Holiday rentals in Cayman Islands

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Top-rated holiday rentals in Cayman Islands

Guests agree: these stays are highly rated for location, cleanliness and more.

Guest favourite

Apartment in West Bay

5.0 out of 5 average rating, 58 reviews

Ocean View w King Bed next to Ritz Carlton

Escape to tropical bliss in this stunning 1 bedroom condo on Seven Mile Beach in the Cayman Islands! This 853 sq ft paradise boasts ocean views from the living room and is just steps away from the sand, where you can soak up the sun and swim in the crystal blue waters. Located between the Ritz Carlton and Westin hotels, this prime stretch of beach is considered the most sought-after on the island and offers the perfect combination of comfort and tranquility. ♥Make memories to last a lifetime♥

28 Aug – 4 Sep

$527 SGD per night
Guest favourite

Home in Stake Bay

5.0 out of 5 average rating, 33 reviews

Modern Oceanfront, 2Primary Suites, sleeps 6, pool

We offer a Hurricane Worry-free Guarantee. Only a short 25-minute flight from Grand Cayman, this newer home provides stunning oceanfront vistas with all modern amenities to enjoy barefoot luxury. Large windows and the open concept floor plan allow for breathtaking views of the pool and sea and include a fully-equipped kitchen, dining, and living areas. Also overlooking the ocean are two master king-size bed suites with tiled baths. A third bedroom has a queen bed and views of tropical foliage.

30 Sep – 7 Oct

$605 SGD per night
Guest favourite

Apartment in George Town

4.93 out of 5 average rating, 149 reviews

Cayman Reef Resort on Seven Mile Beach

At the heart of Seven Mile Beach, our home is in the middle of everything and far from nothing. Extensively renovated and well maintained, the condo is designed for you to enjoy a tranquil beach getaway in a luxurious setting with all the comforts of home. Picture perfect views, top of the line amenities and our local touch provide a warm welcome and cozy stay. We are fully licenced and our rate includes the 13% tourist accommodation tax. 20% discount from list price for local residents!

18–25 Jun

$332 SGD per night

Popular amenities for Cayman Islands holiday rentals

Other great holiday rentals in Cayman Islands

Guest favourite

Cottage in East End

5.0 out of 5 average rating, 76 reviews

Hidden Gem at Grapetree Cove

10–17 Oct

$377 SGD per night
Guest favourite

Apartment in West Bay

4.96 out of 5 average rating, 27 reviews

Ocean View Seven Mile Beach Villa

24 Sep – 1 Oct

$618 SGD per night
Guest favourite

Home in North Side

5.0 out of 5 average rating, 54 reviews

Ocean's Edge: Beachfront Home with Rooftop Views

27 Oct – 3 Nov

$910 SGD per night
Guest favourite

Home in George Town

4.88 out of 5 average rating, 17 reviews

Paradise Beach House in South Sound, George Town

5–12 Mar

$1,046 SGD per night
Superhost

Home in Creek

5.0 out of 5 average rating, 15 reviews

FREE Wi-fi and direct Ocean views!

18–25 Feb

$234 SGD per night
Guest favourite

Flat in Grand Cayman

4.98 out of 5 average rating, 92 reviews

Adorable Boho Beach Villa

18–25 Mar

$326 SGD per night
Guest favourite

Home in Blossom Village

4.94 out of 5 average rating, 17 reviews

Gorgeous Beach House in Little Cayman

10–17 Mar

$448 SGD per night
Guest favourite

Flat in Bodden Town

5.0 out of 5 average rating, 15 reviews

Close to the beach, restaurants and supermarket

10–17 Feb

$205 SGD per night
Guest favourite

Flat in Savannah

5.0 out of 5 average rating, 37 reviews

Cozy, peaceful 1-bedroom rental with free parking

26 Apr – 3 May

$175 SGD per night
Guest favourite

Home in Cayman Brac

4.86 out of 5 average rating, 71 reviews

Southern Exposure, Secluded Paradise, Cayman Brac

20–27 Jul

$253 SGD per night
Guest favourite

Villa in West Bay

4.96 out of 5 average rating, 57 reviews

Ocean Front Relaxation Villa

17–24 Aug

$1,414 SGD per night
Guest favourite

Home in Bodden Town

5.0 out of 5 average rating, 27 reviews

Casa Avi - Beachfront bliss & luxury in Cayman

8–15 Nov

$1,223 SGD per night

Destinations to explore