Swim with Dolphins in Grand Cayman
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Plan Your Vacation in Grand Cayman

Luxury Grand Cayman Vacation Rentals

Grand Cayman Villas offers many options for Private Oceanfront Villas. From 1 bedroom villas for a romantic getaway to a 6-7 bedroom home for a family vacation, we can help you find the perfect vacation rental with a gorgeous view. We can also put together multiple adjacent villas for a larger family vacation.

Private Villas

1BR-Mahogany Cove - Cottage

1BR/1BA Mahogany Cove Apartment is directly oceanfront in the Cottage District on the south coast in the middle of the island. Offering excellent snorkeling directly behind the house and from the adjacent dock next door, a sandy beach for long walks or a hammock for lazy afternoons, this apartment’s single King Suite is a perfect couple’s retreat. If rented, the upstairs 3BR villa will be vacant during your stay. The backyard is sandy, with a hammock shaded by the cabana and a Propane grill. A wide screened porch looks out onto sparkling ocean views and the palm-shaded beach.

10BR-Coconut Reef - Rum Point

Comprised of 5BR Reef Romance and 5BR Coconut Beach, 10BR COMBINATION Villa Coconut Reef can sleep up to twenty guests in unparalleled comfort. Both villas are directly oceanfront in Rum Point on the north coast- separated by only one house and a vacant lot, offering 7 Kings, 1 Queen, 4 Twins, and 9.5 bathrooms. With two pools, a beachfront thatched cabana & bar, volleyball net and plenty of sandy, private beach, 10BR Coconut Beach has room for the whole family (or multiple families!) to spread out and relax.

20% Discount for Sep/Oct Bookings


2/3BR-Sea Cove - Cayman Kai Cove

2-3BR Sea Cove is directly waterfront, within the exclusive Cayman Kai community near Rum Point. Featuring a gorgeous oceanfront screened porch and sundeck, along with a private dock and a pleasant, sandy beach--perfect for rented boats or waverunners, children looking to play in the sand, or just long afternoons spent lounging by the water. The popular Rum Point Club is a short walk away, so guests can pop out for watersports, drinks, lunch or dinner. Sea Cove is an exceptional home for families, comfortably sleeping up to six guests with plenty of room for everyone.

Lower rates available for fewer guests; click "Details" to see more. 

2BR-Castle Guesthouse - East End

2BR/2BA "Castle Guesthouse" is directly oceanfront, and while it shares a 2 acre gated estate and large private white-sand beach with the larger 5BR Cayman Castle, it is actually 80 feet from the Castle (more than the combined setbacks between most oceanfront neighbors). The Guesthouse boasts its own driveway, utilities, garage, satellite dish, grill and freshwater pool.

2BR-Cayman Dream - Rum Point

2BR/2BA Cayman Dream Villa is directly oceanfront in Rum Point on the north coast. Featuring Caribbean style architecture and a sizable oceanfront pool, Cayman Dream is a great getaway for a small family or two couples. The sandy beach is perfect for long walks or just lounging by the water with a novel; the water offers fantastic snorkeling, with plenty of sea life for guests to investigate! Landscaping and a privacy wall keep Cayman Dream quietly tucked away from the neighboring properties, so you can relax, kick back, and enjoy your beach home without interruption.

2BR-Conch'ed Out - Old Man Bay

2BR/2BA "Conch'ed Out" Villa is a recently renovated oceanfront cottage in Old Man Bay on the north coast. This Caribbean-style 2BR very private villa offers excellent snorkeling directly behind the oceanfront pool, and a sandy private backyard that leads to the pebbly beach. Oceanfront doors to the sea connect to the full-width screened-in porch, adjacent to both the beach and the pool. Very deep lot (450') and heavily landscaped from the neighboring homes. Oceanfront freshwater pool with lounge chairs and palm trees. Many shade and coconut trees on the property.

