27Kaia Kamina #28Kaia Kamina #29Kaia Kamina #30Kaia Kamina #31Kaia Kamina #32Kaia Kamina #33Kaia Kamina #34Kaia Kamina #35Kaia Kamina #36
Starting at $3,100 /night.

Moon Kai

Cayman Kai, Cayman Islands

6 Bedrooms, Sleeps 12

Moon KaiMoon Kai #2Moon Kai #3Moon Kai #4Moon Kai #5Moon Kai #6Moon Kai #7Moon Kai #8Moon Kai #9Moon Kai #10Moon Kai #11Moon Kai #12Moon Kai #13Moon Kai #14Moon Kai #15Moon Kai #16Moon Kai #17Moon Kai #18
Starting at $2,500 /night.
Seascape VillaSeascape Villa #2Seascape Villa #3Seascape Villa #4Seascape Villa #5Seascape Villa #6Seascape Villa #7Seascape Villa #8Seascape Villa #9Seascape Villa #10Seascape Villa #11Seascape Villa #12Seascape Villa #13Seascape Villa #14Seascape Villa #15Seascape Villa #16Seascape Villa #17
Starting at $2,400 /night.

Tatenda

Cayman Islands, Caribbean

7 Bedrooms, Sleeps 18

TatendaTatenda #2Tatenda #3Tatenda #4Tatenda #5Tatenda #6Tatenda #7Tatenda #8Tatenda #9Tatenda #10Tatenda #11Tatenda #12Tatenda #13Tatenda #14Tatenda #15Tatenda #16Tatenda #17Tatenda #18Tatenda #19Tatenda #20Tatenda #21Tatenda #22Tatenda #23Tatenda #24Tatenda #25Tatenda #26Tatenda #27Tatenda #28Tatenda #29Tatenda #30Tatenda #31Tatenda #32Tatenda #33Tatenda #34Tatenda #35Tatenda #36Tatenda #37Tatenda #38Tatenda #39
Starting at $2,300 /night.

Oceanus

East End, Cayman Islands

6 Bedrooms, Sleeps 20

OceanusOceanus #2Oceanus #3Oceanus #4Oceanus #5Oceanus #6Oceanus #7Oceanus #8Oceanus #9Oceanus #10Oceanus #11Oceanus #12Oceanus #13Oceanus #14Oceanus #15Oceanus #16Oceanus #17Oceanus #18Oceanus #19Oceanus #20Oceanus #21Oceanus #22Oceanus #23Oceanus #24Oceanus #25Oceanus #26Oceanus #27Oceanus #28Oceanus #29Oceanus #30Oceanus #31Oceanus #32Oceanus #33Oceanus #34
Starting at $2,300 /night.

Evolution

Bodden Town, Cayman Islands

7 Bedrooms, Sleeps 20

EvolutionEvolution #2Evolution #3Evolution #4Evolution #5Evolution #6Evolution #7Evolution #8Evolution #9Evolution #10Evolution #11Evolution #12Evolution #13Evolution #14Evolution #15Evolution #16Evolution #17Evolution #18Evolution #19Evolution #20Evolution #21Evolution #22Evolution #23Evolution #24
Starting at $2,300 /night.

Kaiku

Cayman Kai, Cayman Islands

8 Bedrooms, Sleeps 18

KaikuKaiku #2Kaiku #3Kaiku #4Kaiku #5Kaiku #6Kaiku #7Kaiku #8Kaiku #9Kaiku #10Kaiku #11Kaiku #12Kaiku #13Kaiku #14Kaiku #15Kaiku #16Kaiku #17Kaiku #18
Starting at $1,960 /night.
Pease Bay EstatePease Bay Estate #2Pease Bay Estate #3Pease Bay Estate #4Pease Bay Estate #5Pease Bay Estate #6Pease Bay Estate #7Pease Bay Estate #8Pease Bay Estate #9Pease Bay Estate #10Pease Bay Estate #11Pease Bay Estate #12Pease Bay Estate #13Pease Bay Estate #14Pease Bay Estate #15Pease Bay Estate #16Pease Bay Estate #17Pease Bay Estate #18Pease Bay Estate #19
Starting at $1,950 /night.

