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Cayman Islands vacation rentals

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Top-rated vacation rentals in Cayman Islands

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

SUPERHOST
  1. Entire cottage
  2. Savannah
John John's Hideaway

Cozy 1 bedroom cottage with en-suite bathroom, sitting area, full kitchen, washer and dryer. Located in a quiet neighbourhood, a 2 minute walk away from Pedro St. James Castle. 3 minute drive from a supermarket and local restaurants. 5 minute drive to snorkel at the picturesque Spotts Beach. 20 minute drive from other popular destinations, including shopping centres and other local attractions.

R2,187 ZAR per night
SUPERHOST
  1. Entire cottage
  2. Seven Mile Beach
Luxury Cottage, 1bd/1ba steps to Pool+7 Mile Beach

Our Queen Cottages are part of the Botanica collection of charming island style cottages which won the coveted 2021 Governor's Award for Excellence in Design and Construction. Our focus is casual luxury with dreamy details and high end amenities. Amenity highlight includes a resort style pool with a heated spa set in a tropical oasis with ample space to hang out and enjoy some down time. Be sure to check out our other listings under my profile. Non Smoking Complex.

R4,759 ZAR per night
  1. Entire condo
  2. George Town
Paradise on Seven Mile Beach

Prepare to leave all your hurries behind and kick back and relax in this calm, modern oasis. This beauitful modern stylish 2BR/2B Ocean Front condo is nestled on Seven Mile Beach at the Grandview Condominiums and makes for the perfect vacation getaway experience with the very best #CaymanKind service.

R4,764 ZAR per night

Vacation rentals for every style

Get the amount of space that is right for you

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Cayman Islands house rentals

SUPERHOST
  1. Entire home
  2. Bodden Town
Tranquil Hideaway
R1,417 ZAR per night
  1. Private room
  2. Bodden Town
Gayle's Getaway (GG)
R1,296 ZAR per night
  1. Private room
  2. Savannah
Island Serenity
R1,377 ZAR per night
  1. Entire home
  2. Grand Cayman
Kaibo Dreams by Grand Cayman Villas
R3,979 ZAR per night
  1. Entire home
  2. Grand Cayman
Kai Tana by Grand Cayman Villas
R8,023 ZAR per night
  1. Entire home
  2. Grand Cayman
Pools of the Kai #3 by Grand Cayman Villas
R7,454 ZAR per night
  1. Private room
  2. West Bay
16 Cozy Place-2 Single Bedrooms-1Bathroom
R1,458 ZAR per night
SUPERHOST
  1. Entire home
  2. Little Cayman
Just Chillin in Little Cayman
R2,805 ZAR per night
  1. Private room
  2. West Bay
Shangri-La - Award-Winning- Oleander Room
R3,079 ZAR per night
SUPERHOST
  1. Private room
  2. West Bay
Medlock Guest House (Grey Room)
R1,782 ZAR per night
  1. Entire home
  2. West End
2-bdrm Pool, cabana, sunsets, kayaks, bikes more
R2,836 ZAR per night
SUPERHOST
  1. Entire home
  2. Grand cayman
The Highlands Rooftop Retreat
R6,076 ZAR per night

Cayman Islands condo rentals

SUPERHOST
  1. Entire condo
  2. George Town
Beautiful Modern Condo on 7 Mile Beach
R3,525 ZAR per night
SUPERHOST
  1. Entire condo
  2. West Bay
Modern Penthouse Oceanfront 1 Bdr Condo /w Pool
R5,655 ZAR per night
SUPERHOST
  1. Entire condo
  2. George Town
Beach Living at Seagull Condos BLMI
R3,549 ZAR per night
  1. Entire condo
  2. George Town
On Seven Mile Beach, no cruise ship tourists!!
R3,343 ZAR per night
  1. Entire condo
  2. George Town
One Bedroom Condo-Seven Mile Beach-Cayman Reef #6
R3,241 ZAR per night
SUPERHOST
  1. Entire condo
  2. Grand Harbour
The Sanctuary at the Careenage, Grand Harbour
R2,935 ZAR per night
SUPERHOST
  1. Entire condo
  2. George Town
Beach Living at Island Pine Villas (BLJ)
R3,410 ZAR per night
  1. Entire condo
  2. West Bay
NEW ONE BEDROOM PENTHOUSE OCEANFRONT CONDO
R5,655 ZAR per night
SUPERHOST
  1. Entire condo
  2. George Town
Great 1-Bedroom at Seagull Steps from 7 Mile Beach
R3,484 ZAR per night
  1. Entire condo
  2. West Bay
Condo Kai- Awesome 1B/1B in West Bay, Grand Cayman
R2,836 ZAR per night
SUPERHOST
  1. Entire condo
  2. West Bay
Minutes From 7 Mile Beach
R2,766 ZAR per night
SUPERHOST
  1. Entire condo
  2. George town
Beach condo with sunset view
R5,671 ZAR per night