2BR-Cool Change - Cayman Kai

2BR/2BA Cool Change is the quintessential "Caribbean Island Getaway Cottage." Surrounded by mature palms and casuarina trees, Cool Change offers peace, quiet and privacy, along with a sandy beach on a full-sized lot. It offers comfortable accommodations for up to four adults or a small family of 4.  Featuring bright, airy interiors, Cool Change is is only a few minutes drive from the popular Rum Point club, so guests can pop out anytime for drinks, watersports, equipment rentals, lunch or dinner. Lower rates for 2 adults only.

-Excellent guest cottage to use when renting 5BR Ocean Kai.

2BR-Crystal Cove - Cottage

Crystal Cove- is located on the South Coast of the island just west of the road north to Rum Point. Very impressive island-style architecture, vaulted ceilings, windowed cupola and open rooms to the ocean. Oceanfront verandah and pool with adjacent gazebo. Large spaces, intimate privacy & french doors to ocean all lend a great "Island Feel" to the villa.  Stunning manicured (illuminated) gardens and landscaping really set this villa apart from others on the island, including lush bougainvillea and the zoysia lawn around the pool. 

2BR-Fantasea - Cayman Kai

2BR/2BA Fantasea Villa is a waterfront cottage with private pool in Cayman Kai on the quiet cove.  A cute, Caribbean-style home, Fantasea offers sparkling waters and quiet sunsets from the oceanfront pool and screened porch. This airy beach front home with private dock is within easy walking distance of 2 beach bars, 2 restaurants and a full-service water-sport shop. It is also within a 10 minute drive of a few other restaurants and a grocery store.

2BR-Moon Glow - Cayman Kai

2BR/2BA "Moon Glow" is directly oceanfront in Rum Point on the north coast, only a short walk from the popular Rum Point Club. With cute, sunny interiors that capitalize on the dazzling ocean views, a sandy beach and sizable oceanfront veranda, Moon Glow is a great beach retreat for a small family or two couples. Excellent snorkeling is available just off of the beach, and the oceanfront charcoal grill is perfect for cookouts after a long day of sun, surf and sand!

Lower rates available for fewer guests; click "Details" to see more.
20% Discount Available Sept - Oct.

2BR-Parrot's Haven - Cayman Kai

2BR/2BA Parrot's Haven is a wonderful large cottage tucked away on a half-acre private lot adjoining the Cayman Kai canal to the south...and directly across the street from the (open to the public) Cayman Kai Oceanfront Beach to the north! As all beaches in Grand Cayman are technically public; so 9 days out of 10 you will be the only people on this beach! Freshwater pool, large screened porch, boat dock and ramp, WifI, TVs, King and Queen bedrooms. Central A/C, Hammocks and charcoal grill. Just a great value spot in Cayman Kai and only a short walk to the Rum Point Club and Restaurant.Can sleep 5 in a pinch. No local resident rentals

2BR-Pools of the Kai #6 - Cayman Kai Sound

2BR Pools #6 is absolutely the nicest of the (6) 2BR Pools of the Kai units in Cayman Kai. It has been fully renovated and redecorated down to the tile around the pool and in the bathrooms. New doors, furniture and kitchen give Pools #6 a luxury private feel. 16 feet of sliding glass doors stack against the wall behind the kitchen to open up the entire unit to the screened atrium/pool area with additional furniture for bringing the outdoors inside! Optional Pool Heat year-round for an extra charge.

20% Discount for Sep/Oct Bookings; please call for last-minute rentals.

2BR-Sea Beauty - Cottage

2BR/2BA Sea Beauty is a brand new Cayman Style gingerbread 2BR cottage with very nice amenities located in the Cottage District on the island's south coast. Only 25 minutes to Georgetown, Sea Beauty is unique from other properties we manage in that it has over 300' of private fenced beachfront, but is built across the street from the beach. The beach is all yours while on island, with a gazebo, hammocks, beach chaises, snorkeling and plenty of shade trees. Bone-fishing, kite-boarding, snorkeling, and any other watersports can all be done from this beach. Wheelchair friendly too! 4 Adults max. 6 including small children on pull out sofa.