Fischer's Reef

Rum Point, Cayman Islands

8 Bedrooms, Sleeps 18

Fischer's ReefFischer's Reef #2Fischer's Reef #3Fischer's Reef #4Fischer's Reef #5Fischer's Reef #6Fischer's Reef #7Fischer's Reef #8Fischer's Reef #9Fischer's Reef #10Fischer's Reef #11Fischer's Reef #12Fischer's Reef #13Fischer's Reef #14Fischer's Reef #15Fischer's Reef #16Fischer's Reef #17Fischer's Reef #18Fischer's Reef #19Fischer's Reef #20Fischer's Reef #21Fischer's Reef #22Fischer's Reef #23Fischer's Reef #24Fischer's Reef #25Fischer's Reef #26Fischer's Reef #27
Starting at $1,950 /night.

Nirvana Villa

Cayman Islands, Caribbean

5 Bedrooms, Sleeps 14

Nirvana VillaNirvana Villa #2Nirvana Villa #3Nirvana Villa #4Nirvana Villa #5Nirvana Villa #6Nirvana Villa #7Nirvana Villa #8Nirvana Villa #9Nirvana Villa #10Nirvana Villa #11Nirvana Villa #12Nirvana Villa #13Nirvana Villa #14Nirvana Villa #15Nirvana Villa #16Nirvana Villa #17Nirvana Villa #18Nirvana Villa #19Nirvana Villa #20Nirvana Villa #21Nirvana Villa #22Nirvana Villa #23Nirvana Villa #24Nirvana Villa #25Nirvana Villa #26Nirvana Villa #27Nirvana Villa #28Nirvana Villa #29Nirvana Villa #30Nirvana Villa #31Nirvana Villa #32
Starting at $1,900 /night.

Villa Mora

South Sound, Cayman Islands

7 Bedrooms, Sleeps 18

Villa MoraVilla Mora #2Villa Mora #3Villa Mora #4Villa Mora #5Villa Mora #6Villa Mora #7Villa Mora #8Villa Mora #9Villa Mora #10Villa Mora #11Villa Mora #12Villa Mora #13Villa Mora #14Villa Mora #15Villa Mora #16Villa Mora #17Villa Mora #18Villa Mora #19Villa Mora #20Villa Mora #21Villa Mora #22Villa Mora #23
Starting at $1,900 /night.

Amarone

South Sound, Cayman Islands

6 Bedrooms, Sleeps 12

AmaroneAmarone #2Amarone #3Amarone #4Amarone #5Amarone #6Amarone #7Amarone #8Amarone #9Amarone #10Amarone #11Amarone #12Amarone #13Amarone #14Amarone #15Amarone #16Amarone #17Amarone #18Amarone #19Amarone #20Amarone #21Amarone #22Amarone #23
Starting at $1,850 /night.

Stepping Stone

East End, Cayman Islands

4 Bedrooms, Sleeps 8

Stepping StoneStepping Stone #2Stepping Stone #3Stepping Stone #4Stepping Stone #5Stepping Stone #6Stepping Stone #7Stepping Stone #8Stepping Stone #9Stepping Stone #10Stepping Stone #11Stepping Stone #12Stepping Stone #13Stepping Stone #14Stepping Stone #15Stepping Stone #16Stepping Stone #17Stepping Stone #18Stepping Stone #19Stepping Stone #20Stepping Stone #21
Starting at $1,778 /night.
Cayman Castle & GuesthouseCayman Castle & Guesthouse #2Cayman Castle & Guesthouse #3Cayman Castle & Guesthouse #4Cayman Castle & Guesthouse #5Cayman Castle & Guesthouse #6Cayman Castle & Guesthouse #7Cayman Castle & Guesthouse #8Cayman Castle & Guesthouse #9Cayman Castle & Guesthouse #10Cayman Castle & Guesthouse #11Cayman Castle & Guesthouse #12Cayman Castle & Guesthouse #13Cayman Castle & Guesthouse #14Cayman Castle & Guesthouse #15Cayman Castle & Guesthouse #16Cayman Castle & Guesthouse #17Cayman Castle & Guesthouse #18Cayman Castle & Guesthouse #19
Starting at $1,750 /night.
Sea Orchard RetreatSea Orchard Retreat #2Sea Orchard Retreat #3Sea Orchard Retreat #4Sea Orchard Retreat #5Sea Orchard Retreat #6Sea Orchard Retreat #7Sea Orchard Retreat #8Sea Orchard Retreat #9Sea Orchard Retreat #10Sea Orchard Retreat #11Sea Orchard Retreat #12Sea Orchard Retreat #13Sea Orchard Retreat #14Sea Orchard Retreat #15
Starting at $1,750 /night.
Twin Palms VillaTwin Palms Villa #2Twin Palms Villa #3Twin Palms Villa #4Twin Palms Villa #5Twin Palms Villa #6Twin Palms Villa #7Twin Palms Villa #8Twin Palms Villa #9Twin Palms Villa #10Twin Palms Villa #11Twin Palms Villa #12Twin Palms Villa #13Twin Palms Villa #14Twin Palms Villa #15Twin Palms Villa #16Twin Palms Villa #17Twin Palms Villa #18Twin Palms Villa #19
Starting at $1,650 /night.

