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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.

  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.

$135 per night
SUPERHOST
  1. Entire condo
  2. West Bay
Spacious Modern Condo /w Jaw Dropping Ocean View

This brand new modern oceanfront condo features beautiful unobstructed seafront views from the living room, kitchen, and bedroom. You can enjoy the view from inside the condo with the lovely contemporary interior, or outside on the spacious patio area. There are even two pools – an infinity freshwater pool with waterfall and a sea pool allowing easy access to the sea for diving and snorkeling (on a beautiful reef, rated #4 in the world for shore diving).

$306 per night
SUPERHOST
  1. Entire rental unit
  2. Grand Cayman
Adorable Boho Beach Villa

This adorable studio apartment has been fully renovated & has everything you need to enjoy the perfect Caribbean getaway. Calypso Cove is directly across from the famous Seven Mile Beach, where you can swim in the crystal clear blue sea every day. The studio has a balcony so you can enjoy the sunset or a morning coffee. Walking distance to supermarket, restaurants, bank and pharmacy, this apartment is in the perfect location. Keurig coffee machine, deck chairs, fins and mask and beach umbrella.

$190 per night

Vacation rentals for every style

Get the amount of space that is right for you

  • Houses
  • Resorts
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Cayman Islands house rentals

SUPERHOST
  1. Entire home
  2. Bodden Town
Tranquil Hideaway
$106 per night
  1. Private room
  2. Bodden Town
Gayle's Getaway (GG)
$70 per night
SUPERHOST
  1. Entire home
  2. Grand Cayman
Kaibo Dreams
$322 per night
  1. Private room
  2. Savannah
Island Serenity
$85 per night
SUPERHOST
  1. Entire home
  2. Grand Cayman
Pools of the Kai 3
$476 per night
SUPERHOST
  1. Entire home
  2. Little Cayman
Just Chillin in Little Cayman
$170 per night
  1. Entire home
  2. Grand cayman
The Highlands Rooftop Retreat
$375 per night
SUPERHOST
  1. Entire home
  2. KY
Mango Gardens Tropical Oasis near to town centre
$289 per night
  1. Private room
  2. West Bay
16 Cozy Place-2 Single Bedrooms-1Bathroom
$95 per night
SUPERHOST
  1. Entire home
  2. Grand Cayman
Kai Tana
$504 per night
  1. Private room
  2. West Bay
Medlock Guest House (Grey Room)
$110 per night
  1. Entire home
  2. Gun Bay
East End Beach House
$255 per night

Cayman Islands condo rentals

SUPERHOST
  1. Entire condo
  2. George Town
Cayman Reef Resort on Seven Mile Beach
$328 per night
  1. Entire condo
  2. West Bay
Condo Kai- Awesome 1B/1B in West Bay, Grand Cayman
$175 per night
SUPERHOST
  1. Entire condo
  2. Grand Harbour
The Sanctuary at the Careenage, Grand Harbour
$175 per night
  1. Entire condo
  2. George Town
Beach Living at Seagull Condos BLMI
$137 per night
  1. Entire condo
  2. Rum Point
Kaibo Yacht Club Villas Ocean Front Apartment
$250 per night
SUPERHOST
  1. Entire condo
  2. George Town
2 BR beach condo resort with pool and ocean views
$375 per night
SUPERHOST
  1. Entire condo
  2. George Town
World Famous Seven Mile Beach "Cayman Islands"
$255 per night
  1. Entire condo
  2. KY
Luxury quiet beachfront w/coral reef snorkeling
$275 per night
  1. Entire condo
  2. George Town
On Seven Mile Beach, no cruise ship tourists!!
$280 per night
SUPERHOST
  1. Entire condo
  2. West Bay
Penthouse 2Bd/2Bth Oceanfront Condo-Onsite Dining
$294 per night
  1. Entire condo
  2. George Town
Grandview condominium right on the beach!!!
$350 per night
SUPERHOST
  1. Entire condo
  2. Rum Point
Nature's View: Pools of the Kai #2
$282 per night

Cayman Islands villa rentals

  1. Entire villa
  2. West Bay
Modern BeachSide Villa steps from Seven Mile Beach
$208 per night
  1. Entire villa
  2. Old Man Bay
Old Man Bay Villa #1
$145 per night
  1. Entire villa
  2. Rum Point
Three Little Birds - 2+ bedroom
$296 per night
LUXE
Professionally inspected
  1. Entire villa
  2. Rum Point
Tarasand
$950 per night
SUPERHOST
  1. Entire villa
  2. West Bay
Ocean Front Relaxation Villa
$549 per night
  1. Entire villa
  2. West Bay
Beach Living at Conch Point Villa (BLJJ)
$748 per night
SUPERHOST
  1. Private room
  2. George Town
Double Room + External Bath room (Hibiscus Room)
$125 per night
  1. Entire villa
  2. Bodden Town
Oceanfront Villa (Brand New)
$195 per night
  1. Entire villa
  2. Bodden Town
Beachfront Accomodation
$195 per night
  1. Entire villa
  2. North Side
Coco Kai Beach Front Villa heated pool and dock
$799 per night
  1. Entire villa
  2. Bodden Town
Sea Palm Villas Beautiful Beachfront accomodation
$195 per night
SUPERHOST
  1. Entire villa
  2. Grand Cayman
Deluxe Spacious Villa
$455 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.


How do I get around Cayman Islands?

The Cayman Islands are three main islands: Grand Cayman, Little Cayman, and Cayman Brac. International flights arrive at Captain Charles Kirkconnell International Airport (CYB) on Cayman Brac and the George Town-Owen Roberts Airport (GCM) that services Grand Cayman. Once you’ve landed, the best way to navigate around each of the islands is by car. Rental agencies are available outside of all major airport terminals, and due to the relatively small size of the islands, getting around is straightforward. Taxis are also available in most towns and populated areas. If you want to travel between islands, the fastest way is to charter one of the short inter-island flights. Another option is to hire a private boat for the roughly one-hour journey.


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.