Cayman Islands villa rentals

SUPERHOST
  1. Entire villa
  2. West Bay
Modern BeachSide Villa steps from Seven Mile Beach
R3,208 ZAR per night
SUPERHOST
  1. Entire villa
  2. Old Man Bay
Old Man Bay Villa #1
R2,187 ZAR per night
LUXE
Professionally inspected
  1. Entire villa
  2. Rum Point
Tarasand
R15,393 ZAR per night
SUPERHOST
  1. Entire villa
  2. West Bay
Beach Living at Conch Point Villa (BLJJ)
R13,984 ZAR per night
SUPERHOST
  1. Private room
  2. George Town
Queen Room + Bath (Bluebell Room)
R2,025 ZAR per night
  1. Entire villa
  2. Bodden Town
Oceanfront Villa (Brand New)
R3,044 ZAR per night
SUPERHOST
  1. Entire villa
  2. West Bay
Ocean Front Relaxation Villa
R8,896 ZAR per night
  1. Entire villa
  2. North Side
Coco Kai Beach Front Villa heated pool and dock
R10,183 ZAR per night
  1. Entire villa
  2. North Side
Luxury 3bd Beach Front, # 4 Green, Stunning Views
R6,481 ZAR per night
  1. Entire villa
  2. West End
5 Bdrm, POOL, on the water, cabana, sandy beach
R4,958 ZAR per night
  1. Entire villa
  2. East End
OCEAN VIEW at SUNRISE SOLILOQUY - Paradise Villas
R4,278 ZAR per night
SUPERHOST
  1. Entire villa
  2. Grand Cayman
Deluxe Spacious Villa
R7,373 ZAR per night

Your guide to Cayman Islands

All About Cayman Islands

An idyllic island archipelago in the Caribbean, the Cayman Islands offer everything from tranquility and relaxation on the beach to adventures full of water sports, shipwrecks, and night tours of the bioluminescent ecology. Located in the western Caribbean between Jamaica and Cuba, the Cayman Islands have an identity all their own. A diverse range of cultural heritages come together to create a persona unique to the island chain. Dive with turtles in the morning, take part in a guided jungle tour in the afternoon, and eat at one of the many fine-dining restaurants in the evening.

Each of the three islands that make up the territory has its offerings and personality. Stay in the country's capital of George Town on Grand Cayman for a full sweep of island amenities, find adventure on windswept Cayman Brac with its dramatic cliffs and thick jungles, or take it easy on Little Cayman with its postcard-worthy South Hole Sound Lagoon that is perfect for swimming and lazy kayaking.


When is the best time to stay in a vacation rental in Cayman Islands?

The weather in the Cayman Islands is close to perfect all year round, with warm average temperatures that are ideal for the tropical waters and activities the area is known for. The main area of consideration when looking for Cayman Islands house rentals is the high precipitation rate from May through October. Coinciding with the rain is the hurricane season, which lasts from June through November. However, because the islands are in the western part of the Caribbean, they tend to be shielded from most tropical storms and don't get hit too hard.

If your primary concern is the weather, consider booking your vacation rental or condo in the Cayman Islands from November to April, as this is the dry season. If you are interested in checking out the islands’ famous Carnival Batabano, where costumed dancers, street performers, and musicians celebrate the area's diverse cultural heritage, then book your stay during the first month of May.


What are the top things to do in Cayman Islands?

The Crystal Caves

Located on the north shores of Grand Cayman are the mysterious Crystal Caves. Underground lakes, stalactites, and open ceilings that expose the jungle canopy above are all present in this ancient cave system. Navigate at your own pace or hire an expert to journey through the caves and lush jungles outside while getting the formations' ecological and geological history.

Scuba diving the USS Kittiwake

The Cayman Islands are well known for their world-class scuba diving opportunities, including reefs, underwater cave systems, and shipwrecks. For example, the USS Kittiwake was a former US Naval ship intentionally sunk off the coast in 2011. It now serves as a haven for all kinds of sea life, including shrimp, eels, barracuda, turtles, and grouper. This popular dive site can get crowded, so it’s a good idea to book in advance to secure a spot.

Queen Elizabeth II Botanic Park

This nature reserve is home to several protected and rare species of plant and animal life, including the endangered Grand Cayman Blue Iguana. A visitors center, floral garden, and heritage garden are all available for exploration and provide the public with a view into the island's unique ecological makeup without impacting the environment.