Faroway Villa

South Sound, Cayman Islands

4 Bedrooms, Sleeps 8

Faroway VillaFaroway Villa #2Faroway Villa #3Faroway Villa #4Faroway Villa #5Faroway Villa #6Faroway Villa #7Faroway Villa #8Faroway Villa #9Faroway Villa #10Faroway Villa #11
Starting at $1,500 /night.

Olympus

Rum Point, Cayman Islands

5 Bedrooms, Sleeps 12

OlympusOlympus #2Olympus #3Olympus #4Olympus #5Olympus #6Olympus #7Olympus #8
Starting at $1,500 /night.
Great Bluff EstatesGreat Bluff Estates #2Great Bluff Estates #3Great Bluff Estates #4Great Bluff Estates #5Great Bluff Estates #6Great Bluff Estates #7Great Bluff Estates #8Great Bluff Estates #9Great Bluff Estates #10Great Bluff Estates #11Great Bluff Estates #12Great Bluff Estates #13Great Bluff Estates #14Great Bluff Estates #15Great Bluff Estates #16Great Bluff Estates #17Great Bluff Estates #18Great Bluff Estates #19Great Bluff Estates #20Great Bluff Estates #21Great Bluff Estates #22Great Bluff Estates #23Great Bluff Estates #24
10% OFF!!
Starting at $1,425 /night.

Ocean Kai

Cayman Kai, Cayman Islands

5 Bedrooms, Sleeps 10

Ocean KaiOcean Kai #2Ocean Kai #3Ocean Kai #4Ocean Kai #5Ocean Kai #6Ocean Kai #7Ocean Kai #8Ocean Kai #9Ocean Kai #10Ocean Kai #11Ocean Kai #12Ocean Kai #13Ocean Kai #14Ocean Kai #15Ocean Kai #16Ocean Kai #17
Starting at $1,350 /night.
Cayman Castle VillaCayman Castle Villa #2Cayman Castle Villa #3Cayman Castle Villa #4Cayman Castle Villa #5Cayman Castle Villa #6Cayman Castle Villa #7Cayman Castle Villa #8Cayman Castle Villa #9Cayman Castle Villa #10Cayman Castle Villa #11Cayman Castle Villa #12Cayman Castle Villa #13Cayman Castle Villa #14Cayman Castle Villa #15
Starting at $1,350 /night.

Cos Kai

Cayman Kai, Cayman Islands

5 Bedrooms, Sleeps 14

Cos KaiCos Kai #2Cos Kai #3Cos Kai #4Cos Kai #5Cos Kai #6Cos Kai #7Cos Kai #8Cos Kai #9Cos Kai #10Cos Kai #11Cos Kai #12Cos Kai #13Cos Kai #14
Starting at $1,200 /night.

Crystal Blue

East End, Cayman Islands

7 Bedrooms, Sleeps 16

Crystal BlueCrystal Blue #2Crystal Blue #3Crystal Blue #4Crystal Blue #5Crystal Blue #6Crystal Blue #7Crystal Blue #8Crystal Blue #9Crystal Blue #10Crystal Blue #11Crystal Blue #12Crystal Blue #13Crystal Blue #14Crystal Blue #15Crystal Blue #16Crystal Blue #17Crystal Blue #18Crystal Blue #19Crystal Blue #20
Starting at $1,150 /night.
On the Rocks EstateOn the Rocks Estate #2On the Rocks Estate #3On the Rocks Estate #4On the Rocks Estate #5On the Rocks Estate #6On the Rocks Estate #7On the Rocks Estate #8On the Rocks Estate #9On the Rocks Estate #10On the Rocks Estate #11On the Rocks Estate #12On the Rocks Estate #13On the Rocks Estate #14
10% OFF!!
Starting at $1,135 /night.