2BR-Thatch Hill - Cayman Kai

Thatch Hill is located on the Northside of the island, just 300 yards east of the Rum Point Club. Thatch Hill features elevated views of the sparkling Caribbean sea, an oceanfront freshwater pool, and a spacious screened porch for relaxing and watching the sunset after a day of surf and sand. The interiors are colorfully decorated in a typical Caymanian beach cottage style. A protective reef provides excellent snorkeling just steps from your back door!
Lower rates available for just 2 guests; click "Details" to see more. 

2BR-We'll Sea - Cayman Kai

We’ll Sea is on the North side of the island, just 250 yards from the popular and well-loved Rum Point Club. This charming beach cottage features a perfect white-sand beach with clear, shallow waters for barefoot swimming just steps from the two-story screened lanai, light, airy interiors with vaulted ceilings, and classic beach house decor. Guests will love kicking back on the sand or the porch with a drink to watch the dazzling sunsets.

Lower rates available for fewer guests; click "Details" to see more.
20% Discount Available Sep - Oct. 

3BR w/ Loft-Lone Palm - East End

New Listing!- 3BR & Loft "Lone Palm" in Gun Bay, East End is an award-winning floorplan by renowned architect John Doak. Windows and Glass doors across the oceanfront covered verandah flood the villa with sunshine. (2) king bedroom suites on main floor, (1) queen bedroom and a TV loft with another daybed ( trundle underneath) on second floor can sleep a total of 8 persons.  Large white sand beach, private lot and only a short walk to the best dive operation in East End. No screened porch needed, as east end typically has a tradewind breeze to keep the house cool and bug-free!  Lower rates for fewer people.

3BR-Casuarina Cove - Cayman Kai Sound

3BR/3.5BA Luxury Casuarina Cove is located in the quiet neighborhood of Cayman Kai at the end of a private cul-de-sac on the very tip of the sandy peninsula. This lovely new home has a soft sand beach and private dock with clear calm water for shallow swimming. 2 King Suites and a queen bedroom can accommodate up to 6 people. Elevator available for adult guests. Movie Theater room on second floor, multiple plasma TVs. Covered second floor verandah opens to the sunset views of 7 Mile Beach.

3BR-Fingertip - Cayman Kai

3BR/3BA Fingertip is directly waterfront in Cayman Kai (within Rum Point) on the north coast. This one story, extremely private villa is a choice for a honeymoon, anniversary or just a small family vacation. The property ends in a palm-shaded, white sand beach, with lounge chairs and a hammock under the trees. The shallow, clear water offers barefoot swimming and, when combined with the modern, comfortable interior and exceptional privacy, Fingertip promises to be an exceptional island getaway. Many oceanfront windows and sliding doors to the screened porch provide panoramic views of the azure waters off of Cayman Kai.
Lower rates available for fewer guests in Summer Months

3BR-Fishbones - Queen's Highway

3BR/2.5BA Fishbones is located on the Northside of the island, just about 2 miles west of the Morritt's and Royal Reef Resorts. Fishbones is truly an Ultra-Luxury Villa inside and out; professionally designed & decorated with exquisite furniture, drapes and decor, the villa will make you feel like royalty. Amazing elevated Caribbean views of multi-colored water are interrupted only by the occasional dive boat mooring on a popular dive site just outside the reef. The screened lanai overlooks a stunning pool that leads down private stairs to excellent reef-protected snorkeling and swimming over a shallow, sandy bottom. Ages 18 and above only (no children).

3BR-Just For Fun - Cayman Kai Cove

Cottage-Style 3BR Just for Fun in Cayman Kai is cute, convenient, cozy and offers a HUGE freshwater pool/spa as well as full-width screened atrium, dock and outdoor "Tiki-style" shower facility. Formerly two attached two-bedroom homes, Just for Fun has been renovated and offers a spectacular pool, lovely kitchen, and a large screened-in atrium that’s perfect for lounging or entertaining. The Rum Point Club is a two-minute walk away, so guests can pop out for watersports, drinks, lunch or dinner. Vaulted ceilings and great air flow, combined with the bright, open architecture, give Just for Fun a clean, classic beach house feel.


Grand Cayman Villas