In Harmony

Cayman Islands, Caribbean

4 Bedrooms, Sleeps 10

In HarmonyIn Harmony #2In Harmony #3In Harmony #4In Harmony #5In Harmony #6In Harmony #7In Harmony #8In Harmony #9In Harmony #10In Harmony #11In Harmony #12In Harmony #13In Harmony #14In Harmony #15In Harmony #16In Harmony #17In Harmony #18In Harmony #19In Harmony #20In Harmony #21In Harmony #22In Harmony #23In Harmony #24
Starting at $1,100 /night.
Reef Romance VillaReef Romance Villa #2Reef Romance Villa #3Reef Romance Villa #4Reef Romance Villa #5Reef Romance Villa #6Reef Romance Villa #7Reef Romance Villa #8Reef Romance Villa #9Reef Romance Villa #10Reef Romance Villa #11Reef Romance Villa #12Reef Romance Villa #13
Starting at $1,100 /night.
Villa Two RainbowsVilla Two Rainbows #2Villa Two Rainbows #3Villa Two Rainbows #4Villa Two Rainbows #5Villa Two Rainbows #6Villa Two Rainbows #7Villa Two Rainbows #8Villa Two Rainbows #9Villa Two Rainbows #10Villa Two Rainbows #11Villa Two Rainbows #12Villa Two Rainbows #13Villa Two Rainbows #14
Starting at $1,100 /night.

Coral Kai

Rum Point, Cayman Islands

5 Bedrooms, Sleeps 10

Coral KaiCoral Kai #2Coral Kai #3Coral Kai #4Coral Kai #5Coral Kai #6Coral Kai #7Coral Kai #8Coral Kai #9Coral Kai #10Coral Kai #11Coral Kai #12Coral Kai #13Coral Kai #14Coral Kai #15Coral Kai #16Coral Kai #17Coral Kai #18Coral Kai #19
Starting at $1,100 /night.
Show More Properties Top

Need some help?

Let us know what you're looking for and a Reservation Manager will contact you right away with some options.

$0 No Max

Cayman Islands Visitors Guide

With white-sand beaches and crystal-clear water, the Cayman Islands are known as one of the Caribbean's premier destinations. Composed of Grand Cayman, Cayman Brac and Little Cayman, each member of the Cayman Islands offers its own unique advantages, with the larger Grand Cayman offering great dining and shopping, and the little islands offering amazing landscapes and snorkelling. Cayman Islands vacation rentals can also be found in all shapes and sizes as a result and offer accommodation that caters to all price ranges. From affordable apartments to beachfront condos, a variety of rentals can be found, though the islands are, of course, known for their sprawling villas and infinity pools. They're also known for their breathtaking Caribbean beaches, including the world-famous Seven Mile Beach on Grand Cayman. Like any good Caribbean destination, the Caymans also feature a variety of water sports, boat rentals, surfing, and fishing, as well as enough fresh seafood to satisfy anyone.

Saving Money with Cayman Islands Vacation Rentals

If you're looking to save money or simply add value to your trip, Cayman Islands vacation rentals offer plenty of extras you won't find at hotels. The larger ones also feature private pools and added features like wet bars, with owners usually being happy to assist guests with extras like boat rentals as well. If you consider the number of people these villas can accommodate, those traveling with groups or families can often save a great deal of money by choosing a rental over hotel rooms.

Finding Luxury Cayman Islands Vacation Rentals

Those looking to indulge in a little luxury will find no shortage of it the Caymans, as the island have long catered to an affluent crowd. That means that stunning Cayman Islands vacation rentals are not hard to find, with owners and property management companies often also offering a full concierge services for guests as well. Of course, you can even have your villa staffed with cooks and maids, though the price of doing so is higher than it is on other Caribbean islands. Meanwhile, the islands' stunning scenery makes a lovely backdrop for romance, which is why it is an increasingly popular spot for both destination weddings, and honeymoons.

Access your favorites anytime.

You can view your list of favorites anytime by clicking on the favorites icon in the top menu.

You can view your list of favorites anytime by clicking on Your Favorites in the mobile menu.

When you are logged in to your account, we will automatically save your favorites so you can come back later and view them or share them.

Got it.